2-'ALK'benzene-1,4-diol

Page 1

Reaxys

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eMolecules

Reactions (1411)

Substances (38)

Structure

Citations (1158)

Structure/Compound Data Chemical Name: 2-methylbenzene-1,4-diol Reaxys Registry Number: 2041489

CAS Registry Number: 95-71-6 Type of Substance: isocyclic Molecular Formula: C7H8O2

Linear Structure Formula: (CH3)C6H3(OH)2 Molecular Weight: 124.139

InChI Key: CNHDIAIOKMXOLK-UHFFFAOYSA-N

1

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-methylbenzene-1,4-diol, Methylhydroquinone, 2-Methylbenzene-1,4-diol Identification Substance Label (49) Label

Reference

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N° of preparations All Preps | All Reactions 110 prep out of 800 reactions.

Available Data

N° of ref.

Identification Physical Data (101) Spectra (33) Bioactivity (44) Other Data (45)

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III-1

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mH&2%Q

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4

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7

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by-prod12

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MMHQ

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15

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2a

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Label

Reference

Educt to 2

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5d

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8a

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9

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10

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1b

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2, R1=R2=H, R3=Me

Algi, Fatih; Balci, Metin

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8 -> 13, step f

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4f

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2MHQ

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1f

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4b

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I

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prod., Tab. 2, entry 10

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2e

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Tab. 2, react., entry 2

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product, table/run 1

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38

Pfizer Inc.

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2,5-DHT

Venkata Ramana Rao; Ramana Rao

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5c

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2. monomer to MCLCP-2

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S11

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12 R=Me

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QH2 2

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16

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B

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21

Ichihashi, Keiko; Teranishi, Kiyoshi; Ichimura, Akio

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Patent-Specific Data (5)

Prophetic Compound

Related Markush Structure (RN)

Location in Patent

Reference

Page/Page column

FUJIFILM Corporation; MIZUMURA Masatoshi; KATOH Shunya; UEMURA Minoru; ISHIWATAYasuhiro; YOSHIKAWA Masaru; MATSUYAMA Hiroshi

Patent: EP2738155 A1, 2014 ; Title/Abstract Full Text Show Details

23250300

E I du Pont de Nemours and Company

Patent: US8344175 B2, 2013 ; Title/Abstract Full Text Show Details

21278379

LG Chem, Ltd.

Patent: US7910179 B2, 2011 ; Title/Abstract Full Text Show Details

19847381

GENERAL ELECTRIC COMPANY

Patent: WO2005/97721 A1, 2005 ; Title/Abstract Full Text Show Details

prophetic product

Sumitomo Chemical Company, Limited

Patent: EP1248313 A2, 2002 ; Title/Abstract Full Text Show Details

Derivative (4) Comment (Derivative)

Reference

Bis-(3,4,5-trijod-benzoat): F: 238.2-240grad

O'Donnell et al.

Journal of Chemical and Engineering Data, 1963 , vol. 8, p. 608 Full Text View citing articles Show Details

dibenzoyl derivative (mp: 122 degree )

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

compound with 0.5(?) mol phoenicin (mp: 160 degree ) Further Data see Handbook

Posternak

Helvetica Chimica Acta, 1938 , vol. 21, p. 1326,1335 Full Text View citing articles Show Details

p-toluidine salt (mp: 90 degree , leaflets) Further Data see Handbook

Hebebrand

Chemische Berichte, 1882 , vol. 15, p. 1974 Full Text Show Details

Purification (1) Reference Hecker,E.; Meyer,E.


Chemische Berichte, 1964 , vol. 97, p. 1926 - 1939 Full Text View citing articles Show Details

Barker; Hollingworth

Chemicky Prumysl, 1960 , vol. 10, p. 525 Full Text Show Details

Physical Data Melting Point (25) Melting Point

Solvent (Melting Point)

Reference

125 - 126 °C

benzene hexane

Pande, Poorn Prakash

Asian Journal of Chemistry, 2010 , vol. 22, # 4 p. 2549 - 2553 Title/Abstract Full Text View citing articles Show Details

132 - 133 °C

Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud

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126 °C

benzene

Nadkarni, K. K; Kamat, S. P.; Paknikar, S. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994 , vol. 33, # 5 p. 432 - 435 Title/Abstract Full Text Show Details

125 - 128 °C

Kagawa; Tokura; Uchida; Kakushi; Shike; Nakai

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 8 p. 2083 - 2087 Title/Abstract Full Text View citing articles Show Details

126 °C

Malesani, Giorgio; Galiano, Fabio; Ferlin, Maria Grazia; Masiero, Sergio

Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 563 - 569 Title/Abstract Full Text Show Details

124 - 125 °C

Stern et al.

Journal of the American Chemical Society, 1947 , vol. 69, p. 869,874 Full Text View citing articles Show Details

Cohen

Journal of the American Chemical Society, 1947 , vol. 69, p. 1057,1063 Full Text Show Details

Fujita; Sano

Journal of Organic Chemistry, 1979 , vol. 44, p. 2647,2648, 2650 Full Text View citing articles Show Details

129 - 130 °C

Kikkawa et al.

Nippon Kagaku Kaishi, 1977 , p. 695,696 Full Text Show Details

125 - 126 °C

Forsskahl et al.

Carbohydrate Research, 1976 , vol. 48, p. 13,14-21 Full Text Show Details

131.5 - 132 °C

Fujio,M. et al.

Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 2127 - 2133 Full Text View citing articles Show Details

126 - 127 °C

Maruyama et al.

Bulletin of the Chemical Society of Japan, 1973 , vol. 46, p. 2470,2474 Full Text Show Details

127 - 127.5 °C

Nilsson et al.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 2337,2338 Full Text Show Details

123.5 - 124 °C

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

119 - 121 °C

Sequin-Frey,M.; Tamm,C.

Helvetica Chimica Acta, 1971 , vol. 54, # 3 p. 851 - 861 Full Text View citing articles Show Details

124 °C

Nietzki

Chemische Berichte, 1877 , vol. 10, p. 1934,2005 Chemische Berichte, 1878 , vol. 11, p. 1103 Full Text Show Details


Fichter; Ris

Helvetica Chimica Acta, 1924 , vol. 7, p. 810 Full Text Show Details

Kamal et al.

Pakistan Journal of Scientific and Industrial Research, 1970 , vol. 13, p. 236,237-239 Chem.Abstr., 1971 , vol. 74, # 75167w Full Text Show Details

Hanson; Mehta

Journal of the Chemical Society [Section] C: Organic, 1969 , p. 2349 Full Text View citing articles Show Details

125 °C

le Guyader,M.

Bulletin de la Societe Chimique de France, 1966 , p. 1848 - 1858 Full Text View citing articles Show Details

Fichter; Simon

Helvetica Chimica Acta, 1934 , vol. 17, p. 717,719 Full Text Show Details

120 - 122 °C

Schulte; Ruecker

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1964 , vol. 297, p. 182,184 Full Text Show Details

128 - 130 °C

benzene

Muehlstaedt; Scholz

Chemische Berichte, 1964 , vol. 97, p. 1 Full Text Show Details

122 - 125 °C

benzene

Hecker,E.; Meyer,E.

Chemische Berichte, 1964 , vol. 97, p. 1926 - 1939 Full Text View citing articles Show Details

124 - 126 °C

petroleum ether

Zbiral,E. et al.

Monatshefte fuer Chemie, 1960 , vol. 91, p. 331 - 347 Full Text View citing articles Show Details

125 - 127 °C

benzene

Goodwin; Witkop

Journal of the American Chemical Society, 1957 , vol. 79, p. 179,184 Full Text Show Details

Hide facts Melting Point

Solvent (Melting Point)

Comment (Melting Point)

Reference

126 - 127 °C

nach Sublimation.

Cardani et al.

Gazzetta Chimica Italiana, 1955 , vol. 85, p. 1599,1610 Anm. 17 Full Text Show Details

128 °C

Sublimation.

Birkinshaw; Bracken; Raistrick

Biochemical Journal, 1943 , vol. 37, p. 726 Full Text Show Details

benzene petroleum ether

Fieser; Oxford

Journal of the American Chemical Society, 1942 , vol. 64, p. 2063 Full Text Show Details

127 - 128 °C

James; Snell; Weissberger

Journal of the American Chemical Society, 1938 , vol. 60, p. 2084,2085 Full Text Show Details

124 - 125 °C

benzene

Sublimation.

Nevile; Winther

Chemische Berichte, 1882 , vol. 15, p. 2992 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

163 °C

11 Torr

Bayer and Co.

Patent: DE249939 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 1330 Full Text Show Details

Adsorption (MCS) (2) Description (Adsorption (MCS))

Partner (Adsorption (MCS))

Solvent (Adsorption (MCS))

Temperature (Adsorption (MCS))

Reference

Further physical properties of the

smooth platinum electrode

aq. HClO4

22.9 °C

Soriaga, Manuel P.; Hubbard, Arthur T.


adsorbed molecule

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2735 - 2742 Title/Abstract Full Text View citing articles Show Details Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3937 - 3945 Title/Abstract Full Text View citing articles Show Details

Further physical properties of the adsorbed molecule

smooth platinum electrode, iodide ion

aq. HClO4

22.9 °C

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2742 - 2747 Title/Abstract Full Text View citing articles Show Details

Association (MCS) (3) Solvent (Association (MCS))

Description (Association (MCS))

Partner (Association (MCS))

Further physical properties of the complex

5,10,15-triphenyl-20-(3,6-dioxocyclohexa-1,4dienyl)porphyrinatozinc(II)

benzonitrile

D'Souza; Deviprasad

Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4601 - 4609 Title/Abstract Full Text View citing articles Show Details

NMR spectrum of the complex

C144H136O24

CDCl3

25 °C

Robbins, Timothy A.; Knobler, Carolyn B.; Bellew, Donald R.; Cram, Donald J.

Journal of the American Chemical Society, 1994 , vol. 116, # 1 p. 111 - 122 Title/Abstract Full Text View citing articles Show Details

Stability constant of the complex with ...

Bishop; Tong

Journal of the American Chemical Society, 1965 , vol. 87, p. 501,504 Full Text Show Details

Temperature (Association (MCS))

Chromatographic Data (1) Chromatographic data

Reference

GC (Gas chromatography)

Liu, Shaohua; He, Peixin; Tian, Zhaofu; Li, Xiaolan; Xu, Chunping

Journal of the Chilean Chemical Society, 2015 , vol. 60, # 1 p. 2761 - 2768 Title/Abstract Full Text View citing articles Show Details

Crystal Property Description (4) Colour & Other Properties

Reference

brown

Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud

Synthetic Communications, 2002 , vol. 32, # 10 p. 1501 - 1515 Title/Abstract Full Text View citing articles Show Details

Blaettchen

Birkinshaw; Bracken; Raistrick

Biochemical Journal, 1943 , vol. 37, p. 726 Full Text Show Details

Tafeln

Fieser; Oxford

Journal of the American Chemical Society, 1942 , vol. 64, p. 2063 Full Text Show Details

Blaetter

Nevile; Winther

Chemische Berichte, 1882 , vol. 15, p. 2992 Full Text Show Details

Dielectric Constant (1) Reference Rajyam et al.

Current Science, 1971 , vol. 40, p. 62 Full Text Show Details

Reference


Dissociation Exponent (16) Dissociation Exponent (pK)

Dissociation Group

Temperature (Dissociation Exponent)

Solvent (Dissociation Exponent)

Method (Dissociation Exponent)

Type (Dissociation Exponent)

11.96

a1/apparent

Jacobson, Alan R.; Moe, Scott T.; Allen; Fessenden, James D.

Molecular Pharmacology, 2006 , vol. 70, # 1 p. 259 - 266 Title/Abstract Full Text View citing articles Show Details

10.05

H(1+)

a1/apparent

Kalnin'sh

Russian Journal of Applied Chemistry, 2005 , vol. 78, # 11 p. 1727 - 1744 Title/Abstract Full Text View citing articles Show Details

10.14

O-H

25 °C

H2O

spectrophotometric

a1/apparent

Youngblood, Michael P.

Journal of the American Chemical Society, 1989 , vol. 111, # 5 p. 1843 - 1849 Title/Abstract Full Text View citing articles Show Details

12.11

O-H

25 °C

H2O

spectrophotometric

a2/apparent

Youngblood, Michael P.

Journal of the American Chemical Society, 1989 , vol. 111, # 5 p. 1843 - 1849 Title/Abstract Full Text View citing articles Show Details

(pk')pK

Pearce,P.J.; Simkins,R.J.J.

Canadian Journal of Chemistry, 1968 , vol. 46, p. 241 - 248 Full Text View citing articles Show Details

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1968 , vol. 72, p. 567,569, 572 Full Text Show Details

(pk')Ionisier.-Konst. (berechnet aus dem UV-Sp. <220-400 μ> bei versch. pH-Werten): pK(1)= 10.05, pK(2)= 11.5

Bishop; Tong

Journal of the American Chemical Society, 1965 , vol. 87, p. 501,504 Full Text Show Details

10.15

21 °C

H2O

spectrophotometric

a1/apparent

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

10.25

14 °C

H2O

spectrophotometric

a1/apparent

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

11.74

21 °C

H2O

spectrophotometric

a2/apparent

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

11.85

14 °C

H2O

spectrophotometric

a2/apparent

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

10.05

25.5 °C

H2O

spectrophotometric

a1/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

10.1

19.8 °C

H2O

spectrophotometric

a1/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

10.2

13.1 °C

H2O

spectrophotometric

a1/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143

Comment (Dissociation Exponent)

Reference


Full Text Show Details

11.62

25.5 °C

H2O

spectrophotometric

a2/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

11.67

19.8 °C

H2O

spectrophotometric

a2/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

11.72

13.1 °C

H2O

spectrophotometric

a2/apparent

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

Electrical Moment (1) Description (Electrical Moment)

Comment (Electrical Moment)

Reference

Dipole moment

μ

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1968 , vol. 72, p. 567,569, 572 Full Text Show Details

Electrochemical Behaviour (1) Description (Electrochemical Behaviour)

Reference

Polarography

Arai; Onozuka

Nippon Kagaku Kaishi, 1978 , p. 997,998 Full Text Show Details

Electrochemical Characteristics (9) Description (Electrochemical Characteristics)

Solvent (Electrochemical Characteristics)

Temperature (Electrochemical Characteristics)

cyclovoltammetry

tetrahydrofuran

oxidation potential

oxidation potential

Location

Comment (Electrochemical Characteristics)

Reference

25 °C

supporting information

transmitted electrons 1; Anodic peak potential; 1.42 V; Other electrode; potential diagram; Bu4NPF6

Matsuo, Takashi; Tohi, Yuji; Hayashi, Takashi

Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 8946 - 8955 Title/Abstract Full Text View citing articles Show Details

benzonitrile

Biczok, Laszlo; Gupta, Neeraj; Linschitz, Henry

Journal of the American Chemical Society, 1997 , vol. 119, # 51 p. 12601 - 12609 Title/Abstract Full Text View citing articles Show Details

D'Souza; Deviprasad

Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4601 - 4609 Title/Abstract Full Text View citing articles Show Details

Spinner,I.H. et al.

Canadian Journal of Chemistry, 1964 , vol. 42, p. 554 - 559 Full Text View citing articles Show Details

Manecke et al.

Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1970 , vol. 28, p. 139,142 Full Text Show Details

Giza et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 679,681 Full Text Show Details

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details


polarographic halfwave potential

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Masson et al.

Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1975 , vol. 64, p. 175,181 Full Text Show Details

Arai; Onozuka

Nippon Kagaku Kaishi, 1977 , p. 1665,1666 Chem.Abstr., 1978 , # 36877 Full Text Show Details

redox potential

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1968 , vol. 72, p. 567,569, 572 Full Text Show Details

polarographic current/voltage curve

Smith et al.

Journal of the American Chemical Society, 1941 , vol. 63, p. 1018,1019 Journal of the American Chemical Society, 1942 , vol. 64, p. 447,448 Full Text View citing articles Show Details

Wiesner

Collection of Czechoslovak Chemical Communications, 1947 , vol. 12, p. 594,598, 602, 604 Full Text Show Details

redox potential

des Systems Toluchinon/Toluhydrochinon.

Hunter; Kvalnes

Journal of the American Chemical Society, 1932 , vol. 54, p. 2869,2874 Full Text Show Details

redox potential

Oxydations-Reduktionspotential des Systems Toluhydrochinon/Benzochinon in 0,1n-Salzsaeure bei 18grad und 25,4grad.

Biilmann; Jensen; Pedersen

Journal of the Chemical Society, 1925 , vol. 127, p. 207 Full Text Show Details

redox potential

Oxydations-Reduktionspotential des Systems Toluhydrochinon/Toluchinon in 0,1n-Salzsaeure bei 0grad und 25grad.

Conant; Fieser

Journal of the American Chemical Society, 1923 , vol. 45, p. 2205 Journal of the American Chemical Society, 1924 , vol. 46, p. 1877 Anm. 43 Full Text Show Details

Energy Data (MCS) (17) Description (Energy Data (MCS))

Partner (Energy Data (MCS))

Temperature (Energy Data (MCS))

Enthalpy of solution

methanol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

ethanol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

propan-1-ol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

butan-1-ol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

pentan-1-ol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

hexan-1-ol

25 °C

Smirnov, V. I.; Krestov, G. A.

Reference


Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

octanol

25 °C

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Enthalpy of solution

benzene

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

nitrobenzene

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

acetonitrile

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

1,4-dioxane

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

acetone

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

formamide

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

N,N-dimethyl-formamide

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

dimethyl sulfoxide

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

pyridine

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of solution

N,N,N,N,N,N-hexamethylphosphoric triamide

20 °C

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Enthalpy of Formation (1) Enthalpy of Formation

Temperature (Enthalpy of Formation)

Pressure (Enthalpy of Formation)

Reference

-404200 Jmol-1

25 °C

750.06 Torr

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details


Enthalpy of Fusion (1) Enthalpy of Fusion

Reference

27610 Jmol-1

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details

Further Information (6) Description (Further Information)

Reference

Further information

Masson et al.

Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1975 , vol. 64, p. 175,181 Full Text Show Details

Further information

Rajyam et al.

Current Science, 1971 , vol. 40, p. 62 Full Text Show Details

Further information

Aplin; Pike

Chemistry and Industry (London, United Kingdom), 1966 , p. 2009 Full Text Show Details

Further information

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Further information

Manecke; Foerster

Makromolekulare Chemie, 1962 , vol. 52, p. 147,153,154 Full Text Show Details

Further information

Beckering; Fowkes

Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1959 , p. 3 Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1960 , # 4150 Full Text Show Details

Heat Capacity Cp (1) Heat Capacity Cp

Temperature (Heat Capacity Cp)

Reference

175.16 Jmol-1K-1

0 - 99.6 °C

Satoh; Sogabe

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1941 , vol. 38, p. 246,248 Chem.Abstr., 1941 , p. 4666 Full Text Show Details

Ionization Potential (4) Ionization Potential

Method (Ionization Potential)

Comment (Ionization Potential)

Reference

7.7 eV

change-transfer equilibrium

Kalnin'sh

Russian Journal of Applied Chemistry, 2005 , vol. 78, # 11 p. 1727 - 1744 Title/Abstract Full Text View citing articles Show Details

7.87 eV

spectrographical

Spange, Stefan; Maenz, Karsten; Stadermann, Dietmar

Liebigs Annalen der Chemie, 1992 , # 10 p. 1033 - 1038 Title/Abstract Full Text Show Details

7.7 eV

spectrographical

Type: not given

Kalnin'sh, K. K.; Safant'evskii, A. A.; Shchukareva, V. V.

Journal of Organic Chemistry USSR (English Translation), 1987 , vol. 23, p. 1942 - 1947 Zhurnal Organicheskoi Khimii, 1987 , vol. 23, # 10 p. 2197 - 2202 Title/Abstract Full Text Show Details

Chi-Sing Tse; Kuwana

Analytical Chemistry, 1978 , vol. 50, p. 1315,1316-1317 Full Text Show Details

Liquid/Liquid Systems (MCS) (2) Description (Liquid/Liquid Systems (MCS))

Partner (Liquid/Liquid Systems (MCS))

Solvent (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

sodium dodecyl sulfate

H2O

Reference Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 996


Title/Abstract Full Text View citing articles Show Details

Distribution between solvent 1 + 2

hexadecyltrimethylammonium bromide

Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 996 Title/Abstract Full Text View citing articles Show Details

H2O

Molecular Deformation (1) Description (Molecular Deformation)

Reference

Force constants

Venkata Ramana Rao; Ramana Rao

Spectrochimica Acta - Part A Molecular and Biomolecular Spectroscopy, 2002 , vol. 58, # 14 p. 3039 - 3065 Title/Abstract Full Text View citing articles Show Details

Other Thermochemical Data (2) Description (Other Thermochemical Data)

Comment (Other Thermochemical Data)

Reference

Heat of combustion at constant volume

834,6 kcal/Mol.

Swietoslawski; Starczewska

Journal de Chimie Physique et de Physico-Chimie Biologique, 1926 , vol. 23, p. 822 Full Text Show Details

Heat of combustion at constant volume

836.3 cal/Mol.

Valeur

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 125, p. 872 Annales de Chimie (Cachan, France), 1900 , vol. <7> 21, p. 478 Full Text Show Details

Partition octan-1-ol/water (MCS) (1) log POW

Reference

1.1

Jacobson, Alan R.; Moe, Scott T.; Allen; Fessenden, James D.

Molecular Pharmacology, 2006 , vol. 70, # 1 p. 259 - 266 Title/Abstract Full Text View citing articles Show Details

Transport Phenomena (MCS) (1)

Description (Transport Phenomena (MCS))

Reference

Diffusion

Iwano

Bulletin of the Chemical Society of Japan, 1969 , vol. 42, p. 2677,2679 Full Text Show Details

Spectra NMR Spectroscopy (8) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

chloroform-d1

Bell, Jeffrey G.; Green, James R.; Wang, Jichang

Journal of Physical Chemistry A, 2014 , vol. 118, # 42 p. 9795 - 9800 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

250 MHz

Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud

Synthetic Communications, 2002 , vol. 32, # 10 p. 1501 - 1515 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

acetone-d6

Conway, Gregory A.; Loeffler, Larry J.

Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1315 - 1320 Title/Abstract Full Text Show Details

Puzari; Baruah, Jubaraj B.

Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2344 - 2349 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

acetone-d6

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 2960 Title/Abstract Full Text View citing articles Show Details

Reference


Puzari; Baruah, Jubaraj B.

Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2344 - 2349 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

Matovic, Radomir; Cekovic, Zivorad

Gazzetta Chimica Italiana, 1997 , vol. 127, # 9 p. 483 - 488 Title/Abstract Full Text Show Details

Chemical shifts

1H

dimethylsulfoxide

40 °C

Karpov, O. N.

Journal of Applied Spectroscopy, 1996 , vol. 63, # 3 p. 393 - 397 Zhurnal Prikladnoi Spektroskopii, 1996 , vol. 63, # 3 p. 472 - 476 Title/Abstract Full Text Show Details

Chemical shifts

1H

CDCl3

25 °C

Robbins, Timothy A.; Knobler, Carolyn B.; Bellew, Donald R.; Cram, Donald J.

Journal of the American Chemical Society, 1994 , vol. 116, # 1 p. 111 - 122 Title/Abstract Full Text View citing articles Show Details

NMR

Fujio,M. et al.

Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 2127 - 2133 Full Text View citing articles Show Details

Sequin-Frey; Tamm

Helvetica Chimica Acta, 1971 , vol. 54, p. 851,852-854,859,860 Full Text Show Details

Nilsson et al.

Journal of the Chemical Society, Perkin Transactions 1: Organic and BioOrganic Chemistry (1972-1999), 1973 , p. 2337,2338 Full Text Show Details

Kamal et al.

Pakistan Journal of Scientific and Industrial Research, 1970 , vol. 13, p. 236,237-239 Chem.Abstr., 1971 , vol. 74, # 75167w Full Text Show Details

IR Spectroscopy (11) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Bands

tetrahydrofuran

Kalnin'sh

Russian Journal of Applied Chemistry, 2005 , vol. 78, # 11 p. 1727 - 1744 Title/Abstract Full Text View citing articles Show Details

Bands

KBr

Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud

Synthetic Communications, 2002 , vol. 32, # 10 p. 1501 - 1515 Title/Abstract Full Text View citing articles Show Details

Venkata Ramana Rao; Ramana Rao

Spectrochimica Acta - Part A Molecular and Biomolecular Spectroscopy, 2002 , vol. 58, # 14 p. 3039 - 3065 Title/Abstract Full Text View citing articles Show Details

Bands

neat (no solvent)

Puzari; Baruah, Jubaraj B.

Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2344 - 2349 Title/Abstract Full Text View citing articles Show Details

Bands

neat (no solvent)

3322 - 818 cm**(-1)

Matovic, Radomir; Cekovic, Zivorad

Gazzetta Chimica Italiana, 1997 , vol. 127, # 9 p. 483 - 488 Title/Abstract Full Text Show Details

Bands

KBr

3350 cm**(-1)

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

Bands

3618 cm**(-1)

Kalnin'sh, K. K.; Safant'evskii, A. A.; Shchukareva, V. V.

Journal of Organic Chemistry USSR (English Translation), 1987 , vol. 23, p. 1942 - 1947 Zhurnal Organicheskoi Khimii, 1987 , vol. 23, # 10 p. 2197 - 2202 Title/Abstract Full Text Show Details

Bands

KBr

1198 - 3298 cm**(-1)

Malesani, Giorgio; Galiano, Fabio; Ferlin, Maria Grazia; Masiero, Sergio

Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 563 - 569 Title/Abstract Full Text Show Details

IR

Sequin-Frey,M.; Tamm,C.

Helvetica Chimica Acta, 1971 , vol. 54, # 3 p. 851 - 861 Full Text View citing articles Show Details

Reference


le Guyader,M.

Bulletin de la Societe Chimique de France, 1966 , p. 1848 - 1858 Full Text View citing articles Show Details

Beckering et al.

Analytical Chemistry, 1964 , vol. 36, p. 2412 Full Text View citing articles Show Details

Bands

KBr

3311 cm**(-1) OH-Valenzschwingung.

Musso; v. Grunelius

Chemische Berichte, 1959 , vol. 92, p. 3101,3105 Full Text Show Details

Bands

CCl4

3605 cm**(-1) OH-Valenzschwingung.

Musso; v. Grunelius

Chemische Berichte, 1959 , vol. 92, p. 3101,3105 Full Text Show Details

Spectrum

Beckering; Fowkes

Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1959 , p. 3 Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1960 , # 4150 Full Text Show Details

Mass Spectrometry (4) Description (Mass Spectrometry)

Comment (Mass Spectrometry)

spectrum

Kanaly, Robert A.; In, Seon Kim; Hur, Hor-Gil

Journal of Agricultural and Food Chemistry, 2005 , vol. 53, # 16 p. 6426 - 6431 Title/Abstract Full Text View citing articles Show Details

Hailu, Solomon Legese; Nair, Balachandran Unni; Redi-Abshiro, Mesfin; Diaz, Isabel; Aravindhan, Rathinam; Tessema, Merid

Chinese Journal of Catalysis, 2016 , vol. 37, # 1 p. 135 - 145 Title/Abstract Full Text Show Details

spectrum chemical ionization (CI)

Iida, Yoshio; Daishima, Shigeki; Shibata, Akihiro

Organic Mass Spectrometry, 1993 , vol. 28, # 4 p. 433 - 436 Title/Abstract Full Text Show Details

spectrum

positive secondary ions

Nourse, B. D.; Brodbelt, J. S.; Cooks, R. G.

Organic Mass Spectrometry, 1991 , vol. 26, # 6 p. 575 - 582 Title/Abstract Full Text Show Details

Aplin; Pike

Chemistry and Industry (London, United Kingdom), 1966 , p. 2009 Full Text Show Details

Reference

UV/VIS Spectroscopy (7) Description (UV/VIS Spectroscopy)

Solvent (UV/VIS Spectroscopy)

Absorption Maxima (UV/VIS)

Comment (UV/VIS Spectroscopy)

Spectrum

290 nm

Bell, Jeffrey G.; Green, James R.; Wang, Jichang

Journal of Physical Chemistry A, 2014 , vol. 118, # 42 p. 9795 - 9800 Title/Abstract Full Text View citing articles Show Details

Absorption maxima

Arai; Onozuka

Nippon Kagaku Kaishi, 1977 , p. 1665,1666 Chem.Abstr., 1978 , # 36877 Full Text Show Details

Bishop; Tong

Journal of the American Chemical Society, 1965 , vol. 87, p. 501,504 Full Text Show Details

UV/VIS

Tyman

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 1639,1645 Full Text Show Details

Sequin-Frey; Tamm

Helvetica Chimica Acta, 1971 , vol. 54, p. 851,852-854,859,860 Full Text Show Details

Forrester; Gaucher

Biochemistry, 1972 , vol. 11, p. 1102,1103 Full Text Show Details

Kamal et al.

Pakistan Journal of Scientific and Industrial Research, 1970 , vol. 13, p. 236,237-239 Chem.Abstr., 1971 , vol. 74, # 75167w Full Text Show Details

Arshad et al.

Revue Roumaine de Chimie, 1970 , vol. 15, p. 1653,1656,1658,1660

Reference


Full Text Show Details

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1969 , vol. 73, p. 203 Full Text Show Details

Absorption maxima

butan-1-ol

293.5 nm

Barker; Hollingworth

Journal of Applied Chemistry, 1959 , vol. 9, p. 16,21 Full Text Show Details

Spectrum

H2O

220 - 350 nm

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

Spectrum

ethanol

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details

Spectrum

John; Dietzel; Guenther

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1938 , vol. 252, p. 208,220 Full Text Show Details

ESR Spectroscopy (2) Description (ESR Spectroscopy)

Comment (ESR Spectroscopy)

Reference

Spectrum

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

Spectrum

des bei der Autoxidation in alkal. wss.-aethanol. Loesung erhaltenen 2-Methyl<1,4>benzosemichinon-Anions.

Venkataraman et al.

Journal of Chemical Physics, 1959 , vol. 30, p. 1006,1010 Full Text Show Details

Raman Spectroscopy (1) Description (Raman Spectroscopy)

Reference

Bands

Venkata Ramana Rao; Ramana Rao

Spectrochimica Acta - Part A Molecular and Biomolecular Spectroscopy, 2002 , vol. 58, # 14 p. 3039 - 3065 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (42) 1 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Sequin-Frey,M.; Tamm,C.

Helvetica Chimica Acta, 1971 , vol. 54, # 3 p. 851 - 861 Full Text View citing articles Show Details

Pospisil,J.; Taimr,L.

Collection of Czechoslovak Chemical Communications, 1964 , Full Text View citing articles Show Details

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , Full Text View citing articles Show Details

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , Full Text View citing articles Show Details

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , Full Text View citing articles Show Details

Seiko Kagaku Kabushiki Kaisha

Patent: EP812816 A1, 1997 ;

vol. 29, p. 381 - 389 vol. 30, p. 843 - 852 vol. 31, p. 98 - 105 vol. 37, p. 3599 - 3606

Title/Abstract Full Text Show Details

Zbiral,E. et al.

Monatshefte fuer Chemie, 1960 , vol. 91, p. 331 - 347 Full Text View citing articles Show Details

Agency of Industrial Science and Technology; Mitsui Toatsu Chemicals, Incorporated


Patent: US4066707 A1, 1978 ; Title/Abstract Full Text Show Details

Spinner,I.H. et al.

Canadian Journal of Chemistry, 1964 , vol. 42, p. 554 - 559 Full Text View citing articles Show Details

Pearce,P.J.; Simkins,R.J.J.

Canadian Journal of Chemistry, 1968 , vol. 46, p. 241 - 248 Full Text View citing articles Show Details

Hecker,E.; Meyer,E.

Chemische Berichte, 1964 , vol. 97, p. 1926 - 1939 Full Text View citing articles Show Details

Warner-Lambert Company

Patent: US4351950 A1, 1982 ; Title/Abstract Full Text Show Details

Bohlmann,F. et al.

Chemische Berichte, 1975 , vol. 108, p. 2818 - 2821 Full Text View citing articles Show Details

Buckman Laboratories, Inc.

Patent: US4293559 A1, 1981 ; Title/Abstract Full Text Show Details

E. I. Du Pont de Nemours and Co.

Patent: US4306094 A1, 1981 ; Title/Abstract Full Text Show Details

Sun Tech, Inc.

Patent: US4482756 A1, 1984 ; Title/Abstract Full Text Show Details

Ciba-Geigy AG

Patent: US4608435 A1, 1986 ; Title/Abstract Full Text Show Details

Sanofi

Patent: US4675419 A1, 1987 ; Title/Abstract Full Text Show Details

Sumitomo Chemical Company, Limited

Patent: EP1248313 A2, 2002 ; Title/Abstract Full Text Show Details

Buess,C.M. et al.

Journal of Medicinal Chemistry, 1965 , vol. 8, p. 469 - 474 Full Text View citing articles Show Details

2 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Witty,T.R.; Remers,W.A.

Journal of Medicinal Chemistry, 1973 , vol. 16, p. 1280 - 1284 Full Text View citing articles Show Details

Diana,G.D. et al.

Journal of Medicinal Chemistry, 1978 , vol. 21, p. 689 - 692 Full Text View citing articles Show Details

Jurd,L. et al.

Tetrahedron, 1979 , vol. 35, p. 1041 - 1054 Full Text View citing articles Show Details

Schildknecht,H. et al.

Angewandte Chemie, 1963 , vol. 75, p. 762 - 771 Full Text View citing articles Show Details

Musso,H.

Angewandte Chemie, 1963 , vol. 75, p. 965 - 977 Full Text View citing articles Show Details

Kurosawa,E.

Bulletin of the Chemical Society of Japan, 1961 , vol. 34, p. 300 - 304 Full Text View citing articles Show Details

Fujio,M. et al.

Bulletin of the Chemical Society of Japan, 1975 , vol. 48, p. 2127 - 2133 Full Text View citing articles Show Details

Temple University of the Commonwealth System of Higher Education

Patent: US4975463 A1, 1990 ; Title/Abstract Full Text Show Details

Miyagi,Y. et al.

Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 3019 - 3026 Full Text View citing articles Show Details

Deschamps,J. et al.

Bulletin de la Societe Chimique de France, 1965 , p. 2694 Full Text View citing articles Show Details

le Guyader,M.

Bulletin de la Societe Chimique de France, 1966 , p. 1848 - 1858 Full Text View citing articles Show Details

Behringwerke Aktiengesellschaft


Patent: US5519018 A1, 1996 ; Title/Abstract Full Text Show Details

Murata; Satoh; Nohara; et al.

European Journal of Medicinal Chemistry, 1977 , vol. 12, # 1 p. 17 - 20 Title/Abstract Full Text View citing articles Show Details

Eastman Kodak Company

Patent: US5107003 A1, 1992 ; Title/Abstract Full Text Show Details

Reynolds,D.D.

Journal of Heterocyclic Chemistry, 1970 , vol. 7, p. 1397 - 1400 Full Text View citing articles Show Details

Reynolds,D.D.; Cossar,B.C.

Journal of Heterocyclic Chemistry, 1971 , vol. 8, p. 611 - 615 Full Text View citing articles Show Details

Hoechst Celanese Corporation

Patent: US5130467 A1, 1992 ; Title/Abstract Full Text Show Details

Brown,E.R. et al.

Journal of Organic Chemistry, 1971 , vol. 36, # 19 p. 2849 - 2853 Full Text View citing articles Show Details

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

BASF AKTIENGESELLSCHAFT

Patent: WO2004/50596 A1, 2004 ; Title/Abstract Full Text Show Details

3 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Mahalingam, Rathinam Jothi; Ashtekar, Sunil; Thampi, Jegadeesh; Kumbhar, Pramod Shankar

Patent: US2005/137380 A1, 2005 ; Title/Abstract Full Text Show Details

Ashtekar, Sunil; Kumbhar, Pramod; Lens, Jan-Pleun; Mahalingam, Rathinam Jothi; Pradeep, Nadkarni; Thampi, Jegadeesh

Patent: US2005/137409 A1, 2005 ; Title/Abstract Full Text Show Details

COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH

Patent: WO2005/63664 A1, 2005 ; Title/Abstract Full Text Show Details

Thampi, Jegadeesh; Ashtekar, Sunil; Kumbhar, Pramod; Mahalingam, Rathinam Jothi

Patent: US2006/25634 A1, 2006 ; Title/Abstract Full Text Show Details

TOKYO OHKA KOGYO CO., LTD.

Patent: WO2006/80178 A1, 2006 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

FUJIFILM Corporation

Patent: WO2007/49779 A1, 2007 ; Title/Abstract Full Text Show Details

IRM LLC

Patent: WO2007/56366 A2, 2007 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

E. I. DU PONT DE NEMOURS AND COMPANY

Patent: WO2007/120459 A2, 2007 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

Kehrmann

Justus Liebigs Annalen der Chemie, 1910 , vol. 372, p. 312 Justus Liebigs Annalen der Chemie, 1918 , vol. 414, p. 172 Full Text View citing articles Show Details

Fieser; Hartwell

Journal of the American Chemical Society, 1935 , vol. 57, p. 1479,1481 Full Text View citing articles Show Details


Bernatek; Bo

Acta Chemica Scandinavica (1947-1973), 1959 , vol. 13, p. 337,340 Full Text Show Details

Ludwig et al.

Journal of the American Chemical Society, 1955 , vol. 77, p. 5751 Full Text View citing articles Show Details

Green et al.

Journal of the Chemical Society, 1959 , p. 3362,3369 Full Text View citing articles Show Details

Smith et al.

Journal of the American Chemical Society, 1941 , vol. 63, p. 1018,1019 Journal of the American Chemical Society, 1942 , vol. 64, p. 447,448 Full Text View citing articles Show Details

Marcinkiewicz et al.

Journal of the Chemical Society, 1959 , p. 3377 Full Text View citing articles Show Details

Pendse; Karrer

Helvetica Chimica Acta, 1958 , vol. 41, p. 396,399 Full Text View citing articles Show Details

Stern et al.

Journal of the American Chemical Society, 1947 , vol. 69, p. 869,874 Full Text View citing articles Show Details

4 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Karrer; Fritzsche

Helvetica Chimica Acta, 1939 , vol. 22, p. 260,263 Full Text View citing articles Show Details

Inouye et al.

Chemical and Pharmaceutical Bulletin, 1958 , vol. 6, p. 653 Full Text View citing articles Show Details

Posternak

Helvetica Chimica Acta, 1938 , vol. 21, p. 1326,1335 Full Text View citing articles Show Details

Waldmann; Poppe

Justus Liebigs Annalen der Chemie, 1937 , vol. 527, p. 190,191 Full Text View citing articles Show Details

Green

Chemische Berichte, 1893 , vol. 26, p. 2778 Journal of the Chemical Society, 1893 , vol. 63, p. 1404 Full Text Show Details

Bamberger

Chemische Berichte, 1900 , vol. 33, p. 949 Full Text Show Details

Burke; Weatherbee

Journal of the American Chemical Society, 1950 , vol. 72, p. 4691,4693 Full Text Show Details

Goodwin; Witkop

Journal of the American Chemical Society, 1957 , vol. 79, p. 179,184 Full Text Show Details

Desai; Mavani

Proceedings - Indian Academy of Sciences, Section A, 1947 , # 25 p. 327,329 Full Text Show Details

Desai; Mavani

Proceedings - Indian Academy of Sciences, Section A, 1942 , # 15 p. 11,14 Full Text Show Details

Mustafa

Nature (London, United Kingdom), 1948 , vol. 162, p. 856 Chem.Abstr., 1949 , p. 6515 Full Text View citing articles Show Details

Fieser; Oxford

Journal of the American Chemical Society, 1942 , vol. 64, p. 2063 Full Text Show Details

Bamberger

Justus Liebigs Annalen der Chemie, 1920 , vol. 420, p. 137 Full Text Show Details

Chem. Fabr. Schering

Patent: DE81068 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 127 Full Text Show Details

Kumagai; Wolffenstein

Chemische Berichte, 1908 , vol. 41, p. 298 Full Text Show Details

Nietzki

Chemische Berichte, 1877 , vol. 10, p. 1934,2005 Chemische Berichte, 1878 , vol. 11, p. 1103 Full Text Show Details

Clark

American Chemical Journal, 1892 , vol. 14, p. 571 Full Text Show Details

Brunner

Monatshefte fuer Chemie, 1889 , vol. 10, p. 174 Full Text Show Details

Nietzki; Bernard


Chemische Berichte, 1898 , vol. 31, p. 1336 Full Text Show Details

Valeur

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1897 , vol. 125, p. 872 Annales de Chimie (Cachan, France), 1900 , vol. <7> 21, p. 478 Full Text Show Details

5 of 42

6 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Sabatier; Mailhe

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1908 , vol. 146, p. 458 Annales de Chimie (Cachan, France), 1909 , vol. <8> 16, p. 88 Full Text Show Details

Nietzki

Chemische Berichte, 1878 , vol. 11, p. 1279 Justus Liebigs Annalen der Chemie, 1882 , vol. 215, p. 160 Full Text Show Details

Nevile; Winther

Chemische Berichte, 1882 , vol. 15, p. 2992 Full Text Show Details

Nietzki

Justus Liebigs Annalen der Chemie, 1882 , vol. 215, p. 155 Chemische Berichte, 1892 , vol. 25, p. 282,284 Full Text Show Details

Fichter; Stocker

Chemische Berichte, 1914 , vol. 47, p. 2016 Full Text Show Details

Bayer and Co.

Patent: DE249939 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 1330 Full Text Show Details

Bach

Chem. Zentralbl., 1916 , vol. 87, # II p. 743 Full Text Show Details

Fichter; Ackermann

Helvetica Chimica Acta, 1919 , vol. 2, p. 595 Full Text Show Details

Schmid

Monatshefte fuer Chemie, 1911 , vol. 32, p. 437 Full Text Show Details

Fichter; Ris

Helvetica Chimica Acta, 1924 , vol. 7, p. 810 Full Text Show Details

Swietoslawski; Starczewska

Journal de Chimie Physique et de Physico-Chimie Biologique, 1926 , vol. 23, p. 822 Full Text Show Details

Biilmann; Jensen; Pedersen

Journal of the Chemical Society, 1925 , vol. 127, p. 207 Full Text Show Details

Erdtman

Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences, 1934 , vol. 143, p. 196,197 Chem. Zentralbl., 1934 , vol. 105, # I p. 3054 Full Text Show Details

John; Dietzel; Guenther

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1938 , vol. 252, p. 208,220 Full Text Show Details

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Hunter; Kvalnes

Journal of the American Chemical Society, 1932 , vol. 54, p. 2869,2874 Full Text Show Details

Marini-Bettolo; Trucco

Gazzetta Chimica Italiana, 1943 , vol. 73, p. 300,304 Full Text Show Details

Luettringhaus; Gralheer

Justus Liebigs Annalen der Chemie, 1942 , vol. 550, p. 67,83 Full Text Show Details

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

Hoffmann-La Roche

Patent: DE753627 , 1940 ; DRP/DRBP Org.Chem. Full Text Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details


Cohen

Journal of the American Chemical Society, 1947 , vol. 69, p. 1057,1063 Full Text Show Details

Fichter; Simon

Helvetica Chimica Acta, 1934 , vol. 17, p. 717,719 Full Text Show Details

Birkinshaw; Bracken; Raistrick

Biochemical Journal, 1943 , vol. 37, p. 726 Full Text Show Details

Neunhoeffer; Pelz

Chemische Berichte, 1939 , vol. 72, p. 433,439 Full Text Show Details

Dodgson

Journal of the Chemical Society, 1930 , p. 2498,2500 Full Text Show Details

Pennsylvania Coal Prod. Co.

Patent: US2041593 , 1934 ; Full Text Show Details

James; Snell; Weissberger

Journal of the American Chemical Society, 1938 , vol. 60, p. 2084,2085 Full Text Show Details

Eastman Kodak Co.

Patent: US2533203 , 1948 ; Full Text Show Details

Brockmann; Mueller

Justus Liebigs Annalen der Chemie, 1939 , vol. 540, p. 51,62 Full Text Show Details

Musso; v. Grunelius

Chemische Berichte, 1959 , vol. 92, p. 3101,3105 Full Text Show Details

v. Euler; Adler; Caspersson

Arkiv foer Kemi, 1943 , vol. 16 A, # 11 p. 11 Full Text Show Details

Mayer; Stark

Chemische Berichte, 1931 , vol. 64, p. 2003,2007 Full Text Show Details

Underwood; Walsh

Journal of the American Chemical Society, 1936 , vol. 58, p. 646 Organic Syntheses, 1943 , vol. Coll. Vol. II, p. 553 Full Text View citing articles Show Details

Sondheimer; Elad

Journal of the American Chemical Society, 1957 , vol. 79, p. 5542,5545 Full Text Show Details

Friedmann et al.

Biochimica et Biophysica Acta, 1954 , vol. 13, p. 260,264 Full Text Show Details

Wender et al.

Journal of the American Chemical Society, 1952 , vol. 74, p. 4079,4082 Full Text Show Details

Wessely; Schinzel

Monatshefte fuer Chemie, 1953 , vol. 84, p. 969,976, 987 Full Text View citing articles Show Details

Barker; Hollingworth

Journal of Applied Chemistry, 1959 , vol. 9, p. 16,21 Full Text Show Details

Staude; Teupel

Zeitschrift fuer Elektrochemie und Angewandte Physikalische Chemie, 1957 , vol. 61, p. 181,186 Full Text Show Details

7 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Venkataraman et al.

Journal of Chemical Physics, 1959 , vol. 30, p. 1006,1010 Full Text Show Details

Baxendale; Hardy

Transactions of the Faraday Society, 1953 , vol. 49, p. 1140,1143 Full Text Show Details

Baxendale; Hardy

Transactions of the Faraday Society, 1954 , vol. 50, p. 808,811 Full Text Show Details

Boscott

Chemistry and Industry (London, United Kingdom), 1955 , p. 201 Full Text Show Details

Kharasch et al.

Journal of Organic Chemistry, 1956 , vol. 21, p. 925,927 Full Text Show Details

Mamalis et al.

Journal of the Chemical Society, 1959 , p. 3350,3356 Full Text Show Details

Inouye; Takano

Chemical and Pharmaceutical Bulletin, 1958 , vol. 6, p. 655,658 Full Text Show Details


Eastman Kodak Co.

Patent: US2732300 , 1953 ; Full Text Show Details

Bamberger

Chemische Berichte, 1895 , vol. 28, p. 248 Chemische Berichte, 1894 , vol. 27, p. 1348 Full Text Show Details

Henderson; Boyd

Journal of the Chemical Society, 1910 , vol. 97, p. 1661 Full Text Show Details

Satoh; Sogabe

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1941 , vol. 38, p. 246,248 Chem.Abstr., 1941 , p. 4666 Full Text Show Details

Nietzki

Chemische Berichte, 1877 , vol. 10, p. 835 Justus Liebigs Annalen der Chemie, 1882 , vol. 215, p. 160 Full Text Show Details

Posner; Lipsky

Justus Liebigs Annalen der Chemie, 1904 , vol. 336, p. 159 Full Text Show Details

Kehrmann; Brasch

Journal fuer Praktische Chemie (Leipzig), 1889 , vol. <2> 39, p. 378 Full Text Show Details

Hebebrand

Chemische Berichte, 1882 , vol. 15, p. 1974 Full Text Show Details

Conant; Fieser

Journal of the American Chemical Society, 1923 , vol. 45, p. 2205 Journal of the American Chemical Society, 1924 , vol. 46, p. 1877 Anm. 43 Full Text Show Details

Angeletti

Atti della Accademia delle Scienze di Torino, Classe di Scienze Fisiche, Matematiche e Naturali, 1934 , vol. # 70, p. 326,328 Full Text Show Details

Wiesner

Collection of Czechoslovak Chemical Communications, 1947 , vol. 12, p. 594,598, 602, 604 Full Text Show Details

Velasco

Anales de la Real Sociedad Espanola de Fisica y Quimica, 1934 , vol. 32, p. 345,365, 369 Full Text Show Details

Angeletti

Atti della Accademia delle Scienze di Torino, Classe di Scienze Fisiche, Matematiche e Naturali, 1935 , vol. # 70, p. 326,328 Full Text Show Details

8 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Angeletti

Gazzetta Chimica Italiana, 1934 , vol. 64, p. 346,347 Full Text Show Details

Pickholz

Journal of the Chemical Society, 1946 , p. 685 Full Text Show Details

Brunner

Monatshefte fuer Chemie, 1881 , vol. 2, p. 465 Full Text Show Details

Bamberger; Blangey

Justus Liebigs Annalen der Chemie, 1911 , vol. 384, p. 291 Chemische Berichte, 1903 , vol. 36, p. 1627 Full Text Show Details

Bamberger; Brun

Helvetica Chimica Acta, 1923 , vol. 6, p. 946,947 Helvetica Chimica Acta, 1924 , vol. 7, p. 112,114 Full Text Show Details

Kurosawa

Nippon Kagaku Zasshi, 1957 , vol. 78, p. 312 Chem.Abstr., 1960 , p. 374 Full Text Show Details

Macbeth; Price; Winzor

Journal of the Chemical Society, 1935 , p. 325,327 Full Text Show Details

Fierz-David; Blangey; Streiff

Helvetica Chimica Acta, 1946 , vol. 29, p. 1718,1758 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Waldmann; Mathiowetz

Chemische Berichte, 1931 , vol. 64, p. 1713,1721 Full Text Show Details

Cardani et al.

Gazzetta Chimica Italiana, 1955 , vol. 85, p. 1599,1610 Anm. 17 Full Text Show Details


Sorrie; Thomson

Journal of the Chemical Society, 1955 , p. 2233,2235 Full Text Show Details

Gatenbeck

Acta Chemica Scandinavica (1947-1973), 1959 , vol. 13, p. 705,709 Full Text Show Details

Noelting; Werner

Chemische Berichte, 1890 , vol. 23, p. 3255 Full Text Show Details

Bamberger

Justus Liebigs Annalen der Chemie, 1912 , vol. 390, p. 189 Full Text Show Details

Jacob; Sutcliffe; Todd

Journal of the Chemical Society, 1940 , p. 327,329 Full Text Show Details

Zemplen; Bognar; Morvay

Chemische Berichte, 1943 , vol. 76, p. 1165,1169 Full Text Show Details

Moerner

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1921 , vol. 117, p. 69,73 Full Text Show Details

Heller

Justus Liebigs Annalen der Chemie, 1912 , vol. 392, p. 47 Chemische Berichte, 1915 , vol. 48, p. 1288 Full Text Show Details

Bamberger

Justus Liebigs Annalen der Chemie, 1912 , vol. 390, p. 175 Chemische Berichte, 1907 , vol. 40, p. 1903 Full Text Show Details

9 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Moerner

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1910 , vol. 69, p. 355,361 Full Text Show Details

Bruce; Thomson

Journal of the Chemical Society, 1952 , p. 2759,2765 Journal of the Chemical Society, 1955 , p. 1089,1095 Full Text Show Details

Shirai et al.

Chemistry Letters, 1975 , p. 915 Full Text Show Details

Pelizzetti et al.

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1978 , p. 623 Full Text Show Details

Iwano

Bulletin of the Chemical Society of Japan, 1969 , vol. 42, p. 2677,2679 Full Text Show Details

Tyman

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 1639,1645 Full Text Show Details

Kikkawa et al.

Nippon Kagaku Kaishi, 1977 , p. 695,696 Full Text Show Details

Aplin; Pike

Chemistry and Industry (London, United Kingdom), 1966 , p. 2009 Full Text Show Details

Kaufman et al.

Journal of Organic Chemistry, 1967 , vol. 32, p. 504 Full Text View citing articles Show Details

Mesnard; Bertucat

Bollettino Chimico Farmaceutico, 1962 , vol. 101, p. 519,521 Full Text Show Details

Muehlstaedt; Scholz

Chemische Berichte, 1964 , vol. 97, p. 1 Full Text Show Details

Sequin-Frey; Tamm

Helvetica Chimica Acta, 1971 , vol. 54, p. 851,852-854,859,860 Full Text Show Details

Forrester; Gaucher

Biochemistry, 1972 , vol. 11, p. 1102,1103 Full Text Show Details

Nilsson et al.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1973 , p. 2337,2338 Full Text Show Details

Fujita; Sano

Journal of Organic Chemistry, 1979 , vol. 44, p. 2647,2648, 2650 Full Text View citing articles Show Details

Reinschmiedt et al.

Inorganic Chemistry, 1973 , vol. 12, p. 1639 Full Text View citing articles Show Details

Rao; Hayon

Journal of Physical Chemistry, 1975 , vol. 79, p. 397,400 Full Text Show Details


Vesely; Schmerling

Journal of Organic Chemistry, 1970 , vol. 35, p. 4028,4030 Full Text Show Details

Pelizetti et al.

Inorganic Chemistry, 1978 , vol. 17, p. 1688 Full Text View citing articles Show Details

Pelizzetti et al.

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1975 , p. 794,795-798 Full Text Show Details

10 of 42

11 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Santhanam; Krishnan

Zeitschrift fuer Physikalische Chemie (Muenchen, Germany), 1963 , vol. 39, p. 137,139 Full Text Show Details

Masson et al.

Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1975 , vol. 64, p. 175,181 Full Text Show Details

Clemmer et al.

Inorganic Chemistry, 1979 , vol. 18, p. 2567,2570, 2571 Full Text View citing articles Show Details

Rajyam et al.

Current Science, 1971 , vol. 40, p. 62 Full Text Show Details

Manecke et al.

Journal of Electroanalytical Chemistry and Interfacial Electrochemistry, 1970 , vol. 28, p. 139,142 Full Text Show Details

Chi-Sing Tse; Kuwana

Analytical Chemistry, 1978 , vol. 50, p. 1315,1316-1317 Full Text Show Details

Pelizzetti et al.

Journal of Physical Chemistry, 1976 , vol. 80, p. 2979 Full Text View citing articles Show Details

Mentasti; Pelizzetti

Transition Metal Chemistry (Dordrecht, Netherlands), 1976 , vol. 1, p. 281,283 Full Text Show Details

Arai; Onozuka

Nippon Kagaku Kaishi, 1977 , p. 1665,1666 Chem.Abstr., 1978 , # 36877 Full Text Show Details

Upjohn Co.

Patent: US3683034 , 1970 ; Chem.Abstr., vol. 77, # 114031 Full Text Show Details

Arai; Onozuka

Nippon Kagaku Kaishi, 1978 , p. 997,998 Full Text Show Details

Kamal et al.

Pakistan Journal of Scientific and Industrial Research, 1970 , vol. 13, p. 236,237-239 Chem.Abstr., 1971 , vol. 74, # 75167w Full Text Show Details

Forsskahl et al.

Carbohydrate Research, 1976 , vol. 48, p. 13,14-21 Full Text Show Details

Arshad et al.

Revue Roumaine de Chimie, 1970 , vol. 15, p. 1653,1656,1658,1660 Full Text Show Details

Maruyama et al.

Bulletin of the Chemical Society of Japan, 1973 , vol. 46, p. 2470,2474 Full Text Show Details

Manecke; Foerster

Makromolekulare Chemie, 1962 , vol. 52, p. 147,153,154 Full Text Show Details

Ashworth; Dixon

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1972 , p. 1130,1131 Full Text Show Details

Barker; Hollingworth

Chemicky Prumysl, 1960 , vol. 10, p. 525 Full Text Show Details

Beckering et al.

Analytical Chemistry, 1964 , vol. 36, p. 2412 Full Text View citing articles Show Details

O'Donnell et al.

Journal of Chemical and Engineering Data, 1963 , vol. 8, p. 608 Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1969 , vol. 73, p. 203 Full Text Show Details


Beckering; Fowkes

Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1959 , p. 3 Bur. Mines Rep. Invest. Nr. 5505Chem.Abstr., 1960 , # 4150 Full Text Show Details

Sunkel; Staude

Berichte der Bunsen-Gesellschaft, 1968 , vol. 72, p. 567,569, 572 Full Text Show Details

Giza et al.

Journal of Organic Chemistry, 1962 , vol. 27, p. 679,681 Full Text Show Details

Bishop; Tong

Journal of the American Chemical Society, 1965 , vol. 87, p. 501,504 Full Text Show Details

Schildknecht; Kraemer

Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, 1962 , vol. 17, p. 701 Full Text Show Details

Hanson; Mehta

Journal of the Chemical Society [Section] C: Organic, 1969 , p. 2349 Full Text View citing articles Show Details

Schildknecht; Holoubek

Angewandte Chemie, 1961 , vol. 73, p. 1,5 Full Text Show Details

Schulte; Ruecker

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1964 , vol. 297, p. 182,184 Full Text Show Details

Sartori, Giovanni; Casnati, Giuseppe; Bigi, Franca; Foglio, Federica

Gazzetta Chimica Italiana, 1990 , vol. 120, # 1 p. 13 - 19 Title/Abstract Full Text Show Details

Duprat, Arthur Francois; Capdevielle, Patrice; Maumy, Michel

Journal of the Chemical Society, Chemical Communications, 1991 , # 7 p. 464 - 466 Title/Abstract Full Text View citing articles Show Details

Kajigaeshi, Shoji; Morikawa, Yukihiro; Fujisaki, Shizuo; Kakinami, Takaaki; Nishihira, Keigo

Bulletin of the Chemical Society of Japan, 1991 , vol. 64, # 1 p. 336 - 338 Title/Abstract Full Text Show Details

Pirrung, Michael C.; Nunn, David S.

Tetrahedron Letters, 1988 , vol. 29, # 2 p. 163 - 166 Title/Abstract Full Text View citing articles Show Details

Rao, Darvasula V.; Stuber, Fred A.

Tetrahedron Letters, 1981 , vol. 22, # 25 p. 2337 - 2340 Title/Abstract Full Text View citing articles Show Details

Bloomer, James L.; Gazzillo, Joseph A.

Tetrahedron Letters, 1989 , vol. 30, # 10 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details

Sartori, Giovanni; Casnati, Giuseppe; Bigi, Franca; Robles, Pasquale

Tetrahedron Letters, 1987 , vol. 28, # 14 p. 1533 - 1536 Title/Abstract Full Text View citing articles Show Details

Fischer, A.; Henderson, N.

Tetrahedron Letters, 1980 , vol. 21, p. 701 - 704 Title/Abstract Full Text View citing articles Show Details

Laatsch

1980 , vol. NO. 5, p. 814 - 818 Title/Abstract Full Text View citing articles Show Details

Malesani, Giorgio; Galiano, Fabio; Ferlin, Maria Grazia; Masiero, Sergio

Journal of Heterocyclic Chemistry, 1980 , vol. 17, p. 563 - 569 Title/Abstract Full Text Show Details

Timpe, Hans-Joachim; Dietrich, Reinhard; Boeckelmann, Juergen; Friedel, Ingrid; Boegel, Horst; Haucke, Guenther

Collection of Czechoslovak Chemical Communications, 1981 , vol. 46, # 1 p. 219 - 239 Title/Abstract Full Text Show Details

12 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Conway, Gregory A.; Loeffler, Larry J.

Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 1315 - 1320 Title/Abstract Full Text Show Details

Hiranuma Hidetoshi; Miller, Sidney I.

Journal of Organic Chemistry, 1982 , vol. 47, # 26 p. 5083 - 5088 Title/Abstract Full Text View citing articles Show Details

Minisci, Francesco; Citterio, Attilio; Vismara, Elena; Fontana, Francesca; Bernardinis, Silvia De; Correale, Mariano

Journal of Organic Chemistry, 1989 , vol. 54, # 3 p. 728 - 731 Title/Abstract Full Text View citing articles Show Details

Fischer, Alfred; Henderson, George N.

Synthesis, 1985 , # 6/7 p. 641 - 643 Title/Abstract Full Text Show Details

Ishii, Fumio; Kishi, Ken-ichi

Synthesis, 1980 , # 9 p. 706 - 708 Title/Abstract Full Text Show Details

Takata, Toshikazu; Tajima, Rieko; Ando, Wataru

Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4764 - 4766 Title/Abstract Full Text View citing articles Show Details

Nourse, B. D.; Brodbelt, J. S.; Cooks, R. G.

Organic Mass Spectrometry, 1991 , vol. 26, # 6 p. 575 - 582 Title/Abstract Full Text Show Details

Muathen, H A

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1991 , vol. 30, # 5 p. 522 - 524


Title/Abstract Full Text Show Details

Saa, Jose M.; Morey, Jeroni; Suner, Guillem; Frontera, Antoni; Costa, Antoni

Tetrahedron Letters, 1991 , vol. 32, # 49 p. 7313 - 7316 Title/Abstract Full Text View citing articles Show Details

McKillop, Alexander; Tarbin, Jonathan A.

Tetrahedron, 1987 , vol. 43, # 8 p. 1753 - 1758 Title/Abstract Full Text View citing articles Show Details

Mehta; Murthy; Reddy

Tetrahedron Letters, 1987 , vol. 28, # 13 p. 1467 - 1468 Title/Abstract Full Text View citing articles Show Details

Cossio, Fernando P.; Lopez, Concepcion M.; Palomo, Claudio

Tetrahedron, 1987 , vol. 43, # 17 p. 3963 - 3974 Title/Abstract Full Text View citing articles Show Details

Chawla, H. Mohindra; Sharma, S. K.; Chakrabarty, K.; Bhanumati, S.

Tetrahedron, 1988 , vol. 44, # 4 p. 1227 - 1234 Title/Abstract Full Text View citing articles Show Details

Lecea, B.; Aizpurua, J. M.; Palomo, C.

Tetrahedron, 1985 , vol. 41, # 20 p. 4657 - 4666 Title/Abstract Full Text View citing articles Show Details

Kalnin'sh, K. K.; Safant'evskii, A. A.; Shchukareva, V. V.

Journal of Organic Chemistry USSR (English Translation), 1987 , vol. 23, p. 1942 - 1947 Zhurnal Organicheskoi Khimii, 1987 , vol. 23, # 10 p. 2197 - 2202 Title/Abstract Full Text Show Details

Pratt, Daniel V.; Ruan, Fuqiang; Hopkins, Paul B.

Journal of Organic Chemistry, 1987 , vol. 52, # 22 p. 5053 - 5055 Title/Abstract Full Text View citing articles Show Details

Stern, Alan; Swenton, John S.

Journal of Organic Chemistry, 1987 , vol. 52, # 13 p. 2763 - 2768 Title/Abstract Full Text View citing articles Show Details

Paraskevas, Spyridon M.; Konstantinidis, Demetrios; Vassilara, Georgia

Synthesis, 1988 , # 11 p. 897 - 899 Title/Abstract Full Text Show Details

Youngblood, Michael P.

Journal of the American Chemical Society, 1989 , vol. 111, # 5 p. 1843 - 1849 Title/Abstract Full Text View citing articles Show Details

Willis, John P.; Gogins, Kitty A.; Miller, Larry L.

Journal of Organic Chemistry, 1981 , vol. 46, # 16 p. 3215 - 3218 Title/Abstract Full Text View citing articles Show Details

13 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Herron, David K.; Goodson, Theodore; Bollinger, Nancy G.; Swanson-Bean, Dorothy; Wright, Ian G.; et al.

Journal of Medicinal Chemistry, 1992 , vol. 35, # 10 p. 1818 - 1828 Title/Abstract Full Text View citing articles Show Details

Inoue, Masami; Uragaki, Toshitaka; Enomoto, Saburo

Chemistry Letters, 1986 , p. 2075 - 2078 Title/Abstract Full Text Show Details

Tsuda; Nunozawa; Nitta; Yamamoto

Chemical and Pharmaceutical Bulletin, 1980 , vol. 28, # 3 p. 920 - 925 Title/Abstract Full Text View citing articles Show Details

Cossio, Fernando P.; Aizpurua, Jesus M.; Palomo, Claudio

Canadian Journal of Chemistry, 1986 , vol. 64, p. 225 - 231 Title/Abstract Full Text Show Details

Aizpurua, Jesus M.; Lecea, Begona; Palomo, Claudio

Canadian Journal of Chemistry, 1986 , vol. 64, p. 2342 - 2347 Title/Abstract Full Text Show Details

Juaristi, M.; Aizpurua, J. M.; Lecea, B.; Palomo, C.

Canadian Journal of Chemistry, 1984 , vol. 62, p. 2941 - 2944 Title/Abstract Full Text Show Details

Pelzl, Gerhard; Oertel, Birgit; Mohr, Kristina; Demus, Dietrich

Zeitschrift fuer Chemie (Stuttgart, Germany), 1986 , vol. 26, # 2 p. 63 - 64 Title/Abstract Full Text Show Details

Lichszteld, K.; Kruk, I.

Zeitschrift fuer Physikalische Chemie (Leipzig), 1981 , vol. 262, # 4 p. 673 - 682 Title/Abstract Full Text Show Details

Schaefer, Wolfgang; Deutscher, Hans-Joachim

Zeitschrift fuer Chemie (Stuttgart, Germany), 1982 , vol. 22, # 12 p. 447 - 448 Title/Abstract Full Text Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2735 - 2742 Title/Abstract Full Text View citing articles Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2742 - 2747 Title/Abstract Full Text View citing articles Show Details

King, Michael M.; Cohen, Louis A.

Journal of the American Chemical Society, 1983 , vol. 105, # 9 p. 2752 - 2760 Title/Abstract Full Text View citing articles Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3937 - 3945 Title/Abstract Full Text View citing articles Show Details

Sircar; Hoefle; Maxwell

Journal of Medicinal Chemistry, 1983 , vol. 26, # 7 p. 1020 - 1027 Title/Abstract Full Text View citing articles Show Details

Spange, Stefan; Maenz, Karsten; Stadermann, Dietmar


Liebigs Annalen der Chemie, 1992 , # 10 p. 1033 - 1038 Title/Abstract Full Text Show Details

Vuolle, Mikko; Maekelae, Reijo; Eloranta, Jorma

Journal of the Chemical Society, Faraday Transactions, 1992 , vol. 88, # 15 p. 2173 - 2178 Title/Abstract Full Text View citing articles Show Details

Morey; Saa

Tetrahedron, 1993 , vol. 49, # 1 p. 105 - 112 Title/Abstract Full Text View citing articles Show Details

Haga, Naoki; Endo, Yasuyuki; Kataoka, Ken-Ichiro; Yamaguchi, Kentaro; Shudo, Koichi

Journal of the American Chemical Society, 1992 , vol. 114, # 25 p. 9795 - 9806 Title/Abstract Full Text View citing articles Show Details

Tatsuoka; Suzuki; Imao; Satoh; Ishihara; Hirotsu; Kihara; Hatta; Horikawa; Sumoto; Miyano

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 9 p. 2382 - 2386 Title/Abstract Full Text View citing articles Show Details

Kagawa; Tokura; Uchida; Kakushi; Shike; Nakai

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 8 p. 2083 - 2087 Title/Abstract Full Text View citing articles Show Details

14 of 42

15 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Carlson, Brian W.; Miller, Larry L.

Journal of the American Chemical Society, 1985 , vol. 107, # 2 p. 479 - 485 Title/Abstract Full Text View citing articles Show Details

Cassis, R.; Valderrama, J. A.

Synthetic Communications, 1983 , vol. 13, # 5 p. 347 - 356 Title/Abstract Full Text Show Details

Mori, Akira; Mametsuka, Hiroaki; Takeshita, Hitoshi

Bulletin of the Chemical Society of Japan, 1985 , vol. 58, # 7 p. 2072 - 2077 Title/Abstract Full Text Show Details

Rao, A. V. Rama; Deshpande, V. H.; Ravichandran, K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1985 , vol. 24, p. 233 - 235 Title/Abstract Full Text Show Details

Iida, Yoshio; Daishima, Shigeki; Shibata, Akihiro

Organic Mass Spectrometry, 1993 , vol. 28, # 4 p. 433 - 436 Title/Abstract Full Text Show Details

Smirnov, V. I.; Perlovich, G. L.; Fridman, A. Ya.

Russian Journal of Physical Chemistry, 1992 , vol. 66, # 8 p. 1080 - 1082 Zhurnal Fizicheskoi Khimii, 1992 , vol. 66, p. 2025 - 2030 Title/Abstract Full Text Show Details

Patil; Curtin; I. C. Paul

Journal of the American Chemical Society, 1984 , vol. 106, # 2 p. 348 - 353 Title/Abstract Full Text View citing articles Show Details

Lopez, C.; Gonzalez, A.; Cossio, F. P.; Palomo, C.

Synthetic Communications, 1985 , vol. 15, # 13 p. 1197 - 1212 Title/Abstract Full Text Show Details

Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 - 996 Title/Abstract Full Text View citing articles Show Details

Roemer, Axel

Organic Magnetic Resonance, 1982 , vol. 19, # 2 p. 66 - 68 Title/Abstract Full Text Show Details

Gesson, Jean-Pierre; Jacquesy, Jean-Claude; Jouannetaud, Marie-Paule

Journal of the Chemical Society, Chemical Communications, 1980 , # 23 p. 1128 - 1129 Title/Abstract Full Text View citing articles Show Details

Roemer, A.; Sammet, M.

Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983 , vol. 38, # 7 p. 866 - 872 Title/Abstract Full Text Show Details

Korenskii, V. I.; Skoboleva, V. D.; Kolenko, I. P.; Volkov, V. L.; Gus'kova, L. M.

J. Appl. Chem. USSR (Engl. Transl.), 1981 , vol. <2> 54, # 10 p. 2510 - 2514,2215 - 2218 Title/Abstract Full Text Show Details

Page, Philip C. Bulman; Carefull, John F.; Powell, Laurence H.; Sutherland, Ian O.

Journal of the Chemical Society, Chemical Communications, 1985 , # 12 p. 822 - 823 Title/Abstract Full Text Show Details

Schroeder

Molecular crystals and liquid crystals, 1980 , vol. 61, # 3-4 p. 229 - 240 Title/Abstract Full Text View citing articles Show Details

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Costa, Giovanna; Nora, Angelo; Trefiletti, Vincenzo; Valenti, Barbara

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 79 - 96 Title/Abstract Full Text Show Details

Valenti, Barbara; Trefiletti, Vincenzo; Silanus, Franca; Costa, Giovanna

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 155, p. 511 - 520 Title/Abstract Full Text Show Details

Smith, Colin W.; Ambler, Samantha J.; Steggles, David J.

Tetrahedron Letters, 1993 , vol. 34, # 46 p. 7447 - 7450 Title/Abstract Full Text View citing articles Show Details

Pandey, Bipin; Dalvi, Pramod V.

Angewandte Chemie, 1993 , vol. 105, # 11 p. 1724 - 1726 Title/Abstract Full Text Show Details

Comment

Bioactivities present


(Pharmacological Data)

16 of 42

Reference

Smirnov, V. I.; Krestov, G. A.

Russian Journal of Physical Chemistry, 1994 , vol. 68, # 2 p. 228 - 231 Zhurnal Fizicheskoi Khimii, 1994 , vol. 68, # 2 p. 258 - 261 Title/Abstract Full Text Show Details

Allan, Andrew C.; Walker, John R. L.

Phytochemistry (Elsevier), 1988 , vol. 27, # 10 p. 3075 - 3076 Title/Abstract Full Text View citing articles Show Details

Patolia, R. J.; Trivedi, K. N.

Journal of the Indian Chemical Society, 1980 , vol. 57, p. 532 - 535 Title/Abstract Full Text Show Details

Deacon, Glen B.; O'Donoghue, Michael F.; McKillop, Alexander; Young, Derek W.

Synthetic Communications, 1980 , vol. 10, # 8 p. 615 - 622 Title/Abstract Full Text Show Details

Sassa, Takeshi; Nukina, Manabu

Agricultural and Biological Chemistry, 1984 , vol. 48, # 7 p. 1923 - 1926 Title/Abstract Full Text Show Details

Rathore; Bosch; Kochi

Tetrahedron, 1994 , vol. 50, # 23 p. 6727 - 6758 Title/Abstract Full Text View citing articles Show Details

Robbins, Timothy A.; Knobler, Carolyn B.; Bellew, Donald R.; Cram, Donald J.

Journal of the American Chemical Society, 1994 , vol. 116, # 1 p. 111 - 122 Title/Abstract Full Text View citing articles Show Details

Kretzschmann, H.; Meier, H.

Journal fuer Praktische Chemie/Chemiker-Zeitung, 1994 , vol. 336, # 3 p. 247 - 254 Title/Abstract Full Text Show Details

Sain, Bir; Murthy, Pappu S.; Venkateshwar Rao; Prasada Rao; Joshi, Girish C.

Tetrahedron Letters, 1994 , vol. 35, # 28 p. 5083 - 5084 Title/Abstract Full Text View citing articles Show Details

Sartori, Giovanni; Bigi, Franca; Maggi, Raimondo; Pastorio, Andrea; Porta, Cecilia; Bonfanti, Gianmarco

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994 , # 13 p. 1879 - 1882 Title/Abstract Full Text View citing articles Show Details

Soll, Juergen; Shultz, Gernot

Phytochemistry (Elsevier), 1980 , vol. 19, p. 215 - 218 Title/Abstract Full Text View citing articles Show Details

Matsuo, Koji; Shiraki, Ryuji; Okubo, Masao

Journal of Physical Organic Chemistry, 1994 , vol. 7, # 10 p. 567 - 577 Title/Abstract Full Text Show Details

Costantini; D'Ischia; Prota

Synthesis, 1994 , # 12 p. 1399 - 1400 Title/Abstract Full Text View citing articles Show Details

Fujibayashi, Shinya; Nakayama, Kouichi; Nishiyama, Yutaka; Ishii, Yasutaka

Chemistry Letters, 1994 , # 7 p. 1345 - 1348 Title/Abstract Full Text Show Details

Sartori, Giovanni; Bigi, Franca; Goffredi, Gino; Maggi, Raimondo; Portioli, Roberto; Casnati, Giuseppe

Journal of Chemical Research, Miniprint, 1993 , # 8 p. 2061 - 2079 Title/Abstract Full Text Show Details

Jahromi, S.; Mijs, W. J.

Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994 , vol. 250, p. 209 - 222 Title/Abstract Full Text Show Details

Chawla, H. Mohindra; Sharma, S. Kumar; Chakrabarty, K.; Bhanumati, S.

Journal of the Chemical Society, Chemical Communications, 1988 , # 2 p. 128 - 129 Title/Abstract Full Text View citing articles Show Details

Bhaumik, Asim; Kumar, Rajiv

Journal of the Chemical Society, Chemical Communications, 1995 , # 3 p. 349 - 350 Title/Abstract Full Text View citing articles Show Details

Nadkarni, K. K; Kamat, S. P.; Paknikar, S. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994 , vol. 33, # 5 p. 432 - 435 Title/Abstract Full Text Show Details

Buchanan, J. Grant; Hill, David G.; Wightman, Richard H.; Boddy, Ian K.; Hewitt, Brian D.

Tetrahedron, 1995 , vol. 51, # 21 p. 6033 - 6050 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Novak; Kovacs; Pirok; Kolonits; Szabo; Fekete; Weiszfeiler; Szantay

Synthesis, 1995 , # 6 p. 693 - 698 Title/Abstract Full Text View citing articles Show Details

Bae; Sandifer; Lee; Tryk; Sukenik; Scherson

Analytical Chemistry, 1995 , vol. 67, # 24 p. 4508 - 4513 Title/Abstract Full Text View citing articles Show Details

Kossmehl, Gerhard; Hirsch, Barbara

Zeitschrift fuer Naturforschung, B: Chemical Sciences, 1995 , vol. 50, # 8 p. 1265 - 1274 Title/Abstract Full Text Show Details

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details

Pirrung, Michael C.; Nunn, David S.

Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details

Hochmuth, Detlev H.; Koenig, Wilfried A.

Liebigs Annales, 1996 , # 6 p. 947 - 951


Title/Abstract Full Text View citing articles Show Details

Alegria, Antonio E.; Lopez, Marcos; Guevara, Norberto

Journal of the Chemical Society - Faraday Transactions, 1996 , vol. 92, # 24 p. 4965 - 4968 Title/Abstract Full Text View citing articles Show Details

Andersch, Jens; Tschierske, Carsten; Diele, Siegmar; Lose, Dirk

Journal of Materials Chemistry, 1996 , vol. 6, # 8 p. 1297 - 1307 Title/Abstract Full Text View citing articles Show Details

Arehart, Stephen V.; Pugh, Coleen

Journal of the American Chemical Society, 1997 , vol. 119, # 13 p. 3027 - 3037 Title/Abstract Full Text View citing articles Show Details

Sakamoto, Takaaki; Yonehara, Hisatomo; Pac, Chyongjin

Journal of Organic Chemistry, 1997 , vol. 62, # 10 p. 3194 - 3199 Title/Abstract Full Text View citing articles Show Details

Karpov, O. N.

Journal of Applied Spectroscopy, 1996 , vol. 63, # 3 p. 393 - 397 Zhurnal Prikladnoi Spektroskopii, 1996 , vol. 63, # 3 p. 472 - 476 Title/Abstract Full Text Show Details

Gallois, Eric; Defoin, Albert

Bulletin des Societes Chimiques Belges, 1997 , vol. 106, # 5 p. 273 - 280 Title/Abstract Full Text Show Details

Lub, Johan; Broer, Dirk Jan; Van Den Brock, Nel

Liebigs Annales, 1997 , # 11 p. 2281 - 2288 Title/Abstract Full Text View citing articles Show Details

Matovic, Radomir; Cekovic, Zivorad

Gazzetta Chimica Italiana, 1997 , vol. 127, # 9 p. 483 - 488 Title/Abstract Full Text Show Details

Eastmond; Paprotny

Synthesis, 1998 , # 6 p. 894 - 898 Title/Abstract Full Text View citing articles Show Details

Kalnin'sh; Pavlova

Russian Journal of Physical Chemistry A, 1997 , vol. 71, # 10 p. 1596 - 1600 Title/Abstract Full Text View citing articles Show Details

Choure; Bamatraf; Rao; Das; Mohan; Mittal

Journal of Physical Chemistry A, 1997 , vol. 101, # 51 p. 9837 - 9845 Title/Abstract Full Text View citing articles Show Details

Makino, Mitsuko; Endoh, Toshinari; Ogawa, Yoshio; Watanabe, Kazuko; Fujimoto, Yasuo

Heterocycles, 1998 , vol. 48, # 9 p. 1931 - 1934 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa; Saran, Manfred

Journal of the Chemical Society - Faraday Transactions, 1998 , vol. 94, # 13 p. 1835 - 1840 Title/Abstract Full Text View citing articles Show Details

Hwang, Der-Ren; Chu, Chang-Ying; Wang, Sheng-Kai; Uang, Biing-Jiun

Synlett, 1999 , # 1 p. 77 - 78 Title/Abstract Full Text View citing articles Show Details

17 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Biczok, Laszlo; Gupta, Neeraj; Linschitz, Henry

Journal of the American Chemical Society, 1997 , vol. 119, # 51 p. 12601 - 12609 Title/Abstract Full Text View citing articles Show Details

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 4 p. 871 - 876 Title/Abstract Full Text View citing articles Show Details

Sembiring, Seri Bima; Colbran, Stephen B.; Craig, Donald C.

Journal of the Chemical Society - Dalton Transactions, 1999 , # 10 p. 1543 - 1554 Title/Abstract Full Text View citing articles Show Details

Ichihashi, Keiko; Teranishi, Kiyoshi; Ichimura, Akio

Chemistry Letters, 1999 , # 9 p. 957 - 958 Title/Abstract Full Text View citing articles Show Details

Park, Byung-Ik; Bozzelli, Joseph W.; Booty, Michael R.; Bernhard, Mary J.; Mesuere, Karel; Pettigrew, Charles A.; Shi, Ji-Chun; Simonich, Staci L.

Environmental Science and Technology, 1999 , vol. 33, # 15 p. 2584 - 2592 Title/Abstract Full Text View citing articles Show Details

Arevalo; Benito; De Jesus; De La Mata; Flores; Gomez

Journal of Organometallic Chemistry, 1999 , vol. 592, # 2 p. 265 - 270 Title/Abstract Full Text View citing articles Show Details

Puzari; Baruah, Jubaraj B.

Journal of Organic Chemistry, 2000 , vol. 65, # 8 p. 2344 - 2349 Title/Abstract Full Text View citing articles Show Details

Gomez-Lara; Gutierrez-Perez; Penieres-Carrillo; Lopez-Cortes; Escudero-Salas; Alvarez-Toledano

Synthetic Communications, 2000 , vol. 30, # 15 p. 2713 - 2720 Title/Abstract Full Text View citing articles Show Details

Waterlot, C.; Couturier, D.; Hasiak, B.

Journal of Chemical Research, Miniprint, 2000 , # 3 p. 417 - 429 Title/Abstract Full Text Show Details

Martinez-Ruiz; Behnisch; Schweikart; Hanack; Lueer; Oelkrug

Chemistry - A European Journal, 2000 , vol. 6, # 8 p. 1294 - 1301 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly; Barsukova, Tatyana

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 7 p. 1575 - 1582 Title/Abstract Full Text View citing articles Show Details


Stanton, James L.; Cahill, Edna; Dotson, Ronald; Tan, Jenny; Tomaselli, Hollis C.; Wasvary, Jong M.; Stephan, Zouhair F.; Steele, Ronald E.

Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 15 p. 1661 - 1663 Title/Abstract Full Text View citing articles Show Details

Diez, David; Moro, Rosalina F.; Marcos, Isidro S.; Lopez, Jose Ma Sanchez; Urones, Julio G.

Synlett, 2000 , # 6 p. 794 - 796 Title/Abstract Full Text View citing articles Show Details

Takabatake, Tohru; Miyazawa, Tomoyuki; Kojo, Mahiro; Hasegawa, Minoru

Heterocycles, 2000 , vol. 53, # 10 p. 2151 - 2162 Title/Abstract Full Text View citing articles Show Details

Fuganti, Claudio; Serra, Stefano

Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 22 p. 3758 - 3764 Title/Abstract Full Text View citing articles Show Details

Peeters, Emiel; Van Hal, Paul A.; Knol, Joop; Brabec, Christoph J.; Sariciftci, N. Serdar; Hummelen; Janssen, Rene A. J.

Journal of Physical Chemistry B, 2000 , vol. 104, # 44 p. 10174 - 10190 Title/Abstract Full Text View citing articles Show Details

Hisaindee, Soleiman; Clive, Derrick L.J.

Tetrahedron Letters, 2001 , vol. 42, # 12 p. 2253 - 2255 Title/Abstract Full Text View citing articles Show Details

Krohn, Karsten; Vitz, Juergen

Advanced Synthesis and Catalysis, 2000 , vol. 342, # 8 p. 825 - 827 Title/Abstract Full Text View citing articles Show Details

Ficht, Simon; Muelbaier, Marcel; Giannis, Athanassios

Tetrahedron, 2001 , vol. 57, # 23 p. 4863 - 4866 Title/Abstract Full Text View citing articles Show Details

18 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Sugiono, Erli; Metzroth, Thorsten; Detert, Heiner

Advanced Synthesis and Catalysis, 2001 , vol. 343, # 4 p. 351 - 359 Title/Abstract Full Text View citing articles Show Details

D'Souza; Deviprasad

Journal of Organic Chemistry, 2001 , vol. 66, # 13 p. 4601 - 4609 Title/Abstract Full Text View citing articles Show Details

Ramos; Rispens; Van Duren; Hummelen; Janssen

Journal of the American Chemical Society, 2001 , vol. 123, # 27 p. 6714 - 6715 Title/Abstract Full Text View citing articles Show Details

Villemin, Didier; Hammadi, Mohamed; Hachemi, Messaoud

Synthetic Communications, 2002 , vol. 32, # 10 p. 1501 - 1515 Title/Abstract Full Text View citing articles Show Details

Ling, Taotao; Poupon, Erwan; Rueden, Erik J.; Kim, Sun H.; Theodorakis, Emmanuel A.

Journal of the American Chemical Society, 2002 , vol. 124, # 41 p. 12261 - 12267 Title/Abstract Full Text View citing articles Show Details

Macias, Francisco A; Marin, David; Chinchilla, David; Molinillo, Jose M.G

Tetrahedron Letters, 2002 , vol. 43, # 36 p. 6417 - 6420 Title/Abstract Full Text View citing articles Show Details

Cook, Anthony; Badriya, Samer; Greenfield, Simon; McKeown, Neil B.

Journal of Materials Chemistry, 2002 , vol. 12, # 9 p. 2675 - 2683 Title/Abstract Full Text View citing articles Show Details

Singh, Vasundhara; Sapehiyia, Varinder; Kad, Goverdhan L.

Synthesis, 2003 , # 2 p. 198 - 200 Title/Abstract Full Text View citing articles Show Details

Venkata Ramana Rao; Ramana Rao

Spectrochimica Acta - Part A Molecular and Biomolecular Spectroscopy, 2002 , vol. 58, # 14 p. 3039 - 3065 Title/Abstract Full Text View citing articles Show Details

Horikawa, Yoshiteru; Uchino, Yuki; Sako, Takeshi

Chemistry Letters, 2003 , vol. 32, # 3 p. 232 - 233 Title/Abstract Full Text View citing articles Show Details

Macias, Francisco A.; Chinchilla, David; Molinillo, Jose M. G.; Marin, David; Varela, Rosa M.; Torres, Ascension

Tetrahedron, 2003 , vol. 59, # 10 p. 1679 - 1683 Title/Abstract Full Text View citing articles Show Details

Franchi, Emanuela; Ingrosso, Giovanni; Marchetti, Fabio; Pinzino, Calogero

Tetrahedron, 2003 , vol. 59, # 27 p. 5003 - 5018 Title/Abstract Full Text View citing articles Show Details

Arevalo, Silvia; Bonillo, M. Rufina; de Jesus, Ernesto; de la Mata, F. Javier; Flores, Juan C.; Gomez, Rafael; Gomez-Sal, Pilar; Ortega, Paula

Journal of Organometallic Chemistry, 2003 , vol. 681, # 1-2 p. 228 - 236 Title/Abstract Full Text View citing articles Show Details

Oh, Moonhyun; Reingold, Jeffrey A.; Carpenter, Gene B.; Sweigart, Dwight A.

Journal of Organometallic Chemistry, 2003 , vol. 687, # 1 p. 78 - 84 Title/Abstract Full Text View citing articles Show Details

Small, Aaron C.; Pugh, Coleen

Macromolecules, 2002 , vol. 35, # 6 p. 2105 - 2115 Title/Abstract Full Text View citing articles Show Details

Goerner, Helmut

Photochemistry and Photobiology, 2003 , vol. 78, # 5 p. 440 - 448 Title/Abstract Full Text View citing articles Show Details

Millaruelo; Oriol; Serrano; Pinol; Saez

Molecular Crystals and Liquid Crystals, 2004 , vol. 411, p. 451/[1493]-466/[1508] Title/Abstract Full Text View citing articles Show Details

Niedermeyer, Timo H. J.; Mikolasch, Annett; Lalk, Michael

Journal of Organic Chemistry, 2005 , vol. 70, # 6 p. 2002 - 2008 Title/Abstract Full Text View citing articles Show Details

Sharghi, Hashem; Beni, Ali Reza Salimi

Synthesis, 2004 , # 17 p. 2900 - 2904 Title/Abstract Full Text View citing articles Show Details


Novak, Michael; Glover, Stephen A.

Journal of the American Chemical Society, 2005 , vol. 127, # 22 p. 8090 - 8097 Title/Abstract Full Text View citing articles Show Details

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Reference

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Journal of Agricultural and Food Chemistry, 2005 , vol. 53, # 16 p. 6426 - 6431 Title/Abstract Full Text View citing articles Show Details

Mazzini, Francesco; Salvadori, Piero

Synthesis, 2005 , # 15 art. no. P05605SS, p. 2479 - 2481 Title/Abstract Full Text View citing articles Show Details

Akachi, Yosuke; Koide, Naoyuki

Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2001 , vol. 365, p. 427 - 437 Title/Abstract Full Text View citing articles Show Details

Ali, Mohammed Hashmat; Niedbalski, Melinda; Bohnert, Gary; Bryant, Daniel

Synthetic Communications, 2006 , vol. 36, # 12 p. 1751 - 1759 Title/Abstract Full Text View citing articles Show Details

Algi, Fatih; Balci, Metin

Synthetic Communications, 2006 , vol. 36, # 16 p. 2293 - 2297 Title/Abstract Full Text View citing articles Show Details

Van Der Veen, Marleen H.; De Boer, Bert; Stalmach, Ulf; Van De Wetering, Karin I.; Hadziioannou, Georges

Macromolecules, 2004 , vol. 37, # 10 p. 3673 - 3684 Title/Abstract Full Text View citing articles Show Details

Scheepers, Brent A.; Klein, Rosalyn; Davies-Coleman, Michael T.

Tetrahedron Letters, 2006 , vol. 47, # 47 p. 8243 - 8246 Title/Abstract Full Text View citing articles Show Details

Zhou, Guanglian; Zheng, Deping; Da, Shijun; Xie, Zhixiang; Li, Ying

Tetrahedron Letters, 2006 , vol. 47, # 20 p. 3349 - 3352 Title/Abstract Full Text View citing articles Show Details

Zhang, Zhonghui; Hong, Qing; Xu, Jianghong; Zhang, Xiaozhou; Li, Shunpeng

Biodegradation, 2006 , vol. 17, # 3 p. 275 - 283 Title/Abstract Full Text View citing articles Show Details

Kim, Dong Wook; Choi, Jin Joo; Lim, Jong-Sun; Lee, Changjin

Molecular Crystals and Liquid Crystals, 2007 , vol. 463, # 1 p. 43 - 53 Title/Abstract Full Text View citing articles Show Details

Jacobson, Alan R.; Moe, Scott T.; Allen; Fessenden, James D.

Molecular Pharmacology, 2006 , vol. 70, # 1 p. 259 - 266 Title/Abstract Full Text View citing articles Show Details

Kalnin'sh

Russian Journal of Applied Chemistry, 2005 , vol. 78, # 11 p. 1727 - 1744 Title/Abstract Full Text View citing articles Show Details

Bojanowska-Czajka, Anna; Drzewicz, Przemyslaw; Kozyra, Czeslaw; Nalecz-Jawecki, Grzegorz; Sawicki, Jozef; Szostek, Bogdan; Trojanowicz, Marek

Ecotoxicology and Environmental Safety, 2006 , vol. 65, # 2 p. 265 - 277 Title/Abstract Full Text View citing articles Show Details

Olsen, Bradley D.; Segalman, Rachel A.

Macromolecules, 2005 , vol. 38, # 24 p. 10127 - 10137 Title/Abstract Full Text View citing articles Show Details

Witayakran, Suteera; Zettili, Abdullah; Ragauskas, Arthur J.

Tetrahedron Letters, 2007 , vol. 48, # 17 p. 2983 - 2987 Title/Abstract Full Text View citing articles Show Details

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

Couladouros, Elias A.; Moutsos, Vassilios I.; Lampropoulou, Maria; Little, James L.; Hyatt, John A.

Journal of Organic Chemistry, 2007 , vol. 72, # 18 p. 6735 - 6741 Title/Abstract Full Text View citing articles Show Details

Kostikov, Alexey P.; Popik, Vladimir V.

Journal of Organic Chemistry, 2007 , vol. 72, # 24 p. 9190 - 9194 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

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BASF Aktiengesellschaft

Patent: US5712416 A1, 1998 ; Title/Abstract Full Text Show Details

Dainippon Ink and Chemicals, Inc.

Patent: US6169186 A, 2001 ; Title/Abstract Full Text Show Details


Degussa Aktiengesellschaft

Patent: US4590305 A1, 1986 ; Title/Abstract Full Text Show Details

E. I. Du Pont de Nemours and Company

Patent: US4766256 A1, 1988 ; Title/Abstract Full Text Show Details

Warner-Lambert Company

Patent: US5760050 A1, 1998 ; Title/Abstract Full Text Show Details

OGATA, KAZUMI; NAKAO, HIDETOSHI; ITO, KAZUHIKO; SAKAUE, TAKAHIRO; INOUE, SACHIKO; IEMURA, MASAHITO

Patent: US2001/8893 A1, 2001 ; Title/Abstract Full Text Show Details

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

Chen, Pinhong; Wang, Junhua; Liu, Kun; Li, Chaozhong

Journal of Organic Chemistry, 2008 , vol. 73, # 1 p. 339 - 341 Title/Abstract Full Text View citing articles Show Details

Hong, Mei Peng; Webster, Richard D.

Journal of Organic Chemistry, 2008 , vol. 73, # 6 p. 2169 - 2175 Title/Abstract Full Text View citing articles Show Details

Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu

Chemistry Letters, 2008 , vol. 37, # 3 p. 360 - 361 Title/Abstract Full Text View citing articles Show Details

Hubbard, Colin D.; Bajaj, Hari C.; Eldik, Rudi van; Burgess, John; Blundell, Nicholas J.

Inorganica Chimica Acta, 1991 , vol. 183, p. 1 - 8 Full Text View citing articles Show Details

Abd-El-Aziz, Alaa S.; Schriemer, David C.; Denus, Christine R. de

Organometallics, 1994 , vol. 13, p. 374 - 384 Full Text View citing articles Show Details

DONGJIN SEMICHEM CO., LTD.

Patent: WO2008/102962 A1, 2008 ; Title/Abstract Full Text Show Details

Chouchane, Salem; Wooten, Jan B.; Tewes, Franz J.; Wittig, Arno; Mueller, Boris P.; Veltel, Detlef; Diekmann, Joerg

Chemical Research in Toxicology, 2006 , vol. 19, # 12 p. 1602 - 1610 Title/Abstract Full Text View citing articles Show Details

Khoumeri, Omar; Montana, Marc; Terme, Thierry; Vanelle, Patrice

Tetrahedron, 2008 , vol. 64, # 49 p. 11237 - 11242 Title/Abstract Full Text View citing articles Show Details

Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu

Angewandte Chemie - International Edition, 2008 , vol. 47, # 42 p. 8093 - 8095 Title/Abstract Full Text View citing articles Show Details

E. I. DU PONT DE NEMOURS AND COMPANY

Patent: WO2009/23759 A2, 2009 ; Title/Abstract Full Text Show Details

Kim, Chulwoo; Choi, Hyunbong; Kim, Sanghoon; Baik, Chul; Song, Kihyung; Kang, Moon-Sung; Sang, Ook Kang; Ko, Jaejung

Journal of Organic Chemistry, 2008 , vol. 73, # 18 p. 7072 - 7079 Title/Abstract Full Text View citing articles Show Details

Chaikovskaya; Sokolova; Karetnikova; Mal'Kov; Kuz'Mina

Russian Journal of Applied Chemistry, 2009 , vol. 82, # 3 p. 396 - 401 Title/Abstract Full Text View citing articles Show Details

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Reference

Symeonidis, Theodoros; Chamilos, Michael; Hadjipavlou-Litina, Dimitra J.; Kallitsakis, Michael; Litinas, Konstantinos E.

Bioorganic and Medicinal Chemistry Letters, 2009 , vol. 19, # 4 p. 1139 - 1142 Title/Abstract Full Text View citing articles Show Details

Mansoori; Sarvari; Zamanloo; Imanzadeh

Russian Journal of Organic Chemistry, 2009 , vol. 45, # 1 p. 154 - 157 Title/Abstract Full Text View citing articles Show Details

Arkoudis, Elias; Lykakis, Ioannis N.; Gryparis, Charis; Stratakis, Manolis

Organic Letters, 2009 , vol. 11, # 14 p. 2988 - 2991 Title/Abstract Full Text View citing articles Show Details

Goto, Hideyuki; Terao, Yoshiyasu; Akai, Shuji

Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 4 p. 346 - 360 Title/Abstract Full Text View citing articles Show Details

Kim, Sungjin; Kim, Daehwan; Park, Jaiwook

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 16 p. 2573 - 2578 Title/Abstract Full Text View citing articles Show Details

TRANSITIONS OPTICAL, INC.

Patent: US2009/326186 A1, 2009 ; Title/Abstract Full Text Show Details

Pfizer Inc.

Patent: WO2003/106446 A1, 2003 ; Title/Abstract Full Text Show Details


Nippon Oil Corporation

Patent: EP1428823 A1, 2004 ; Title/Abstract Full Text Show Details

Chisso Corporation; CHISSO SEKIYU KAGAKU KK

Patent: JP2005/112850 A, 2005 ; Title/Abstract Full Text Show Details

GENERAL ELECTRIC COMPANY

Patent: WO2005/97721 A1, 2005 ; Title/Abstract Full Text Show Details

Gallagher, Brian D.; Taft, Benjamin R.; Lipshutz, Bruce H.

Organic Letters, 2009 , vol. 11, # 23 p. 5374 - 5377 Title/Abstract Full Text View citing articles Show Details

DONGJIN SEMICHEM CO., LTD.

Patent: US2010/71763 A1, 2010 ; Title/Abstract Full Text Show Details

Derikvand, Fatemeh; Bigi, Franca; Maggi, Raimondo; Piscopo, Calogero Giancarlo; Sartori, Giovanni

Journal of Catalysis, 2010 , vol. 271, # 1 p. 99 - 103 Title/Abstract Full Text View citing articles Show Details

Menichetti, Stefano; Amorati, Riccardo; Bartolozzi, Maria Grazia; Pedulli, Gian Franco; Salvini, Antonella; Viglianisi, Caterina

European Journal of Organic Chemistry, 2010 , # 11 p. 2218 - 2225 Title/Abstract Full Text View citing articles Show Details

Liu, Xin; Ou, Yingyong; Chen, Shaopeng; Lu, Xin; Cheng, Hao; Jia, Xian; Wang, Decai; Zhou, Guo-Chun

European Journal of Medicinal Chemistry, 2010 , vol. 45, # 6 p. 2147 - 2153 Title/Abstract Full Text View citing articles Show Details

METABOLEX, INC.; SHI, Dong Fang; SONG, Jiangao; MA, Jingyuan; NOVACK, Aaron; PHAM, Phuongly; NASHASHIBI, Imad; RABBAT, Christopher J.; CHEN, Xin

Patent: WO2010/80537 A1, 2010 ; Title/Abstract Full Text Show Details

Pande, Poorn Prakash

Asian Journal of Chemistry, 2010 , vol. 22, # 4 p. 2549 - 2553 Title/Abstract Full Text View citing articles Show Details

Mehta, Goverdhan; Khan, Tabrez Babu; Sunil Kumar

Tetrahedron Letters, 2010 , vol. 51, # 39 p. 5116 - 5119 Title/Abstract Full Text View citing articles Show Details

FOREST LABORATORIES HOLDINGS LIMITED; SARMA, Pakala Kumara, Savithru; ACHARYA, Vinod, Parameshwaran; KASIBHATLA, Srinivas, Rao; TIWARI, Atul; REDDY, Vantaddu, Nagarjuna; BISCHOFF, Alexander

Patent: WO2010/127208 A1, 2010 ; Title/Abstract Full Text Show Details

Katsumata, Hideyuki; Okada, Toshiko; Kaneco, Satoshi; Suzuki, Tohru; Ohta, Kiyohisa

Ultrasonics Sonochemistry, 2010 , vol. 17, # 1 p. 200 - 206 Title/Abstract Full Text View citing articles Show Details

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Reference

IRM LLC

Patent: WO2007/56497 A1, 2007 ; Title/Abstract Full Text Show Details

Miyamura, Hiroyuki; Maehata, Kanako; Kobayashi, Shu

Chemical Communications, 2010 , vol. 46, # 42 p. 8052 - 8054 Title/Abstract Full Text View citing articles Show Details

Smirnova; Zharnikova; Donnio; Brus

Russian Journal of General Chemistry, 2010 , vol. 80, # 7 p. 1331 - 1340 Title/Abstract Full Text View citing articles Show Details

Amemiya, Takashi; Wang, Jichang

Journal of Physical Chemistry A, 2010 , vol. 114, # 51 p. 13347 - 13352 Title/Abstract Full Text View citing articles Show Details

DOW AGROSCIENCES LLC

Patent: US2011/54173 A1, 2011 ; Title/Abstract Full Text Show Details

DOW AGROSCIENCES LLC; BREWSTER, William; DEMETER, David; ERICKSON, W.; LOWE, Christian; KLITTICH, Carla; NUGENT, Jaime; RIEDER, Brent; SIDDALL, Thomas; YAO, Chenglin; YERKES, Carla; ZHU, Yuanming

Patent: WO2011/25505 A1, 2011 ; Title/Abstract Full Text Show Details

LG Chem, Ltd.

Patent: US7910179 B2, 2011 ; Title/Abstract Full Text Show Details

Fakhari, Ali Reza; Ahmar, Hamid; Hosseiny Davarani, Saied Saeed; Shaabani, Ahmad; Nikjah, Sanaz; Maleki, Ali

Synthetic Communications, 2011 , vol. 41, # 4 p. 561 - 568 Title/Abstract Full Text View citing articles Show Details

Takeuchi, Saeka; Saito, Hiroaki; Miyairi, Shinichi; Takabatake, Tohru

Heterocycles, 2011 , vol. 83, # 3 p. 531 - 534 Title/Abstract Full Text View citing articles Show Details

Tang, Ying; Wei, Zhenhong; Zhong, Wei; Liu, Xiaoming

European Journal of Inorganic Chemistry, 2011 , # 7 p. 1112 - 1120


Title/Abstract Full Text View citing articles Show Details

Cai, Guang-Rong; Guan, Zhi; He, Yan-Hong

Synthetic Communications, 2011 , vol. 41, # 20 p. 3016 - 3025 Title/Abstract Full Text View citing articles Show Details

Liu, Hao; Li, Yongjun; Zhang, Sen; Yang, Dong; Hu, Jianhua; Huang, Xiaoyu

Journal of Polymer Science, Part A: Polymer Chemistry, 2011 , vol. 49, # 1 p. 11 - 22 Title/Abstract Full Text View citing articles Show Details

MERCK PATENT GESELLSCHAFT MIT BESCHRANKTER HAFTUNG

Patent: US2011/261311 A1, 2011 ; Title/Abstract Full Text Show Details

Liu, Hao; Zhang, Sen; Li, Yongjun; Yang, Dong; Hu, Jianhua; Huang, Xiaoyu

Polymer, 2010 , vol. 51, # 22 p. 5198 - 5206 Title/Abstract Full Text View citing articles Show Details

Singh, Prabhpreet; Lamanna, Giuseppe; Menard-Moyon, Cecilia; Toma, Francesca Maria; Magnano, Elena; Bondino, Federica; Prato, Maurizio; Verma, Sandeep; Bianco, Alberto

Angewandte Chemie - International Edition, 2011 , vol. 50, # 42 p. 9893 - 9897 Title/Abstract Full Text View citing articles Show Details

Huang, Peng; Jin, Baokang; Liu, Peng; Cheng, Longjiu; Cheng, Wangxing; Zhang, Shengyi

Journal of Organometallic Chemistry, 2012 , vol. 697, # 1 p. 57 - 64 Title/Abstract Full Text View citing articles Show Details

METABOLEX, INC.; SHI, Dong Fang; SONG, Jiangao; MA, Jingyuan; NOVACK, Aaron; PHAM, Phuongly; NASHASHIBI, Imad; RABBAT, Christopher J.; CHEN, Xin

Patent: WO2011/159297 A1, 2011 ; Title/Abstract Full Text Show Details

Pourali, Ali Reza; Goli, Arezou

Journal of Chemical Sciences, 2011 , vol. 123, # 1 p. 63 - 67 Title/Abstract Full Text View citing articles Show Details

Maggi, Raimondo; Piscopo, Calogero G.; Sartori, Giovanni; Storaro, Loretta; Moretti, Elisa

Applied Catalysis A: General, 2012 , vol. 411-412, p. 146 - 152 Title/Abstract Full Text View citing articles Show Details

Rolic AG

Patent: US8105662 B2, 2012 ; Title/Abstract Full Text Show Details

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Reference

Kidwai, Mazaahir; Jain, Arti; Sharma, Abha; Kuhad, Ramesh Chander

Journal of Molecular Catalysis B: Enzymatic, 2012 , vol. 74, # 3-4 p. 236 - 240 Title/Abstract Full Text View citing articles Show Details

Hajdok, Szilvia; Conrad, Juergen; Beifuss, Uwe

Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 445 - 459 Title/Abstract Full Text View citing articles Show Details

Tchaikovskaya, Olga N.; Karetnikova, Elena A.; Sokolova, Irina V.; Mayer, Georgy V.; Shvornev, Dmitry A.

Journal of Photochemistry and Photobiology A: Chemistry, 2012 , vol. 228, # 1 p. 8 - 14 Title/Abstract Full Text View citing articles Show Details

Norcott, Philip; Spielman, Calan; McErlean, Christopher S. P.

Green Chemistry, 2012 , vol. 14, # 3 p. 605 - 609 Title/Abstract Full Text View citing articles Show Details

MacHonkin, Timothy E.; Doerner, Amy E.

Biochemistry, 2011 , vol. 50, # 41 p. 8899 - 8913 Title/Abstract Full Text View citing articles Show Details

Turrado, Carlos; Puig, Teresa; Garcia-Carceles, Javier; Artola, Marta; Benhamu, Bellinda; Ortega-Gutierrez, Silvia; Relat, Joana; Oliveras, Gloria; Blancafort, Adriana; Haro, Diego; Marrero, Pedro F.; Colomer, Ramon; Lopez-Rodriguez, Maria L.

Journal of Medicinal Chemistry, 2012 , vol. 55, # 11 p. 5013 - 5023 Title/Abstract Full Text View citing articles Show Details

Dongjin Semichem Co., Ltd.

Patent: US8288542 B2, 2012 ; Title/Abstract Full Text Show Details

Wu, Guangwei; Ma, Hongyan; Zhu, Tianjiao; Li, Jing; Gu, Qianqun; Li, Dehai

Tetrahedron, 2012 , vol. 68, # 47 p. 9745 - 9749,5 Title/Abstract Full Text Show Details

Tell, Volkmar; Mahmoud, Kazem Ahmed; Hilgeroth, Andreas; Holzer, Max; Herrmann, Lydia; Schaechtele, Christoph; Totzke, Frank

Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 22 p. 6914 - 6918,5 Title/Abstract Full Text Show Details

Aptula, Aynur O.; Roberts, David W.; Cronin, Mark T. D.; Schultz, T. Wayne

Chemical Research in Toxicology, 2005 , vol. 18, # 5 p. 844 - 854 Title/Abstract Full Text View citing articles Show Details

Reuman, Michael; Hu, Zhiyong; Kuo, Gee-Hong; Li, Xun; Russell, Ronald K.; Shen, Lan; Youells, Scott; Zhang, Yongzheng

Organic Process Research and Development, 2007 , vol. 11, # 6 p. 1010 - 1014 Title/Abstract Full Text View citing articles Show Details

Matsuo, Takashi; Tohi, Yuji; Hayashi, Takashi

Journal of Organic Chemistry, 2012 , vol. 77, # 20 p. 8946 - 8955 Title/Abstract Full Text View citing articles Show Details

Galindo, Jose L.G.; MacIas, Mariola; Molinillo, Jose M.G.; Munoz-Suano, Alba; Torres, Ascension; Varela, Rosa M.; Garcia-Cozar, Francisco; MacIas, Francisco A.

Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 22 p. 6662 - 6668 Title/Abstract Full Text View citing articles Show Details

E I du Pont de Nemours and Company

Patent: US8344175 B2, 2013 ;


Title/Abstract Full Text Show Details

Kidwai, Mazaahir; Jain, Arti; Sharma, Abha; Kuhad, Ramesh Chander

Catalysis Science and Technology, 2013 , vol. 3, # 1 p. 230 - 234 Title/Abstract Full Text View citing articles Show Details

Jia, Honghua; Zhong, Chao; Huang, Fan; Wang, Chunming; Jia, Lisha; Zhou, Hua; Wei, Ping

ChemPlusChem, 2013 , vol. 78, # 5 p. 451 - 458 Title/Abstract Full Text View citing articles Show Details

Kidwai, Mazaahir; Jain, Arti; Sharma, Abha; Kuhad, Ramesh Chander

Comptes Rendus Chimie, 2013 , vol. 16, # 8 p. 728 - 735 Title/Abstract Full Text View citing articles Show Details

Cronin, Mark T.D.; Aptula, Aynur O.; Duffy, Judith C.; Netzeva, Tatiana I.; Rowe, Philip H.; Valkova, Iva V.; Schultz, T. Wayne

Chemosphere, 2002 , vol. 49, # 10 p. 1201 - 1221 Title/Abstract Full Text View citing articles Show Details

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Ikeda, Atsushi; Hoshino, Kazuya; Komatsuzaki, Hidehito; Satoh, Minoru; Nakazawa, Jun; Hikichi, Shiro

New Journal of Chemistry, 2013 , vol. 37, # 8 p. 2377 - 2383 Title/Abstract Full Text View citing articles Show Details

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Reference

Gan, Maoluo; Liu, Yufeng; Bai, Yinlei; Guan, Yan; Li, Li; Gao, Rongmei; He, Weiying; You, Xuefu; Li, Yuhuan; Yu, Liyan; Xiao, Chunling

Journal of Natural Products, 2013 , vol. 76, # 9 p. 1535 - 1540 Title/Abstract Full Text View citing articles Show Details

Portalier, Francois; Bourdreux, Flavien; Marrot, Jeroime; Moreau, Xavier; Coeffard, Vincent; Greck, Christine

Organic Letters, 2013 , vol. 15, # 22 p. 5642 - 5645 Title/Abstract Full Text View citing articles Show Details

Jiang, Zhen; Xu, Ming; Li, Fuyou; Yu, Yanlei

Journal of the American Chemical Society, 2013 , vol. 135, # 44 p. 16446 - 16453 Title/Abstract Full Text View citing articles Show Details

EADY, Elizabeth, Anne; QURESHI, Andleeb

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

EADY, Elizabeth, Anne; FITZGERALD, Daniel, James; COVE, Jonathan, Howard; SEVILLE, Scott

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

Chen, Xingwu; Wang, Ling; Chen, Yinjie; Li, Chenyue; Hou, Guoyan; Liu, Xin; Zhang, Xiaoguang; He, Wanli; Yang, Huai

Chemical Communications, 2014 , vol. 50, # 6 p. 691 - 694 Title/Abstract Full Text View citing articles Show Details

QSAR & combinatorial science, 2005 , vol. 24, # 3 p. 385 - 396 Title/Abstract Full Text Show Details

Lee, Yi-Huan; Chang, Chun-Jie; Yang, Yi-Lung; Chiang, Chi-Ju; Lee, Yu-Ping; Shen, Ching; Tsai, Kang-Ting; Chen, Yi-Fan; Dai, Chi-An

Polymer (United Kingdom), 2014 , vol. 55, # 10 p. 2481 - 2490 Title/Abstract Full Text View citing articles Show Details

Mulani, Khudbudin B.; Ganjave, Nitin V.; Chavan, Nayaku N.

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014 , vol. 53, # 5 p. 591 - 596 Title/Abstract Full Text View citing articles Show Details

FUJIFILM Corporation; MIZUMURA Masatoshi; KATOH Shunya; UEMURA Minoru; ISHIWATAYasuhiro; YOSHIKAWA Masaru; MATSUYAMA Hiroshi

Patent: EP2738155 A1, 2014 ; Title/Abstract Full Text Show Details

Garcia-Marquez, Alfonso Ramon; Heinrich, Benoit; Beyer, Nicolas; Guillon, Daniel; Donnio, Bertrand

Macromolecules, 2014 , vol. 47, # 15 p. 5198 - 5210 Title/Abstract Full Text View citing articles Show Details

Bell, Jeffrey G.; Green, James R.; Wang, Jichang

Journal of Physical Chemistry A, 2014 , vol. 118, # 42 p. 9795 - 9800 Title/Abstract Full Text View citing articles Show Details

Yang, Wei; Wang, Shan; Zhang, Qian; Liu, Qun; Xu, Xianxiu

Chemical Communications, 2015 , vol. 51, # 4 p. 661 - 664 Title/Abstract Full Text View citing articles Show Details

Xie, Ying; Lei, Zheng-Lin; Luo, Yan-Ping

Letters in Drug Design and Discovery, 2014 , vol. 11, # 9 p. 1124 - 1132 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

Suljic, Sanel; Pietruszka, Jörg; Worgull, Dennis

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 8 p. 1822 - 1830 Title/Abstract Full Text View citing articles Show Details

Liu, Shaohua; He, Peixin; Tian, Zhaofu; Li, Xiaolan; Xu, Chunping

Journal of the Chilean Chemical Society, 2015 , vol. 60, # 1 p. 2761 - 2768 Title/Abstract Full Text View citing articles Show Details

Norcott; McErlean

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 24 p. 6866 - 6878 Title/Abstract Full Text View citing articles Show Details

Piscopo, Calogero G.

ChemistryOpen, 2015 , vol. 4, # 3 p. 383 - 388 Title/Abstract Full Text View citing articles Show Details

Cannatelli, Mark D.; Ragauskas, Arthur J.

Journal of Molecular Catalysis B: Enzymatic, 2015 , vol. 119, p. 85 - 89


Title/Abstract Full Text View citing articles Show Details

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26 of 42

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Reference

Du, Yongli; Ling, Hao; Zhang, Meng; Shen, Jingkang; Li, Qunyi

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 15 p. 4891 - 4898 Title/Abstract Full Text View citing articles Show Details

Hasegawa, Masatoshi; Ishigami, Tomohiro; Ishii, Junichi

Polymer (United Kingdom), 2015 , vol. 74, p. 1 - 15 Title/Abstract Full Text View citing articles Show Details

Martella, Daniele; Parmeggiani, Camilla; Wiersma, Diederik Sybolt; Piol, Milagros; Oriol, Luis

Journal of Materials Chemistry C, 2015 , vol. 3, # 34 p. 9003 - 9010 Title/Abstract Full Text View citing articles Show Details

Ali, Mohammed Hashmat; Welker, Andrea; York, Crystal

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Zhao, Jianqiang; Yu, Yanlei

Molecular Crystals and Liquid Crystals, 2014 , vol. 601, # 1 p. 134 - 141 Title/Abstract Full Text View citing articles Show Details

Dennig, Alexander; Busto, Eduardo; Kroutil, Wolfgang; Faber, Kurt

ACS Catalysis, 2015 , vol. 5, # 12 p. 7503 - 7506 Title/Abstract Full Text View citing articles Show Details

Zhang, Li-Pei; Xing, Yun-Peng; Liu, Lan-Hua; Zhou, Xiao-Hong; Shi, Han-Chang

Sensors and Actuators, B: Chemical, 2016 , vol. 225, p. 593 - 599 Title/Abstract Full Text Show Details

Hailu, Solomon Legese; Nair, Balachandran Unni; Redi-Abshiro, Mesfin; Diaz, Isabel; Aravindhan, Rathinam; Tessema, Merid

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Prasetyo, Endry Nugroho; Semlitsch, Stefan; Nyanhongo, Gibson S.; Lemmouchi, Yahia; Guebitz, Georg M.

Chemosphere, 2016 , vol. 144, p. 652 - 660 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

Schlippert, Max; Mikolasch, Annett; Hahn, Veronika; Schauer, Frieder

Journal of Molecular Catalysis B: Enzymatic, 2016 , vol. 126, p. 106 - 114 Title/Abstract Full Text View citing articles Show Details

Shirley, Harry J.; Bray, Christopher D.

European Journal of Organic Chemistry, 2016 , vol. 2016, # 8 p. 1504 - 1507 Title/Abstract Full Text View citing articles Show Details

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García-Caballero; Blacher; Paupert; Quesada; Medina; Noël

British Journal of Pharmacology, 2016 , vol. 173, # 12 p. 1966 - 1987 Title/Abstract Full Text View citing articles Show Details

He, Wan-Li; Wang, Xin; Yang, Zhou; Wang, Dong; Cao, Hui

Liquid Crystals, 2016 , vol. 43, # 7 p. 874 - 885 Title/Abstract Full Text View citing articles Show Details

Baysal, Mustafa; Yürüm, Yuda

Biofuels, 2016 , vol. 7, # 2 p. 181 - 189 Title/Abstract Full Text View citing articles Show Details

Liu, Jingchao; Fu, Junjie; Li, Wenlong; Zou, Yu; Huang, Zhangjian; Xu, Jinyi; Peng, Sixun; Zhang, Yihua

Tetrahedron, 2016 , vol. 72, # 27-28 p. 4103 - 4110 Title/Abstract Full Text View citing articles Show Details

Lui, Matthew Y.; Lokare, Kapil S.; Hemming, Ellen; Stanley, Jessica N.G.; Perosa, Alvise; Selva, Maurizio; Masters, Anthony F.; Maschmeyer, Thomas

RSC Advances, 2016 , vol. 6, # 63 p. 58443 - 58451 Title/Abstract Full Text View citing articles Show Details

Baysal, Mustafa; Yürüm, Yuda

Biofuels, 2016 , vol. 7, # 2 p. 181 - 189 Title/Abstract Full Text Show Details

Kockler, Katrin B.; Fleischhaker, Friederike; Barner-Kowollik, Christopher

Polymer Chemistry, 2016 , vol. 7, # 26 p. 4342 - 4351 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Ting, Jeffrey M.; Navale, Tushar S.; Jones, Seamus D.; Bates, Frank S.; Reineke, Theresa M.

ACS Biomaterials Science and Engineering, 2015 , vol. 1, # 10 p. 978 - 990 Title/Abstract Full Text Show Details

Cannatelli, Mark D.; Ragauskas, Arthur J.

Tetrahedron Letters, 2016 , vol. 57, # 33 p. 3749 - 3753 Title/Abstract Full Text View citing articles Show Details

McBride, Kevin; Gaide, Tom; Vorholt, Andreas; Behr, Arno; Sundmacher, Kai

Chemical Engineering and Processing: Process Intensification, 2016 , vol. 99, p. 97 - 106 Title/Abstract Full Text View citing articles Show Details

McBride, Kevin; Gaide, Tom; Vorholt, Andreas; Behr, Arno; Sundmacher, Kai

Chemical Engineering and Processing: Process Intensification, 2016 , vol. 99, p. 97 - 106 Title/Abstract Full Text Show Details

Saad, Mohamed El Khames; Rabaaoui, Nejmeddine; Elaloui, Elimame; Moussaoui, Younes


Separation and Purification Technology, 2016 , vol. 171, p. 157 - 163 Title/Abstract Full Text View citing articles Show Details

Xu, Lun; Liu, Fengyi; Xu, Li-Wen; Gao, Ziwei; Zhao, Yu-Ming

Organic Letters, 2016 , vol. 18, # 15 p. 3698 - 3701 Title/Abstract Full Text View citing articles Show Details

Nakanishi, Ikuo; Ohkubo, Kei; Ogawa, Yukihiro; Matsumoto, Ken-Ichiro; Ozawa, Toshihiko; Fukuzumi, Shunichi

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 33 p. 7956 - 7961 Title/Abstract Full Text View citing articles Show Details

Kamps; Hoeks; Kung; Lens; McCloskey; Noordover; Heuts

Polymer Chemistry, 2016 , vol. 7, # 33 p. 5294 - 5303 Title/Abstract Full Text Show Details

Lee, Sang Jae; Lee, In-Gyun; Lee, Ki-Young; Kim, Dong-Gyun; Eun, Hyun-Jong; Yoon, Hye-Jin; Chae, Susanna; Song, Sung-Hyun; Kang, SaOuk; Seo, Min-Duk; Kim, Hyoun Sook; Park, Sung Jean; Lee, Bong-Jin

Proceedings of the National Academy of Sciences of the United States of America, 2016 , vol. 113, # 35 p. E5202 - E5211 Title/Abstract Full Text Show Details

Dehua, Ma; Cong, Liu; Xiaobiao, Zhu; Rui, Liu; Lujun, Chen

Environmental Science and Pollution Research, 2016 , vol. 23, # 18 p. 18343 - 18352 Title/Abstract Full Text Show Details

Li, Jing; Dai, Jianjun; Liu, Guangqing; Zhang, Hedong; Gao, Zuopeng; Fu, Jie; He, Yanfeng; Huang, Yan

Biomass and Bioenergy, 2016 , vol. 94, p. 228 - 244 Title/Abstract Full Text Show Details

Li, Jing; Dai, Jianjun; Liu, Guangqing; Zhang, Hedong; Gao, Zuopeng; Fu, Jie; He, Yanfeng; Huang, Yan

Biomass and Bioenergy, 2016 , vol. 94, p. 228 - 244 Title/Abstract Full Text Show Details

Moreira, Francisca C.; Boaventura, Rui A.R.; Brillas, Enric; Vilar, Vítor J.P.

Applied Catalysis B: Environmental, 2017 , vol. 202, p. 217 - 261 Title/Abstract Full Text Show Details

Moreira, Francisca C.; Boaventura, Rui A.R.; Brillas, Enric; Vilar, Vítor J.P.

Applied Catalysis B: Environmental, 2017 , vol. 202, p. 217 - 261 Title/Abstract Full Text Show Details

Zhang, Yuhan; Guo, Yonghong; Li, Zhongle; Xie, Zhixiang

Organic Letters, 2016 , vol. 18, # 18 p. 4578 - 4581 Title/Abstract Full Text Show Details

Widhalm, Joshua R.; Rhodes, David

Horticulture Research, 2016 , vol. 3, art. no. 16046 Title/Abstract Full Text Show Details

JNC Corporation; JNC Petrochemical Corporation; OOTSUKI, DAISUKE; INAGAKI, JUNICHI

Patent: JP5803076 B2, 2015 ; Title/Abstract Full Text Show Details

DOW AGROSCIENCES LLC; BREWSTER, WILLIAM; KLITTICH, CARLA; RIEDER, BRENT; SIDDALL, THOMAS; YAO, CHENGLIN

Patent: JP5781090 B2, 2015 ; Title/Abstract Full Text Show Details

Naik, Desavath V.; Kumar, Ranjan; Tripathi, Deependra; Singh, Raghuvir; Kanaujia, Pankaj K.

Journal of Analytical and Applied Pyrolysis, 2016 , vol. 121, p. 360 - 368 Title/Abstract Full Text Show Details

Yagofarov, Mikhail I.; Nagrimanov, Ruslan N.; Solomonov, Boris N.

Journal of Chemical Thermodynamics, 2017 , vol. 105, p. 50 - 57 Title/Abstract Full Text Show Details

27 of 42

Comment (Pharmacological Data)

Bioactivities present

Reference

Yagofarov, Mikhail I.; Nagrimanov, Ruslan N.; Solomonov, Boris N.

Journal of Chemical Thermodynamics, 2017 , vol. 105, p. 50 - 57 Title/Abstract Full Text Show Details

Zhao, Qian; Liu, Yu

Biotechnology Advances, 2016 , vol. 34, # 5 p. 1064 - 1072 Title/Abstract Full Text Show Details

Peixoto de Abreu Lima, Alejandro; Graziano, Natali; Pandolfi, Enrique

Green Chemistry Letters and Reviews, 2016 , vol. 9, # 4 p. 210 - 215 Title/Abstract Full Text Show Details

Li, Xuesong; Markandeya, Nagula; Jonusauskas, Gediminas; McClenaghan, Nathan D.; Maurizot, Victor; Denisov, Sergey A.; Huc, Ivan

Journal of the American Chemical Society, 2016 , vol. 138, # 41 p. 13568 - 13578 Title/Abstract Full Text Show Details

FUJIFILM CORPORATION; Katoh, Shunya; Matsuyama, Hiroshi; Yoshikawa, Masaru

Patent: US9464228 B2, 2016 ; Title/Abstract Full Text Show Details

FUJIFILM CORPORATION; KATOH, SHUNYA; NAKAZAWA, YUKI

Patent: JP2015/163596 A, 2015 ; Title/Abstract Full Text Show Details

Menichetti, Stefano; Amorati, Riccardo; Meoni, Valentina; Tofani, Lorenzo; Caminati, Gabriella; Viglianisi, Caterina

Organic Letters, 2016 , vol. 18, # 21 p. 5464 - 5467 Title/Abstract Full Text Show Details

Zhu, Chao; Wang, Runyu; Jin, Hui; Lian, Xiaoyan; Guo, Liejin; Huang, Jianbing

International Journal of Hydrogen Energy, 2016 , vol. 41, # 36 p. 16002 - 16008 Title/Abstract Full Text Show Details

Zhu, Chao; Wang, Runyu; Jin, Hui; Lian, Xiaoyan; Guo, Liejin; Huang, Jianbing

International Journal of Hydrogen Energy, 2016 , vol. 41, # 36 p. 16002 - 16008 Title/Abstract Full Text Show Details

Fuji Photo Film Co., Ltd.; Kato, Syunya; Yoshikawa, Masaru

Patent: KR101634475 B1, 2016 ;


Title/Abstract Full Text Show Details

DIC Corporation; Horiguchi, Masahiro; Aoki, Yoshio; Hayashi, Masanao; Kusumoto, Tetsuo

Patent: JP5988087 B2, 2016 ; Title/Abstract Full Text Show Details

Fujifilm Corporation; Nakamura, Takaki; Shimamura, Satoshi; Imoto, Junichi; Watanabe, Katsuyuki

Patent: JP5728313 B2, 2015 ; Title/Abstract Full Text Show Details

28 of 42

29 of 42

30 of 42

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

García-Caballero; Blacher; Paupert; Quesada; Medina; Noël

British Journal of Pharmacology, 2016 , vol. 173, # 12 p. 1966 - 1987 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

pharmacokinetics

Species or TestSystem (Pharmacological Data)

2,6-dichlorohydroquinone 1,2-dioxygenase of Sphingobium chlorophenolicum ATCC 39723

Kind of Dosing (Pharmacological Data)

comparative comp. incubated in the presence of saturated air buffer

Further Details (Pharmacological Data)

spectrophotometry; Michaelis-Menten constant (Km)

Type (Pharmacological Data)

Km

Value of Type (Pharmacological Data)

41 μmol/l

Reference

MacHonkin, Timothy E.; Doerner, Amy E.

Biochemistry, 2011 , vol. 50, # 41 p. 8899 - 8913 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 3 - activity asainst P. acnes (other quinones)A series of quinones was tested with zinc pyrithione (ZP) in a similar manner to that described in Example 1. The MIC and MBC results are shown in Table 4 below and the (S)DDA results in Tables 5 (unsupplemented assays) and 6 (assays supplemented with salt and lipid). All results are collated from a number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of 2-t-butyl-p-benzoquinone which was used at 50 μg per disc in unsupplemented and 100 μg per disc in supplemented assays. The test compounds were dissolved in DMSO, with the exception of /?-benzoquinone and thymoquinone which were dissolved in ethanol.Table 4 Table 5 (unsupplemented (S)DDAs)Table 6 (supplemented (S)DDAs) (SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)Again these data demonstrate a synergistic antimicrobial interaction when a quinone is combined with zinc pyrithione, there being a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in nearly all cases in the presence of salt and lipid; furthermore the activity of the quinones alone appears in all cases to be enhanced by the presence of the supplements. Indeed, in some cases, for example the combination of 2-methyl-/?hydroquinone or 2- ethyl-p-hydroquinone with zinc pyrithione, antimicrobial synergy appears to be far more marked under the supplemented conditions than the unsupplemented ones, indicating the potential value of such a combination in topical skin treatment formulations, in particular to treat acne.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

62.5 μg/ml

Results

MBC is 125 μg/ml, MIC/MBC is 0.5

Location

Page/Page column 22-24; 28

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details


31 of 42

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 3 - activity asainst P. acnes (other quinones)A series of quinones was tested with zinc pyrithione (ZP) in a similar manner to that described in Example 1. The MIC and MBC results are shown in Table 4 below and the (S)DDA results in Tables 5 (unsupplemented assays) and 6 (assays supplemented with salt and lipid). All results are collated from a number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of 2-t-butyl-p-benzoquinone which was used at 50 μg per disc in unsupplemented and 100 μg per disc in supplemented assays. The test compounds were dissolved in DMSO, with the exception of /?-benzoquinone and thymoquinone which were dissolved in ethanol.Table 4 Table 5 (unsupplemented (S)DDAs)Table 6 (supplemented (S)DDAs) (SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)Again these data demonstrate a synergistic antimicrobial interaction when a quinone is combined with zinc pyrithione, there being a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in nearly all cases in the presence of salt and lipid; furthermore the activity of the quinones alone appears in all cases to be enhanced by the presence of the supplements. Indeed, in some cases, for example the combination of 2-methyl-/?hydroquinone or 2- ethyl-p-hydroquinone with zinc pyrithione, antimicrobial synergy appears to be far more marked under the supplemented conditions than the unsupplemented ones, indicating the potential value of such a combination in topical skin treatment formulations, in particular to treat acne.

Results

unsupplemented disc diffusion assay value is 0.0 mm, supplemented (Triolein at 1percent v/v, sodium chloride, 100 mM) disc diffusion assay value is 36.13 mm

Location

Page/Page column 22-25; 28-30

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

32 of 42

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 8 - activity against P. acnes (other quinones)A number of different quinones was tested with both copper (II) sulphate pentahydrate (CSPH) and copper (II) silicate (CSL) against P. acnes NCTC 737 using (S)DDA tests as described in Example 1.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc, with the exception of copper (II) silicate (62 μg/disc) and 2-t-butyl-l,4- benzoquinone (100 μg/disc). The quinones were dissolved in DMSO and the copper (II) sulphate pentahydrate in deionised water, whilst the copper (II) silicate was used as a 0.62 percent (w/w) solution in water.All the quinones were sourced from Thermo Fisher Scientific, UK with the exception of 2-t-butyl-l,4-benzoquinone (Sigma- Aldrich) and 2-ethyl-p-hydroquinone (Apin Chemicals Ltd, UK).The DDA results are shown in Table 13 below and the SDDA results in Tables 14 and 15 (unsupplemented assays) and 16 and 17 (supplemented assays).Table 13 f-lpercent(v/v) trioleinTable 14Table 15Table 16 (SL SDDA = SDDA with salt and lipid (1percent (v/v) triolein) supplements)Table 17(SL SDDA = SDDA with salt and lipid (1percent (v/v) triolein) supplements)These data demonstrate synergistic antimicrobial activity against P. acnes NCTC 737 for a range of different benzo- and hydroquinones with copper salts. On the whole these synergies are retained under the supplemented conditions.

Results

title compound demonstrated an antimicrobial activity with zone of diameter of 13.64 mm (DDA) and 35.18 mm (DDA + salt and lipid)

Location

Page/Page column 47-49

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

33 of 42

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Staphylococcus aureus ATCC 29213

Method (Pharmacological Data)

Example 9 - activity against S. aureus (other quinones)Two further quinones, 2-methyl- and 2-ethyl:p-hydroquinone, were tested with both copper (II) sulphate pentahydrate (CSPH) and copper (II) silicate (CSL) against S. aureus ATCC 29213 using (S)DDA tests as described in Example 3.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of copper (II) silicate which was added at 62 μg/disc. The quinones were dissolved in DMSO and the copper (II) sulphate pentahydrate in deionised water, whilst the copper (II) silicate was used as a 0.62 percent (w/w) solution in water. All (S)DDA experiments were conducted in triplicate.The DDA results are shown in Table 18 below and the SDDA results in Tables 19 and 20 (unsupplemented assays) and 21 and 22 (supplemented assays).Table 18Table 19Table 20 Table 21(SS SDDA = SDDA with salt and serum supplements)Table 22(SS SDDA = SDDA with salt and serum supplements)These data demonstrate that a synergistic antimicrobial interaction against S. aureus ATCC 29213 can be observed not only for TBHQ with copper salts but also for other benzo- and hydroquinones with copper salts. The synergies are retained under the supplemented conditions.

Results

title compound demonstrated an antimicrobial activity with zone of diameter of 25.77 mm (DDA) and 26.91 mm (DDA + salt and lipid)

Location

Page/Page column 49-51

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details


34 of 42

35 of 42

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

rabbit sceletal muscle sarcoplasmic reticulum membranes

Concentration (Pharmacological Data)

1 mmol/l

Method (Pharmacological Data)

RyR1 activity monitored by specific binding of 5 nmol/l <3H>ryanodine to 10 μg vesicles in presence of title comp. after shaking at 37 deg C for 2 to 3 h in HEPES, pH 7.4; after rapid filtration amount of <3H>ryanodine bound to filter determined by LSC

Further Details (Pharmacological Data)

RyR1: ryanodine receptor isoform 1; LSC: liquid scintillation counting

Comment (Pharmacological Data)

No effect

Reference

Jacobson, Alan R.; Moe, Scott T.; Allen; Fessenden, James D.

Molecular Pharmacology, 2006 , vol. 70, # 1 p. 259 - 266 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as

described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

36 of 42

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted


benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

37 of 42

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as

described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Results

title compound resulted in a 25.70 mm disc diffusion assay (DDA); title compound resulted in a 22.49 mm disc diffusion assay (DDA) in the presence of salt; title compound resulted in a 24.68 mm disc diffusion assay (DDA) in the presence of a lipid; title compound resulted in a 18.74 mm disc diffusion assay (DDA) in the presence of blood

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

38 of 42

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

3T3 cells of BALB/c mouse embryo

Kind of Dosing (Pharmacological Data)

title comp. added to culture medium

Method (Pharmacological Data)

neutral red uptake assay; cells in Dulbecco's Modified Eagle's Medium with fetal bovine serum treated with title comp. for 24 h; after exposure to title comp. cells incubated with neutral red (nr) for 3 h; conc. of nr determined spectrophotometrically

Further Details (Pharmacological Data)

EC50: conc. that decreased number of viable cells by 50percent relative to solvent control

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.011 mmol/l


39 of 42

40 of 42

41 of 42

42 of 42

Reference

Chouchane, Salem; Wooten, Jan B.; Tewes, Franz J.; Wittig, Arno; Mueller, Boris P.; Veltel, Detlef; Diekmann, Joerg

Chemical Research in Toxicology, 2006 , vol. 19, # 12 p. 1602 - 1610 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

growth inhibitory effect against L 1210 leukemia cells (IC50=5 μg/mL)

Reference

Makino, Mitsuko; Endoh, Toshinari; Ogawa, Yoshio; Watanabe, Kazuko; Fujimoto, Yasuo

Heterocycles, 1998 , vol. 48, # 9 p. 1931 - 1934 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

inhibitory effect on AA-induced platelet aggregation

Reference

Kagawa; Tokura; Uchida; Kakushi; Shike; Nakai

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 8 p. 2083 - 2087 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

inotropic and chronotropic effects (isolated guinea pig atria)

Reference

Kagawa; Tokura; Uchida; Kakushi; Shike; Nakai

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 8 p. 2083 - 2087 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

no self-growth inhibiting activity

Reference

Sassa, Takeshi; Nukina, Manabu

Agricultural and Biological Chemistry, 1984 , vol. 48, # 7 p. 1923 - 1926 Title/Abstract Full Text Show Details

Ecotoxicology (2) 1 of 2

2 of 2

Effect (Ecotoxicology)

electrophysiology; effect on

Species or TestSystem (Ecotoxicology)

antenna of Tribolium confusum (du Val), flour beetle

Sex

male and female

Concentration (Ecotoxicology)

1 - 1E6 ng

Kind of Dosing (Ecotoxicology)

title comp. impregnated in a piece of 0.5-cm2 filter paper

Method (Ecotoxicology)

insect antenna mounted between 2 glass electrodes; exposed to title comp. puff by means of a stimulus controller; EAG responses recorded

Further Details (Ecotoxicology)

control: n-hexane; active control: 10 μg of title comp.; EAG: electroantennography

Comment (Ecotoxicology)

No effect

Reference

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

toxicity to bacteria

Species or TestSystem (Ecotoxicology)

Vibrio fischeri

Method (Ecotoxicology)

title comp. toxicity measured 24 after γ-radiation; Microtox assay

Further Details (Ecotoxicology)

EC50: conc. that causes 50 percent reduction of the bioluminescence after 15 min incubation

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

0.30 mg/l

Reference

Bojanowska-Czajka, Anna; Drzewicz, Przemyslaw; Kozyra, Czeslaw; Nalecz-Jawecki, Grzegorz; Sawicki, Jozef; Szostek, Bogdan; Trojanowicz, Marek

Ecotoxicology and Environmental Safety, 2006 , vol. 65, # 2 p. 265 - 277


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Other Data Use (36) Use Pattern

Reference

Antimicrobial

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin structure conditions

SYNTOPIX LIMITED

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Acne

SYNTOPIX LIMITED

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Eczema

SYNTOPIX LIMITED

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Superficial infected traumatic lesions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

wounds

SYNTOPIX LIMITED

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Burns

SYNTOPIX LIMITED

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ulcers

SYNTOPIX LIMITED

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Folliculitis

SYNTOPIX LIMITED

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Mycoses

SYNTOPIX LIMITED

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Acne lesions

SYNTOPIX LIMITED

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Bacteria associated with acne

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin conditions

SYNTOPIX LIMITED

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Staphylococcal infection

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details


SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Atopic dermatitis

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Primary skin infections

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Secondary skin infections

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Primary skin structure infections

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Secondary skin structure infections

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Acne-related scarring

Title/Abstract Full Text Show Details

Hide facts Laboratory Use and Handling

Use Pattern

Reference

methicillin resistant S. aureus (MRSA)-associated infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin care

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Hair care

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Cosmeceutical preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Toiletry product

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Laundry product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Fabric treatment product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Bath additive

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Shower additive

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details


Cleansing preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Agricultural product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Horticultural product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

veterinary preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Polymerization-inhibitor

TOKYO OHKA KOGYO CO., LTD.

Patent: WO2006/80178 A1, 2006 ; Title/Abstract Full Text Show Details

Inhibitor of polymerisation

BASF AKTIENGESELLSCHAFT

Patent: WO2004/50596 A1, 2004 ; Title/Abstract Full Text Show Details

antioxidant

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details

Isolation from Natural Product (9) Isolation from Natural Product

Reference

cultures of Penicillium sp. strain I09F 484, isolated from the rhizosphere soil of the plant Picea asperata, collected from Kanas Lake, Buerjin County, Altay Prefecture, Xinjiang Uygur Autonomous Region, China

Gan, Maoluo; Liu, Yufeng; Bai, Yinlei; Guan, Yan; Li, Li; Gao, Rongmei; He, Weiying; You, Xuefu; Li, Yuhuan; Yu, Liyan; Xiao, Chunling

Journal of Natural Products, 2013 , vol. 76, # 9 p. 1535 - 1540 Title/Abstract Full Text View citing articles Show Details

strain Penicillium crustosum PRB-2; collected in Prydz Bay

Wu, Guangwei; Ma, Hongyan; Zhu, Tianjiao; Li, Jing; Gu, Qianqun; Li, Dehai

Tetrahedron, 2012 , vol. 68, # 47 p. 9745 - 9749,5 Title/Abstract Full Text Show Details

Penicillium vulpinum

Makino, Mitsuko; Endoh, Toshinari; Ogawa, Yoshio; Watanabe, Kazuko; Fujimoto, Yasuo

Heterocycles, 1998 , vol. 48, # 9 p. 1931 - 1934 Title/Abstract Full Text View citing articles Show Details

Pyrolae Herba (mixt. of Pyrola rotundifolia, Pyrola incarnata, Pyrola japonica)

Kagawa; Tokura; Uchida; Kakushi; Shike; Nakai

Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 8 p. 2083 - 2087 Title/Abstract Full Text View citing articles Show Details

Vork. in Phana

Sequin-Frey,M.; Tamm,C.

Helvetica Chimica Acta, 1971 , vol. 54, # 3 p. 851 - 861 Full Text View citing articles Show Details

Im 'Pulverdampf' von Bombardierkaefern und anderen Kaefern

Schildknecht,H. et al.

Angewandte Chemie, 1963 , vol. 75, p. 762 - 771 Full Text View citing articles Show Details

in den Abwehrblasen von Tenebrio molitor, Forficula auricularia, Schizophyllium sabulorium

Schildknecht; Kraemer

Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, 1962 , vol. 17, p. 701 Full Text Show Details

In den Bombardierkaefern Brachynus sclopeta u. anderen Brachynus-Arten sowie in Pheropsophus catiorei

Schildknecht; Holoubek

Angewandte Chemie, 1961 , vol. 73, p. 1,5 Full Text Show Details

Vorkommen in Tribolium confusum und Tribolium castaneum

Hackman; Pryor; Todd


Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

Chemical Name: 2-ethylhydroquinone

2

Reaxys Registry Number: 1936246

CAS Registry Number: 2349-70-4 Type of Substance: isocyclic Molecular Formula: C8H10O2

Linear Structure Formula: C6H4O2H2CH2CH2

Molecular Weight: 138.166

InChI Key: VJIDDJAKLVOBSE-UHFFFAOYSA-N

33 prep out of 98 reactions.

Identification Physical Data (21) Spectra (10) Bioactivity (15) Other Data (36)

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-ethylhydroquinone, 2-ethyl-1,4-dihydroxybenzene, 3-ethyl-4-hydroxyphenol, 2-Ethylhydroquinone, ethylhydroquinone, 2-ethyl-1,4-hydroquinone, 2-ethyl-benzene-1,4-diol Identification Substance Label (13) Label

Reference

2ag

Xia, Zilei; Hu, Jiadong; Shen, Zhigao; Yao, Qizheng; Xie, Weiqing

RSC Advances, 2015 , vol. 5, # 48 p. 38499 - 38502 Title/Abstract Full Text View citing articles Show Details

4b

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

1c

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

14

Rocha, Daniele F.O.; Wouters, Felipe C.; Zampieri, Davila S.; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J.

Molecules, 2013 , vol. 18, # 9 p. 11429 - 11451 Title/Abstract Full Text View citing articles Show Details

Intermediate LXXXIII

JUBILANT BIOSYS LTD.; SARMA, Pakala Kumara Savithru; ACHARYA, Vinod Parameshwaran; KASIBHATLA, Srinivas Rao; VISWANADHAN, Vellarkad Narayana; TIWARI, Atul; SINGHA, Rakesh Kumar; BISCHOFF, Alexander

Patent: WO2012/90219 A2, 2012 ; Title/Abstract Full Text Show Details

8b

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

11a

Yakubovskaya; Pokhilo; Mishchenko; Anufriev

Russian Chemical Bulletin, 2007 , vol. 56, # 4 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

EHQ

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

3a

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

product, table/run 4

Horikawa, Yoshiteru; Uchino, Yuki; Sako, Takeshi

Chemistry Letters, 2003 , vol. 32, # 3 p. 232 - 233 Title/Abstract Full Text View citing articles Show Details

71


2a

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

12 R=Et

Stanton, James L.; Cahill, Edna; Dotson, Ronald; Tan, Jenny; Tomaselli, Hollis C.; Wasvary, Jong M.; Stephan, Zouhair F.; Steele, Ronald E.

Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 15 p. 1661 - 1663 Title/Abstract Full Text View citing articles Show Details

QH2 3

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 4 p. 871 - 876 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly; Barsukova, Tatyana

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 7 p. 1575 - 1582 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (2) Prophetic Compound

Location in Patent

Reference

prophetic product

The Procter and Gamble Company

Patent: US3957424 A1, 1976 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2003/66140 A1, 2003 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2003/135935 A1, 2003 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2004/19980 A1, 2004 ; Title/Abstract Full Text Show Details

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ;

Claim

Title/Abstract Full Text Show Details

Standard Oil Company

Patent: US4307012 A1, 1981 ; Title/Abstract Full Text Show Details

Huels Aktiengesellschaft

Patent: US4614808 A1, 1986 ; Title/Abstract Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

dibenzoyl derivative (mp: 89 degree )

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

Physical Data Melting Point (15) Melting Point

Solvent (Melting Point)

Comment (Melting Point)

Reference

112 - 113 °C

chloroform

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

104 - 106 °C

toluene

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

108 - 110 °C

hexane

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

112 °C

diethyl ether

Gocmen,M. et al.


petroleum ether

Bulletin de la Societe Chimique de France, 1973 , p. 562 - 569 Full Text View citing articles Show Details

111 - 112 °C

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

115 - 116 °C

benzene

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

112 - 113 °C

Bayrac

Bulletin de la Societe Chimique de France, 1894 , vol. <3> 11, p. 1130,1133 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 55,56, 68 Full Text Show Details

Ehrhart

Angewandte Chemie, 1963 , vol. 75, p. 855 Full Text Show Details

113 °C

benzene

Stern et al.

Journal of the American Chemical Society, 1957 , vol. 79, p. 5797,5800 Full Text View citing articles Show Details

114 °C

H2O

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

112 °C

Desai; Mavani

Proceedings - Indian Academy of Sciences, Section A, 1942 , # 15 p. 11,14 Full Text Show Details

113 - 115 °C

benzene

Kenner; Statham

Journal of the Chemical Society, 1935 , p. 299,301 Chemische Berichte, 1936 , vol. 69, p. 16,17 Full Text Show Details

112 °C

H2O

sublimiert in Nadeln.

Clemmensen

Chemische Berichte, 1914 , vol. 47, p. 62 Full Text Show Details

112 °C

CHCl3

sublimiert in Nadeln.

Clemmensen

Chemische Berichte, 1914 , vol. 47, p. 62 Full Text Show Details

112 °C

benzene

sublimiert in Nadeln.

Clemmensen

Chemische Berichte, 1914 , vol. 47, p. 62 Full Text Show Details

113 - 114 °C

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

166 - 170 °C

14 Torr

Landa; Macak

Collection of Czechoslovak Chemical Communications, 1960 , vol. 25, p. 761,762 Full Text Show Details

Crystal Property Description (4) Colour & Other Properties

Reference

light-yellow

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

Tafeln

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

Nadeln

Kenner; Statham

Journal of the Chemical Society, 1935 , p. 299,301 Chemische Berichte, 1936 , vol. 69, p. 16,17


Full Text Show Details

Bayrac

Bulletin de la Societe Chimique de France, 1894 , vol. <3> 11, p. 1130,1133 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 55,56, 68 Full Text Show Details

Nadeln oder Tafeln

Electrochemical Characteristics (1) Description (Electrochemical Characteristics)

Reference

polarographic half-wave potential

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Spectra NMR Spectroscopy (4) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

dimethylsulfoxide-d6

500 MHz

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

acetone-d6

250.13 MHz

Yakubovskaya; Pokhilo; Mishchenko; Anufriev

Russian Chemical Bulletin, 2007 , vol. 56, # 4 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

acetone-d6

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Chemical shifts

1H

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

Reference

IR Spectroscopy (2) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Reference

Bands

CHCl3

Yakubovskaya; Pokhilo; Mishchenko; Anufriev

Russian Chemical Bulletin, 2007 , vol. 56, # 4 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

Bands

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

Mass Spectrometry (2) Description (Mass Spectrometry)

Location

Reference

high resolution mass spectrometry (HRMS) electron impact (EI) gas chromatography mass spectrometry (GCMS) time-of-flight mass spectra (TOFMS) spectrum

supporting information

Rocha, Daniele F.O.; Wouters, Felipe C.; Zampieri, Davila S.; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J.

Molecules, 2013 , vol. 18, # 9 p. 11429 - 11451 Title/Abstract Full Text View citing articles Show Details

spectrum electron impact (EI)

Yakubovskaya; Pokhilo; Mishchenko; Anufriev

Russian Chemical Bulletin, 2007 , vol. 56, # 4 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

UV/VIS Spectroscopy (2) Description (UV/VIS Spectroscopy)

Solvent (UV/VIS Spectroscopy)

Reference

Spectrum

Moser; Cassidy

Journal of Organic Chemistry, 1965 , vol. 30, p. 2602,2603 Full Text Show Details


Spectrum

ethanol

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details

Bioactivity Pharmacological Data (14) 1 of 14

Comment (Pharmacological Data)

Bioactivities present

Reference

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

The Procter and Gamble Company

Patent: US3957424 A1, 1976 ; Title/Abstract Full Text Show Details

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ; Title/Abstract Full Text Show Details

Standard Oil Company

Patent: US4307012 A1, 1981 ; Title/Abstract Full Text Show Details

Allen Jr.; Pidacks; Weiss

Journal of the American Chemical Society, 1966 , vol. 88, # 11 p. 2536 - 2544 Title/Abstract Full Text View citing articles Show Details

Huels Aktiengesellschaft

Patent: US4614808 A1, 1986 ; Title/Abstract Full Text Show Details

Schildknecht,H. et al.

Angewandte Chemie, 1963 , vol. 75, p. 762 - 771 Full Text View citing articles Show Details

Gocmen,M. et al.

Bulletin de la Societe Chimique de France, 1973 , p. 562 - 569 Full Text View citing articles Show Details

Murata; Satoh; Nohara; et al.

European Journal of Medicinal Chemistry, 1977 , vol. 12, # 1 p. 17 - 20 Title/Abstract Full Text View citing articles Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2003/66140 A1, 2003 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2003/135935 A1, 2003 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division of Conopco, Inc.

Patent: US2004/19980 A1, 2004 ; Title/Abstract Full Text Show Details

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

Ramage; Stead

Journal of the Chemical Society, 1953 , p. 3602,3605 Full Text View citing articles Show Details

Stern et al.

Journal of the American Chemical Society, 1957 , vol. 79, p. 5797,5800 Full Text View citing articles Show Details


2 of 14

Comment (Pharmacological Data)

Bioactivities present

Reference

Desai; Mavani

Proceedings - Indian Academy of Sciences, Section A, 1942 , # 15 p. 11,14 Full Text Show Details

Mehta et al.

Journal of the Indian Chemical Society, 1956 , vol. 33, p. 135,138 Full Text Show Details

Kenner; Statham

Journal of the Chemical Society, 1935 , p. 299,301 Chemische Berichte, 1936 , vol. 69, p. 16,17 Full Text Show Details

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

Clemmensen

Chemische Berichte, 1914 , vol. 47, p. 62 Full Text Show Details

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Hackman; Pryor; Todd

Biochemical Journal, 1948 , vol. 43, p. 474,477 Full Text Show Details

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details

Kuroda; Wada

Proceedings of the Imperial Academy (Tokyo), 1936 , vol. 12, p. 239 Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1755 Full Text Show Details

Updegraff; Cassidy

Journal of the American Chemical Society, 1949 , vol. 71, p. 407 Full Text View citing articles Show Details

Loconti; Roth

Ann. Entomol. Soc. Am., 1953 , vol. 46, p. 281,283 Full Text Show Details

Eastman Kodak Co.

Patent: US2533203 , 1948 ; Full Text Show Details

Bayrac

Bulletin de la Societe Chimique de France, 1894 , vol. <3> 11, p. 1130,1133 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 55,56, 68 Full Text Show Details

Ono

Helvetica Chimica Acta, 1927 , vol. 10, p. 46,47, 51 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Ashworth; Dixon

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1972 , p. 1130,1131 Full Text Show Details

Alberola et al.

Anales de Quimica (1968-1979), 1977 , vol. 73, p. 1227 Full Text Show Details

Landa; Macak

Collection of Czechoslovak Chemical Communications, 1960 , vol. 25, p. 761,762 Full Text Show Details

Ehrhart

Angewandte Chemie, 1963 , vol. 75, p. 855 Full Text Show Details

Moser; Cassidy

Journal of Organic Chemistry, 1965 , vol. 30, p. 2602,2603 Full Text Show Details

3 of 14

Comment (Pharmacological Data)

Bioactivities present

Reference

Schildknecht; Kraemer

Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, 1962 , vol. 17, p. 701 Full Text Show Details

Langlais et al.

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1961 , vol. 253, p. 2364 Full Text Show Details

Pelzl, Gerhard; Oertel, Birgit; Mohr, Kristina; Demus, Dietrich

Zeitschrift fuer Chemie (Stuttgart, Germany), 1986 , vol. 26, # 2 p. 63 - 64 Title/Abstract Full Text Show Details

Schaefer, Wolfgang; Deutscher, Hans-Joachim

Zeitschrift fuer Chemie (Stuttgart, Germany), 1982 , vol. 22, # 12 p. 447 - 448 Title/Abstract Full Text Show Details


Wissner, A.; Carroll, M. L.; Green, K. E.; Kerwar, S. S.; Pickett, W. C.; et al.

Journal of Medicinal Chemistry, 1992 , vol. 35, # 9 p. 1650 - 1662 Title/Abstract Full Text View citing articles Show Details

Elliger, Carl A.

Synthetic Communications, 1985 , vol. 15, # 14 p. 1315 - 1324 Title/Abstract Full Text Show Details

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Kneppe, H.; Schneider, F.

Molecular Crystals and Liquid Crystals (1969-1991), 1983 , vol. 97, p. 219 - 230 Title/Abstract Full Text Show Details

Wu, Shao-Yong; Ito, Shigekazu; Eto, Morifusa

Agricultural and Biological Chemistry, 1987 , vol. 51, # 11 p. 2935 - 2942 Title/Abstract Full Text Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa; Saran, Manfred

Journal of the Chemical Society - Faraday Transactions, 1998 , vol. 94, # 13 p. 1835 - 1840 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 4 p. 871 - 876 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly; Barsukova, Tatyana

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 7 p. 1575 - 1582 Title/Abstract Full Text View citing articles Show Details

Stanton, James L.; Cahill, Edna; Dotson, Ronald; Tan, Jenny; Tomaselli, Hollis C.; Wasvary, Jong M.; Stephan, Zouhair F.; Steele, Ronald E.

Bioorganic and Medicinal Chemistry Letters, 2000 , vol. 10, # 15 p. 1661 - 1663 Title/Abstract Full Text View citing articles Show Details

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

Horikawa, Yoshiteru; Uchino, Yuki; Sako, Takeshi

Chemistry Letters, 2003 , vol. 32, # 3 p. 232 - 233 Title/Abstract Full Text View citing articles Show Details

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Yakubovskaya; Pokhilo; Mishchenko; Anufriev

Russian Chemical Bulletin, 2007 , vol. 56, # 4 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

4 of 14

Comment (Pharmacological Data)

Bioactivities present

Reference

4SC AG

Patent: EP1947103 A1, 2008 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2009/74792 A2, 2009 ; Title/Abstract Full Text Show Details

Gholap, Shivajirao L.; Woo, Christina M.; Ravikumar; Herzon, Seth B.

Organic Letters, 2009 , vol. 11, # 19 p. 4322 - 4325 Title/Abstract Full Text View citing articles Show Details

Tasler, Stefan; Baumgartner, Roland; Ammendola, Astrid; Schachtner, Josef; Wieber, Tanja; Blisse, Marcus; Rath, Sandra; Zaja, Mirko; Klahn, Philipp; Quotschalla, Udo; Ney, Peter

Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 20 p. 6108 - 6115 Title/Abstract Full Text View citing articles Show Details

JUBILANT BIOSYS LTD.; SARMA, Pakala Kumara Savithru; ACHARYA, Vinod Parameshwaran; KASIBHATLA, Srinivas Rao; VISWANADHAN, Vellarkad Narayana; TIWARI, Atul; SINGHA, Rakesh Kumar; BISCHOFF, Alexander

Patent: WO2012/90219 A2, 2012 ; Title/Abstract Full Text Show Details

Rocha, Daniele F.O.; Wouters, Felipe C.; Zampieri, Davila S.; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J.

Molecules, 2013 , vol. 18, # 9 p. 11429 - 11451 Title/Abstract Full Text View citing articles Show Details

EADY, Elizabeth, Anne; QURESHI, Andleeb

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

EADY, Elizabeth, Anne; FITZGERALD, Daniel, James; COVE, Jonathan, Howard; SEVILLE, Scott

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923


Title/Abstract Full Text View citing articles Show Details

Xia, Zilei; Hu, Jiadong; Shen, Zhigao; Yao, Qizheng; Xie, Weiqing

RSC Advances, 2015 , vol. 5, # 48 p. 38499 - 38502 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

5 of 14

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 3 - activity asainst P. acnes (other quinones)A series of quinones was tested with zinc pyrithione (ZP) in a similar manner to that described in Example 1. The MIC and MBC results are shown in Table 4 below and the (S)DDA results in Tables 5 (unsupplemented assays) and 6 (assays supplemented with salt and lipid). All results are collated from a number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of 2-t-butyl-p-benzoquinone which was used at 50 μg per disc in unsupplemented and 100 μg per disc in supplemented assays. The test compounds were dissolved in DMSO, with the exception of /?-benzoquinone and thymoquinone which were dissolved in ethanol.Table 4 Table 5 (unsupplemented (S)DDAs)Table 6 (supplemented (S)DDAs) (SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)Again these data demonstrate a synergistic antimicrobial interaction when a quinone is combined with zinc pyrithione, there being a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in nearly all cases in the presence of salt and lipid; furthermore the activity of the quinones alone appears in all cases to be enhanced by the presence of the supplements. Indeed, in some cases, for example the combination of 2-methyl-/?hydroquinone or 2- ethyl-p-hydroquinone with zinc pyrithione, antimicrobial synergy appears to be far more marked under the supplemented conditions than the unsupplemented ones, indicating the potential value of such a combination in topical skin treatment formulations, in particular to treat acne.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

MBC is 31.25 μg/ml, MIC/MBC is 0.25

Location

Page/Page column 22-24; 28

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

6 of 14

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 3 - activity asainst P. acnes (other quinones)A series of quinones was tested with zinc pyrithione (ZP) in a similar manner to that described in Example 1. The MIC and MBC results are shown in Table 4 below and the (S)DDA results in Tables 5 (unsupplemented assays) and 6 (assays supplemented with salt and lipid). All results are collated from a number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of 2-t-butyl-p-benzoquinone which was used at 50 μg per disc in unsupplemented and 100 μg per disc in supplemented assays. The test compounds were dissolved in DMSO, with the exception of /?-benzoquinone and thymoquinone which were dissolved in ethanol.Table 4 Table 5 (unsupplemented (S)DDAs)Table 6 (supplemented (S)DDAs) (SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)Again these data demonstrate a synergistic antimicrobial interaction when a quinone is combined with zinc pyrithione, there being a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in nearly all cases in the presence of salt and lipid; furthermore the activity of the quinones alone appears in all cases to be enhanced by the presence of the supplements. Indeed, in some cases, for example the combination of 2-methyl-/?hydroquinone or 2- ethyl-p-hydroquinone with zinc pyrithione, antimicrobial synergy appears to be far more marked under the supplemented conditions than the unsupplemented ones, indicating the potential value of such a combination in topical skin treatment formulations, in particular to treat acne.

Results

unsupplemented disc diffusion assay value is 0.0 mm, supplemented (Triolein at 1percent v/v, sodium chloride, 100 mM) disc diffusion assay value is 26.16 mm

Location

Page/Page column 22-25; 28-30

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

7 of 14

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method

Example 8 - activity against P. acnes (other quinones)A number of different quinones was tested with both copper (II) sulphate pentahydrate (CSPH) and


(Pharmacological Data)

copper (II) silicate (CSL) against P. acnes NCTC 737 using (S)DDA tests as described in Example 1.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc, with the exception of copper (II) silicate (62 μg/disc) and 2-t-butyl-l,4- benzoquinone (100 μg/disc). The quinones were dissolved in DMSO and the copper (II) sulphate pentahydrate in deionised water, whilst the copper (II) silicate was used as a 0.62 percent (w/w) solution in water.All the quinones were sourced from Thermo Fisher Scientific, UK with the exception of 2-t-butyl-l,4-benzoquinone (Sigma- Aldrich) and 2-ethyl-p-hydroquinone (Apin Chemicals Ltd, UK).The DDA results are shown in Table 13 below and the SDDA results in Tables 14 and 15 (unsupplemented assays) and 16 and 17 (supplemented assays).Table 13 f-lpercent(v/v) trioleinTable 14Table 15Table 16 (SL SDDA = SDDA with salt and lipid (1percent (v/v) triolein) supplements)Table 17(SL SDDA = SDDA with salt and lipid (1percent (v/v) triolein) supplements)These data demonstrate synergistic antimicrobial activity against P. acnes NCTC 737 for a range of different benzo- and hydroquinones with copper salts. On the whole these synergies are retained under the supplemented conditions.

Results

title compound demonstrated an antimicrobial activity with zone of diameter of 9.95 mm (DDA) and 33.74 mm (DDA + salt and lipid)

Location

Page/Page column 47-49

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

8 of 14

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Staphylococcus aureus ATCC 29213

Method (Pharmacological Data)

Example 9 - activity against S. aureus (other quinones)Two further quinones, 2-methyl- and 2-ethyl:p-hydroquinone, were tested with both copper (II) sulphate pentahydrate (CSPH) and copper (II) silicate (CSL) against S. aureus ATCC 29213 using (S)DDA tests as described in Example 3.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc with the exception of copper (II) silicate which was added at 62 μg/disc. The quinones were dissolved in DMSO and the copper (II) sulphate pentahydrate in deionised water, whilst the copper (II) silicate was used as a 0.62 percent (w/w) solution in water. All (S)DDA experiments were conducted in triplicate.The DDA results are shown in Table 18 below and the SDDA results in Tables 19 and 20 (unsupplemented assays) and 21 and 22 (supplemented assays).Table 18Table 19Table 20 Table 21(SS SDDA = SDDA with salt and serum supplements)Table 22(SS SDDA = SDDA with salt and serum supplements)These data demonstrate that a synergistic antimicrobial interaction against S. aureus ATCC 29213 can be observed not only for TBHQ with copper salts but also for other benzo- and hydroquinones with copper salts. The synergies are retained under the supplemented conditions.

Results

title compound demonstrated an antimicrobial activity with zone of diameter of 24.12 mm (DDA) and 25.26 mm (DDA + salt and lipid)

Location

Page/Page column 49-51

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

9 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details


10 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as

described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

11 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone)

and ethanol (for TBHQ, thymoquinone, phydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Results

title compound resulted in a 21.06 mm disc diffusion assay (DDA); title compound resulted in a 24.59 mm disc diffusion assay (DDA) in the presence of salt; title compound resulted in a 23.04 mm disc diffusion assay (DDA) in the presence of a lipid; title compound resulted in a 17.74 mm disc diffusion assay (DDA) in the presence of blood

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

12 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method

Example 6 - activity against P. acnes -MIC, MBC


(Pharmacological Data)

(S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

13 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 6 - activity against P. acnes -MIC, MBC (S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described

above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each compound

was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

31.25 μg/ml

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

14 of 14

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 6 - activity against P. acnes -MIC, MBC (S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described

above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each compound

was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a


benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent. Results

title compound resulted in a 9.90 mm disc diffusion assay (DDA); title compound resulted in a 9.38 mm disc diffusion assay (DDA) in the presence of salt; title compound resulted in a 0 mm disc diffusion assay (DDA) in the presence of a lipid

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

Ecotoxicology (1) 1 of 1

Effect (Ecotoxicology)

electrophysiology; effect on

Species or TestSystem (Ecotoxicology)

antenna of Tribolium confusum (du Val), flour beetle

Sex

male and female

Concentration (Ecotoxicology)

1 - 1E5 ng

Kind of Dosing (Ecotoxicology)

title comp. impregnated in a piece of 0.5-cm2 filter paper

Method (Ecotoxicology)

insect antenna mounted between 2 glass electrodes; exposed to title comp. puff by means of a stimulus controller; EAG responses recorded

Further Details (Ecotoxicology)

control: n-hexane; active control: 10 μg of title comp.; EAG: electroantennography

Comment (Ecotoxicology)

No effect

Reference

Verheggen; Ryne; Olsson; Arnaud; Lognay; Hoegberg; Persson; Haubruge; Loefstedt

Journal of Chemical Ecology, 2007 , vol. 33, # 3 p. 525 - 539 Title/Abstract Full Text View citing articles Show Details

Other Data Use (33) Use Pattern

Reference

Antimicrobial

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin structure conditions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Eczema

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Superficial infected traumatic lesions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

wounds

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Burns

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;


Title/Abstract Full Text Show Details

ulcers

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Folliculitis

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Mycoses

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne lesions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Bacteria associated with acne

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin conditions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Staphylococcal infection

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Atopic dermatitis

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Primary skin infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Secondary skin infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Primary skin structure infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Secondary skin structure infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne-related scarring

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Hide facts Use Pattern

Reference

methicillin resistant S. aureus (MRSA)-associated infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin care

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;


Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Hair care

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Cosmeceutical preparation

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Toiletry product

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Laundry product

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Fabric treatment product

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Bath additive

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Shower additive

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Cleansing preparation

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Agricultural product

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

Horticultural product

Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;

veterinary preparation

Title/Abstract Full Text Show Details

Isolation from Natural Product (3) Isolation from Natural Product

Reference

Chavesincola inexpectabilis

Rocha, Daniele F.O.; Wouters, Felipe C.; Zampieri, Davila S.; Brocksom, Timothy J.; Machado, Glauco; Marsaioli, Anita J.

Molecules, 2013 , vol. 18, # 9 p. 11429 - 11451 Title/Abstract Full Text View citing articles Show Details

in d. Sekreten v. Ohrwuermern

Schildknecht,H. et al.

Angewandte Chemie, 1963 , vol. 75, p. 762 - 771 Full Text View citing articles Show Details

Abwehrblasen v. Forficula auricularia

Schildknecht; Kraemer

Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys.,, 1962 , vol. 17, p. 701 Full Text Show Details

Chemical Name:

16 prep

Identification

17


2-Propylhydroquinone

3

Reaxys Registry Number: 1941519

CAS Registry Number: 4693-31-6 Type of Substance: isocyclic Molecular Formula: C9H12O2

Linear Structure Formula: C9H12O2

Molecular Weight: 152.193

InChI Key: NJRNUAVVFBHIPT-UHFFFAOYSA-N

out of 29 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-Propylhydroquinone, n-propylhydroquinone, 2-propyl-hydroquinone, 2-Propyl-hydrochinon, 2.5-Dihydroxy-1-propyl-benzol, 2-propylhydroquinone, 2-n-Propyl-hydrochinon Identification Substance Label (6) Label

Reference

3b

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

2b

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

3, R=CH2CH3

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

n=3

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Ic

Kaufman et al.

Journal of Organic Chemistry, 1967 , vol. 32, p. 504 Full Text View citing articles Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

Patent-Specific Data (2) Related Markush Structure (RN)

Location in Patent

Reference

11326765

FORSKARPATENT I SYD AB

Patent: WO2004/2224 A1, 2004 ; Title/Abstract Full Text Show Details

Claim

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (9) Melting Point

Solvent (Melting Point)

Reference

Physical Data (11) Spectra (2) Bioactivity (2)


92 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

88 - 90 °C

benzene

Kaufman et al.

Journal of Organic Chemistry, 1967 , vol. 32, p. 504 Full Text View citing articles Show Details

88 °C

benzene hexane

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

91.5 - 92 °C

H2O

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

89 - 90 °C

benzene petroleum ether

Eastman Kodak Co.

Patent: US2533203 , 1948 ;

88 °C

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

87 °C

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

90 °C

benzene

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

86 °C

benzene

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

Full Text Show Details

Crystal Property Description (2) Colour & Other Properties

Reference

light-yellow

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

Nadeln

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

Spectra NMR Spectroscopy (1) Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

CD3 OD

400 MHz

Original Text (NMR Spectroscopy)

Signals

Kind of signal

Comment (NMR Spectroscopy)

Reference

NMR (400 MHz, CD3 OD) δ 6.56 (d, 1H), 6.51 (d, 1H), 6.43 (dd, 1H), 2.48 (t, 2H), 1.58 (m, 2H), 0.96 (t, 3H)

6.56 ppm 6.51 ppm 6.43 ppm 2.48 ppm 1.58 ppm 0.96 ppm

d, 1H d, 1H dd, 1H t, 2H m, 2H t, 3H

Signals given

Merck and Co., Inc.

Patent: US6090836 A1, 2000 ; Title/Abstract Full Text Show Details

UV/VIS Spectroscopy (1) Description (UV/VIS Spectroscopy)

Solvent (UV/VIS Spectroscopy)

Reference

Spectrum

ethanol

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details


Bioactivity Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ; Title/Abstract Full Text Show Details

Merck and Co., Inc.

Patent: US6090836 A1, 2000 ; Title/Abstract Full Text Show Details

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Johnson; Hodge

Journal of the American Chemical Society, 1913 , vol. 35, p. 1019 Full Text Show Details

Baddeley; Kenner

Journal of the Chemical Society, 1934 , p. 633 Full Text Show Details

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

Alexander; Barton

Biochemical Journal, 1943 , vol. 37, p. 463 Full Text Show Details

Eastman Kodak Co.

Patent: US2533203 , 1948 ; Full Text Show Details

Hiraiwa

Yakugaku Zasshi, 1940 , vol. 60, p. 569,574 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Kaufman et al.

Journal of Organic Chemistry, 1967 , vol. 32, p. 504 Full Text View citing articles Show Details

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

FORSKARPATENT I SYD AB

Patent: WO2004/2224 A1, 2004 ; Title/Abstract Full Text Show Details

2 of 2

Effect (Pharmacological Data)

antifeedant

Species or TestSystem (Pharmacological Data)

Hylobius abietis

Method (Pharmacological Data)

Structure Code name | Source* | AFI/ED 50 Compound type I DHCNOH Synthesis 0. 96 2. 0 hou HO- -A Cn-epox Synthesis 1. 000. 52 B2 Synthesis 0. 82 O. xx ... Her . B34 Synthesis 0. 59 i Ho Compound type II No.40 Synthesis 1. 00 CHO HO No.54 Synthesis 1. 00 Me No.55 Synthesis 0. 77 rr "HO No.56 Commercial 1. 00 C8, 068-7 CHO B5 alt. CE7 Synthesis 1. 00 Me Mea"- HO CE8 Synthesis 1. 00 Me CE10 Synthesis 0. 94 OMe CE11 Synthesis 1. 00 sqzCHO MeO+OMe CE14 Synthesis 0. 84 Mem OMe Compound type 111 oit No.3 Commercial 1. 00 met 39, 082-8 No.8 Commercial 1. 00 Me H 16, 737-1 + I OMe No.14 Commercial 0. 74 Me CHO 14, 375-8 Me OH No.18 Commercial 0. 74 i D4, 740-4 No.19 Synthesis 0. 42 OH OH No.22 Commercial 0. 87 Ruz 179-1 HO No.45 Commercial 1. 00 P4, 910-4 No.47 Synthesis 0. 94 OH OH i jfY OH No.51 Commercial 0. 83 T7, 650-3 oH o Hq Commercial 1. 00 Oxx XD H4, 700-3 _ B 11 Commercial 1. 00 CHO 10, 962-2 Me *The commercial chemicals are bought from Aldrich. Denominations are their catalogue numbers from the 2000-2001 catalogue. AFI in the table above has been determined in accordance with the following. In order to fulfil the need for testing small amounts of synthetic compounds and extracts a micro feeding test was developed. Alternative substrates for testing of antifeedant compounds with regard to the pine weevil, Hylobius abietis, was searched for, as host plant-twigtest consumes too large amounts of compound for routine testing of series of synthetic compounds or extracts or their fractions. Furthermore, the twig cortex consumption a long time for exposure and determination. A simple set-up consisting of 5 x 5 mm


pieces of thin layer chromatography plates was made. They were used in pair for the choice of biotest, attached to a strip of double adhesive tape in a 9 cm Petri dish. After application of 1.5 [U. L] of 10 percent solutions and evaporation of the solvent, each plate obtained a 5 [J-D] amount of 1 M of succrose in water as feeding stimulant. A 1 day starvation which is enough for the twig test replaced a 6-7 days of starvation which gave a significant death prior to or after the test. The test period is 4 hrs, the plates and the animals were kept at [+25°C,] 65percent RH, 2000 lux and 20: 4 light: dark cycle. The correlation of biological non-eating activity with that of the twig test was excellent, which shows a good accuracy. For a simple comparison between different types of feeding tests, [ANTIFEEDANTINDEX,] AFI, was used: Amount fed at Control-Amount fed at Treatment [ AFI =] Amount fed at Control + Amount fed at Treatment An AFI = 1 indicates a total protection against feeding (feed intake) (maximal anti-gnaw effect), an AFI = 0 is no effect, while an AFI =-1 indicates perfect feed stimulation (i. e., gnawing). Results

AFI=0.94

Location

Page 11

Comment (Pharmacological Data)

potential area of application: agro

Reference

FORSKARPATENT I SYD AB

Patent: WO2004/2224 A1, 2004 ; Title/Abstract Full Text Show Details

Chemical Name: 2-isopropylhydroquinone

4

Reaxys Registry Number: 2043546

CAS Registry Number: 2349-71-5 Type of Substance: isocyclic Molecular Formula: C9H12O2

Linear Structure Formula: C9H12O2

Molecular Weight: 152.193

InChI Key: HIGSPBFIOSHWQG-UHFFFAOYSA-N

10 prep out of 23 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-isopropylhydroquinone, 1,4-dihydroxy-2-isopropylbenzene, 2-Isopropylhydroquinone, isopropylhydroquinone, 2-isopropykhydroquinone, 2isopropyl-hydroquinone, 2.5-Dihydroxy-1-isopropyl-benzol Identification Substance Label (9) Label

Reference

4c

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

1d

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

8c

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

table 5, R=i-Pr

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

3h

Dhekne et al.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977 , vol. 15, p. 755 Full Text Show Details

Ib

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

III

Balba; Casida

Identification Physical Data (8) Spectra (2) Bioactivity (3)

25


Journal of Agricultural and Food Chemistry, 1968 , vol. 16, p. 561,562,563 Full Text View citing articles Show Details

I

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

4

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Patent-Specific Data (1)

Location in Patent

Reference

Claim

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ; Title/Abstract Full Text Show Details

Rhone-Poulenc Industries

Patent: US4487975 A1, 1984 ; Title/Abstract Full Text Show Details

Huels Aktiengesellschaft

Patent: US4614808 A1, 1986 ; Title/Abstract Full Text Show Details

UOP Inc.

Patent: US4323714 A1, 1982 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (6) Melting Point

Solvent (Melting Point)

Reference

129.5 - 131 °C

chloroform Petroleum ether

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

129.5 - 131 °C

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

127.5 - 130 °C

Balba; Casida

Journal of Agricultural and Food Chemistry, 1968 , vol. 16, p. 561,562,563 Full Text View citing articles Show Details

129.5 - 131 °C

benzene

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

130 - 131 °C

H2O

Bogoljubsski

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

Bogoljubskii

J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 869,862 Chem.Abstr., 1963 , vol. 58, # 2391 Full Text Show Details

130 - 131 °C

Bayrac

Bulletin de la Societe Chimique de France, 1895 , vol. <3> 13, p. 979 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 66,73 Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Bogoljubsski

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

Bayrac


Bulletin de la Societe Chimique de France, 1895 , vol. <3> 13, p. 979 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 66,73 Full Text Show Details

Electrochemical Characteristics (1) Description (Electrochemical Characteristics)

Reference

polarographic half-wave potential

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

dimethylsulfoxide-d6

500 MHz

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

acetone-d6

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Reference

Bioactivity Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Reference

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

Matsuyama Petrochemicals Inc.; Maruzen Oil Co., Ltd.

Patent: US4189603 A1, 1980 ; Title/Abstract Full Text Show Details

Rhone-Poulenc Industries

Patent: US4487975 A1, 1984 ; Title/Abstract Full Text Show Details

Huels Aktiengesellschaft

Patent: US4614808 A1, 1986 ; Title/Abstract Full Text Show Details

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Calcott; Tinker; Weinmayr

Journal of the American Chemical Society, 1939 , vol. 61, p. 1010,1014 Full Text Show Details

Bush Inc.

Patent: US2291804 , 1939 ; Full Text Show Details

Bogoljubsski

Zhurnal Obshchei Khimii, 1962 , vol. 32, p. 869,870 J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 862,863 Full Text Show Details

Zenker; Jorgensen

Journal of Organic Chemistry, 1959 , vol. 24, p. 1351 Full Text View citing articles Show Details

Bayrac

Bulletin de la Societe Chimique de France, 1895 , vol. <3> 13, p. 979 Annales de Chimie (Cachan, France), 1897 , vol. <7> 10, p. 66,73 Full Text Show Details

Dhekne et al.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1977 , vol. 15, p. 755


Full Text Show Details

Vesely; Schmerling

Journal of Organic Chemistry, 1970 , vol. 35, p. 4028,4030 Full Text Show Details

Balba; Casida

Journal of Agricultural and Food Chemistry, 1968 , vol. 16, p. 561,562,563 Full Text View citing articles Show Details

Bogoljubskii

J. Gen. Chem. USSR (Engl. Transl.), 1962 , vol. 32, p. 869,862 Chem.Abstr., 1963 , vol. 58, # 2391 Full Text Show Details

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Murase; Shimizu; Hayashi

Bioscience, Biotechnology and Biochemistry, 1994 , vol. 58, # 5 p. 900 - 905 Title/Abstract Full Text View citing articles Show Details

Shadyro; Timoshchuk; Polozov; Povalishev; Andreeva; Zhelobkovich

Pharmaceutical Chemistry Journal, 1999 , vol. 33, # 7 p. 366 - 369 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

2 of 3

Comment (Pharmacological Data)

Bioactivities present

Reference

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

UOP Inc.

Patent: US4323714 A1, 1982 ; Title/Abstract Full Text Show Details

Elam, Christopher; Lape, Michael; Deye, Joel; Zultowsky, Jodie; Stanton, David T.; Paula, Stefan

European Journal of Medicinal Chemistry, 2011 , vol. 46, # 5 p. 1512 - 1523 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

3 of 3

Comment (Pharmacological Data)

stimulation of nerve growth factor synthesis/secretion in mouse astroglial cells in culture

Reference

Murase; Shimizu; Hayashi

Bioscience, Biotechnology and Biochemistry, 1994 , vol. 58, # 5 p. 900 - 905 Title/Abstract Full Text View citing articles Show Details

Chemical Name: tert-butylhydroquinone

5

Reaxys Registry Number: 637923

CAS Registry Number: 1948-33-0 Type of Substance: isocyclic Molecular Formula: C10H14O2

Linear Structure Formula: C6H3C(CH3)3(OH)2 Molecular Weight: 166.22

InChI Key: BGNXCDMCOKJUMV-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms tert-butylhydroquinone, TBHQ Identification Substance Label (42) Label

Reference

21 prep out of 247 reactions.

Identification Physical Data (27) Spectra (31) Bioactivity (559) Other Data (94)

570


tBHQ

Shertzer, Howard G.; Vasiliou, Vasilis; Liu, Rui-Ming; Tabor, M. Wilson; Nebert, Daniel W.

Chemical Research in Toxicology, 1995 , vol. 8, # 3 p. 431 - 436 Title/Abstract Full Text View citing articles Show Details

Nakagawa, Yoshio

Toxicology Letters, 1996 , vol. 84, # 2 p. 63 - 68 Title/Abstract Full Text View citing articles Show Details

Dobo; Eastmond

Environmental and Molecular Mutagenesis, 1994 , vol. 24, # 4 p. 293 - 300 Title/Abstract Full Text View citing articles Show Details

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Schrenk, Dieter; Baus, Petra R.; Ermel, Nadine; Klein, Christopher; Vorderstemann, Birgit; Kauffmann, Hans-Martin

Toxicology Letters, 2001 , vol. 120, # 1-3 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Lamb, John G.; Franklin, Michael R.

Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Solis, Willy A.; Dalton, Timothy P.; Dieter, Matthew Z.; Freshwater, Sarah; Harrer, Judy M.; He, Lei; Shertzer, Howard G.; Nebert, Daniel W.

Biochemical Pharmacology, 2002 , vol. 63, # 9 p. 1739 - 1754 Title/Abstract Full Text View citing articles Show Details

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Sherratt, Philip J.; McLellan, Lesley I.; Hayes, John D.

Biochemical Pharmacology, 2003 , vol. 66, # 1 p. 51 - 61 Title/Abstract Full Text View citing articles Show Details

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Apopa, Patrick L.; He, Xiaoqing; Ma, Qiang

Journal of Biochemical and Molecular Toxicology, 2008 , vol. 22, # 1 p. 63 - 76 Title/Abstract Full Text View citing articles Show Details

Wu, Jiaguo; Wang, Hongyan; Tang, Xiuwen

Biochemical and Biophysical Research Communications, 2014 , vol. 452, # 3 p. 554 - 559 Title/Abstract Full Text View citing articles Show Details

Chen, Jianping; Yan, Artemis L.; Lam, Kelly Y. C.; Lam, Candy T. W.; Li, Ning; Yao, Ping; Xiong, Aizhen; Dong, Tina T. X.; Tsim, Karl W. K.

Phytotherapy Research, 2014 , vol. 28, # 11 p. 1727 - 1730 Title/Abstract Full Text View citing articles Show Details

China Pharmaceutical University; You, Qidong; Yang, Tingting; Sun, Haopeng; Xi, Meiyang; Zhu, Junfeng

Patent: CN105566323 A, 2016 ; Title/Abstract Full Text Show Details

TBHQ

Okubo, Tomoko; Nagai, Fumiko; Ushiyama, Keiko; Kano, Itsu

Toxicology Letters, 1997 , vol. 90, # 1 p. 11 - 18 Title/Abstract Full Text View citing articles Show Details

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Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

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Peters, Melanie M. C. G.; Lau, Serrine S.; Dulik, Deanne; Murphy, Darlene; Van Ommen, Ben; Van Bladeren, Peter J.; Monks, Terrence J.

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SYNTOPIX LIMITED

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%t&BHQ

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13

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6b

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Organic Letters, 2016 , vol. 18, # 14 p. 3422 - 3425 Title/Abstract Full Text View citing articles Show Details

t-BHQ

Anderson; Phillips

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Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

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7

Bonafoux, Dominique; Zihao, Hua; Wang, Beihan; Ojima, Iwao

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Song, Kebiao; Xu, Xing; Liu, Peng; Chen, Lili; Shen, Xu; Liu, Junhua; Hu, Lihong

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2c

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Cannatelli, Mark D.; Ragauskas, Arthur J.

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BHQ

Hasegawa, Masatoshi; Ishigami, Tomohiro; Ishii, Junichi

Polymer (United Kingdom), 2015 , vol. 74, p. 1 - 15 Title/Abstract Full Text View citing articles Show Details


86

Oda, Shingo; Fujiwara, Ryoichi; Kutsuno, Yuki; Fukami, Tatsuki; Itoh, Tomoo; Yokoi, Tsuyoshi; Nakajima, Miki

Drug Metabolism and Disposition, 2015 , vol. 43, # 6 p. 812 - 818 Title/Abstract Full Text View citing articles Show Details

38

The United States of America, as represented by the Secretary, Department of Health and Human Services; Zudaire, Enrique; Aparicio, Marta; Cuttitta, Frank

Patent: US9186365 B2, 2015 ; Title/Abstract Full Text Show Details

4d

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei

Canadian Journal of Chemistry, 2015 , vol. 94, # 1 p. 44 - 49 Title/Abstract Full Text View citing articles Show Details

1e

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Maeda, Yuki

Tetrahedron, 2014 , vol. 71, # 23 p. 3915 - 3923 Title/Abstract Full Text View citing articles Show Details

1b

Jawale, Dhanaji V.; Gravel, Edmond; Geertsen, Valerie; Li, Haiyan; Shah, Nimesh; Namboothiri, Irishi N. N.; Doris, Eric

ChemCatChem, 2014 , vol. 6, # 3 p. 719 - 723 Title/Abstract Full Text View citing articles Show Details

4h

Komeyama, Kimihiro; Kashihara, Tetsuya; Takaki, Ken

Tetrahedron Letters, 2013 , vol. 54, # 9 p. 1084 - 1086 Title/Abstract Full Text View citing articles Show Details

6f; 6g

Kidwai, Mazaahir; Jain, Arti; Sharma, Abha; Kuhad, Ramesh Chander

Comptes Rendus Chimie, 2013 , vol. 16, # 8 p. 728 - 735 Title/Abstract Full Text View citing articles Show Details

VIII

Bausch and Lomb Incorporated

Patent: US7825257 B1, 2010 ; Title/Abstract Full Text Show Details

15a

Zaytsev, Andrey V.; Anderson, Rosaleen J.; Bedernjak, Alexandre; Groundwater, Paul W.; Huang, Yongxue; Perry, John D.; Orenga, Sylvain; Dalbert-Roger, Celine; James, Arthur

Organic and Biomolecular Chemistry, 2008 , vol. 6, # 6 p. 682 - 692 Title/Abstract Full Text View citing articles Show Details

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4a

Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu

Chemistry Letters, 2008 , vol. 37, # 3 p. 360 - 361 Title/Abstract Full Text View citing articles Show Details

Table 1, entry 3, subs.

Bar-Nahum, Itsik; York, John T.; Young Jr., Victor G.; Tolman, William B.

Angewandte Chemie - International Edition, 2008 , vol. 47, # 3 p. 533 - 536 Title/Abstract Full Text View citing articles Show Details

3

Huang, Wei; Song, Yuming; Wang, Jing; Cao, Guoying; Zheng, Zhuo

Tetrahedron, 2004 , vol. 60, # 46 SPEC. ISS. p. 10469 - 10477 Title/Abstract Full Text View citing articles Show Details

Storr, Tim; Merkel, Michael; Song-Zhao, George X.; Scott, Lauren E.; Green, David E.; Bowen, Meryn L.; Thompson, Katherine H.; Patrick, Brian O.; Schugar, Harvey J.; Orvig, Chris

Journal of the American Chemical Society, 2007 , vol. 129, # 23 p. 7453 - 7463 Title/Abstract Full Text View citing articles Show Details

8d

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

p-HO-m-t-BuC6H3OH

Shang, Yongjia; But, Tracy Yuen Sze; Togo, Hideo; Toy, Patrick H.

Synlett, 2007 , # 1 p. 67 - 70 Title/Abstract Full Text View citing articles Show Details

XXIV

Cholli, Ashok L.; Kumar, Vijayendra; Kumar, Javant; Parmar, Virinder Singh; Samuelson, Lynne Ann; Bruno, Ferdinando F.

Patent: US2007/154430 A1, 2007 ; Title/Abstract Full Text Show Details

NSC no. 4972

St. George, Stephanie; Bishop, Jeanette V.; Titus, Richard G.; Selitrennikoff, Claude P.

Antimicrobial Agents and Chemotherapy, 2006 , vol. 50, # 2 p. 474 - 479


Title/Abstract Full Text View citing articles Show Details

1f

Ali, Mohammed Hashmat; Niedbalski, Melinda; Bohnert, Gary; Bryant, Daniel

Synthetic Communications, 2006 , vol. 36, # 12 p. 1751 - 1759 Title/Abstract Full Text View citing articles Show Details

3c

Maeda, Chihiro; Shinokubo, Hiroshi; Osuka, Atsuhiro

Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 200 - 202 Title/Abstract Full Text View citing articles Show Details

Tab. 2, entry 19, subs.

Tajbakhsh, Mahmood; Lakouraj, Moslem Mansour; Ramzanian-Lehmali, Farhad

Synlett, 2006 , # 11 p. 1724 - 1728 Title/Abstract Full Text View citing articles Show Details

1

Ponticelli, Fabio; Trendafilova, Antoaneta; Valoti, Massimo; Saponara, Simona; Sgaragli, GianPietro

Carbohydrate Research, 2001 , vol. 330, # 4 p. 459 - 468 Title/Abstract Full Text View citing articles Show Details

Song, Yuming; Chen, Huilin; Hu, Xinquan; Bai, Changmin; Zheng, Zhuo

Tetrahedron Letters, 2003 , vol. 44, # 37 p. 7081 - 7085 Title/Abstract Full Text View citing articles Show Details

Panella, Lavinia; Broos, Jaap; Jin, Jianfeng; Fraaije, Marco W.; Janssen, Dick B.; Jeronimus-Stratingh, Margot; Feringa, Ben L.; Minnaard, Adriaan J.; De Vries, Johannes G.

Chemical Communications, 2005 , # 45 p. 5656 - 5658 Title/Abstract Full Text View citing articles Show Details

1d

Shivarama Holla; Narayana Poojary; Sooryanarayana Rao; Shivananda

European Journal of Medicinal Chemistry, 2002 , vol. 37, # 6 p. 511 - 517 Title/Abstract Full Text View citing articles Show Details

Iwasa, Seiji; Fakhruddin, Ahmad; Widagdo, Herman Setyo; Nishiyama, Hisao

Advanced Synthesis and Catalysis, 2005 , vol. 347, # 4 p. 517 - 520 Title/Abstract Full Text View citing articles Show Details

1g

Niedermeyer, Timo H. J.; Mikolasch, Annett; Lalk, Michael

Journal of Organic Chemistry, 2005 , vol. 70, # 6 p. 2002 - 2008 Title/Abstract Full Text View citing articles Show Details

BQ

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

educt to 14

Verboom, Renzo C.; Plietker, Bernd J.; Baeckvall, Jan-E.

Journal of Organometallic Chemistry, 2003 , vol. 687, # 2 p. 508 - 517 Title/Abstract Full Text View citing articles Show Details

25

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

10

Michman, Michael; Oron, Miriam; Schaefer, Hans J.

Collection of Czechoslovak Chemical Communications, 2000 , vol. 65, # 6 p. 924 - 940 Title/Abstract Full Text View citing articles Show Details

Table 1, TBHQ

Bock, Karl Walter; Eckle, Tilman; Ouzzine, Mohamed; Fournel-Gigleux, Sylvie

Biochemical Pharmacology, 2000 , vol. 59, # 5 p. 467 - 470 Title/Abstract Full Text View citing articles Show Details

QH2 4

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 4 p. 871 - 876 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly; Barsukova, Tatyana

Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 7 p. 1575 - 1582 Title/Abstract Full Text View citing articles Show Details

C

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details

THQ

Feng, Wei; Liu, Guohua; Xia, Ruohong; Abramson, Jonathan J.; Pessah, Isaac N.

Molecular Pharmacology, 1999 , vol. 55, # 5 p. 821 - 831 Title/Abstract Full Text View citing articles Show Details

MTBHQ

Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

Akasaka; Teshima; Ikebuchi; Sawada

Inflammation Research, 1996 , vol. 45, # 12 p. 583 - 589 Title/Abstract Full Text View citing articles Show Details


Teshima; Onose; Ikebuchi; Sawada

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Patent-Specific Data (4) Prophetic Compound

Related Markush Structure (RN)

Location in Patent

Reference

Page/Page column

Herrmann, Andreas; Berthier, Damien; Paret, Nicolas; Therrien, Mylène

Patent: US2014/275288 A1, 2014 ; Title/Abstract Full Text Show Details

11325124

Aasbo, Kari; Granli, Tom; Breivik, Harald

Patent: US2004/10166 A1, 2004 ; Title/Abstract Full Text Show Details

prophetic product

Claim

NIPPON SODA CO., LTD.

Patent: EP1113112 A1, 2001 ; Title/Abstract Full Text Show Details

Givaudan Corporation

Patent: US4713473 A1, 1987 ; Title/Abstract Full Text Show Details

Kurita Water Industries Ltd.

Patent: US5079000 A1, 1992 ; Title/Abstract Full Text Show Details

prophetic product

Ciba Geigy Corporation

Patent: US4519805 A1, 1985 ; Title/Abstract Full Text Show Details

Adams Veterinary Research Laboratories

Patent: US4668666 A1, 1987 ; Title/Abstract Full Text Show Details

Related Structure (1) Related Structure

Reference

Ueber ein ebenfalls unter dieser Konstitution beschriebenes Praeparat (F: 149-150grad); aus Hydrochinon und #tert!-Butylakohol mit Hilfe von ZnCl2 hergestellt).

Eastman Kodak Co.

Patent: US2511193 , 1947 ; Full Text Show Details

Physical Data Melting Point (4) Melting Point

Reference

128 - 129 °C

Fujita; Sano

Journal of Organic Chemistry, 1979 , vol. 44, p. 2647,2648, 2650 Full Text View citing articles Show Details

130 - 132 °C

Kikkawa et al.

Nippon Kagaku Kaishi, 1977 , p. 695,696 Full Text Show Details

128 °C

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

Pilar et al.

Collection of Czechoslovak Chemical Communications, 1970 , vol. 35, p. 489,490 Full Text Show Details

129 °C

Stroh et al.

Angewandte Chemie, 1957 , vol. 69, p. 699,700 Full Text Show Details

Adsorption (MCS) (2)


Description (Adsorption (MCS)) Further physical properties of the adsorbed molecule

Partner (Adsorption (MCS))

Solvent (Adsorption (MCS))

Temperature (Adsorption (MCS))

smooth platinum electrode

aq. HClO4

22.9 °C

Reference Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2735 - 2742 Title/Abstract Full Text View citing articles Show Details Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3937 - 3945 Title/Abstract Full Text View citing articles Show Details

Further physical properties of the adsorbed molecule

smooth platinum electrode, iodide ion

aq. HClO4

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2742 - 2747 Title/Abstract Full Text View citing articles Show Details

22.9 °C

Chromatographic Data (2) Chromatographic data

Reference

TLC (Thin layer chromatography)

Noreen; Farman

Asian Journal of Chemistry, 2016 , vol. 28, # 5 p. 1007 - 1010 Title/Abstract Full Text View citing articles Show Details

HPLC (High performance liquid chromatography)

Wang, Peijin; Meng, Dongling; Yang, Yaling

Journal of the Chemical Society of Pakistan, 2013 , vol. 35, # 5 p. 1268 - 1274 Title/Abstract Full Text View citing articles Show Details

Conformation (1) Object of Investigation

Reference

Conformation

Ingold,K.U.; Taylor,D.R.

Canadian Journal of Chemistry, 1961 , vol. 39, p. 471 - 480 Full Text View citing articles Show Details

Crystal Property Description (1) Colour & Other Properties

Location

Reference

white

Paragraph 0030; 0037; 0044; 0051

Guangzhou Taibang Food Technology Co., Ltd.; Lu, Junqing

Patent: CN103864581 B, 2016 ; Title/Abstract Full Text Show Details

Dissociation Exponent (3) Dissociation Exponent (pK)

Dissociation Group

Temperature (Dissociation Exponent)

Solvent (Dissociation Exponent)

Method (Dissociation Exponent)

Type (Dissociation Exponent)

Comment (Dissociation Exponent)

10.7

OH

22 °C

H2O various solvent(s)

potentiometric

a1/thermodynamic

Dohrmann, Juergen K.; Bergmann, Barbara

Journal of Physical Chemistry, 1995 , vol. 99, # 4 p. 1218 - 1227 Title/Abstract Full Text View citing articles Show Details

13.6

OH

22 °C

H2O various solvent(s)

potentiometric

a2/thermodynamic

Dohrmann, Juergen K.; Bergmann, Barbara

Journal of Physical Chemistry, 1995 , vol. 99, # 4 p. 1218 - 1227 Title/Abstract Full Text View citing articles Show Details

(pk')pK(a)

Clemmer et al.

Inorganic Chemistry, 1979 , vol. 18, p. 2567,2570, 2571 Full Text View citing articles Show Details

Electrochemical Characteristics (7) Description

Solvent

pH-Value

Temperature

Product XRN

Comment

Reference


(Electrochemical Characteristics)

(Electrochemical Characteristics)

(Electrochemical Characteristics)

(Electrochemical Characteristics)

(Electrochemical Characteristics)

Product

(Electrochemical Characteristics)

Reference

cyclovoltammetry

7

Saturated silver chloride electrode; potential diagram; 0.05 mol/L tris-HCl solution

dos Santos Moretti, Ederson; de Oliveira, Fernanda Midori; Scheel, Guilherme Luiz; DalĺAntônia, Luiz Henrique; Borsato, Dionísio; Kubota, Lauro Tatsuo; Segatelli, Mariana Gava; Tarley, César Ricardo Teixeira Electrochimica Acta, 2016 , vol. 212, p. 322 - 332 Title/Abstract Full Text View citing articles Show Details

cyclovoltammetry

water

23 °C

Saturated silver chloride electrode; potential diagram; 0.10 M LiClO4 containing 0.10 M sodium dodecyl sulfate

Ziyatdinova; Saveliev; Evtugyn; Budnikov

Electrochimica Acta, 2014 , vol. 137, p. 114 - 120 Title/Abstract Full Text Show Details

Electrochemical characteristics given

Wang, Jinyan; Zhang, Dongli; Chu, Qingcui; Ye, Jiannong

Chinese Journal of Chemistry, 2010 , vol. 28, # 2 p. 313 - 319 Title/Abstract Full Text View citing articles Show Details

oxidation potential

acetonitrile

Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

oxidation potential

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details

redox potential

acetic acid

20 °C

1860944

2-tert-butyl1,4benzoquinone

0.57 V Product: /BRN= 1860944/. No. of transm. electrons: 2. Method: coulometry. Description: against 0.5 M HClO4 relative to aq. AgCl electrode, reference electrode potential 0.212 V, indicator electrode platinum needle

Abdullin, I. F.; Bufatina, M. A.; Samuilov, Ya. D.; Budnikov, G. K.; Mannafov, T. G.

J. Gen. Chem. USSR (Engl. Transl.), 1991 , vol. 61, # 6.1. p. 1280 - 1282,1162 - 1164 Title/Abstract Full Text Show Details

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

polarographic halfwave potential

Enthalpy of Formation (1) Enthalpy of Formation

Temperature (Enthalpy of Formation)

Pressure (Enthalpy of Formation)

Reference

-470400 Jmol-1

25 °C

750.06 Torr

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details

Enthalpy of Fusion (1) Enthalpy of Fusion

Reference

27740 Jmol-1

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131


Title/Abstract Full Text View citing articles Show Details

Further Information (2) Description (Further Information)

Reference

behaviour as inhibitor

Hwang, Hong-Sik; Winkler-Moser, Jill K.; Bakota, Erica L.; Berhow, Mark A.; Liu, Sean X.

JAOCS, Journal of the American Oil Chemists' Society, 2013 , vol. 90, # 5 p. 659 - 666 Title/Abstract Full Text View citing articles Show Details

Further information

Isaguljanz et al.

J. Appl. Chem. USSR (Engl. Transl.), 1964 , vol. 37, p. 2729,2689 Full Text Show Details

Liquid/Liquid Systems (MCS) (2) Description (Liquid/Liquid Systems (MCS))

Partner (Liquid/Liquid Systems (MCS))

Solvent (Liquid/Liquid Systems (MCS))

Distribution between solvent 1 + 2

sodium dodecyl sulfate

H2O

Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 996 Title/Abstract Full Text View citing articles Show Details

Distribution between solvent 1 + 2

hexadecyltrimethylammonium bromide

H2O

Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 996 Title/Abstract Full Text View citing articles Show Details

Reference

Solubility (MCS) (1) Comment (Solubility (MCS))

Reference

insoluble in CDCl3

Hwang, Hong-Sik; Winkler-Moser, Jill K.

Journal of the American Oil Chemists' Society, 2014 , vol. 91, # 10 p. 1745 - 1761 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Chemical shifts

1H

CDCl3

Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Izumi, Tatsuo; Tsukamoto, Shuichi

Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4161 - 4165 Title/Abstract Full Text View citing articles Show Details

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 8706 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

acetone-d6

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 2960 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 8706 Title/Abstract Full Text View citing articles Show Details

Reference

IR Spectroscopy (3) Description (IR Spectroscopy)

Reference

ATR (attenuated total reflectance) Spectrum

Grecu, Tudor; Adams, Harry; Hunter, Christopher A.; McCabe, James F.; Portell, Anna; Prohens, Rafel

Crystal Growth and Design, 2014 , vol. 14, # 4 p. 1749 - 1755 Title/Abstract Full Text View citing articles Show Details


Intensity of IR bands Bands Spectrum

Dereli; Erdogdu; Gulluoglu; Tuerkkan; Oezmen; Sundaraganesan

Journal of Molecular Structure, 2012 , vol. 1012, p. 168 - 176 Title/Abstract Full Text View citing articles Show Details

IR

Ingold,K.U.; Taylor,D.R.

Canadian Journal of Chemistry, 1961 , vol. 39, p. 471 - 480 Full Text View citing articles Show Details

Mass Spectrometry (2)

Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 - 8706 Title/Abstract Full Text View citing articles Show Details

spectrum

Mizuno, Masashi; Toda, Masaya; Danno, Gen-ichi; Kanazawa, Kazuki; Natake, Masato

Agricultural and Biological Chemistry, 1988 , vol. 52, # 11 p. 2843 - 2850 Title/Abstract Full Text Show Details

UV/VIS Spectroscopy (21) Description (UV/VIS Spectroscopy)

Solvent (UV/VIS Spectroscopy)

Absorption Maxima (UV/VIS)

Ext./Abs. Coefficient

Location

Reference

Spectrum

206 nm 227 nm 292 nm

Li, Jun; Bi, Yanlan; Liu, Wei; Sun, Shangde

Journal of Agricultural and Food Chemistry, 2015 , vol. 63, # 38 p. 8584 8591 Title/Abstract Full Text View citing articles Show Details

Spectrum

ethyl acetate

290 nm

Bekdeser, Burcu; Oezyuerek, Mustafa; Gueclue, Kubilay; Apak, Resat

Analytical Chemistry, 2011 , vol. 83, # 14 p. 5652 - 5660 Title/Abstract Full Text View citing articles Show Details

in the presence of additive(s) Spectrum

aq. buffer

290 nm

3000 l·mol-1cm-1

supporting information

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

acetic acid

296.1 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

acetone

326.7 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

acetonitrile

296.1 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

butan-1-ol

295.5 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

iso-butanol

297.1 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

chloroform

297.1 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

dichloromethane

297.5 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details


Solvatochromism

diethyl ether

295 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

N,N-dimethyl-formamide

297.1 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

dimethyl sulfoxide

299.6 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

ethyl acetate

295 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

ethanol

295 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

hexane

298 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

methanol

295.5 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

pentan-1-ol

296.7 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

isopropyl alcohol

303.6 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Solvatochromism

water

292 nm

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Hide facts Solvent (UV/VIS Spectroscopy)

Absorption Maxima (UV/VIS)

various solvent(s)

290 nm

Comment (UV/VIS Spectroscopy)

Reference

in the presence of inorganic compounds. Object(s) of Study: in the presence of organic compounds

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

ESR Spectroscopy (1) Description (ESR Spectroscopy)

Reference

ESR

Foster et al.

Canadian Journal of Chemistry, 1978 , vol. 56, p. 869 Full Text Show Details

Raman Spectroscopy (1) Description (Raman Spectroscopy)

Reference

Raman

Dereli; Erdogdu; Gulluoglu; Tuerkkan; Oezmen; Sundaraganesan

Journal of Molecular Structure, 2012 , vol. 1012, p. 168 - 176 Title/Abstract Full Text View citing articles Show Details


Bioactivity Pharmacological Data (549) 1 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Pospisil,J.; Taimr,L.

Collection of Czechoslovak Chemical Communications, 1964 , Full Text View citing articles Show Details

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , Full Text View citing articles Show Details

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , Full Text View citing articles Show Details

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , Full Text View citing articles Show Details

Seiko Kagaku Kabushiki Kaisha

Patent: EP812816 A1, 1997 ;

vol. 29, p. 381 - 389 vol. 30, p. 843 - 852 vol. 31, p. 98 - 105 vol. 34, p. 1991 - 2001

Title/Abstract Full Text Show Details

Ingold,K.U.; Taylor,D.R.

Canadian Journal of Chemistry, 1961 , vol. 39, p. 471 - 480 Full Text View citing articles Show Details

Horswill,E.C.; Ingold,K.U.

Canadian Journal of Chemistry, 1966 , vol. 44, p. 269 - 277 Full Text View citing articles Show Details

Cuntze,U.; Musso,H.

Chemische Berichte, 1970 , vol. 103, p. 62 - 70 Full Text View citing articles Show Details

Anic S.p.A.

Patent: US4469897 A1, 1984 ; Title/Abstract Full Text Show Details

Ciba Geigy Corporation

Patent: US4519805 A1, 1985 ; Title/Abstract Full Text Show Details

Ciba-Geigy AG

Patent: US4558131 A1, 1985 ; Title/Abstract Full Text Show Details

NIPPON SODA CO., LTD.

Patent: EP1113112 A1, 2001 ; Title/Abstract Full Text Show Details

Givaudan Corporation

Patent: US4713473 A1, 1987 ; Title/Abstract Full Text Show Details

Buess,C.M. et al.

Journal of Medicinal Chemistry, 1965 , vol. 8, p. 469 - 474 Full Text View citing articles Show Details

Jorgensen,E.C.; Reid,J.A.W.

Journal of Medicinal Chemistry, 1965 , vol. 8, p. 533 - 536 Full Text View citing articles Show Details

Lam; Pai; Wattenberg

Journal of Medicinal Chemistry, 1979 , vol. 22, # 5 p. 569 - 571 Title/Abstract Full Text View citing articles Show Details

McKillop,A. et al.

Tetrahedron, 1970 , vol. 26, p. 4031 - 4039 Full Text View citing articles Show Details

Vicari; Richard; Aslam; Mohammad; Ray; Wilson B.; Davenport; Kenneth G.; Dammel; Ralph; Lingnau; Juergen; Doessel; Karl-Friedrich

Patent: US4965400 A1, 1990 ; Title/Abstract Full Text Show Details

Rhone-Poulenc Rorer Pharmaceuticals Inc.

Patent: US5480883 A1, 1996 ; Title/Abstract Full Text Show Details

Behringwerke Aktiengesellschaft

Patent: US5519018 A1, 1996 ; Title/Abstract Full Text Show Details

2 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

National Science Council

Patent: US6060575 A1, 2000 ;


Title/Abstract Full Text Show Details

Sankyo Company, Limited

Patent: US5104888 A1, 1992 ; Title/Abstract Full Text Show Details

Reynolds,D.D.; Cossar,B.C.

Journal of Heterocyclic Chemistry, 1971 , vol. 8, p. 611 - 615 Full Text View citing articles Show Details

Menicon Co., Ltd.

Patent: US5147902 A1, 1992 ; Title/Abstract Full Text Show Details

Sankyo Company, Limited

Patent: US6432993 B1, 2002 ; Title/Abstract Full Text Show Details

Hoechst Marion Roussel, Inc.

Patent: US5608095 A1, 1997 ; Title/Abstract Full Text Show Details

Aventis Pharmaceuticals Inc.

Patent: EP942896 B1, 2003 ; Title/Abstract Full Text Show Details

Aasbo, Kari; Granli, Tom; Breivik, Harald

Patent: US2004/10166 A1, 2004 ; Title/Abstract Full Text Show Details

Oshlack, Benjamin; Huang, Hua-Pin; Goliber, Philip; Mannion, Richard

Patent: US2003/229111 A1, 2003 ; Title/Abstract Full Text Show Details

L'OREAL S.A.

Patent: US2004/253283 A1, 2004 ; Title/Abstract Full Text Show Details

RECKITT BENCKISER (AUSTRALIA) PTY LIMITED; RECKITT BENCKISER (UK) LIMITED

Patent: WO2005/20686 A1, 2005 ; Title/Abstract Full Text Show Details

Board of Trustees of Michigan State University

Patent: US2005/59727 A1, 2005 ; Title/Abstract Full Text Show Details

ABBOTT LABORATORIES

Patent: WO2005/23762 A1, 2005 ; Title/Abstract Full Text Show Details

Alcon, Inc.

Patent: US2005/137146 A1, 2005 ; Title/Abstract Full Text Show Details

Alcon, Inc.

Patent: US2005/137147 A1, 2005 ; Title/Abstract Full Text Show Details

COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH

Patent: WO2005/63664 A1, 2005 ; Title/Abstract Full Text Show Details

RANBAXY LABORATORIES LIMITED

Patent: WO2005/87706 A1, 2005 ; Title/Abstract Full Text Show Details

ISAGRO S.P.A.

Patent: WO2005/94580 A1, 2005 ; Title/Abstract Full Text Show Details

GPC BIOTECH AG

Patent: WO2005/120479 A1, 2005 ; Title/Abstract Full Text Show Details

Glinski, Jan

Patent: US2006/93571 A1, 2006 ; Title/Abstract Full Text Show Details

3 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details


Galileo Pharmaceuticals, Inc.

Patent: US2006/128790 A1, 2006 ; Title/Abstract Full Text Show Details

Southwest Research Institute

Patent: US7098359 B2, 2006 ; Title/Abstract Full Text Show Details

GEORGIA TECH RESEARCH CORPORATION

Patent: WO2006/99162 A2, 2006 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

VALENT BIOSCIENCES CORPORATION

Patent: WO2006/107905 A1, 2006 ; Title/Abstract Full Text Show Details

IOLAB CORPORATION

Patent: EP274844 B1, 1991 ; Title/Abstract Full Text Show Details

SUNTORY LIMITED

Patent: WO2007/4689 A1, 2007 ; Title/Abstract Full Text Show Details

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details

CAMLIN LTD.

Patent: WO2007/15260 A2, 2007 ; Title/Abstract Full Text Show Details

E.I. DU PONT DE NEMOURS AND COMPANY

Patent: US2007/59344 A1, 2007 ; Title/Abstract Full Text Show Details

Giner, Victor Casana

Patent: US2007/77308 A1, 2007 ; Title/Abstract Full Text Show Details

DENTSPLY DETREY GmbH

Patent: EP1776943 A1, 2007 ; Title/Abstract Full Text Show Details

BRAIN N' BEYOND BIOTECH PVT. LTD.

Patent: WO2007/52308 A2, 2007 ; Title/Abstract Full Text Show Details

BRAIN N' BEYOND BIOTECH PVT. LTD.

Patent: WO2007/54977 A2, 2007 ; Title/Abstract Full Text Show Details

MARINUS PHARMACEUTICALS

Patent: WO2007/62266 A2, 2007 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

4 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

Eastman Kodak Co.


Patent: US2758119 , 1953 ; Full Text Show Details

Stroh et al.

Angewandte Chemie, 1957 , vol. 69, p. 699,700 Full Text Show Details

Eastman Kodak Co.

Patent: US2511193 , 1947 ; Full Text Show Details

Universal Oil Prod. Co.

Patent: US2781404 , 1953 ; Full Text Show Details

Eastman Kodak Co.

Patent: US2722556 , 1952 ; Full Text Show Details

Eastman Kodak Co.

Patent: US2776321 , 1953 ; Full Text Show Details

Eastman Kodak Co.

Patent: US2801268 , 1953 ; Full Text Show Details

Eastman Kodak Co.

Patent: US2682563 , 1951 ; Full Text Show Details

Shirai et al.

Chemistry Letters, 1975 , p. 915 Full Text Show Details

Kikkawa et al.

Nippon Kagaku Kaishi, 1977 , p. 695,696 Full Text Show Details

Fujita; Sano

Journal of Organic Chemistry, 1979 , vol. 44, p. 2647,2648, 2650 Full Text View citing articles Show Details

Ruetgerswerke AG

Patent: DE1159961 , 1962 ; Chem.Abstr., 1964 , vol. 60, # 7955f Full Text Show Details

Clemmer et al.

Inorganic Chemistry, 1979 , vol. 18, p. 2567,2570, 2571 Full Text View citing articles Show Details

Foster et al.

Canadian Journal of Chemistry, 1978 , vol. 56, p. 869 Full Text Show Details

Aivazyan; Vardanyan

Kinetics and Catalysis, 1978 , vol. 19, p. 1153 p. 1424 Full Text Show Details

Pilar et al.

Collection of Czechoslovak Chemical Communications, 1970 , vol. 35, p. 489,490 Full Text Show Details

Ashworth; Dixon

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1972 , p. 1130,1131 Full Text Show Details

Horswill et al.

Canadian Journal of Chemistry, 1966 , vol. 44, p. 985,989 Full Text Show Details

Isaguljanz et al.

J. Appl. Chem. USSR (Engl. Transl.), 1964 , vol. 37, p. 2729,2689 Full Text Show Details

5 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Bayer AG

Patent: US3051762 , 1958 ; Chem.Abstr., 1963 , vol. 58, # 1402f Full Text Show Details

Fischer, Alfred; Henderson, George N.

Synthesis, 1985 , # 6/7 p. 641 - 643 Title/Abstract Full Text Show Details

Ishii, Fumio; Kishi, Ken-ichi

Synthesis, 1980 , # 9 p. 706 - 708 Title/Abstract Full Text Show Details

Kamitori, Yasuhiro; Hojo, Masaru; Masuda, Ryoichi; Izumi, Tatsuo; Tsukamoto, Shuichi

Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4161 - 4165 Title/Abstract Full Text View citing articles Show Details

Takata, Toshikazu; Tajima, Rieko; Ando, Wataru

Journal of Organic Chemistry, 1983 , vol. 48, # 24 p. 4764 - 4766 Title/Abstract Full Text View citing articles Show Details


McKillop, Alexander; Tarbin, Jonathan A.

Tetrahedron, 1987 , vol. 43, # 8 p. 1753 - 1758 Title/Abstract Full Text View citing articles Show Details

Hewgill, Frank R.; Legge, Frank

Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1983 , p. 653 - 660 Title/Abstract Full Text Show Details

Hewgill, Frank R.; Greca, Bart La; Legge, Frank; Roga, Peter E.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983 , # 1 p. 131 - 134 Title/Abstract Full Text View citing articles Show Details

Pratt, Daniel V.; Ruan, Fuqiang; Hopkins, Paul B.

Journal of Organic Chemistry, 1987 , vol. 52, # 22 p. 5053 - 5055 Title/Abstract Full Text View citing articles Show Details

Abdullin, I. F.; Bufatina, M. A.; Samuilov, Ya. D.; Budnikov, G. K.; Mannafov, T. G.

J. Gen. Chem. USSR (Engl. Transl.), 1991 , vol. 61, # 6.1. p. 1280 - 1282,1162 - 1164 Title/Abstract Full Text Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2735 - 2742 Title/Abstract Full Text View citing articles Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2742 - 2747 Title/Abstract Full Text View citing articles Show Details

Soriaga, Manuel P.; Hubbard, Arthur T.

Journal of the American Chemical Society, 1982 , vol. 104, # 14 p. 3937 - 3945 Title/Abstract Full Text View citing articles Show Details

Sircar; Hoefle; Maxwell

Journal of Medicinal Chemistry, 1983 , vol. 26, # 7 p. 1020 - 1027 Title/Abstract Full Text View citing articles Show Details

Rockcliffe, David A.; Martell, Artur E.

Journal of the Chemical Society, Chemical Communications, 1992 , # 24 p. 1758 - 1760 Title/Abstract Full Text View citing articles Show Details

Wissner, A.; Carroll, M. L.; Green, K. E.; Kerwar, S. S.; Pickett, W. C.; et al.

Journal of Medicinal Chemistry, 1992 , vol. 35, # 9 p. 1650 - 1662 Title/Abstract Full Text View citing articles Show Details

Eubanks, J. R. I.; Pacifici, J. G.

Synthetic Communications, 1987 , vol. 17, # 7 p. 829 - 836 Title/Abstract Full Text Show Details

Cassis, R.; Valderrama, J. A.

Synthetic Communications, 1983 , vol. 13, # 5 p. 347 - 356 Title/Abstract Full Text Show Details

Barker, Peter; Finke, Paul; Thompson, Kevan

Synthetic Communications, 1989 , vol. 19, # 1, 2 p. 257 - 266 Title/Abstract Full Text Show Details

McKay, Peter G.; Mitchell, Anthony S.

Australian Journal of Chemistry, 1989 , vol. 42, # 12 p. 2295 - 2297 Title/Abstract Full Text Show Details

6 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Pelizzetti, Ezio; Pramauro, Edmondo

Journal of Physical Chemistry, 1984 , vol. 88, # 5 p. 990 - 996 Title/Abstract Full Text View citing articles Show Details

Eloeve, Guelnur A.; Schauble, J. Herman

Magnetic Resonance in Chemistry, 1987 , vol. 25, p. 194 - 200 Title/Abstract Full Text Show Details

Witiak, Donald T.; Kim, Sung K.; Tehim, Ashok K.; Sternitzke, Kent D.; McCreery, Richard L.; et al.

Journal of Medicinal Chemistry, 1988 , vol. 31, # 7 p. 1437 - 1445 Title/Abstract Full Text View citing articles Show Details

Chang, Sukbok; Heid, Richard M.; Jacobsen, Eric N.

Tetrahedron Letters, 1994 , vol. 35, # 5 p. 669 - 672 Title/Abstract Full Text View citing articles Show Details

Mukai, Kazuo; Takamatsu, Kimiko; Ishizu, Kazuhiko

Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 12 p. 3507 - 3510 Title/Abstract Full Text Show Details

Mizuno, Masashi; Toda, Masaya; Danno, Gen-ichi; Kanazawa, Kazuki; Natake, Masato

Agricultural and Biological Chemistry, 1988 , vol. 52, # 11 p. 2843 - 2850 Title/Abstract Full Text Show Details

Deacon, Glen B.; O'Donoghue, Michael F.; McKillop, Alexander; Young, Derek W.

Synthetic Communications, 1980 , vol. 10, # 8 p. 615 - 622 Title/Abstract Full Text Show Details

Lam; Garg; Swanson; Pezzuto

Journal of Pharmaceutical Sciences, 1988 , vol. 77, # 5 p. 393 - 395 Title/Abstract Full Text View citing articles Show Details

Costantini; D'Ischia; Prota

Synthesis, 1994 , # 12 p. 1399 - 1400 Title/Abstract Full Text View citing articles Show Details

Dohrmann, Juergen K.; Bergmann, Barbara

Journal of Physical Chemistry, 1995 , vol. 99, # 4 p. 1218 - 1227 Title/Abstract Full Text View citing articles Show Details

Byrne, Lindsay T.; Hewgill, Frank R.; Legge, Frank; Skelton, Brian W.; White, Allan H.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982 , # 12 p. 2855 - 2862 Title/Abstract Full Text View citing articles Show Details

Hewgill, Frank R.; Legge, Frank

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982 , # 12 p. 2863 - 2866 Title/Abstract Full Text View citing articles Show Details


Novak; Kovacs; Pirok; Kolonits; Szabo; Fekete; Weiszfeiler; Szantay

Synthesis, 1995 , # 6 p. 693 - 698 Title/Abstract Full Text View citing articles Show Details

Mure, Minae; Klinman, Judith P.

Journal of the American Chemical Society, 1995 , vol. 117, # 34 p. 8698 - 8706 Title/Abstract Full Text View citing articles Show Details

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama

Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details

Kuenzel, Antje; Sokolow, Maxim; Liu, Feng-Quan; Roesky, Herbert W.; Noltemeyer, Mathias; Schmidt, Hans-Georg; Uson, Isabel

Journal of the Chemical Society - Dalton Transactions, 1996 , # 6 p. 913 - 919 Title/Abstract Full Text View citing articles Show Details

Pirrung, Michael C.; Nunn, David S.

Tetrahedron, 1996 , vol. 52, # 16 p. 5707 - 5738 Title/Abstract Full Text View citing articles Show Details

Pospisil, Paul J.; Carsten, Douglas H.; Jacobsen, Eric N.

Chemistry--A European Journal, 1996 , vol. 2, # 8 p. 974 - 980 Title/Abstract Full Text Show Details

Tamami, Bahman; Yeganeh, Hamid

Tetrahedron, 1997 , vol. 53, # 23 p. 7889 - 7896 Title/Abstract Full Text View citing articles Show Details

Carman, Raymond M.; Kanizaj, Nicholas; Taylor, Richard J.K.

Australian Journal of Chemistry, 1997 , vol. 50, # 5 p. 515 - 516 Title/Abstract Full Text View citing articles Show Details

7 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Hall III, Clifford A.; Cuppett, Susan L.; Dussault, Pat

Journal of Agricultural and Food Chemistry, 1998 , vol. 46, # 4 p. 1303 - 1310 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa; Saran, Manfred

Journal of the Chemical Society - Faraday Transactions, 1998 , vol. 94, # 13 p. 1835 - 1840 Title/Abstract Full Text View citing articles Show Details

Wang, Haibo; Nair, Muraleedharan G.; Strasburg, Gale M.; Booren, Alden M.; Gray, J. Ian

Journal of Natural Products, 1999 , vol. 62, # 1 p. 86 - 88 Title/Abstract Full Text View citing articles Show Details

Hwang, Der-Ren; Chu, Chang-Ying; Wang, Sheng-Kai; Uang, Biing-Jiun

Synlett, 1999 , # 1 p. 77 - 78 Title/Abstract Full Text View citing articles Show Details

Shertzer, Howard G.; Vasiliou, Vasilis; Liu, Rui-Ming; Tabor, M. Wilson; Nebert, Daniel W.

Chemical Research in Toxicology, 1995 , vol. 8, # 3 p. 431 - 436 Title/Abstract Full Text View citing articles Show Details

Okubo, Tomoko; Nagai, Fumiko; Ushiyama, Keiko; Kano, Itsu

Toxicology Letters, 1997 , vol. 90, # 1 p. 11 - 18 Title/Abstract Full Text View citing articles Show Details

Nakagawa, Yoshio

Toxicology Letters, 1996 , vol. 84, # 2 p. 63 - 68 Title/Abstract Full Text View citing articles Show Details

Nagai, Fumiko; Okubo, Tomoko; Ushiyama, Keiko; Satoh, Kanako; Kano, Itsu

Toxicology Letters, 1996 , vol. 89, # 2 p. 163 - 167 Title/Abstract Full Text View citing articles Show Details

Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

Environmental Toxicology and Chemistry, 1997 , vol. 16, # 9 p. 1930 - 1934 Title/Abstract Full Text View citing articles Show Details

Verevkin, Sergey P.

Physical Chemistry Chemical Physics, 1999 , vol. 1, # 1 p. 127 - 131 Title/Abstract Full Text View citing articles Show Details

Kubo, Isao; Lee, Sang Hwa

Journal of Agricultural and Food Chemistry, 1998 , vol. 46, # 10 p. 4052 - 4055 Title/Abstract Full Text View citing articles Show Details

Roginsky, Vitaly A.; Pisarenko, Leonid M.; Bors, Wolf; Michel, Christa

Journal of the Chemical Society. Perkin Transactions 2, 1999 , # 4 p. 871 - 876 Title/Abstract Full Text View citing articles Show Details

Ikeda; Sapienza; Ross

Food and Chemical Toxicology, 1998 , vol. 36, # 11 p. 907 - 914 Title/Abstract Full Text View citing articles Show Details

Sreerama, Lakshmaiah; Rekha, Ganaganur K.; Sladek, Norman E.

Biochemical Pharmacology, 1995 , vol. 49, # 5 p. 669 - 676 Title/Abstract Full Text View citing articles Show Details

Peters, Melanie M. C. G.; Lau, Serrine S.; Dulik, Deanne; Murphy, Darlene; Van Ommen, Ben; Van Bladeren, Peter J.; Monks, Terrence J.

Chemical Research in Toxicology, 1996 , vol. 9, # 1 p. 133 - 139 Title/Abstract Full Text View citing articles Show Details

Dobo; Eastmond

Environmental and Molecular Mutagenesis, 1994 , vol. 24, # 4 p. 293 - 300 Title/Abstract Full Text View citing articles Show Details

Anderson; Phillips

Food and Chemical Toxicology, 1999 , vol. 37, # 9-10 p. 1015 - 1025 Title/Abstract Full Text View citing articles Show Details

Gibson, David P.; Brauninger, Roger; Shaffi, Hussain S.; Kerckaert, Gary A.; LeBoeuf, Robert A.; Isfort, Robert J.; Aardema, Marilyn J.

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 1997 , vol. 392, # 1-2 p. 61 - 70 Title/Abstract Full Text View citing articles Show Details

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details


Vachal; Jacobsen

Organic letters, 2000 , vol. 2, # 6 p. 867 - 870 Title/Abstract Full Text View citing articles Show Details

8 of 549

9 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

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Collection of Czechoslovak Chemical Communications, 2000 , vol. 65, # 6 p. 924 - 940 Title/Abstract Full Text View citing articles Show Details

Sun, Mingzhou; Sakakibara, Hiroyuki; Ashida, Hitoshi; Danno, Gen-Ichi; Kanazawa, Kazuki

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Ponticelli, Fabio; Trendafilova, Antoaneta; Valoti, Massimo; Saponara, Simona; Sgaragli, GianPietro

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Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Ready; Jacobsen

Journal of the American Chemical Society, 2001 , vol. 123, # 11 p. 2687 - 2688 Title/Abstract Full Text View citing articles Show Details

Akasaka; Teshima; Ikebuchi; Sawada

Inflammation Research, 1996 , vol. 45, # 12 p. 583 - 589 Title/Abstract Full Text View citing articles Show Details

Schrenk, Dieter; Baus, Petra R.; Ermel, Nadine; Klein, Christopher; Vorderstemann, Birgit; Kauffmann, Hans-Martin

Toxicology Letters, 2001 , vol. 120, # 1-3 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Bonafoux, Dominique; Zihao, Hua; Wang, Beihan; Ojima, Iwao

Journal of Fluorine Chemistry, 2001 , vol. 112, # 1 p. 101 - 108 Title/Abstract Full Text View citing articles Show Details

Okubo, Tomoko; Nagai, Fumiko; Seto, Takako; Satoh, Kanako; Ushiyama, Keiko; Kano, Itsu

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 2 p. 199 - 203 Title/Abstract Full Text View citing articles Show Details

Pelotier, Beatrice; Anson, Mike S.; Campbell, Ian B.; Macdonald, Simon J. F.; Priem, Ghislaine; Jackson, Richard F. W.

Synlett, 2002 , # 7 p. 1055 - 1060 Title/Abstract Full Text View citing articles Show Details

Shivarama Holla; Narayana Poojary; Sooryanarayana Rao; Shivananda

European Journal of Medicinal Chemistry, 2002 , vol. 37, # 6 p. 511 - 517 Title/Abstract Full Text View citing articles Show Details

Bock, Karl Walter; Eckle, Tilman; Ouzzine, Mohamed; Fournel-Gigleux, Sylvie

Biochemical Pharmacology, 2000 , vol. 59, # 5 p. 467 - 470 Title/Abstract Full Text View citing articles Show Details

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Choi, Jinah; Liu, Rui-Ming; Forman, Henry Jay

Biochemical Pharmacology, 1997 , vol. 53, # 7 p. 987 - 993 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

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Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Song, Yuming; Chen, Huilin; Hu, Xinquan; Bai, Changmin; Zheng, Zhuo

Tetrahedron Letters, 2003 , vol. 44, # 37 p. 7081 - 7085 Title/Abstract Full Text View citing articles Show Details

Franchi, Emanuela; Ingrosso, Giovanni; Marchetti, Fabio; Pinzino, Calogero

Tetrahedron, 2003 , vol. 59, # 27 p. 5003 - 5018 Title/Abstract Full Text View citing articles Show Details

Solis, Willy A.; Dalton, Timothy P.; Dieter, Matthew Z.; Freshwater, Sarah; Harrer, Judy M.; He, Lei; Shertzer, Howard G.; Nebert, Daniel W.

Biochemical Pharmacology, 2002 , vol. 63, # 9 p. 1739 - 1754 Title/Abstract Full Text View citing articles Show Details


Oh, Moonhyun; Reingold, Jeffrey A.; Carpenter, Gene B.; Sweigart, Dwight A.

Journal of Organometallic Chemistry, 2003 , vol. 687, # 1 p. 78 - 84 Title/Abstract Full Text View citing articles Show Details

Verboom, Renzo C.; Plietker, Bernd J.; Baeckvall, Jan-E.

Journal of Organometallic Chemistry, 2003 , vol. 687, # 2 p. 508 - 517 Title/Abstract Full Text View citing articles Show Details

Teshima; Onose; Ikebuchi; Sawada

Inflammation Research, 1998 , vol. 47, # 8 p. 328 - 333 Title/Abstract Full Text View citing articles Show Details

Feng, Wei; Liu, Guohua; Xia, Ruohong; Abramson, Jonathan J.; Pessah, Isaac N.

Molecular Pharmacology, 1999 , vol. 55, # 5 p. 821 - 831 Title/Abstract Full Text View citing articles Show Details

Sugatani, Junko; Yamakawa, Kasumi; Tonda, Eri; Nishitani, Shinichi; Yoshinari, Kouichi; Degawa, Masakuni; Abe, Ikuro; Noguchi, Hiroshi; Miwa, Masao

Biochemical Pharmacology, 2004 , vol. 67, # 5 p. 989 - 1000 Title/Abstract Full Text View citing articles Show Details

Niedermeyer, Timo H. J.; Mikolasch, Annett; Lalk, Michael

Journal of Organic Chemistry, 2005 , vol. 70, # 6 p. 2002 - 2008 Title/Abstract Full Text View citing articles Show Details

Huang, Wei; Song, Yuming; Wang, Jing; Cao, Guoying; Zheng, Zhuo

Tetrahedron, 2004 , vol. 60, # 46 SPEC. ISS. p. 10469 - 10477 Title/Abstract Full Text View citing articles Show Details

Iwasa, Seiji; Fakhruddin, Ahmad; Widagdo, Herman Setyo; Nishiyama, Hisao

Advanced Synthesis and Catalysis, 2005 , vol. 347, # 4 p. 517 - 520 Title/Abstract Full Text View citing articles Show Details

Miao, Weimin; Hu, Lianggao; Kandouz, Mustapha; Hamilton, David; Batist, Gerald

Biochemical Pharmacology, 2004 , vol. 67, # 10 p. 1897 - 1905 Title/Abstract Full Text View citing articles Show Details

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

Tajbakhsh; Hosseinzadeh; Sadatshahabi

Synthetic Communications, 2005 , vol. 35, # 11 p. 1547 - 1554 Title/Abstract Full Text View citing articles Show Details

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Falkner, K. Cameron; Rushmore, Thomas H.; Linder, Mark W.; Prough, Russell A.

Molecular Pharmacology, 1998 , vol. 53, # 6 p. 1016 - 1026 Title/Abstract Full Text View citing articles Show Details

Remenar, Julius F.; Wenslow, Robert; Ostovic, Drazen; Peresypkin, Andrey

Pharmaceutical Research, 2004 , vol. 21, # 1 p. 185 - 188 Title/Abstract Full Text View citing articles Show Details

Tajbakhsh, Mahmoud; Lakouraj, Moslem-Mansor; Yadoolahzadeh, Khadijeh

Phosphorus, Sulfur and Silicon and the Related Elements, 2005 , vol. 180, # 11 p. 2431 - 2437 Title/Abstract Full Text View citing articles Show Details

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Biochemical Pharmacology, 2003 , vol. 66, # 1 p. 51 - 61 Title/Abstract Full Text View citing articles Show Details

10 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

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Antimicrobial Agents and Chemotherapy, 2006 , vol. 50, # 2 p. 474 - 479 Title/Abstract Full Text View citing articles Show Details

Boerboom, Anne-Marie J.F.; Vermeulen, Martijn; van der Woude, Hester; Bremer, Birgit I.; Lee-Hilz, Yee Y.; Kampman, Ellen; van Bladeren, Peter J.; Rietjens, Ivonne M.C.M.; Aarts, Jac M.M.J.G.

Biochemical Pharmacology, 2006 , vol. 72, # 2 p. 217 - 226 Title/Abstract Full Text View citing articles Show Details

Ali, Mohammed Hashmat; Niedbalski, Melinda; Bohnert, Gary; Bryant, Daniel

Synthetic Communications, 2006 , vol. 36, # 12 p. 1751 - 1759 Title/Abstract Full Text View citing articles Show Details

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Rousseau, Ingrid A.; Qin, Haihu; Mather, Patrick T.

Macromolecules, 2005 , vol. 38, # 10 p. 4103 - 4113 Title/Abstract Full Text View citing articles Show Details

Lau, Tim K.; Chu, Wei; Graham, Nigel J. D.

Environmental Science and Technology, 2007 , vol. 41, # 2 p. 613 - 619 Title/Abstract Full Text View citing articles Show Details

Maeda, Chihiro; Shinokubo, Hiroshi; Osuka, Atsuhiro

Organic and Biomolecular Chemistry, 2006 , vol. 4, # 2 p. 200 - 202 Title/Abstract Full Text View citing articles Show Details

Panella, Lavinia; Broos, Jaap; Jin, Jianfeng; Fraaije, Marco W.; Janssen, Dick B.; Jeronimus-Stratingh, Margot; Feringa, Ben L.; Minnaard, Adriaan J.; De Vries, Johannes G.

Chemical Communications, 2005 , # 45 p. 5656 - 5658 Title/Abstract Full Text View citing articles Show Details

Ono, Takashi; Fujii, Shunsuke; Nobori, Tadahito; Lehn, Jean-Marie

Chemical Communications, 2007 , # 1 p. 46 - 48


Title/Abstract Full Text View citing articles Show Details

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Liu, Guo-Yu; Bu, Xuexian; Yan, Hang; Jia, William W.-G.

Journal of Natural Products, 2007 , vol. 70, # 2 p. 259 - 264 Title/Abstract Full Text View citing articles Show Details

Tajbakhsh, Mahmood; Lakouraj, Moslem Mansour; Ramzanian-Lehmali, Farhad

Synlett, 2006 , # 11 p. 1724 - 1728 Title/Abstract Full Text View citing articles Show Details

Storr, Tim; Merkel, Michael; Song-Zhao, George X.; Scott, Lauren E.; Green, David E.; Bowen, Meryn L.; Thompson, Katherine H.; Patrick, Brian O.; Schugar, Harvey J.; Orvig, Chris

Journal of the American Chemical Society, 2007 , vol. 129, # 23 p. 7453 - 7463 Title/Abstract Full Text View citing articles Show Details

Doyle, Abigail G.; Jacobsen, Eric N.

Angewandte Chemie - International Edition, 2007 , vol. 46, # 20 p. 3701 - 3705 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2007 , vol. 48, # 47 p. 8334 - 8337 Title/Abstract Full Text View citing articles Show Details

Shang, Yongjia; But, Tracy Yuen Sze; Togo, Hideo; Toy, Patrick H.

Synlett, 2007 , # 1 p. 67 - 70 Title/Abstract Full Text View citing articles Show Details

Miyazawa, Toshifumi; Hamada, Manabu; Morimoto, Ryohei; Murashima, Takashi; Yamada, Takashi

Tetrahedron Letters, 2008 , vol. 49, # 1 p. 175 - 178 Title/Abstract Full Text View citing articles Show Details

Xie, Chaoyu; Sullivan, Kevin A.; Laurila, Michael E.; Mitchell, David N.; Pu, Y. John

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Adams Veterinary Research Laboratories

Patent: US4668666 A1, 1987 ; Title/Abstract Full Text Show Details

11 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Ciba-Geigy AG

Patent: US4484000 A1, 1984 ; Title/Abstract Full Text Show Details

Ciba-Geigy AG

Patent: US4835323 A1, 1989 ; Title/Abstract Full Text Show Details

Konishiroku Photo Industry Co., Ltd.

Patent: US4394315 A1, 1983 ; Title/Abstract Full Text Show Details

Hoechst Celanese Corporation

Patent: US4927956 A1, 1990 ; Title/Abstract Full Text Show Details

Hoechst Celanese Corporation

Patent: US4933495 A1, 1990 ; Title/Abstract Full Text Show Details

Hoechst Marion Roussel, Inc.

Patent: US6114572 A1, 2000 ; Title/Abstract Full Text Show Details

Kurita Water Industries Ltd.

Patent: US5079000 A1, 1992 ; Title/Abstract Full Text Show Details

OGATA, KAZUMI; NAKAO, HIDETOSHI; ITO, KAZUHIKO; SAKAUE, TAKAHIRO; INOUE, SACHIKO; IEMURA, MASAHITO

Patent: US2001/8893 A1, 2001 ; Title/Abstract Full Text Show Details

Rhone-Poulenc Rorer Pharmaceuticals, Inc.

Patent: US36256 E1, 1999 ; Title/Abstract Full Text Show Details

Tanabe Seiyaku Co., Ltd.

Patent: US5849732 A1, 1998 ; Title/Abstract Full Text Show Details

Unilever Home and Personal Care USA, Division Of Conopco, Inc.

Patent: US2006/110341 A1, 2006 ; Title/Abstract Full Text Show Details

Zaytsev, Andrey V.; Anderson, Rosaleen J.; Bedernjak, Alexandre; Groundwater, Paul W.; Huang, Yongxue; Perry, John D.; Orenga, Sylvain; Dalbert-Roger, Celine; James, Arthur

Organic and Biomolecular Chemistry, 2008 , vol. 6, # 6 p. 682 - 692 Title/Abstract Full Text View citing articles Show Details


Apopa, Patrick L.; He, Xiaoqing; Ma, Qiang

Journal of Biochemical and Molecular Toxicology, 2008 , vol. 22, # 1 p. 63 - 76 Title/Abstract Full Text View citing articles Show Details

Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu

Chemistry Letters, 2008 , vol. 37, # 3 p. 360 - 361 Title/Abstract Full Text View citing articles Show Details

Bar-Nahum, Itsik; York, John T.; Young Jr., Victor G.; Tolman, William B.

Angewandte Chemie - International Edition, 2008 , vol. 47, # 3 p. 533 - 536 Title/Abstract Full Text View citing articles Show Details

Minero, C.; Pramauro, E.; Pelizzetti, E.; Blundell, N. J.; Burgess, J.; Radulovic, S.

Inorganica Chimica Acta, 1990 , vol. 173, p. 43 - 52 Full Text View citing articles Show Details

AKPHARMA INC.

Patent: US2008/107743 A1, 2008 ; Title/Abstract Full Text Show Details

National Starch and Chemical Investment Holding Corporation

Patent: US2008/112987 A1, 2008 ; Title/Abstract Full Text Show Details

MARINUS PHARMACEUTICALS

Patent: WO2008/66899 A2, 2008 ; Title/Abstract Full Text Show Details

Nippon Oil Corporation

Patent: EP1990339 A1, 2008 ; Title/Abstract Full Text Show Details

12 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

VALENT BIOSCIENCES CORPORATION

Patent: WO2008/143961 A1, 2008 ; Title/Abstract Full Text Show Details

VALENT BIOSCIENCES CORPORATION

Patent: WO2008/143969 A1, 2008 ; Title/Abstract Full Text Show Details

Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Khaledi, Hamid

Journal of the Chinese Chemical Society, 2008 , vol. 55, # 1 p. 239 - 243 Title/Abstract Full Text View citing articles Show Details

Miyamura, Hiroyuki; Shiramizu, Mika; Matsubara, Ryosuke; Kobayashi, Shu

Angewandte Chemie - International Edition, 2008 , vol. 47, # 42 p. 8093 - 8095 Title/Abstract Full Text View citing articles Show Details

Lakouraj, Moslem Mansour; Tajbakhsh, Mahmood; Ramzanian-Lehmali, Farhad

Phosphorus, Sulfur and Silicon and the Related Elements, 2008 , vol. 183, # 6 p. 1388 - 1395 Title/Abstract Full Text View citing articles Show Details

Air Products and Chemicals, Inc.

Patent: EP2050753 A1, 2009 ; Title/Abstract Full Text Show Details

Azizi; Chaichi; Yousefi

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2009 , vol. 73, # 1 p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

SYNTOPIX LIMITED

Patent: WO2009/74792 A2, 2009 ; Title/Abstract Full Text Show Details

Shiri, Lotfi; Ghorbani-Choghamarani, Arash

Phosphorus, Sulfur and Silicon and the Related Elements, 2009 , vol. 184, # 2 p. 492 - 498 Title/Abstract Full Text View citing articles Show Details

Albrecht, Marcel; Schneider, Oliver; Schmidt, Andreas

Organic and Biomolecular Chemistry, 2009 , vol. 7, # 7 p. 1445 - 1453 Title/Abstract Full Text View citing articles Show Details

Kim, Sungjin; Kim, Daehwan; Park, Jaiwook

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 16 p. 2573 - 2578 Title/Abstract Full Text View citing articles Show Details

Pei, Zhonghua; Li, Xiaofeng; Longenecker, Kenton L.; Sham, Hing L.; Wiedeman, Paul E.

Patent: US2005/131019 A1, 2005 ; Title/Abstract Full Text Show Details

Hu, Jinlian; Zeng, Fang; Li, Pei

Patent: US2005/232880 A1, 2005 ; Title/Abstract Full Text Show Details

Tran, Thu-Ba Thi; Younathan, Janet Nadya


Patent: US2010/22606 A1, 2010 ; Title/Abstract Full Text Show Details

El-Ghorab, Ahmed; Shaaban, Hamdy A.; El-Massry, Khaled F.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2008 , vol. 56, # 13 p. 5021 - 5025 Title/Abstract Full Text View citing articles Show Details

Yi, Wei; Cao, Ri-Hui; Chen, Zhi-Yong; Yu, Liang; Ma, Lin; Song, Hua-Can

Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 11 p. 1273 - 1277 Title/Abstract Full Text View citing articles Show Details

Ando, Kaori; Suzuki, Yusaku

Tetrahedron Letters, 2010 , vol. 51, # 17 p. 2323 - 2325 Title/Abstract Full Text View citing articles Show Details

El-Massrry, Khaled F.; El-Ghorab, Ahmed H.; Shaaban, Hamdy A.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 12 p. 5265 - 5270 Title/Abstract Full Text View citing articles Show Details

13 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Liu, Xin; Ou, Yingyong; Chen, Shaopeng; Lu, Xin; Cheng, Hao; Jia, Xian; Wang, Decai; Zhou, Guo-Chun

European Journal of Medicinal Chemistry, 2010 , vol. 45, # 6 p. 2147 - 2153 Title/Abstract Full Text View citing articles Show Details

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Rupasinghe, H. P. Vasantha; Erkan, Naciye; Yasmin, Afsana

Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 2 p. 1233 - 1239 Title/Abstract Full Text View citing articles Show Details

Wang, Jinyan; Zhang, Dongli; Chu, Qingcui; Ye, Jiannong

Chinese Journal of Chemistry, 2010 , vol. 28, # 2 p. 313 - 319 Title/Abstract Full Text View citing articles Show Details

Cholli, Ashok L.; Kumar, Vijayendra; Kumar, Javant; Parmar, Virinder Singh; Samuelson, Lynne Ann; Bruno, Ferdinando F.

Patent: US2007/154430 A1, 2007 ; Title/Abstract Full Text Show Details

Wu, Raymond P.; Hayashi, Tomoko; Cottam, Howard B.; Jin, Guangyi; Yao, Shiyin; Wu, Christina C. N.; Rosenbach, Michael D.; Corr, Maripat; Schwab, Richard B.; Carson, Dennis A.

Proceedings of the National Academy of Sciences of the United States of America, 2010 , vol. 107, # 16 p. 7479 - 7484 Title/Abstract Full Text View citing articles Show Details

Bausch and Lomb Incorporated

Patent: US7825257 B1, 2010 ; Title/Abstract Full Text Show Details

Kim, Kyu-Han; Jeong, Jae-Yeon; Surh, Young-Joon; Kim, Kyu-Won

Nucleic Acids Research, 2010 , vol. 38, # 1 art. no. GKP865, p. 48 - 59 Title/Abstract Full Text View citing articles Show Details

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Saito, Yukako; Yoshimura, Yuichi; Takahata, Hiroki

Tetrahedron Letters, 2010 , vol. 51, # 52 p. 6915 - 6917 Title/Abstract Full Text View citing articles Show Details

Chen, Chien-Tien; Kao, Jun-Qi; Salunke, Santosh B.; Lin, Ya-Hui

Organic Letters, 2011 , vol. 13, # 1 p. 26 - 29 Title/Abstract Full Text View citing articles Show Details

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Kiritsakis, Kostas; Kontominas; Kontogiorgis; Hadjipavlou-Litina; Moustakas; Kiritsakis

JAOCS, Journal of the American Oil Chemists' Society, 2010 , vol. 87, # 4 p. 369 - 376 Title/Abstract Full Text View citing articles Show Details

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Elam, Christopher; Lape, Michael; Deye, Joel; Zultowsky, Jodie; Stanton, David T.; Paula, Stefan

European Journal of Medicinal Chemistry, 2011 , vol. 46, # 5 p. 1512 - 1523 Title/Abstract Full Text View citing articles Show Details

Rene, Alice; Abasq, Marie-Laurence; Hauchard, Didier; Hapiot, Philippe

Analytical Chemistry, 2010 , vol. 82, # 20 p. 8703 - 8710 Title/Abstract Full Text View citing articles Show Details

Salunke, Santosh B.; Babu, N.Seshu; Chen, Chien-Tien

Advanced Synthesis and Catalysis, 2011 , vol. 353, # 8 p. 1234 - 1240 Title/Abstract Full Text View citing articles Show Details

Rupasinghe, Vasantha Handukutti Pathirannehalage; Huber, Marie Gwendolyn; Yasmin, Afsana; Erkan, Naciye

Patent: US2011/152371 A1, 2011 ; Title/Abstract Full Text Show Details

Hur, Wooyoung; Sun, Zheng; Jiang, Tao; Mason, Daniel E.; Peters, Eric C.; Zhang, Donna D.; Luesch, Hendrik; Schultz, Peter G.; Gray, Nathanael S.

Chemistry and Biology, 2010 , vol. 17, # 5 p. 537 - 547 Title/Abstract Full Text View citing articles Show Details

Kalow, Julia A.; Doyle, Abigail G.

Journal of the American Chemical Society, 2011 , vol. 133, # 40 p. 16001 - 16012 Title/Abstract Full Text View citing articles Show Details


14 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Pourali, Ali Reza; Goli, Arezou

Journal of Chemical Sciences, 2011 , vol. 123, # 1 p. 63 - 67 Title/Abstract Full Text View citing articles Show Details

Smirnova, Natalya A.; Haskew-Layton, Renee E.; Basso, Manuela; Hushpulian, Dmitry M.; Payappilly, Jimmy B.; Speer, Rachel E.; Ahn, Young-Hoon; Rakhman, Ilay; Cole, Philip A.; Pinto, John T.; Ratan, Rajiv R.; Gazaryan, Irina G.

Chemistry and Biology, 2011 , vol. 18, # 6 p. 752 - 765 Title/Abstract Full Text View citing articles Show Details

Maggi, Raimondo; Piscopo, Calogero G.; Sartori, Giovanni; Storaro, Loretta; Moretti, Elisa

Applied Catalysis A: General, 2012 , vol. 411-412, p. 146 - 152 Title/Abstract Full Text View citing articles Show Details

Bekdeser, Burcu; Oezyuerek, Mustafa; Gueclue, Kubilay; Apak, Resat

Analytical Chemistry, 2011 , vol. 83, # 14 p. 5652 - 5660 Title/Abstract Full Text View citing articles Show Details

Higgins, Larry G.; Hayes, John D.

Chemico-Biological Interactions, 2011 , vol. 192, # 1-2 p. 37 - 45 Title/Abstract Full Text View citing articles Show Details

Dereli; Erdogdu; Gulluoglu; Tuerkkan; Oezmen; Sundaraganesan

Journal of Molecular Structure, 2012 , vol. 1012, p. 168 - 176 Title/Abstract Full Text View citing articles Show Details

STRATEGIC ENZYME APPLICATIONS, INC.; ALBIZATI, Kim; TRACEWELL, Cara

Patent: WO2012/75053 A2, 2012 ; Title/Abstract Full Text Show Details

COLGATE-PALMOLIVE COMPANY; DU-THUMM, Laurence; SCHAEFFER-KORBYLO, Lyndsay; SANTOS, David; JARACZ, Stanislav

Patent: WO2012/78135 A1, 2012 ; Title/Abstract Full Text Show Details

Chen; Zhou; Qiu

Asian Journal of Chemistry, 2010 , vol. 22, # 9 p. 6867 - 6878 Title/Abstract Full Text View citing articles Show Details

Wu, Zhengrong; Zheng, Lifang; Li, Yang; Su, Feng; Yue, Xiaoxuan; Tang, Wei; Ma, Xiaoyan; Nie, Junyu; Li, Hongyu

Food Chemistry, 2012 , vol. 134, # 2 p. 1128 - 1131 Title/Abstract Full Text View citing articles Show Details

Designer Molecules, Inc.

Patent: US8288591 B2, 2012 ; Title/Abstract Full Text Show Details

Schreiber, Thomas D.; Kohle, Christoph; Buckler, Felicitas; Schmohl, Stefan; Braeuning, Albert; Schmiechen, Alexander; Schwarz, Michael; Munzel, Peter A.

Drug Metabolism and Disposition, 2006 , vol. 34, # 7 p. 1096 - 1101 Title/Abstract Full Text View citing articles Show Details

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Comment (Pharmacological Data)

Bioactivities present

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Bioactivities present

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Comment (Pharmacological Data)

Bioactivities present

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Comment (Pharmacological Data)

Bioactivities present

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Comment (Pharmacological Data)

Bioactivities present

Reference

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20 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

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Oriental Journal of Chemistry, 2016 , vol. 32, # 2 p. 1061 - 1066 Title/Abstract Full Text View citing articles Show Details

Hanson; Urriola; Johnston; Shurson

Journal of Animal Science, 2015 , vol. 93, # 8 p. 4070 - 4078 Title/Abstract Full Text View citing articles Show Details

Sivaraman, Balasubramanian; Shakila, Robinson Jeya; Jeyasekaran, Geevaretnam; Sukumar, Durairaj; Manimaran, Uthaman; Sumathi, Ganesan

Food Science and Biotechnology, 2016 , vol. 25, # 3 p. 665 - 672 Title/Abstract Full Text View citing articles Show Details

Goyal, Sumit; Goyal, Gyanendra Kumar

Critical Reviews in Food Science and Nutrition, 2016 , vol. 56, # 8 p. 1253 - 1261 Title/Abstract Full Text View citing articles Show Details

Skouta, Rachid

Neural Regeneration Research, 2016 , vol. 11, # 4 p. 566 - 567 Title/Abstract Full Text View citing articles Show Details

Kiewlicz, Justyna; Szymusiak, Henryk; Zieliński, Ryszard

Zywnosc. Nauka. Technologia. Jakosc/Food. Science Technology. Quality, 2015 , vol. 22, # 4 p. 188 - 200 Title/Abstract Full Text View citing articles Show Details

Muthusamy, Sasikumar; Peng, Cheng; Ng, Jack C.

Toxicology Research, 2016 , vol. 5, # 4 p. 1160 - 1171 Title/Abstract Full Text View citing articles Show Details

Sainsbury, Jeanine; Grypa, Roman; Ellingworth, John; Duodu, Kwaku G.; De Kock, Henriëtta L.

Food Chemistry, 2016 , vol. 213, p. 230 - 237 Title/Abstract Full Text View citing articles Show Details

Guitard, Romain; Paul, Jean-François; Nardello-Rataj, Véronique; Aubry, Jean-Marie

Food Chemistry, 2016 , vol. 213, p. 284 - 295 Title/Abstract Full Text View citing articles Show Details

Melo, Priscilla Siqueira; Arrivetti, Leandro de Oliveira Rodrigues; de Alencar, Severino Matias; Skibsted, Leif H.

Food Chemistry, 2016 , vol. 213, p. 440 - 449 Title/Abstract Full Text View citing articles Show Details

Delfanian, Mojtaba; Esmaeilzadeh Kenari, Reza; Sahari, Mohammad Ali

International Journal of Food Properties, 2016 , vol. 19, # 5 p. 958 - 973 Title/Abstract Full Text Show Details

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Reference

Joo, Min Sung; Kim, Won Dong; Lee, Ki Young; Kim, Ji Hyun; Koo, Ja Hyun; Kim, Sang Geon

Molecular and Cellular Biology, 2016 , vol. 36, # 14 p. 1931 - 1942 Title/Abstract Full Text View citing articles Show Details

Navas-Navarro, Paloma; Rojo-Ruiz, Jonathan; Rodriguez-Prados, Macarena; Ganfornina, María Dolores; Looger, Loren L.; Alonso, María Teresa; García-Sancho, Javier

Cell Chemical Biology, 2016 , vol. 23, # 6 p. 738 - 745 Title/Abstract Full Text View citing articles Show Details

Gabr, Ahmed M. M.; Mabrok, Hoda B.; Ghanem, Kadry Z.; Blaut, Michael; Smetanska, Iryna

Plant Cell, Tissue and Organ Culture, 2016 , vol. 126, # 2 p. 255 - 267 Title/Abstract Full Text View citing articles Show Details

Chen, Weimin; Li, Shanshan; Li, Jinwei; Zhou, Wen; Wu, Shouhai; Xu, Shengmei; Cui, Ke; Zhang, Donna D.; Liu, Bo

FASEB Journal, 2016 , vol. 30, # 7 p. 2500 - 2510 Title/Abstract Full Text View citing articles Show Details

Feng, Lifang; Shi, Chunwei; Bei, Ziye; Li, Yayun; Yuan, Dongxia; Gong, Yingchun; Han, Jianzhong

International Journal of Food Properties, 2016 , vol. 19, # 10 p. 2338 - 2348 Title/Abstract Full Text View citing articles Show Details

Kaur, Davinder; Kaur, Arvinder; Arora, Saroj

SpringerPlus, 2016 , vol. 5, # 1 art. no. 1037 Title/Abstract Full Text View citing articles Show Details

Nejadmansouri, Maryam; Hosseini, Seyed Mohammad Hashem; Niakosari, Mehrdad; Yousefi, Gholam Hossein; Golmakani, Mohammad


Taghi

Food Hydrocolloids, 2016 , vol. 61, p. 801 - 811 Title/Abstract Full Text View citing articles Show Details

Xu, Li-Li; Zhang, Xian; Jiang, Zheng-Yu; You, Qi-Dong

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 16 p. 3540 - 3547 Title/Abstract Full Text View citing articles Show Details

dos Santos Moretti, Ederson; de Oliveira, Fernanda Midori; Scheel, Guilherme Luiz; DalĺAntônia, Luiz Henrique; Borsato, Dionísio; Kubota, Lauro Tatsuo; Segatelli, Mariana Gava; Tarley, César Ricardo Teixeira

Electrochimica Acta, 2016 , vol. 212, p. 322 - 332 Title/Abstract Full Text View citing articles Show Details

Dadhania, Vivekkumar P.; Trivedi, Priyanka P.; Vikram, Ajit; Tripathi, Durga N.

Current Neuropharmacology, 2016 , vol. 14, # 6 p. 627 - 640 Title/Abstract Full Text View citing articles Show Details

de Angelis-Pereira, Michel Cardoso; Barcelos, Maria de Fátima Piccolo; Pereira, Rafaela Corrêa; Pereira, Juciane de Abreu Ribeiro; de Sousa, Raimundo Vicente

Nutrition and Food Science, 2016 , vol. 46, # 4 p. 504 - 516 Title/Abstract Full Text View citing articles Show Details

Gelis, Coralie; Bekkaye, Mathieu; Lebée, Clément; Blanchard, Florent; Masson, Géraldine

Organic Letters, 2016 , vol. 18, # 14 p. 3422 - 3425 Title/Abstract Full Text View citing articles Show Details

Salami; Guinguina; Agboola; Omede; Agbonlahor; Tayyab

Animal, 2016 , vol. 10, # 8 p. 1375 - 1390 Title/Abstract Full Text View citing articles Show Details

Xu, Bing-Can; Long, Hui-Bao; Luo, Ke-Qin

Scientific Reports, 2016 , vol. 6, art. no. 29589 Title/Abstract Full Text View citing articles Show Details

Shi, Xiaojing; Li, Yang; Hu, Jun; Yu, Bo

International Journal of Molecular Medicine, 2016 , vol. 38, # 1 p. 123 - 130 Title/Abstract Full Text View citing articles Show Details

Beker, Sabrina Anderson; da Silva, Yara Patricia; Bücker, Francielle; Cazarolli, Juciana Clarice; de Quadros, Patrícia Dörr; Peralba, Maria do Carmo Ruaro; Piatnicki, Clarisse Maria Sartori; Bento, Fátima Menezes

Fuel, 2016 , vol. 184, p. 701 - 707 Title/Abstract Full Text View citing articles Show Details

Beker, Sabrina Anderson; da Silva, Yara Patricia; Bücker, Francielle; Cazarolli, Juciana Clarice; de Quadros, Patrícia Dörr; Peralba, Maria do Carmo Ruaro; Piatnicki, Clarisse Maria Sartori; Bento, Fátima Menezes

Fuel, 2016 , vol. 184, p. 701 - 707 Title/Abstract Full Text Show Details

Ooi; Eady; Cove; O'Neill

Journal of Antimicrobial Chemotherapy, 2016 , vol. 71, # 7 p. 1841 - 1844 Title/Abstract Full Text View citing articles Show Details

Rashidi, Ladan; Gholami, Zahra; Nanvazadeh, Sara; Shabani, Zhila

Food Analytical Methods, 2016 , vol. 9, # 9 p. 2682 - 2690 Title/Abstract Full Text View citing articles Show Details

Nogueira; Kessuane; Lobo Ladd; Cogliati; Castro

British Journal of Nutrition, 2016 , vol. 116, # 2 p. 258 - 269 Title/Abstract Full Text View citing articles Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Jin, Sang-Keun; Choi, Jung-Seok; Jeong, Jin-Yeon; Kim, Gap-Don

Journal of the Science of Food and Agriculture, 2016 , vol. 96, # 12 p. 4089 - 4097 Title/Abstract Full Text View citing articles Show Details

Hawashin, Majed D.; Al-Juhaimi, Fahad; Ahmed, Isam A. Mohamed; Ghafoor, Kashif; Babiker, Elfadil E.

Meat Science, 2016 , vol. 122, p. 32 - 39 Title/Abstract Full Text View citing articles Show Details

Le Rouzic, Olivier; Koné, Bachirou; Kluza, Jerome; Marchetti, Philippe; Hennegrave, Florence; Olivier, Cécile; Kervoaze, Gwenola; Vilain, Eva; Mordacq, Clémence; Just, Nicolas; Perez, Thierry; Bautin, Nathalie; Pichavant, Muriel; Gosset, Philippe

Respiratory Research, 2016 , vol. 17, # 1 art. no. 94, p. 1 - 1 Title/Abstract Full Text View citing articles Show Details

Zhou, Jian; Xiong, Yun; Xu, Shihai

Fuel, 2016 , vol. 184, p. 808 - 814 Title/Abstract Full Text View citing articles Show Details

Zhou, Jian; Xiong, Yun; Xu, Shihai

Fuel, 2016 , vol. 184, p. 808 - 814 Title/Abstract Full Text Show Details

Song, Hui-Peng; Wu, Si-Qi; Qi, Lian-Wen; Long, Fang; Jiang, Li-Feng; Liu, Ke; Zeng, Hao; Xu, Zhi-Meng; Li, Ping; Yang, Hua

Journal of Chromatography A, 2016 , vol. 1456, p. 176 - 186 Title/Abstract Full Text View citing articles Show Details

Van, Tho Dinh Son; Trung, Nghia Phan; Anh, Vu Nguyen; Lan, Huong Nguyen; Kim, Anh To

International Journal of Green Energy, 2016 , vol. 13, # 7 p. 720 - 729 Title/Abstract Full Text View citing articles Show Details

Dai, Yunlong; Li, Xueyan; Fan, Limei; Lu, Xiaojing; Kan, Xianwen

Biosensors and Bioelectronics, 2016 , vol. 86, p. 741 - 747 Title/Abstract Full Text View citing articles Show Details

Hajazimi, Ensieh; Landberg, Rikard; Zamaratskaia, Galia

LWT - Food Science and Technology, 2016 , vol. 74, p. 128 - 134 Title/Abstract Full Text View citing articles Show Details

Nejadmansouri, Maryam; Hosseini, Seyed Mohammad Hashem; Niakosari, Mehrdad; Yousefi, Gholam Hossein; Golmakani, Mohammad Taghi

Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2016 , vol. 506, p. 821 - 832 Title/Abstract Full Text View citing articles Show Details

Czaplicki; Tańska; Konopka

Italian Journal of Food Science, 2016 , vol. 28, # 3 p. 412 - 425 Title/Abstract Full Text View citing articles Show Details


Loboda, Agnieszka; Damulewicz, Milena; Pyza, Elzbieta; Jozkowicz, Alicja; Dulak, Jozef

Cellular and Molecular Life Sciences, 2016 , vol. 73, # 17 p. 3221 - 3247 Title/Abstract Full Text View citing articles Show Details

Guitard, Romain; Nardello-Rataj, Véronique; Aubry, Jean-Marie

International Journal of Molecular Sciences, 2016 , vol. 17, # 8 art. no. 1220 Title/Abstract Full Text View citing articles Show Details

Lee, Hanki; Jin, Wook; Jeong, Byeong-Chul; Suh, Joo-Won

Scientific Reports, 2016 , vol. 6, art. no. 30642 Title/Abstract Full Text View citing articles Show Details

Gao, Xiao-yun; Wang, Sheng-nan; Yang, Xiao-hong; Lan, Wen-jian; Chen, Zi-wei; Chen, Jing-kao; Xie, Jian-hui; Han, Yi-fan; Pi, Rong-biao; Yang, Xiao-bo

Neurochemical Research, 2016 , vol. 41, # 9 p. 2267 - 2277 Title/Abstract Full Text View citing articles Show Details

Saluja, Rajesh Kumar; Kumar, Vineet; Sham, Radhey

Renewable and Sustainable Energy Reviews, 2016 , vol. 62, p. 166 - 181 Title/Abstract Full Text View citing articles Show Details

Ebabe Elle, Raymond; Rahmani, Saher; Lauret, Céline; Morena, Marion; Bidel, Luc Philippe Régis; Boulahtouf, Abdelhay; Balaguer, Patrick; Cristol, Jean-Paul; Durand, Jean-Olivier; Charnay, Clarence; Badia, Eric

Molecular Pharmaceutics, 2016 , vol. 13, # 8 p. 2647 - 2660 Title/Abstract Full Text View citing articles Show Details

Figueroa, Johnny D.; Serrano-Illan, Miguel; Licero, Jenniffer; Cordero, Kathia; Miranda, Jorge D.; De Leon, Marino

Journal of Neurotrauma, 2016 , vol. 33, # 15 p. 1436 - 1449 Title/Abstract Full Text View citing articles Show Details

Karatoprak, Gökçe Şeker; Ilgün, Selen; Koşar, Müberra

Turkish Journal of Pharmaceutical Sciences, 2016 , vol. 13, # 2 p. 201 - 212 Title/Abstract Full Text View citing articles Show Details

Massini, Laura; Rico, Daniel; Martin-Diana, Ana Belen; Barry-Ryan, Catherine

European Food Research and Technology, 2016 , vol. 242, # 9 p. 1459 - 1469 Title/Abstract Full Text View citing articles Show Details

23 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Allard, Sébastien; Criquet, Justine; Prunier, Anaïs; Falantin, Cécilia; Le Person, Annaïg; Yat-Man Tang, Janet; Croué, Jean-Philippe

Water Research, 2016 , vol. 103, p. 453 - 461 Title/Abstract Full Text View citing articles Show Details

Zhang, Kai Ming; Wang, Jia Wan; Guo, Mei Li; Du, Wen Li; Wu, Rong Hua; Wang, Xian

Journal of Plant Physiology, 2016 , vol. 204, p. 1 - 7 Title/Abstract Full Text View citing articles Show Details

Allard, Sébastien; Criquet, Justine; Prunier, Anaïs; Falantin, Cécilia; Le Person, Annaïg; Yat-Man Tang, Janet; Croué, Jean-Philippe

Water Research, 2016 , vol. 103, p. 453 - 461 Title/Abstract Full Text Show Details

Choi, Seung-Hyun; Kim, Jae-Min; Choi, Sun-Il; Jung, Tae-Dong; Oh, Ji-Won; Cho, Bong-Yeon; Lee, Jin-Ha; Lee, Ok-Hwan

Journal of the Korean Society of Food Science and Nutrition, 2016 , vol. 45, # 7 p. 1065 - 1070 Title/Abstract Full Text View citing articles Show Details

Skowyra, Monika; Janiewicz, Urszula; Salejda, Anna Marietta; Krasnowska, Grazyna; Almajano, María Pilar

Food Technology and Biotechnology, 2015 , vol. 53, # 4 p. 419 - 427 Title/Abstract Full Text View citing articles Show Details

Hefnawy, Hefnawy T.; El-Shourbagy, Gehan A.; Ramadan, Mohamed Fawzy

Journal of Food Measurement and Characterization, 2016 , vol. 10, # 3 p. 576 - 583 Title/Abstract Full Text View citing articles Show Details

Hosseinihashemi, Seyyed Khalil; Nazari, Latif; Lashgari, Amir; Salem, Mohamed Z.M.

BioResources, 2016 , vol. 11, # 1 p. 1505 - 1517 Title/Abstract Full Text View citing articles Show Details

Ghorbani Gorji, Sara; Smyth, Heather E.; Sharma, Mary; Fitzgerald, Melissa

Trends in Food Science and Technology, 2016 , vol. 56, p. 88 - 102 Title/Abstract Full Text View citing articles Show Details

Zhu, Xindi; Cheng, Yanling; Chen, Paul; Peng, Peng; Liu, Shiyu; Li, Dong; Ruan, Roger

Innovative Food Science and Emerging Technologies, 2016 , vol. 37, p. 91 - 97 Title/Abstract Full Text View citing articles Show Details

Ramalingam, Senthil; Rajendran, Silambarasan; Ganesan, Pranesh

Fuel, 2016 , vol. 185, p. 804 - 809 Title/Abstract Full Text View citing articles Show Details

Ramalingam, Senthil; Rajendran, Silambarasan; Ganesan, Pranesh

Fuel, 2016 , vol. 185, p. 804 - 809 Title/Abstract Full Text Show Details

Chakraborty, Kajal; Chakkalakal, Selsa J.; Joseph, Deepu

Journal of Aquatic Food Product Technology, 2016 , vol. 25, # 5 p. 666 - 683 Title/Abstract Full Text View citing articles Show Details

Jung, Ji Young; Park, Han-Min; Yang, Jae-Kyung

Wood Science and Technology, 2016 , vol. 50, # 5 p. 1037 - 1055 Title/Abstract Full Text View citing articles Show Details

Mousavi, Seyedeh Neda; Koohdani, Fariba; Shidfar, Farzad; Shafiei-Neek, Leila

Journal of Family and Reproductive Health, 2016 , vol. 10, # 2 p. 85 - 91 Title/Abstract Full Text Show Details

Bodoira, Romina M.; Penci, María C.; Ribotta, Pablo D.; Martínez, Marcela L.

LWT - Food Science and Technology, 2017 , vol. 75, p. 107 - 113 Title/Abstract Full Text View citing articles Show Details

Kamps; Hoeks; Kung; Lens; McCloskey; Noordover; Heuts

Polymer Chemistry, 2016 , vol. 7, # 33 p. 5294 - 5303 Title/Abstract Full Text Show Details

Sapawe; Samion, Syahrullail; Zulhanafi; Nor Azwadi; Hanafi

Tribology Transactions, 2016 , vol. 59, # 5 p. 883 - 888 Title/Abstract Full Text Show Details

Dalefield, Rosalind R.; Gosse, Michelle A.; Mueller, Utz


Regulatory Toxicology and Pharmacology, 2016 , vol. 81, p. 146 - 154 Title/Abstract Full Text Show Details

Zhou, Jing; Chao, Gao; Li, YuLei; Wu, Min; Zhong, ShuZhi; Feng, ZunYong

Neuroscience Letters, 2016 , vol. 632, p. 92 - 97 Title/Abstract Full Text Show Details

Mittal, Smriti P.K.; Khole, Swati; Jagadish, Nidhi; Ghosh, Debjani; Gadgil, Vijay; Sinkar, Vilas; Ghaskadbi, Saroj S.

Biochimica et Biophysica Acta - General Subjects, 2016 , vol. 1860, # 11 p. 2377 - 2390 Title/Abstract Full Text Show Details

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25 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Ban, Lan; Patel, Neil M.; Schroeder, William D.

JAOCS, Journal of the American Oil Chemists' Society, 2016 , vol. 93, # 9 p. 1183 - 1190 Title/Abstract Full Text Show Details

Sapawe; Samion, Syahrullail; Zulhanafi; Nor Azwadi; Hanafi

Tribology Transactions, 2016 , vol. 59, # 5 p. 883 - 888 Title/Abstract Full Text Show Details

Mohan, Nimmy; Sudheesh; Francis, Nimmy; Anderson, Richard; Laishram, Rakesh S.

Nucleic Acids Research, 2015 , vol. 43, # 14 p. 7005 - 7020 Title/Abstract Full Text Show Details

Ju, Yanlun; Zhang, Ang; Fang, Yulin; Liu, Min; Zhao, Xianfang; Wang, Hua; Zhang, Zhenwen

Spanish Journal of Agricultural Research, 2016 , vol. 14, # 3 art. no. E0805, p. 13 Title/Abstract Full Text Show Details

Rathod, Richa S.; Khaire, Amrita A.; Kale, Anvita A.; Joshi, Sadhana R.

Biochimie, 2016 , vol. 128-129, p. 201 - 208 Title/Abstract Full Text Show Details

Wieczorek, Dorota; Marchut-Mikolajczyk, Olga; Strzelecki, Bartosz; Gajewska, Malgorzata; Polewczyk, Arkadiusz; Antczak, Tadeusz

International Biodeterioration and Biodegradation, 2016 , vol. 115, p. 205 - 211 Title/Abstract Full Text Show Details

Masondo, Nqobile A.; Kulkarni, Manoj G.; Rengasamy, Kannan R.R.; Pendota, Srinivasa C.; Finnie, Jeffrey F.; Van Staden, Johannes

Acta Physiologiae Plantarum, 2016 , vol. 38, # 10 art. no. 236 Title/Abstract Full Text Show Details

Motamedi-Tehrani; Ebrahimi-Dorcheh; Malekpouri; Goli

Journal of Applied Ichthyology, 2016 , vol. 32, # 5 p. 906 - 912 Title/Abstract Full Text Show Details

Tao, Chun; Chen, Juming; Huang, Aiwen; Zhang, Jing; Lin, Bing; Liu, Zhihong; Zhang, Minxin; Chen, Xu; Zeng, Lingjun; Zhang, Lingna; Song, Hongtao

International Journal of Pharmaceutics, 2016 , vol. 513, # 1-2 p. 255 - 261 Title/Abstract Full Text Show Details

Giacobbo, Alexandre; Bernardes, Andréa Moura; de Pinho, Maria Norberta

Separation and Purification Technology, 2017 , vol. 173, p. 49 - 54 Title/Abstract Full Text Show Details

Yu, Danmeng; Pu, Wenjun; Li, Dengwu; Wang, Dongmei; Liu, Qiaoxiao; Wang, Yongtao

Chemistry and Biodiversity, 2016 , vol. 13, # 9 p. 1140 - 1148 Title/Abstract Full Text Show Details

Zhao, Yang; Liu, Dong; Proksch, Peter; Yu, Siwang; Lin, Wenhan

Chemistry and Biodiversity, 2016 , vol. 13, # 9 p. 1186 - 1193 Title/Abstract Full Text Show Details

Czochara, Robert; Kusio, Jarosław; Symonowicz, Michał; Litwinienko, Grzegorz

Industrial and Engineering Chemistry Research, 2016 , vol. 55, # 37 p. 9887 - 9894 Title/Abstract Full Text Show Details

Yu, Yong-Jie; Ni, Sui; Wu, Fan; Sang, Wei-Guo

Journal of Essential Oil-Bearing Plants, 2016 , vol. 19, # 5 p. 1170 - 1180 Title/Abstract Full Text Show Details

Pinteus, Susete; Silva, Joana; Alves, Celso; Horta, André; Fino, Nádia; Rodrigues, Ana Inês; Mendes, Susana; Pedrosa, Rui

Food Chemistry, 2017 , vol. 218, p. 591 - 599 Title/Abstract Full Text Show Details

Savoia, Dianella

Current Drug Targets, 2016 , vol. 17, # 6 p. 731 - 738 Title/Abstract Full Text Show Details

Bhandari, Shiva Ram; Lee, Jun Gu

Journal of Analytical Methods in Chemistry, 2016 , vol. 2016, art. no. 5498618 Title/Abstract Full Text Show Details

Im, Seon-Yeong; Jang, Ka-Hee; Farooq, Muhammad; Lee, Dong-Jin

Journal of Herbs, Spices and Medicinal Plants, 2016 , vol. 22, # 4 p. 327 - 336 Title/Abstract Full Text Show Details

Devi, Anuchaya; Das, Vijay K.; Deka, Dhanapati

Fuel, 2017 , vol. 187, p. 306 - 314 Title/Abstract Full Text Show Details

Jo, Cheorun; Khan, Faisal Fareed; Khan, Muhammad Issa; Iqbal, Javed

Food Reviews International, 2017 , vol. 33, # 1 p. 44 - 61 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

Bioactivities present

Reference

Devi, Anuchaya; Das, Vijay K.; Deka, Dhanapati

Fuel, 2017 , vol. 187, p. 306 - 314 Title/Abstract Full Text Show Details

Jadon, Nimisha; Jain, Rajeev; Sharma, Swati; Singh, Kshiti

Talanta, 2016 , vol. 161, p. 894 - 916 Title/Abstract Full Text Show Details


Barthel, Sebastian Robert; Medvedev, Regina; Heinrich, Thekla; Büchner, Sarah Manon; Kettern, Nadja; Hildt, Eberhard

Cellular and Molecular Life Sciences, 2016 , vol. 73, # 21 p. 4121 - 4140 Title/Abstract Full Text Show Details

Hussein, Ahmed M.S.; Lotfy, Shereen N.; Kamil, Mohie M.

International Journal of PharmTech Research, 2016 , vol. 9, # 8 p. 228 - 236 Title/Abstract Full Text Show Details

Borjian Borojeni; Goli; Gharachourloo

Journal of Agricultural Science and Technology, 2016 , vol. 18, # 6 p. 1531 - 1542 Title/Abstract Full Text Show Details

Eça, Kaliana Sitonio; Sartori, Tanara; Menegalli, Florencia Cecilia

Brazilian Journal of Food Technology, 2014 , vol. 17, # 2 p. 98 - 112 Title/Abstract Full Text Show Details

Cortese-Krott, Miriam M; Pullmann, David; Feelisch, Martin

Pharmacological Research, 2016 , vol. 113, p. 490 - 499 Title/Abstract Full Text Show Details

Czochara, Robert; Kusio, Jarosław; Symonowicz, Michał; Litwinienko, Grzegorz

Industrial and Engineering Chemistry Research, 2016 , vol. 55, # 37 p. 9887 - 9894 Title/Abstract Full Text Show Details

Thanksgiving Food Science and Tecnology Co., Ltd. of Dongguan City; Wang, Li

Patent: CN105294403 A, 2016 ; Title/Abstract Full Text Show Details

Guangzhou Taibang Food Technology Co., Ltd.; Lu, Junqing

Patent: CN103864581 B, 2016 ; Title/Abstract Full Text Show Details

China Pharmaceutical University; You, Qidong; Yang, Tingting; Sun, Haopeng; Xi, Meiyang; Zhu, Junfeng

Patent: CN105566323 A, 2016 ; Title/Abstract Full Text Show Details

Márquez-Mota, Claudia C.; Rodriguez-Gaytan, Cinthya; Adjibade, Pauline; Mazroui, Rachid; Gálvez, Amanda; Granados, Omar; Tovar, Armando R.; Torres, Nimbe

Nutrients, 2016 , vol. 8, # 9 art. no. 573 Title/Abstract Full Text Show Details

Jiang, Jiang; Xiong, Youling L.

Meat Science, 2016 , vol. 120, p. 107 - 117 Title/Abstract Full Text Show Details

Carlisi; Buttitta; Di Fiore; Scerri; Drago-Ferrante; Vento; Tesoriere

Cell Death and Disease, 2016 , vol. 7, # 4 art. no. E2194 Title/Abstract Full Text Show Details

Rafiee, Zahra; Barzegar, Mohsen; Sahari, Mohammad Ali; Maherani, Behnoush

Food Chemistry, 2017 , vol. 220, p. 115 - 122 Title/Abstract Full Text Show Details

Xu, Zhou; Wang, Handong; Wang, Bulei; Fu, Liang; Yuan, Ming; Liu, Jing; Zhou, Lijun; Ding, Chunbang

International Journal of Biological Macromolecules, 2016 , vol. 92, p. 148 - 155 Title/Abstract Full Text Show Details

Saddawi-Konefka, Robert; Seelige, Ruth; Gross, Emilie T.E.; Levy, Eric; Searles, Stephen C.; Washington, Allen; Santosa, Endi K.; Liu, Beichen; O'Sullivan, Timothy E.; Harismendy, Olivier; Bui, Jack D.

Cell Reports, 2016 , vol. 16, # 9 p. 2348 - 2358 Title/Abstract Full Text Show Details

Wu, Long; Yin, Wenmin; Tang, Kun; Li, Dian; Shao, Kang; Zuo, Yunpeng; Ma, Jing; Liu, Jiawei; Han, Heyou

Analytica Chimica Acta, 2016 , vol. 933, p. 89 - 96 Title/Abstract Full Text Show Details

TANG, Jing-Jing; GENG, Xiao-Ting; WANG, Ya-Jing; ZHENG, Tian-Yu; LU, Jin-Rong; HU, Rong

Chinese Journal of Natural Medicines, 2016 , vol. 14, # 6 p. 462 - 472 Title/Abstract Full Text Show Details

Zhou, Jian; Xiong, Yun; Liu, Xiao

Fuel, 2017 , vol. 188, p. 61 - 68 Title/Abstract Full Text Show Details

26 of 549

Comment (Pharmacological Data)

Bioactivities present

Reference

Zhou, Jian; Xiong, Yun; Liu, Xiao

Fuel, 2017 , vol. 188, p. 61 - 68 Title/Abstract Full Text Show Details

Ghorbanpour; Hadian; Hatami; Salehi-Arjomand; Aliahmadi

Journal of Medicinal Plants, 2016 , vol. 15, # 59 p. 58 - 72 Title/Abstract Full Text Show Details

Tang, Jing; Wang, Wei; Zheng, Shengbiao; Zhang, Yan; Wei, Jumeng; Wang, Jianfei

Food Analytical Methods, 2016 , vol. 9, # 11 p. 3044 - 3052 Title/Abstract Full Text Show Details

Zhang; Han; Bridges; Dawson

Poultry Science, 2016 , vol. 95, # 10 p. 2435 - 2440 Title/Abstract Full Text Show Details

Çelik, Mehmet

Applied Thermal Engineering, 2016 , vol. 108, p. 1178 - 1189 Title/Abstract Full Text Show Details

Song, JuHee; Jang, Eun Yeong; Kim, Mi-Ja; Kim, Young-Jun; Lee, JaeHwan

International Journal of Food Science and Technology, 2016 , vol. 51, # 11 p. 2424 - 2432 Title/Abstract Full Text Show Details

Çelik, Mehmet

Applied Thermal Engineering, 2016 , vol. 108, p. 1178 - 1189 Title/Abstract Full Text Show Details

Rafiquzzaman; Ahmad, Moin Uddin; Lee, Jong Min; Kim, Eun -Young; Kim, Young -Ok; Kim, Dong -Gyun; Kong, In -Soo


Journal of Food Processing and Preservation, 2016 , vol. 40, # 5 p. 1074 - 1083 Title/Abstract Full Text Show Details

Ashrafi, Reza; Yon, Marianne; Pickavance, Lucy; Yanni Gerges, Joseph; Davis, Gershan; Wilding, John; Jian, Kun; Zhang, Henggui; Hart, George; Boyett, Mark

Journal of Obesity, 2016 , vol. 2016, art. no. 7127898 Title/Abstract Full Text Show Details

Li, Xinran; Chen, Fengli; Li, Shuangyang; Jia, Jun; Gu, Huiyan; Yang, Lei

Industrial Crops and Products, 2016 , vol. 94, p. 834 - 847 Title/Abstract Full Text Show Details

Sharayei, Parvin; Farhoosh, Reza

European Journal of Lipid Science and Technology, 2016 , vol. 118, # 10 p. 1495 - 1506 Title/Abstract Full Text Show Details

Liu, Cuifang; Li, Jun; Bi, Yanlan; Wang, Xuede; Sun, Shangde; Yang, Guolong

Journal of Oleo Science, 2016 , vol. 65, # 9 p. 739 - 748 Title/Abstract Full Text Show Details

Palliyaguru, Dushani L.; Chartoumpekis, Dionysios V.; Wakabayashi, Nobunao; Skoko, John J.; Yagishita, Yoko; Singh, Shivendra V.; Kensler, Thomas W.

Free Radical Biology and Medicine, 2016 , vol. 101, p. 116 - 128 Title/Abstract Full Text Show Details

Williams, Larissa M.; Lago, Briony A.; McArthur, Andrew G.; Raphenya, Amogelang R.; Pray, Nicholas; Saleem, Nabil; Salas, Sophia; Paulson, Katherine; Mangar, Roshni S.; Liu, Yang; Vo, Andy H.; Shavit, Jordan A.

Aquatic Toxicology, 2016 , vol. 180, p. 141 - 154 Title/Abstract Full Text Show Details

Pal, Gaurav Kumar; Suresh

Innovative Food Science and Emerging Technologies, 2016 , vol. 37, # Part B p. 201 - 215 Title/Abstract Full Text Show Details

Gutsche, Katrin; Randi, Elisa B.; Blank, Volker; Fink, Daniel; Wenger, Roland H.; Leo, Cornelia; Scholz, Carsten C.

Free Radical Biology and Medicine, 2016 , vol. 101, p. 129 - 142 Title/Abstract Full Text Show Details

Stalter, Daniel; O'Malley, Elissa; Von Gunten, Urs; Escher, Beate I.

Environmental Science: Water Research and Technology, 2016 , vol. 2, # 5 p. 875 - 883 Title/Abstract Full Text Show Details

Naskar, Sagar; Mazumder

Iranian Journal of Pharmacology and Therapeutics, 2015 , vol. 14, # 2 p. 1 - 9 Title/Abstract Full Text Show Details

Chen, Xin; Shi, Xianping; Zhao, Chong; Li, Xiaofen; Lan, Xiaoying; Liu, Shouting; Huang, Hongbiao; Liu, Ningning; Liao, Siyan; Zang, Dan; Song, Wenbin; Liu, Quentin; Carter, Bing Z.; Ping Dou; Wang, Xuejun; Liu, Jinbao

Oncotarget, 2014 , vol. 5, # 19 p. 9118 - 9132 Title/Abstract Full Text Show Details

Singh, Bahaderjeet; Sharma, Prince; Kumar, Arun; Chadha, Pooja; Kaur, Ramandeep; Kaur, Amarjeet

Journal of Ethnopharmacology, 2016 , vol. 194, p. 450 - 456 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Landeros, José M.; Belmont-Bernal, Fernando; Pérez-González, Alma Teresa; Pérez-Padrón, Mario Israel; Guevara-Salazar, Patricia; González-Herrera, Irma Gabriela; Guadarrama, Patricia

Materials Science and Engineering C, 2017 , vol. 71, p. 351 - 362 Title/Abstract Full Text Show Details

Zhao, Gongling; Li, Bing; Guo, Yancheng

Journal of the Chemical Society of Pakistan, 2016 , vol. 38, # 4 p. 631 - 637 Title/Abstract Full Text Show Details

Patra, Jayanta Kumar; Singdevsachan, Sameer Kumar; Swain, Manas Ranjan

Agro Food Industry Hi-Tech, 2016 , vol. 27, # 4 p. 29 - 33 Title/Abstract Full Text Show Details

El-Maati, Mohamed F. Abo; Mahgoub, Samir A.; Labib, Salah M.; Al-Gaby, Ali M.A.; Ramadan, Mohamed Fawzy

European Journal of Integrative Medicine, 2016 , vol. 8, # 4 p. 494 - 504 Title/Abstract Full Text Show Details

Liu; Shao; Bai

Animal Feed Science and Technology, 2016 , vol. 221, p. 1 - 11 Title/Abstract Full Text Show Details

Singh Gurau, Virender; Agarwal, Mudit Shankar; Sarin, Amit; Sandhu, Sarbjot Singh

Energy and Fuels, 2016 , vol. 30, # 10 p. 8377 - 8385 Title/Abstract Full Text Show Details

Kim, Ji-Sang

Preventive Nutrition and Food Science, 2016 , vol. 21, # 3 p. 263 - 270 Title/Abstract Full Text Show Details

Ishitsuka, Yosuke; Huebner, Aaron J.; Rice, Robert H.; Koch, Peter J.; Speransky, Vladislav V.; Steven, Alasdair C.; Roop, Dennis R.

Journal of Investigative Dermatology, 2016 , vol. 136, # 8 p. 1656 - 1663 Title/Abstract Full Text Show Details

Nasirizadeh, Navid; Ghaani, Masoud; Shekari, Zahra; Shateri-Khalilabad, Mohammad

Journal of the Brazilian Chemical Society, 2016 , vol. 27, # 9 p. 1577 - 1586 Title/Abstract Full Text Show Details

Bhandari, Shiva Ram; Cho, Myeong-Cheoul; Lee, Jun Gu

Horticulture Environment and Biotechnology, 2016 , vol. 57, # 5 p. 440 - 452 Title/Abstract Full Text Show Details

Fang, Xiaoyi; Vitrac, Olivier

Critical Reviews in Food Science and Nutrition, 2017 , vol. 57, # 2 p. 275 - 312 Title/Abstract Full Text Show Details

Yoon; Choi; Lee

Cell Death and Disease, 2016 , vol. 7, # 2 art. no. E2093 Title/Abstract Full Text Show Details

Holowiecki, Andrew; O'Shields, Britton; Jenny, Matthew J.

Toxicology and Applied Pharmacology, 2016 , vol. 311, p. 74 - 87


Title/Abstract Full Text Show Details

Nakagami, Yasuhiro

Oxidative Medicine and Cellular Longevity, 2016 , vol. 2016, art. no. 7469326 Title/Abstract Full Text Show Details

Bossi, Elisabetta; Tana, Francesca; Punta, Carlo; Cigada, Alberto; De Nardo, Luigi

Food Packaging and Shelf Life, 2016 , vol. 10, p. 106 - 114 Title/Abstract Full Text Show Details

Saundane, Anand Raghunath; Manjunatha, Yarlakatti

Arabian Journal of Chemistry, 2016 , vol. 9, p. S501 - S509 Title/Abstract Full Text Show Details

Abd-Elhakim, Yasmina M.; Mohamed, Wafaa A.M.

Toxicological and Environmental Chemistry, 2016 , vol. 98, # 10 p. 1227 - 1240 Title/Abstract Full Text Show Details

Rakoczy, Roksana; Kopeć, Aneta; Piątkowska, Ewa; Smoleń, Sylwester; Skoczylas, Łukasz; Leszczyńska, Teresa; Sady, Włodzimierz

Biological Trace Element Research, 2016 , vol. 174, # 2 p. 347 - 355 Title/Abstract Full Text Show Details

Williams, Larissa M.; Lago, Briony A.; McArthur, Andrew G.; Raphenya, Amogelang R.; Pray, Nicholas; Saleem, Nabil; Salas, Sophia; Paulson, Katherine; Mangar, Roshni S.; Liu, Yang; Vo, Andy H.; Shavit, Jordan A.

Aquatic Toxicology, 2016 , vol. 180, p. 141 - 154 Title/Abstract Full Text Show Details

Suganya, Arumugampillai Manimehalai; Sanjivkumar, Muthusamy; Chandran, Manohar Navin; Palavesam, Arunachalam; Immanuel, Grasian

Biomedicine and Pharmacotherapy, 2016 , vol. 84, p. 1300 - 1312 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Ishida, Takumi; Takechi, Shinji

PLoS ONE, 2016 , vol. 11, # 11 art. no. E0166100 Title/Abstract Full Text Show Details

Mulvaney, Kathleen M.; Matson, Jacob P.; Siesser, Priscila F.; Tamir, Tigist Y.; Goldfarb, Dennis; Jacobs, Timothy M.; Cloer, Erica W.; Harrison, Joseph S.; Vaziri, Cyrus; Cook, Jeanette G.; Major, Michael B.

Journal of Biological Chemistry, 2016 , vol. 291, # 45 p. 23719 - 23733 Title/Abstract Full Text Show Details

Singh Gurau, Virender; Agarwal, Mudit Shankar; Sarin, Amit; Sandhu, Sarbjot Singh

Energy and Fuels, 2016 , vol. 30, # 10 p. 8377 - 8385 Title/Abstract Full Text Show Details

Andersen, F. Alan; Bergfeld, Wilma F.; Belsito, Donald V.; Hill, Ronald A.; Klaassen, Curtis D.; Liebler, Daniel C.; Marks, James G.; Shank, Ronald C.; Slaga, Thomas J.; Snyder, Paul W.

International Journal of Toxicology, 2010 , vol. 29, # 6_suppl p. S221 - S243 Title/Abstract Full Text Show Details

Kaur, Manjit; Badhan, Raj K.S.

Brain Research, 2017 , vol. 1654, p. 9 - 23 Title/Abstract Full Text Show Details

Neale, Peta A.; Munz, Nicole A.; Aїt-Aїssa, Selim; Altenburger, Rolf; Brion, François; Busch, Wibke; Escher, Beate I.; Hilscherová, Klára; Kienle, Cornelia; Novák, Jiří; Seiler, Thomas-Benjamin; Shao, Ying; Stamm, Christian; Hollender, Juliane

Science of the Total Environment, 2017 , vol. 576, p. 785 - 795 Title/Abstract Full Text Show Details

Sathiyamoorthi; Sankaranarayanan; Pitchandi

Applied Thermal Engineering, 2017 , vol. 112, p. 1421 - 1432 Title/Abstract Full Text Show Details

Zhang, Liu; Zhang, Hui; Li, Xueyan; Jia, Bingjie; Yang, Yuyu; Zhou, Ping; Li, Ping; Chen, Jun

Phytomedicine, 2016 , vol. 23, # 14 p. 1806 - 1813 Title/Abstract Full Text Show Details

Gong, Amy G.W.; Huang, Vincent Y.; Wang, Huai Y.; Lin, Huang Q.; Dong, Tina T.X.; Tsim, Karl W.K.

PLoS ONE, 2016 , vol. 11, # 11 art. no. E0165486 Title/Abstract Full Text Show Details

Benchekroun, Mohamed; Romero, Alejandro; Egea, Javier; León, Rafael; Michalska, Patrycja; Buendía, Izaskun; Jimeno, María Luisa; Jun, Daniel; Janockova, Jana; Sepsova, Vendula; Soukup, Ondrej; Bautista-Aguilera, Oscar M.; Refouvelet, Bernard; Ouari, Olivier; MarcoContelles, José; Ismaili, Lhassane

Journal of Medicinal Chemistry, 2016 , vol. 59, # 21 p. 9967 - 9973 Title/Abstract Full Text Show Details

Rani, Savita; Khabiruddin

Oriental Journal of Chemistry, 2016 , vol. 32, # 5 p. 2803 - 2811 Title/Abstract Full Text Show Details

Wang, Jian; Chen, Guo-Jun

Genes and Diseases, 2016 , vol. 3, # 3 p. 220 - 227 Title/Abstract Full Text Show Details

Rahmanpour, Mahbobe S.; Khalilzadeh, Mohammad A.

Analytical and Bioanalytical Electrochemistry, 2016 , vol. 8, # 7 p. 922 - 930 Title/Abstract Full Text Show Details

Power, Krista A.; Lu, Jenifer T.; Monk, Jennifer M.; Lepp, Dion; Wu, Wenqing; Zhang, Claire; Liu, Ronghua; Tsao, Rong; Robinson, Lindsay E.; Wood, Geoffrey A.; Wolyn, David J.

Molecular Nutrition and Food Research, 2016 , vol. 60, # 11 p. 2396 - 2412 Title/Abstract Full Text Show Details

Tarhan, Leman; Tongul, Burcu

International Biodeterioration and Biodegradation, 2017 , vol. 117, p. 1 - 7 Title/Abstract Full Text Show Details

Eskin, Michael; Clough, Peter; List, Gary

Lipid Technology, 2016 , vol. 28, # 10-11 p. 180 - 183 Title/Abstract Full Text Show Details

Su, Shiau-Tsz; Yeh, Chiu-Li; Hou, Yu-Chen; Pai, Man-Hui; Yeh, Sung-Ling

Journal of Nutritional Biochemistry, 2017 , vol. 40, p. 86 - 94 Title/Abstract Full Text Show Details


Liu, Lei; Zhao, Yong-fu; Han, Wen-hao; Chen, Tao; Hou, Guo-xin; Tong, Xian-zhou

Asian Pacific Journal of Tropical Medicine, 2016 , vol. 9, # 11 p. 1101 - 1104 Title/Abstract Full Text Show Details

Zhao, Jianying

Patent: CN105541560 A, 2016 ; Title/Abstract Full Text Show Details

Sánchez-Rodríguez, Ricardo; Torres-Mena, Julia Esperanza; Quintanar-Jurado, Valeria; Chagoya-Hazas, Victoria; Rojas del Castillo, Emilio; del Pozo Yauner, Luis; Villa-Treviño, Saul; Pérez-Carreón, Julio Isael

Free Radical Biology and Medicine, 2017 , vol. 102, p. 87 - 99 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Yang, Guanhui; Zhang, Yu; Huang, Yanshan; Shakir, Muhammad Imran; Xu, Yuxi

Physical Chemistry Chemical Physics, 2016 , vol. 18, # 46 p. 31361 - 31377 Title/Abstract Full Text Show Details

Li, Jing; Zhou, Jun; Ye, Yuanhua; Liu, Qunying; Wang, Xiaojin; Zhang, Ning; Wang, Xietong

Gynecologic and Obstetric Investigation, 2016 , vol. 81, # 6 p. 543 - 551 Title/Abstract Full Text Show Details

Chen, Ni; Zhang, Rui; Konishi, Teruaki; Wang, Jun

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2017 , vol. 813, p. 10 - 17 Title/Abstract Full Text Show Details

Kumar, Niraj

Fuel, 2017 , vol. 190, p. 328 - 350 Title/Abstract Full Text Show Details

Kumar, Niraj

Fuel, 2017 , vol. 190, p. 328 - 350 Title/Abstract Full Text Show Details

Akcan, Tolga; Estévez, Mario; Serdaroğlu, Meltem

LWT - Food Science and Technology, 2017 , vol. 77, p. 323 - 331 Title/Abstract Full Text Show Details

Kong, Qingkun; Wang, Yanhu; Zhang, Lina; Ge, Shenguang; Yu, Jinghua

Sensors and Actuators, B: Chemical, 2017 , vol. 243, p. 130 - 136 Title/Abstract Full Text Show Details

Comin, Marina; de Souza, Ana C.D.; Roveda, Ana C.; Yahagi, Silvia S.; de Oliveira, Luiz H.; Amaral, Mariana S.; Silva, Cinthia A.A.; Fiorucci, Antonio R.; Gomes, Roberto S.; Caires, Anderson R.L.; Trindade, Magno A.G.

Fuel, 2017 , vol. 191, p. 275 - 282 Title/Abstract Full Text Show Details

Comin, Marina; de Souza, Ana C.D.; Roveda, Ana C.; Yahagi, Silvia S.; de Oliveira, Luiz H.; Amaral, Mariana S.; Silva, Cinthia A.A.; Fiorucci, Antonio R.; Gomes, Roberto S.; Caires, Anderson R.L.; Trindade, Magno A.G.

Fuel, 2017 , vol. 191, p. 275 - 282 Title/Abstract Full Text Show Details

Tanzadehpanah, Hamid; Asoodeh, Ahmad; Mahaki, Hanieh; Mostajabodave, Zeinab; Chamani, Jamshidkhan; Mojallal-Tabatabaei, Zahra; Emtenani, Shirin; Emtenani, Shamsi; Moradi, Mohammad-Reza

Process Biochemistry, 2016 , vol. 51, # 12 p. 2067 - 2075 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Rashed, Marwan M.A.; Tong, Qunyi; Abdelhai, Mandour H.; Gasmalla, Mohammed A.A.; Ndayishimiye, Jean B.; Chen, Long; Ren, Fei

Ultrasonics Sonochemistry, 2016 , vol. 29, p. 39 - 47 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Wu, Zehong; Wang, Yongrui; Liu, Dong; Proksch, Peter; Yu, Siwang; Lin, Wenhan

Tetrahedron, 2016 , vol. 72, # 1 p. 50 - 57 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Chen, Jianping; Lam, Candy T. W.; Li, Zhonggui; Yao, Ping; Lin, Huangquan; Dong, Tina T. X.; Tsim, Karl W. K.

Phytotherapy Research, 2016 , vol. 30, # 2 p. 267 - 271 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Cabrera, Mauricio; Mastandrea, Ignacio; Otero, Gabriel; Cerecetto, Hugo; Gonzlez, Mercedes

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 8 p. 1665 - 1674 Title/Abstract Full Text View citing articles Show Details

Comment

physiological behaviour discussed


(Pharmacological Data) Reference

K-STEMCELL CO., LTD.; Ra, Jeong-Chan; Kang, Sung Keun; Jo, Jung Youn

Patent: US2016/90573 A1, 2016 ; Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Ali, Tarik E.; El-Edfawy, Somaya M.

Research on Chemical Intermediates, 2016 , vol. 42, # 2 p. 1329 - 1347 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Guitard, Romain; Paul, Jean-François; Nardello-Rataj, Véronique; Aubry, Jean-Marie

Food Chemistry, 2016 , vol. 213, p. 284 - 295 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

China Pharmaceutical University; You, Qidong; Yang, Tingting; Sun, Haopeng; Xi, Meiyang; Zhu, Junfeng

Patent: CN105566323 A, 2016 ; Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Kicel, Agnieszka; Michel, Piotr; Owczarek, Aleksandra; Marchelak, Anna; Zyzelewicz, Dorota; Budryn, Grazyna; Oracz, Joanna; Anna Olszewska, Monika

Molecules, 2016 , vol. 21, # 6 art. no. 688 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Xu, Li-Li; Zhang, Xian; Jiang, Zheng-Yu; You, Qi-Dong

Bioorganic and Medicinal Chemistry, 2016 , vol. 24, # 16 p. 3540 - 3547 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Zhao, Yang; Liu, Dong; Proksch, Peter; Yu, Siwang; Lin, Wenhan

Chemistry and Biodiversity, 2016 , vol. 13, # 9 p. 1186 - 1193 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Gong, Amy G.W.; Huang, Vincent Y.; Wang, Huai Y.; Lin, Huang Q.; Dong, Tina T.X.; Tsim, Karl W.K.

PLoS ONE, 2016 , vol. 11, # 11 art. no. E0165486 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Benchekroun, Mohamed; Romero, Alejandro; Egea, Javier; León, Rafael; Michalska, Patrycja; Buendía, Izaskun; Jimeno, María Luisa; Jun, Daniel; Janockova, Jana; Sepsova, Vendula; Soukup, Ondrej; Bautista-Aguilera, Oscar M.; Refouvelet, Bernard; Ouari, Olivier; MarcoContelles, José; Ismaili, Lhassane

Journal of Medicinal Chemistry, 2016 , vol. 59, # 21 p. 9967 - 9973 Title/Abstract Full Text Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Yu, Danmeng; Pu, Wenjun; Li, Dengwu; Wang, Dongmei; Liu, Qiaoxiao; Wang, Yongtao

Chemistry and Biodiversity, 2016 , vol. 13, # 9 p. 1140 - 1148


Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Saundane, Anand R.; Kalpana

Medicinal Chemistry Research, 2015 , vol. 24, # 4 p. 1681 - 1695 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Samatiwat, Papavee; Prawan, Auemduan; Senggunprai, Laddawan; Kukongviriyapan, Veerapol

Naunyn-Schmiedeberg's Archives of Pharmacology, 2015 , vol. 388, # 6 p. 601 - 612 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Chang, Ken-Ming; Liang, Fong-Pin; Chen, I-Li; Yang, Shyh-Chyun; Juang, Shin-Hun; Wang, Tai-Chi; Chen, Yeh-Long; Tzeng, Cherng-Chyi

Bioorganic and Medicinal Chemistry, 2015 , vol. 23, # 13 art. no. 12172, p. 3852 - 3859 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Shen, Tao; Jiang, Tao; Long, Min; Chen, Jun; Ren, Dong-Mei; Wong, Pak Kin; Chapman, Eli; Zhou, Bo; Zhang, Donna D.

Antioxidants and Redox Signaling, 2015 , vol. 23, # 8 p. 651 - 664 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Xu, Li-Li; Zhu, Jun-Feng; Xu, Xiao-Li; Zhu, Jie; Li; Xi, Mei-Yang; Jiang, Zheng-Yu; Zhang, Ming-Ye; Liu, Fang; Lu, Meng-Chen; Bao, Qi-Chao; Li, Qi; Zhang, Chao; Wei, Jin-Lian; Zhang, Xiao-Jin; Zhang, Lian-Shan; You, Qi-Dong; Sun, Hao-Peng

Journal of Medicinal Chemistry, 2015 , vol. 58, # 14 p. 5419 - 5436 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Oda, Shingo; Fujiwara, Ryoichi; Kutsuno, Yuki; Fukami, Tatsuki; Itoh, Tomoo; Yokoi, Tsuyoshi; Nakajima, Miki

Drug Metabolism and Disposition, 2015 , vol. 43, # 6 p. 812 - 818 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Chang, Ken-Ming; Chen, Huang-Hui; Wang, Tai-Chi; Chen, I-Li; Chen, Yu-Tsen; Yang, Shyh-Chyun; Chen, Yeh-Long; Chang, Hsin-Huei; Huang, Chih-Hsiang; Chang, Jang-Yang; Shih, Chuan; Kuo, Ching-Chuan; Tzeng, Cherng-Chyi

European Journal of Medicinal Chemistry, 2015 , vol. 106, p. 60 - 74 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

The United States of America, as represented by the Secretary, Department of Health and Human Services; Zudaire, Enrique; Aparicio, Marta; Cuttitta, Frank

Patent: US9186365 B2, 2015 ; Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Yuan, Yuan; Tian, Jun-Mian; Xiao, Jian; Shao, Qi; Gao, Jin-Ming

Natural Product Research, 2014 , vol. 28, # 4 p. 278 - 281 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed


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Reference

Jiang, Zheng-Yu; Lu, Meng-Chen; Xu, Li-Li; Yang, Ting-Ting; Xi, Mei-Yang; Xu, Xiao-Li; Guo, Xiao-Ke; Zhang, Xiao-Jin; You, Qi-Dong; Sun, Hao-Peng

Journal of Medicinal Chemistry, 2014 , vol. 57, # 6 p. 2736 - 2745 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Shimizu, Mai; Fukami, Tatsuki; Nakajima, Miki; Yokoi, Tsuyoshi

Drug Metabolism and Disposition, 2014 , vol. 42, # 7 p. 1103 - 1109 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Lu, Qiang-Qiang; Tian, Jun-Mian; Wei, Jing; Gao, Jin-Ming

Natural Product Research, 2014 , vol. 28, # 16 p. 1288 - 1292 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Wu, Jiaguo; Wang, Hongyan; Tang, Xiuwen

Biochemical and Biophysical Research Communications, 2014 , vol. 452, # 3 p. 554 - 559 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Chen, Jianping; Yan, Artemis L.; Lam, Kelly Y. C.; Lam, Candy T. W.; Li, Ning; Yao, Ping; Xiong, Aizhen; Dong, Tina T. X.; Tsim, Karl W. K.

Phytotherapy Research, 2014 , vol. 28, # 11 p. 1727 - 1730 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Michel, Piotr; Dobrowolska, Anna; Kicel, Agnieszka; Owczarek, Aleksandra; Olszewska, Monika A.; Bazylko, Agnieszka; Granica, Sebastian; Piwowarski, Jakub P.

Molecules, 2014 , vol. 19, # 12 p. 20498 - 20520 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Masood, Nusrat; Luqman, Suaib

Combinatorial Chemistry and High Throughput Screening, 2014 , vol. 17, # 8 p. 718 - 722 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antioxidative

Species or TestSystem (Pharmacological Data)

neuroblastoma IMR-32 cells of human; genetically modified/infected with: ARE-luc-wt, ARE-luc-mt

Concentration (Pharmacological Data)

10 μmol/l

Further Details (Pharmacological Data)

relative fold activation related to: ARE-luciferase

Type (Pharmacological Data)

relative fold activation

Value of Type (Pharmacological Data)

14.9 fold

Reference

Wang, Rui; Paul, Valerie J.; Luesch, Hendrik

Free Radical Biology and Medicine, 2013 , vol. 57, p. 141 - 153 Title/Abstract Full Text View citing articles Show Details


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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Zhou, Binhua; Li, Baojian; Yi, Wei; Bu, Xianzhang; Ma, Lin

Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 13 p. 3759 - 3763 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Kobayashi, Kaoru; Kajiwara, Eri; Ishikawa, Masayuki; Mimura, Hanaka; Oka, Hidenobu; Ejiri, Yoko; Hosoda, Masaya; Chiba, Kan

Drug Metabolism and Pharmacokinetics, 2013 , vol. 28, # 3 p. 265 - 268 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Saundane, Anand R.; Verma, Vaijinath A.; Vijaykumar, Katkar

Medicinal Chemistry Research, 2013 , vol. 22, # 8 p. 3787 - 3793 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Xi, Mei-Yang; Sun, Zhong-Ying; Sun, Hao-Peng; Jia, Jian-Min; Jiang, Zheng-Yu; Tao, Lei; Ye, Ming; Yang, Xi; Wang, Ya-Jing; Xue, Xin; Huang, Jing-Jie; Gao, Yuan; Guo, Xiao-Ke; Zhang, Sheng-Lie; Yang, Ying-Rui; Guo, Qing-Long; Hu, Rong; You, Qi-Dong

European Journal of Medicinal Chemistry, 2013 , vol. 66, p. 364 - 371 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Xi, Mei-Yang; Jia, Jian-Min; Sun, Hao-Peng; Sun, Zhong-Ying; Jiang, Jie-Wei; Wang, Ya-Jing; Zhang, Min-Ye; Zhu, Jun-Feng; Xu, Li-Li; Jiang, Zheng-Yu; Xue, Xin; Ye, Ming; Yang, Xi; Gao, Yuan; Tao, Lei; Guo, Xiao-Ke; Xu, Xiao-Li; Guo, Qing-Long; Zhang, Xiao-Jin; Hu, Rong; You, QiDong

Journal of Medicinal Chemistry, 2013 , vol. 56, # 20 p. 7925 - 7938 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Zargoosh, Kiomars; Ghayeb, Yousef; Azmoon, Behnaz; Qandalee, Mohammad

Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013 , vol. 112, p. 1 - 6 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Sauer, Tanja; Raithel, Martin; Kressel, Juergen; Muench, Gerald; Pischetsrieder, Monika

Amino Acids, 2013 , vol. 44, # 6 p. 1427 - 1439 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Gharib; Badr; Al-Ghazali; Zahran

Egyptian Journal of Chemistry, 2013 , vol. 56, # 1 p. 1 - 24 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or TestSystem (Pharmacological Data)

tyrosinase

Results

molecular target: tyrosinase

Reference

Wu, Zhengrong; Zheng, Lifang; Li, Yang; Su, Feng; Yue, Xiaoxuan; Tang, Wei; Ma, Xiaoyan; Nie, Junyu; Li, Hongyu

Food Chemistry, 2012 , vol. 134, # 2 p. 1128 - 1131 Title/Abstract Full Text View citing articles Show Details


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73 of 549

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or TestSystem (Pharmacological Data)

tyrosinase

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

Ca. 55 μmol/l

Reference

Wu, Zhengrong; Zheng, Lifang; Li, Yang; Su, Feng; Yue, Xiaoxuan; Tang, Wei; Ma, Xiaoyan; Nie, Junyu; Li, Hongyu

Food Chemistry, 2012 , vol. 134, # 2 p. 1128 - 1131 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

radical-scavenging

Species or TestSystem (Pharmacological Data)

DPPH

Kind of Dosing (Pharmacological Data)

comparative comp. dissolved in ethanol

Further Details (Pharmacological Data)

DPPH: 1,1-di-phenyl-2-picrylhydrazyl

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

Ca. 11 μmol/l

Reference

Wu, Zhengrong; Zheng, Lifang; Li, Yang; Su, Feng; Yue, Xiaoxuan; Tang, Wei; Ma, Xiaoyan; Nie, Junyu; Li, Hongyu

Food Chemistry, 2012 , vol. 134, # 2 p. 1128 - 1131 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

radical scavenging

Species or TestSystem (Pharmacological Data)

1,1-diphenyl-2-picryl hydrazyl

Concentration (Pharmacological Data)

25 - 100 μg/ml

Method (Pharmacological Data)

name of assay/method: Hatano’s method

Further Details (Pharmacological Data)

radical scavenging activity (RSA)

Type (Pharmacological Data)

RSA

Value of Type (Pharmacological Data)

86.44 - 94.06 percent

Reference

Saundane Anand; Walmik, Prabhaker

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012 , vol. 51, # 11 p. 1593 - 1606 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

radical scavenging


74 of 549

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76 of 549

Species or TestSystem (Pharmacological Data)

1,1-diphenyl-2-picryl hydrazyl

Concentration (Pharmacological Data)

25 - 100 μg/ml

Method (Pharmacological Data)

name of assay/method: Hatanos method

Further Details (Pharmacological Data)

radical scavenging activity (RSA)

Type (Pharmacological Data)

RSA

Value of Type (Pharmacological Data)

86.44 - 94.06 percent

Reference

Saundane Anand; Walmik, Prabhaker

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012 , vol. 51, # 11 p. 1593 - 1606 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

radical scavenging

Species or TestSystem (Pharmacological Data)

1,1-diphenyl-2-picryl hydrazyl

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

14.64 μg/ml

Reference

Saundane Anand; Walmik, Prabhaker

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012 , vol. 51, # 11 p. 1593 - 1606 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

reducing power

Species or TestSystem (Pharmacological Data)

potassium ferricyanide

Concentration (Pharmacological Data)

20 - 80 μg/ml

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Type (Pharmacological Data)

reducing power

Value of Type (Pharmacological Data)

0.88 - 1.308

Reference

Saundane Anand; Walmik, Prabhaker

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012 , vol. 51, # 11 p. 1593 - 1606 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Saundane Anand; Kalpana; Manjunatha, Yarlakatti

Indian Journal of Heterocyclic Chemistry, 2012 , vol. 21, # 3 p. 193 - 200 Title/Abstract Full Text View citing articles Show Details


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Effect (Pharmacological Data)

Nrf2 response; activation of

Species or TestSystem (Pharmacological Data)

neuroblastoma SH-SY5Y-Neh2-luc cells of human

Concentration (Pharmacological Data)

16 μmol/l

Further Details (Pharmacological Data)

Nrf2: nuclear factor erythroid 2-related factor 2; activation rate related to: Neh2 domain of Nrf2

Type (Pharmacological Data)

activation rate

Value of Type (Pharmacological Data)

100 percent

Reference

Smirnova, Natalya A.; Haskew-Layton, Renee E.; Basso, Manuela; Hushpulian, Dmitry M.; Payappilly, Jimmy B.; Speer, Rachel E.; Ahn, Young-Hoon; Rakhman, Ilay; Cole, Philip A.; Pinto, John T.; Ratan, Rajiv R.; Gazaryan, Irina G.

Chemistry and Biology, 2011 , vol. 18, # 6 p. 752 - 765 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic fibroblast cells of C57BL/6 mouse; genetically modified/infected with: Nrf2+/+

Further Details (Pharmacological Data)

MTT assay; Nrf2: nuclear factor-erythroid 2 p45-related factor 2; test species pre-treated with 3 μM sulforaphane; the data presented represent LD50 of test species that had been primed with 3μM sulforaphane when expressed as a percentage of LD50 of test species that had not been primed, but were pre-treated with 0.1percent (v/v) DMSO

Type (Pharmacological Data)

relative increase in resistance

Value of Type (Pharmacological Data)

173 percent

Reference

Higgins, Larry G.; Hayes, John D.

Chemico-Biological Interactions, 2011 , vol. 192, # 1-2 p. 37 - 45 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

embryonic fibroblast cells of C57BL/6 mouse; genetically modified/infected with: Nrf2-/-

Further Details (Pharmacological Data)

MTT assay; Nrf2: nuclear factor-erythroid 2 p45-related factor 2; the data presented represent LD50 of test species for the title comp. expressed as a percentage of LD50 of Nrf2+/+ fibroblasts

Type (Pharmacological Data)

relative sensitivity

Value of Type (Pharmacological Data)

44 percent

Reference

Higgins, Larry G.; Hayes, John D.

Chemico-Biological Interactions, 2011 , vol. 192, # 1-2 p. 37 - 45 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem

mammary AREc32 cells of human


(Pharmacological Data)

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82 of 549

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Further Details (Pharmacological Data)

ARE: antioxidant response element; CD: concentration of title comp. required to double luciferase reporter activity

Type (Pharmacological Data)

CD

Value of Type (Pharmacological Data)

1.4 μmol/l

Reference

Higgins, Larry G.; Hayes, John D.

Chemico-Biological Interactions, 2011 , vol. 192, # 1-2 p. 37 - 45 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

5 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in absence of CuCl2; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control

Value of Type (Pharmacological Data)

1.1

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

5 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of CuCl2; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control

Value of Type (Pharmacological Data)

32.6

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological

ARE-luciferase reporter activity; induction of


Data)

84 of 549

85 of 549

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

5 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of CuCl2; cells pretreated with L-buthionine-S,R-sulfoximine plus serum for 24 h; control luciferase activity was set to 1.0; fold of control related to: luciferase

Type (Pharmacological Data)

fold of control

Value of Type (Pharmacological Data)

70

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

5 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of CuCl2; cells pretreated with sulforaphane plus serum for 24 h; control luciferase activity was set to 1.0; fold of control related to: luciferase

Type (Pharmacological Data)

fold of control

Value of Type (Pharmacological Data)

9

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control


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Value of Type (Pharmacological Data)

20

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of CoCl2; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control

Value of Type (Pharmacological Data)

35

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

10 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of NiSO4; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control

Value of Type (Pharmacological Data)

37

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ARE-luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

mammary AREc32 reporter cells of human; genetically modified/infected with: ARE-luciferase

Concentration (Pharmacological Data)

10 μmol/l


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Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

ARE: antioxidant response element; test carried out in presence of FeCl2; control luciferase activity was set to 1.0; fold to control related to: luciferase

Type (Pharmacological Data)

fold to control

Value of Type (Pharmacological Data)

38

Reference

Wang, Xiu Jun; Hayes, John D.; Higgins, Larry G.; Wolf, C. Roland; Dinkova-Kostova, Albena T.

Chemistry and Biology, 2010 , vol. 17, # 1 p. 75 - 85 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

heat-induced lipid oxidation; inhibition of

Species or TestSystem (Pharmacological Data)

eicosapentaenoic acid

Concentration (Pharmacological Data)

20 - 400 μg/ml

Further Details (Pharmacological Data)

PDP value is concentration-dependent and assay-dependent

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

16.2 - 74.5 percent

Reference

Rupasinghe, H. P. Vasantha; Erkan, Naciye; Yasmin, Afsana

Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 2 p. 1233 - 1239 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UV-induced lipid oxidation; inhibition of

Species or TestSystem (Pharmacological Data)

eicosapentaenoic acid

Concentration (Pharmacological Data)

20 - 400 μg/ml

Further Details (Pharmacological Data)

PDP value is concentration-dependent and assay-dependent

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

24.2 - 81.7 percent

Reference

Rupasinghe, H. P. Vasantha; Erkan, Naciye; Yasmin, Afsana

Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 2 p. 1233 - 1239 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

AAPH-induced lipid oxidation; inhibition of

Species or TestSystem (Pharmacological Data)

eicosapentaenoic acid


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Concentration (Pharmacological Data)

20 - 400 μg/ml

Further Details (Pharmacological Data)

PDP value is concentration-dependent and assay-dependent

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

57.9 - 77.8 percent

Reference

Rupasinghe, H. P. Vasantha; Erkan, Naciye; Yasmin, Afsana

Journal of Agricultural and Food Chemistry, 2010 , vol. 58, # 2 p. 1233 - 1239 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Nrf2 signalling; activation of

Species or TestSystem (Pharmacological Data)

liver carcinoma HepG2 cells of human; genetically modified/infected with: FRET β-lactamase reporter system under control of ARE

Further Details (Pharmacological Data)

test cells referred to as ARE-bla HepG2 cells; response ratio defined as FRET activity of Nrf2 GeneBlazer assay of title comp. divided by FRET activity at baseline; ARE: antioxidant response element; Nrf2: nuclear factor erythroid 2-related factor 2; concentration at response ratio of 2 (CRR2); CRR2 related to: Nrf2

Type (Pharmacological Data)

CRR2

Value of Type (Pharmacological Data)

0.95 μmol/l

Reference

Wu, Raymond P.; Hayashi, Tomoko; Cottam, Howard B.; Jin, Guangyi; Yao, Shiyin; Wu, Christina C. N.; Rosenbach, Michael D.; Corr, Maripat; Schwab, Richard B.; Carson, Dennis A.

Proceedings of the National Academy of Sciences of the United States of America, 2010 , vol. 107, # 16 p. 7479 - 7484 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

peripheral blood mononuclear cells of human

Further Details (Pharmacological Data)

LD50: concentration that induces 50percent cytotoxicity; lethal concentration (LD)

Type (Pharmacological Data)

LD50

Value of Type (Pharmacological Data)

65 μmol/l

Reference

Wu, Raymond P.; Hayashi, Tomoko; Cottam, Howard B.; Jin, Guangyi; Yao, Shiyin; Wu, Christina C. N.; Rosenbach, Michael D.; Corr, Maripat; Schwab, Richard B.; Carson, Dennis A.

Proceedings of the National Academy of Sciences of the United States of America, 2010 , vol. 107, # 16 p. 7479 - 7484 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

chronic lymphocytic leukemia peripheral blood mononuclear cells of human

Further Details (Pharmacological Data)

LD50: concentration that induces 50percent cytotoxicity; lethal concentration (LD)

Type (Pharmacological

LD50


Data)

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Value of Type (Pharmacological Data)

6 μmol/l

Reference

Wu, Raymond P.; Hayashi, Tomoko; Cottam, Howard B.; Jin, Guangyi; Yao, Shiyin; Wu, Christina C. N.; Rosenbach, Michael D.; Corr, Maripat; Schwab, Richard B.; Carson, Dennis A.

Proceedings of the National Academy of Sciences of the United States of America, 2010 , vol. 107, # 16 p. 7479 - 7484 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cell viability; inhibition of

Species or TestSystem (Pharmacological Data)

primary brain astrocytes of human

Results

no effect

Reference

Kim, Kyu-Han; Jeong, Jae-Yeon; Surh, Young-Joon; Kim, Kyu-Won

Nucleic Acids Research, 2010 , vol. 38, # 1 art. no. GKP865, p. 48 - 59 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cell viability; inhibition of

Species or TestSystem (Pharmacological Data)

primary cerebral astrocytes of mouse

Results

no effect

Reference

Kim, Kyu-Han; Jeong, Jae-Yeon; Surh, Young-Joon; Kim, Kyu-Won

Nucleic Acids Research, 2010 , vol. 38, # 1 art. no. GKP865, p. 48 - 59 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Nrf2-dependent transcriptional activation of ATF3 gene; increase of

Species or TestSystem (Pharmacological Data)

primary brain astrocytes of human; genetically modified/infected with: pATF3-3.6k-luc-mut

Concentration (Pharmacological Data)

100 μmol/l

Further Details (Pharmacological Data)

effect determined after 24 h incubation; ATF3: activating transcription factor 3; Nrf2: NF-E2-related factor 2

Results

no effect (related to ATF3 gene)

Reference

Kim, Kyu-Han; Jeong, Jae-Yeon; Surh, Young-Joon; Kim, Kyu-Won

Nucleic Acids Research, 2010 , vol. 38, # 1 art. no. GKP865, p. 48 - 59 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Nrf2-dependent transcriptional activation of ATF3 gene; increase of

Species or TestSystem (Pharmacological Data)

primary brain astrocytes of human; genetically modified/infected with: pATF3-3.6k-luc

Concentration (Pharmacological Data)

100 μmol/l

Further Details (Pharmacological Data)

effect determined after 24 h incubation; ATF3: activating transcription factor 3; Nrf2: NF-E2-related factor 2; fold increase related to: ATF3 gene

Type (Pharmacological Data)

fold increase

Value of Type

2


(Pharmacological Data)

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Reference

Kim, Kyu-Han; Jeong, Jae-Yeon; Surh, Young-Joon; Kim, Kyu-Won

Nucleic Acids Research, 2010 , vol. 38, # 1 art. no. GKP865, p. 48 - 59 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UGT1A10 mRNA; induction of

Species or TestSystem (Pharmacological Data)

esophageal squamous carcinoma KYSE70 cells of human; genetically modified/infected with: human UGT1A10 500 bp fragment, pRL-TK

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

fold induction: luciferase activity relative to luciferase activity in test cells transfected with empty pGL3 vector

Type (Pharmacological Data)

fold induction

Value of Type (Pharmacological Data)

2.5

Reference

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UGT1A8 mRNA; induction of

Species or TestSystem (Pharmacological Data)

esophageal squamous carcinoma KYSE70 cells of human; genetically modified/infected with: human UGT1A8 500 bp fragment, pRL-TK

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

fold induction: luciferase activity relative to luciferase activity in test cells transfected with empty pGL3 vector

Type (Pharmacological Data)

fold induction

Value of Type (Pharmacological Data)

2.7

Reference

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UGT1A9 mRNA; induction of

Species or TestSystem (Pharmacological Data)

esophageal squamous carcinoma KYSE70 cells of human; genetically modified/infected with: human UGT1A9 530 bp fragment, pRL-TK

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing

title comp. dissolved in DMSO


(Pharmacological Data)

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Results

no effect

Reference

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UGT1A9 mRNA; induction of

Species or TestSystem (Pharmacological Data)

esophageal squamous carcinoma KYSE70 cells of human; genetically modified/infected with: human UGT1A9 ARE-143 Thr137Gly mutant, pRL-TK

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

fold induction: luciferase activity relative to luciferase activity in test cells transfected with empty pGL3 vector

Type (Pharmacological Data)

fold induction

Value of Type (Pharmacological Data)

1.8

Reference

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

UGT1A9 mRNA; induction of

Species or TestSystem (Pharmacological Data)

esophageal squamous carcinoma KYSE70 cells of human; genetically modified/infected with: human UGT1A9 ARE-143 mut-like 1A10, pRL-TK

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Further Details (Pharmacological Data)

fold induction: luciferase activity relative to luciferase activity in test cells transfected with empty pGL3 vector

Type (Pharmacological Data)

fold induction

Value of Type (Pharmacological Data)

2.1

Reference

Kalthoff, Sandra; Ehmer, Ursula; Freiberg, Nicole; Manns, Michael P.; Strassburg, Christian P.

Journal of Biological Chemistry, 2010 , vol. 285, # 9 p. 5993 - 6002 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

repression of NRF2; induction of

Species or TestSystem (Pharmacological Data)

HeLa cells; genetically modified/infected with: pcDNA-Myc-His-KEAP1, HA-NRF2

Further Details (Pharmacological Data)

KEAP1: adaptor of a Cul3-ubiquitin ligase complex that ubiquitinates NRF2 and marks it for proteasomal degradation; HA: hemagglutinin; NRF2: transcription factor; at 5 h; Western blot; effective concentration related to: NRF2


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Type (Pharmacological Data)

effective concentration

Value of Type (Pharmacological Data)

80 μmol/l

Reference

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

repression of NRF2; induction of

Species or TestSystem (Pharmacological Data)

HeLa cells; genetically modified/infected with: pcDNA-Myc-His-KEAP1, HA-NRF2

Further Details (Pharmacological Data)

KEAP1: adaptor of a Cul3-ubiquitin ligase complex that ubiquitinates NRF2 and marks it for proteasomal degradation; HA: hemagglutinin; NRF2: transcription factor; at 5 h; Western blot

Results

molecular target: NRF2

Reference

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

repression of NRF2; induction of

Species or TestSystem (Pharmacological Data)

HeLa cells; genetically modified/infected with: pcDNA-Myc-His-KEAP1 Cys151S mutant, HA-NRF2

Concentration (Pharmacological Data)

80 μmol/l

Further Details (Pharmacological Data)

KEAP1: adaptor of a Cul3-ubiquitin ligase complex that ubiquitinates NRF2 and marks it for proteasomal degradation; HA: hemagglutinin; NRF2: transcription factor; at 5 h; Western blot

Results

no effect (related to NRF2)

Reference

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

repression of NRF2; induction of

Species or TestSystem (Pharmacological Data)

HeLa cells; genetically modified/infected with: pcDNA-Myc-His-KEAP1 Cys226S mutant, HA-NRF2

Further Details (Pharmacological Data)

KEAP1: adaptor of a Cul3-ubiquitin ligase complex that ubiquitinates NRF2 and marks it for proteasomal degradation; HA: hemagglutinin; NRF2: transcription factor; at 5 h; Western blot; effective concentration related to: NRF2

Type (Pharmacological Data)

effective concentration

Value of Type (Pharmacological Data)

80 μmol/l

Reference

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

repression of NRF2; induction of

Species or TestSystem (Pharmacological

HeLa cells; genetically modified/infected with: pcDNA-Myc-His-KEAP1 Cys226S mutant, HA-NRF2


Data)

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Further Details (Pharmacological Data)

KEAP1: adaptor of a Cul3-ubiquitin ligase complex that ubiquitinates NRF2 and marks it for proteasomal degradation; HA: hemagglutinin; NRF2: transcription factor; at 5 h; Western blot

Results

molecular target: NRF2

Reference

Fourquet, Simon; Guerois, Raphael; Biard, Denis; Toledano, Michel B.

Journal of Biological Chemistry, 2010 , vol. 285, # 11 p. 8463 - 8471 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative stability; increase of

Species or TestSystem (Pharmacological Data)

olive oil

Concentration (Pharmacological Data)

100 ppm

Kind of Dosing (Pharmacological Data)

comparative compound dissolved in DMSO

Further Details (Pharmacological Data)

oxidative stability index for negative control: 22.00 h; negative control: vehicle

Type (Pharmacological Data)

oxidative stability index

Value of Type (Pharmacological Data)

32.33 h

Reference

Kiritsakis, Kostas; Kontominas; Kontogiorgis; Hadjipavlou-Litina; Moustakas; Kiritsakis

JAOCS, Journal of the American Oil Chemists' Society, 2010 , vol. 87, # 4 p. 369 - 376 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free-radical scavenging

Species or TestSystem (Pharmacological Data)

DPPH radical

Concentration (Pharmacological Data)

0.28 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMF

Further Details (Pharmacological Data)

electron spin resonance-DPPH method; DPPH: 1,1-diphenyl-2-picrylhydrazyl

Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

84.9 percent

Reference

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free-radical scavenging

Species or TestSystem (Pharmacological Data)

DPPH radical


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114 of 549

Concentration (Pharmacological Data)

0.28 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMF

Further Details (Pharmacological Data)

electron spin resonance-DPPH method; DPPH: 1,1-diphenyl-2-picrylhydrazyl

Results

molecular target: DPPH radical

Reference

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free-radical scavenging

Species or TestSystem (Pharmacological Data)

hydrogen peroxide

Concentration (Pharmacological Data)

20 - 100 μg/ml

Further Details (Pharmacological Data)

hydrogen peroxide scavenging assay; inhibitory concentration (IC)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

58.17 μg/ml

Reference

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free-radical scavenging

Species or TestSystem (Pharmacological Data)

hydrogen peroxide

Concentration (Pharmacological Data)

20 - 100 μg/ml

Further Details (Pharmacological Data)

hydrogen peroxide scavenging assay

Type (Pharmacological Data)

scavenging rate

Value of Type (Pharmacological Data)

15 - 74 percent

Reference

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free-radical scavenging

Species or TestSystem (Pharmacological Data)

hydrogen peroxide

Concentration (Pharmacological

20 - 100 μg/ml


Data)

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116 of 549

117 of 549

Further Details (Pharmacological Data)

hydrogen peroxide scavenging assay

Results

molecular target: hydrogen peroxide

Reference

El-Ebiary, Nora M. A.; Swellem, Randa H.; Mossa, Abdel-Tawab H.; Nawwar, Galal A. M.

Archiv der Pharmazie, 2010 , vol. 343, # 9 p. 528 - 534 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Kelch-like ECH-associated protein 1 binding

Species or TestSystem (Pharmacological Data)

IMR-32 cells; genetically modified/infected with: hNQO1-ARE-luc reporter gene construct

Further Details (Pharmacological Data)

ARE-luciferase reporter gene assay; ARE: antioxidant response element; NQO: NAD(P)H:quinone oxidoreductase; luc: luciferase; effective concentration (EC)

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

5 - 12 μmol/l

Reference

Hur, Wooyoung; Sun, Zheng; Jiang, Tao; Mason, Daniel E.; Peters, Eric C.; Zhang, Donna D.; Luesch, Hendrik; Schultz, Peter G.; Gray, Nathanael S.

Chemistry and Biology, 2010 , vol. 17, # 5 p. 537 - 547 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Kelch-like ECH-associated protein 1 binding

Species or TestSystem (Pharmacological Data)

IMR-32 cells; genetically modified/infected with: hNQO1-ARE-luc reporter gene construct

Further Details (Pharmacological Data)

ARE-luciferase reporter gene assay; ARE: antioxidant response element; NQO: NAD(P)H:quinone oxidoreductase; luc: luciferase

Results

molecular target: Kelch-like ECH-associated protein 1

Reference

Hur, Wooyoung; Sun, Zheng; Jiang, Tao; Mason, Daniel E.; Peters, Eric C.; Zhang, Donna D.; Luesch, Hendrik; Schultz, Peter G.; Gray, Nathanael S.

Chemistry and Biology, 2010 , vol. 17, # 5 p. 537 - 547 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

chelating capacity

Species or TestSystem (Pharmacological Data)

FeCl2-ferrozine

Concentration (Pharmacological Data)

2 mg/ml

Kind of Dosing (Pharmacological Data)

comparative comp. redissolved in methanol

Further Details (Pharmacological Data)

title comp. chelating rate = 20.22 percent - 68.63 percent at 1 - 20 mg/mL

Type (Pharmacological Data)

chelating rate

Value of Type (Pharmacological Data)

1.61 percent


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119 of 549

120 of 549

Reference

Chen; Zhou; Qiu

Asian Journal of Chemistry, 2010 , vol. 22, # 9 p. 6867 - 6878 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

chelating capacity

Species or TestSystem (Pharmacological Data)

FeCl2-ferrozine

Concentration (Pharmacological Data)

2 mg/ml

Kind of Dosing (Pharmacological Data)

comparative comp. redissolved in methanol

Further Details (Pharmacological Data)

title comp. chelating rate = 41.56 percent - 75.46 percent at 1 - 20 mg/mL

Type (Pharmacological Data)

chelating rate

Value of Type (Pharmacological Data)

1.61 percent

Reference

Chen; Zhou; Qiu

Asian Journal of Chemistry, 2010 , vol. 22, # 9 p. 6867 - 6878 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free radical scavenging

Species or TestSystem (Pharmacological Data)

1,1-diphenyl-2-picrylhydrazyl

Kind of Dosing (Pharmacological Data)

comparative comp. solution in DMSO

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

7.4 μmol/l

Reference

Yi, Wei; Cao, Ri-Hui; Chen, Zhi-Yong; Yu, Liang; Ma, Lin; Song, Hua-Can

Chemical and Pharmaceutical Bulletin, 2009 , vol. 57, # 11 p. 1273 - 1277 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free radical scavenging capacity

Species or TestSystem (Pharmacological Data)

DPPH radical

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

DPPH: 2,2-diphenylpicrylhydrazyl

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

86.4 percent


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122 of 549

123 of 549

Reference

El-Massrry, Khaled F.; El-Ghorab, Ahmed H.; Shaaban, Hamdy A.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 12 p. 5265 - 5270 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

β-carotene bleaching; inhibition of

Species or TestSystem (Pharmacological Data)

β-carotene

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

tested at 20 min

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

87.2 percent

Reference

El-Massrry, Khaled F.; El-Ghorab, Ahmed H.; Shaaban, Hamdy A.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 12 p. 5265 - 5270 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

β-carotene bleaching; inhibition of

Species or TestSystem (Pharmacological Data)

β-carotene

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

tested at 120 min

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

Ca. 80 percent

Reference

El-Massrry, Khaled F.; El-Ghorab, Ahmed H.; Shaaban, Hamdy A.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 12 p. 5265 - 5270 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

free radical scavenging capacity

Species or TestSystem (Pharmacological Data)

DPPH radical

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

DPPH: diphenylpicrylhydrazyl

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

86.4 percent


124 of 549

Reference

El-Massrry, Khaled F.; El-Ghorab, Ahmed H.; Shaaban, Hamdy A.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2009 , vol. 57, # 12 p. 5265 - 5270 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Nrf2 protein expression; effect on

Species or TestSystem (Pharmacological Data)

pRS-hNrf2 vectors transfected into human breast carcinoma MCF7 cells

Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud

Results

Nrf2 protein expression on both whole-cell (Cru) and nuclear extracts were detected after treatment with 10 μM title compound for 24 hours; figure is given

Location

Page/Page column 14; 22-26; 2/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

125 of 549

Effect (Pharmacological Data)

luciferase reporter activity; effect on

Species or TestSystem (Pharmacological Data)

pGL3-nxARE constucts transfected into human breast carcinoma MCF7 cells

Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud

Results

when MCF7 cells transfected with 1x, 2x, 4x, 6x and 8x ARE copies in the pGL3 promoter vector, there was good correlation on the level of induction of luciferase activity by 50 μM title compound; pGL-8xARE transfected into human breast carcinoma MCF7 cells showed the highest level of luciferase activity in 50 μM title compound; figure is given

Location

Page/Page column 15; 22-26; 2/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

126 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological

pGL-GSTA2.41bp-ARE construct transfected into human breast carcinoma MCF7 cells


Data) Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud

Results

luciferase activity in MCF7 cells was induced up to 50-fold by overnight treatment with 50 μM title compound

Location

Page/Page column 22-26; 44-45

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

127 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

pGL-GSTA2.41bp-ARE construct transfected into human hepatoblastoma HepG2 cells

Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud

Results

luciferase activity in HepG2 cells was induced between 2- and 4-fold after an overnight treatment with 50 μM title compound

Location

Page/Page column 22-26; 44-45

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

128 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

pGL-GSTA2.41bp-ARE construct transfected into chinese hamster ovarian carcinoma CHO cells

Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ


pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud Results

luciferase activity in CHO cells was induced between 2- and 4-fold after an overnight treatment with 50 μM title compound

Location

Page/Page column 22-26; 44-45

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

129 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

pGL-GSTA2.41bp-ARE construct transfected into mouse hepatoma Hepa1 cells

Method (Pharmacological Data)

Generation of a stable cell line expressing a functional ARE-driven reporter trans-geneIn this study, a series of ARE-luciferase reporter plasmids containing either one, two, four, six or eight copies of the cis-element common to the rat GSTA2 and mouse gstal gene promoters were made. The ARE sequences are listed in Table 1. These reporter constructs were tested by transient transfection in MCF7 and HepG2 cells. As shown in Figure 2, increasing the number of copies of the ARE in the promoter of pGL3 had no significant effect on the basal level of luciferase activity observed under normal homeostatic conditions. However, there was a good correlation between the number of ARE copies in the pGL3 promoter vector and the level of induction of luciferase activity by tBHQ in the MCF7 cells. These results confirm the findings of Nguyen et al., 1994) in which it was demonstrated that transfection of multiple copies of the rat GSTA2-AKE increased the sensitivity of reporter gene activity (chloramphenicol acetyl transferase) to tBHQ treatment.In order to choose an appropriate cell system for the generation of a stable reporter cell line, ρGL-GSX42.41bρ-ARE was transfected into HepG2, MCF7, CHO, Hepal cells. As shown in Table 2, in transient transfection experiments with this construct, luciferase activity in MCF7 cells was induced up to 50-fold after an overnight treatment with 50 μM tBHQ. By contrast, the reporter gene was only induced between 2- and 4-fold following similar transfection experiments in HepG2, CHO or Hepal cells. Thus, our results showed that MCF7 cells expresses Nrf2 and could provide a sensitive cell system for measuring ARE-driven transcription.We decided to employ pGL-8xARE, which contained eight tandemly arrayed copies of the minimal functional ARE, as the plasmid to generate a reporter stable cell line because this construct gave a reasonably high level of inducible luciferase production following treatment with tBHQ. To this end, pGL-8xARE and pCDNA3.1, which contained a neomycin selectable marker, were stably co- transfected into MCF7 cells and selected in the presence of G418. One hundred and fifty- three G418-resistant clones were isolated. After the first passage, thirty-two clones were kept for further monitoring according to their basal and inducible luciferase activity. Among them, one clone, defined as AREc32, showed low basal and high inducible luciferase activity, and also demonstrated a stable phenotype after more than 20 passages. The rest of the clones were discarded because they showed either a lower induction level (2- to 6-fold) by 10 μM tBHQ, or an unstable phenotype with more passages. Therefore, AREc32 cells were retained for further stud

Results

luciferase activity in Hepa1 cells was induced between 2- and 4-fold after an overnight treatment with 50 μM title compound

Location

Page/Page column 22-26; 44-45

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

130 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells) transiently transfected with the expression construct pHygEF-hNrf2

Method (Pharmacological Data)

Induction of ARE-driven Iuciferase activity in AREc32 cells is mediated by Nrf2In order to confirm that the Iuciferase activity in AREc32 cells was responsive to Nrf2, this CNC bZIP protein was over-expressed in AREc32 cells by transient transfection with the expression construct pHyg-EF-hNrf2. As shown in Figure 3, the control cells where no DNA was included in the transfection mix, gave 13-fold induction of Iuciferase activity when treated with 10 μM tBHQ. When 25 ng of pHyg-EF-hNrf2 plasmid DNA was used per well, neither the basal nor inducible Iuciferase activities were significantly affected. However, following transfection with 50 ng of pHyg-EF-hNrf2 per well, the basal level of Iuciferase activity increased to 2.6-fold, and the inducible level increased to 19-fold. Moreover, following transfection with 100 ng of pHyg-EF-hNrf2, the basal reporter gene activity increased to 4-fold and the inducible level to 25-fold. In different wells, the same amount of pEGFP-Nl, an EGFP expression vector, was transfected into AREc32 cells as a negative control. Neither the basal nor the inducible Iuciferase activities were significantly affected by over-expression of EGFP.To determine whether Nrf2 mediates induction of Iuciferase activity by tBHQ in AREc32 cells, an RNAi vector was used to knockdown its expression. Figure 3 B shows that transfection of AREc32 cells with either pRS-hNr.pound.2 or pRS-GFP vectors did not affect the level of GAPDH mRNA. However, 24h after transfection with pRS-Nrf2, the endogenous mRNA level for Nrf2 was reduced to nearly 40percent of control levels, but its abundance was not affected by transfection with the pRS-GFP vector (Figure 3B). This finding indicates that transfection of pRS-hNrfi specifically suppressed expression of the bZIP factor.Transfection of AREc32 cells with pRS-hNrf2 reduced the basal level of Iuciferase activity to 60percent of control levels (Figure 3C). When 25 ng of pRS-hNrf2 DNA was used per well, the inducibility of Iuciferase activity was not affected significantly, compared to the control cells (10-fold induction) where no DNA was included in the transfection mix. When 50 ng of pRS-hNrf2 DNA was used per well, induction of Iuciferase activity by 10 μM tBHQ was reduced to 8-fold. When 100 ng of pRS-hNrf2 DNA was used per well, only 6-fold induction by tBHQ was detected. In different wells, the basal and inducible Iuciferase activity was not affected when AREc32 cells were transfected with the same amount of pRS-GFP DNA, which targeted GFP mRNA (Figure 3C). These data indicate both basal and inducible luciferase activities in AREc32 cells are mediated by Nrf2 through the ARE. .

Results

treatment with 10μM title compound and transfection with 25 ng of pHyg-EF-hNrf2 per well neither the basal nor inducible luciferase activities were significantly affected; with 50 and 100 ng pHyg-EF-hNrf2 per well, luciferase activity increased 2.6-fold and 4-fold while inducible level increased 19-fold and 25-fold, respectively; figure is given

Location

Page/Page column 15; 22-25; 27-28; 3/26


Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

131 of 549

Effect (Pharmacological Data)

GAPDH mRNA level; effect on

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells) transfected with pRS-hNrf2 vector

Method (Pharmacological Data)

Induction of ARE-driven Iuciferase activity in AREc32 cells is mediated by Nrf2In order to confirm that the Iuciferase activity in AREc32 cells was responsive to Nrf2, this CNC bZIP protein was over-expressed in AREc32 cells by transient transfection with the expression construct pHyg-EF-hNrf2. As shown in Figure 3, the control cells where no DNA was included in the transfection mix, gave 13-fold induction of Iuciferase activity when treated with 10 μM tBHQ. When 25 ng of pHyg-EF-hNrf2 plasmid DNA was used per well, neither the basal nor inducible Iuciferase activities were significantly affected. However, following transfection with 50 ng of pHyg-EF-hNrf2 per well, the basal level of Iuciferase activity increased to 2.6-fold, and the inducible level increased to 19-fold. Moreover, following transfection with 100 ng of pHyg-EF-hNrf2, the basal reporter gene activity increased to 4-fold and the inducible level to 25-fold. In different wells, the same amount of pEGFP-Nl, an EGFP expression vector, was transfected into AREc32 cells as a negative control. Neither the basal nor the inducible Iuciferase activities were significantly affected by over-expression of EGFP.To determine whether Nrf2 mediates induction of Iuciferase activity by tBHQ in AREc32 cells, an RNAi vector was used to knockdown its expression. Figure 3 B shows that transfection of AREc32 cells with either pRS-hNr.pound.2 or pRS-GFP vectors did not affect the level of GAPDH mRNA. However, 24h after transfection with pRS-Nrf2, the endogenous mRNA level for Nrf2 was reduced to nearly 40percent of control levels, but its abundance was not affected by transfection with the pRS-GFP vector (Figure 3B). This finding indicates that transfection of pRS-hNrfi specifically suppressed expression of the bZIP factor.Transfection of AREc32 cells with pRS-hNrf2 reduced the basal level of Iuciferase activity to 60percent of control levels (Figure 3C). When 25 ng of pRS-hNrf2 DNA was used per well, the inducibility of Iuciferase activity was not affected significantly, compared to the control cells (10-fold induction) where no DNA was included in the transfection mix. When 50 ng of pRS-hNrf2 DNA was used per well, induction of Iuciferase activity by 10 μM tBHQ was reduced to 8-fold. When 100 ng of pRS-hNrf2 DNA was used per well, only 6-fold induction by tBHQ was detected. In different wells, the basal and inducible Iuciferase activity was not affected when AREc32 cells were transfected with the same amount of pRS-GFP DNA, which targeted GFP mRNA (Figure 3C). These data indicate both basal and inducible luciferase activities in AREc32 cells are mediated by Nrf2 through the ARE. .

Location

Page/Page column 15; 22-25; 27-28; 4/26

Comment (Pharmacological Data)

No effect

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

132 of 549

Effect (Pharmacological Data)

Nrf2 mRNA level; reduction of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells) transfected with pRS-hNrf2 vector

Method (Pharmacological Data)

Induction of ARE-driven Iuciferase activity in AREc32 cells is mediated by Nrf2In order to confirm that the Iuciferase activity in AREc32 cells was responsive to Nrf2, this CNC bZIP protein was over-expressed in AREc32 cells by transient transfection with the expression construct pHyg-EF-hNrf2. As shown in Figure 3, the control cells where no DNA was included in the transfection mix, gave 13-fold induction of Iuciferase activity when treated with 10 μM tBHQ. When 25 ng of pHyg-EF-hNrf2 plasmid DNA was used per well, neither the basal nor inducible Iuciferase activities were significantly affected. However, following transfection with 50 ng of pHyg-EF-hNrf2 per well, the basal level of Iuciferase activity increased to 2.6-fold, and the inducible level increased to 19-fold. Moreover, following transfection with 100 ng of pHyg-EF-hNrf2, the basal reporter gene activity increased to 4-fold and the inducible level to 25-fold. In different wells, the same amount of pEGFP-Nl, an EGFP expression vector, was transfected into AREc32 cells as a negative control. Neither the basal nor the inducible Iuciferase activities were significantly affected by over-expression of EGFP.To determine whether Nrf2 mediates induction of Iuciferase activity by tBHQ in AREc32 cells, an RNAi vector was used to knockdown its expression. Figure 3 B shows that transfection of AREc32 cells with either pRS-hNr.pound.2 or pRS-GFP vectors did not affect the level of GAPDH mRNA. However, 24h after transfection with pRS-Nrf2, the endogenous mRNA level for Nrf2 was reduced to nearly 40percent of control levels, but its abundance was not affected by transfection with the pRS-GFP vector (Figure 3B). This finding indicates that transfection of pRS-hNrfi specifically suppressed expression of the bZIP factor.Transfection of AREc32 cells with pRS-hNrf2 reduced the basal level of Iuciferase activity to 60percent of control levels (Figure 3C). When 25 ng of pRS-hNrf2 DNA was used per well, the inducibility of Iuciferase activity was not affected significantly, compared to the control cells (10-fold induction) where no DNA was included in the transfection mix. When 50 ng of pRS-hNrf2 DNA was used per well, induction of Iuciferase activity by 10 μM tBHQ was reduced to 8-fold. When 100 ng of pRS-hNrf2 DNA was used per well, only 6-fold induction by tBHQ was detected. In different wells, the basal and inducible Iuciferase activity was not affected when AREc32 cells were transfected with the same amount of pRS-GFP DNA, which targeted GFP mRNA (Figure 3C). These data indicate both basal and inducible luciferase activities in AREc32 cells are mediated by Nrf2 through the ARE. .

Results

24 h after transfection with pRS-Nrf2, the endogenous mRNA level for Nrf2 in 10 μM title compound was reduced to nearly 40percent of control levels; figure is given

Location

Page/Page column 15; 22-25; 27-28; 4/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

133 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or Test-

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells) transfected with pRS-hNrf2 vector


System (Pharmacological Data) Method (Pharmacological Data)

Induction of ARE-driven Iuciferase activity in AREc32 cells is mediated by Nrf2In order to confirm that the Iuciferase activity in AREc32 cells was responsive to Nrf2, this CNC bZIP protein was over-expressed in AREc32 cells by transient transfection with the expression construct pHyg-EF-hNrf2. As shown in Figure 3, the control cells where no DNA was included in the transfection mix, gave 13-fold induction of Iuciferase activity when treated with 10 μM tBHQ. When 25 ng of pHyg-EF-hNrf2 plasmid DNA was used per well, neither the basal nor inducible Iuciferase activities were significantly affected. However, following transfection with 50 ng of pHyg-EF-hNrf2 per well, the basal level of Iuciferase activity increased to 2.6-fold, and the inducible level increased to 19-fold. Moreover, following transfection with 100 ng of pHyg-EF-hNrf2, the basal reporter gene activity increased to 4-fold and the inducible level to 25-fold. In different wells, the same amount of pEGFP-Nl, an EGFP expression vector, was transfected into AREc32 cells as a negative control. Neither the basal nor the inducible Iuciferase activities were significantly affected by over-expression of EGFP.To determine whether Nrf2 mediates induction of Iuciferase activity by tBHQ in AREc32 cells, an RNAi vector was used to knockdown its expression. Figure 3 B shows that transfection of AREc32 cells with either pRS-hNr.pound.2 or pRS-GFP vectors did not affect the level of GAPDH mRNA. However, 24h after transfection with pRS-Nrf2, the endogenous mRNA level for Nrf2 was reduced to nearly 40percent of control levels, but its abundance was not affected by transfection with the pRS-GFP vector (Figure 3B). This finding indicates that transfection of pRS-hNrfi specifically suppressed expression of the bZIP factor.Transfection of AREc32 cells with pRS-hNrf2 reduced the basal level of Iuciferase activity to 60percent of control levels (Figure 3C). When 25 ng of pRS-hNrf2 DNA was used per well, the inducibility of Iuciferase activity was not affected significantly, compared to the control cells (10-fold induction) where no DNA was included in the transfection mix. When 50 ng of pRS-hNrf2 DNA was used per well, induction of Iuciferase activity by 10 μM tBHQ was reduced to 8-fold. When 100 ng of pRS-hNrf2 DNA was used per well, only 6-fold induction by tBHQ was detected. In different wells, the basal and inducible Iuciferase activity was not affected when AREc32 cells were transfected with the same amount of pRS-GFP DNA, which targeted GFP mRNA (Figure 3C). These data indicate both basal and inducible luciferase activities in AREc32 cells are mediated by Nrf2 through the ARE. .

Results

when 50 ng and 100 ng of pRS-hNrf2 DNA was used per well, induction of luciferase activity by 10 μM title compound was reduced to 8-fold and 6-fold, respectively; when 25 ng of pRs-hNrf2 DNA was used per well, induction of luciferase activity by 10 μM title compound was not significantly affected in comparison to the control cells; figure is given

Location

Page/Page column 15; 22-25; 27-28; 5/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

134 of 549

Effect (Pharmacological Data)

luciferase reporter activity; induction of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells)

Method (Pharmacological Data)

Time- and dose-dependent induction of luciferase in AREc32 cellsLuciferase activity in AREc32 cells could be induced by in a time- and dose- dependent manner; after treatment for 24h, luciferase activity was increased 2-fold by 1 μM tBHQ, and 5-fold by 5 μM tBHQ (see Figure 4A and Table 3). A maximum luciferase activity (around 10-fold increase) was seen following treatment with 10 μM tBHQ. Induction of luciferase activity by tBHQ was also timedependent; it increased 4-fold after 8h treatment with 10 μM tBHQ, and reached 10-fold 18h after treatment with the same dose of tBHQ. A similar magnitude of induction of luciferase activity in AREc32 cells was observed after 24h exposure to 10 μM sulforaphane (SUL), a potent NQOl and AKRlC enzyme inducer (Bonnesen et al., 2001).; Method: AREc32 cells were seeded out in 96 well plates and treated with DMSO (control), tBHQ (50 μM), tBHQ + BTB09463 (5 μM) or tBHQ + Retinoic acid (1 μM). After 24 hours incubation, cells were washed and lysed before measuring luciferase activity. BTB09463 is l{4-[(3,4-dichlorobenzyl)oxy]phenyl}ethan-l-one.Results: Luciferase activity is highly inducible by tBHQ in the AREc32 reporter cell line, in this experiment showing a 14-fold induction of expression as compared to the DMSO control. Co-treatment with BTB09463 or Retinoic acid markedly suppressed this induction, by approximately 65percent and 75percent respectively. See Figure 14.

Results

induction of luciferase activity by title compound was time- and dose-dependent; after treatment for 24 h, luciferase activity increased by 2-fold and 5-fold after treatment with 1 and 5 μM title compound, respectively; additionally, induction of luciferase activity increased to 4-fold and 10-fold after 8 h and 18 h of treatment with 10 μM title compound, respectively; at 50 μM, title compound induced luciferase activity to 7.5-14-fold as compared to control; figures are given

Location

Page/Page column 16; 21-25; 28; 46; 6/26; 17/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

135 of 549

Effect (Pharmacological Data)

L-buthioninS,R-sulfoximine (BSO)-induced AKR1C mRNA espression; induction of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells)

Method (Pharmacological Data)

Activation of ARE-driven gene expression by anticancer drugs is redox dependentIn order to examine the whether cellular GSH level has any effect on the ability of anticancer drugs to activate luciferase activity, we pretreated AREc32 cells with 50 μM BSO for 24 h before challenging them with chemotherapeutic agents. As can be seen in Figure 5A, the pre-treatment with BSO caused the induction of luciferase activity by cisplatin and melphalan to be increased to 3and 5-fold, respectively. More remarkably, BSO caused the induction of luciferase activity by chlorambucil and BCNU to be increased to > 10-fold. Such inductions were nearly completely repressed by the addition of 5 mM NAC (Figure 5A). For the treatments of etopside and mitozantrone, we found that BSO pre-treatment did not change luciferase activity significantly (data not shown).To find out whether anticancer drugs similarly activate the expression of an endogenous Nrf2 -regulated gene, we examined expression of AKRlC in AREc32 cells. Without pre-treatment with BSO, the mRNA level of AKRlC was only slightly increased by the treatment of melphalan, cisplatin, chlorambucil. However, when the cells were pre-treated with 50 μM BSO for 24 h, melphalan and cisplatin increased the expression of AKRlC mRNA by 3- and 4-fold, respectively, and chlorambucil increased this mRNA 31 -fold (Figure 5B). Treatment with BCNU induced the expression of AKRlC mRNA 3-fold, and with pre-treatment of BSO BCNU induced AKRlC mRNA 42-fold (Figure 5B). Immunoblotting revealed that AKRlC protein was also increased by these anticancer drugs (Figure 5C). BSO pre-treatment did not further enhance the expression of AKRlC protein by tBHQ treatment. However, this is possibly because the induction of AKRlC by 10 μM tBHQ alone has already reached the maximum level.DISCUSSIONWe have generated a stable ARE-reporter human mammary cell line, AREc32, derived from MCF7 cells, in which only the minimal enhancer


sequence is present to direct expression of the luciferase trans-gene. The ARE employed for this purpose was designed around that found in the promoters of both rat GSTA2 and mouse gstal . In the case gstal, its basal and inducible expression has been shown to be regulated by Nrf2 in vivo (Chanas et al., 2002). We also used the ARE from the promoters of GSTA2 and gstal because, unlike that in human NQOl, it does not contain an embedded API site and the absence of this site within the ARE should facilitate interpretation of induction of reporter gene activity. We have shown that in the AREc32 cells expression of luciferase activity was mediated by Nrf2 and was sensitive to redox status. This cell line gave a 10-fold induction of reporter activity by 10 μM tBHQ, and therefore provides a good model system that can be used to screen chemical libraries in order to identify agonists and antagonists of Nrf2. Results

maximum level of AKR1C induction was reached by treatment with 10 μM title compound; BSO pretreatment did not further enhance the expression of AKR1C protein by title compound treatment; figure is given

Location

Page/Page column 16-17; 22-25; 29-30; 8/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

136 of 549

Effect (Pharmacological Data)

all trans-retinoic acid (ATRA)-induced luciferase activity; suppression of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells)

Method (Pharmacological Data)

Antagonism of inducible ARE-driven gene expression by all trans-retinoic acidThe MCF7-ARE reporter cell line was treated with a number of compounds known to activate the ARE including tBHQ, acrolein, β-naphthoflavone (NF) and SuI. As expected, all of these inducing agents increased luciferase activity in AREc32 cells (Figure 6). Treatment of AREc32 cells with tBHQ, acrolein, NF and SuI in the presence of lμM ATRA however significantly attenuated the increase in ARE-driven luciferase activity affected by the inducing agents. Indeed, following subtraction of the DMSO control from the values obtained, there was almost complete ablation of luciferase activity. In a subsequent experiment (shown in Figure 7A) we examined the dependence of inhibition of the AREdriven response on retinoic acid concentration and also the ability of other retinoid derivates to inhibit the ARE response. Interestingly, all 3 retinoids inhibited the ARE response in a similar dose- dependent manner, the IC50 values being approximately 3 x 10"7M. It is known that these three retinoid

derivatives all bind with approximately equal potency to the retinoic acid receptor suggesting that this mediates the responses observed. In addition, the time dependence of the inhibition of luciferase activity by retinoic acid was determined. As shown in Figure 7B, after a lag phase of approximately 3 hour, luciferase activity in tBHQ-treated cells increased almost linearly over a 24-hour period. However, when AREc32 cells were treated simultaneously with tBHQ and ATRA, the lag phase increased from 3 hour to 16 hours, and thereafter only a modest increase in luciferase activity was between 16 and 24 hours. Results

in the presence of 1 μM all trans-retinoic acid (ATRA), title compound significantly suppressed the increase in luciferase activity of AREc32 cells; after a lag phase of ~3 h, luciferase activity in title compound treated cells increased almost linearly over a 24-hour period; figures are given

Location

Page/Page column 17-18; 30-34; 9/26 - 10/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

137 of 549

Effect (Pharmacological Data)

AKR1C1 gene expression; induction of

Species or TestSystem (Pharmacological Data)

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells)

Method (Pharmacological Data)

All trans-retinoic acid prevents induction of endogenous genes by tBHQIn order to establish whether retinoic acid could inhibit the expression of endogenous genes regulated through the ARE, we investigated the effects of ATRA on the induction of the AKRlCl gene by tBHQ (Figure 8A). In this experiment tBHQ induced the expression of AKRlCl mRNA by approximately 15-fold and this induction was markedly repressed (to just 3-fold induction) by co-incubation with retinoic acid. After subtracting the DMSO control, the inhibition was estimated to be approximately 85percent. We then investigated the effect of ATRA on the induction of AKRlC protein by Western Blot analysis. As can be seen in Figure 8B, the level of this protein was also markedly reduced. Scanning of the Western blots indicated that this reduction was approximately 50percent; this apparent discrepancy between the TaqMan and immunoblotting data is probably due to a lack of specificity in the antibody raised against AKRlCl as it will cross-react with AKRl Cl and probably AKRl C3.In order to investigate whether the observations in MCF7 cells could also be extrapolated to the expression of ARE-regulated genes in vivo, we carried out an experiment where mice were fed a retinoic acid-deficient (i.e. vitamin A-deficient, VAD) diet. Interestingly, in wild-type mice placed on a vitamin A-deficient diet for 6 weeks, a profound induction of the ARE-regulated genes GstM5 GCLC, NQOl and GstAl was observed (Figure 9). The induction of these genes by the VAD diet was dependent on Nrf2 as no increase in GstM5 GCLC, NQOl and GstAl was observed in nrβ'^ mice. On daily administration of ATRA to wildtype mice during the last 2 weeks of them being placed on the VAD diet, the induction of ARE-driven genes was almost completely reversed in the small intestine. This finding demonstrates that the repressive effects of retinoic acid are relevant to the in vivo situation in the GI tract.

Results

title compound treatment at 10 μM induced the expression of AKR1C mRNA by approximately 15-fold; figures are given

Location

Page/Page column 18-19; 30-35; 11/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

138 of 549

Effect (Pharmacological Data)

Nrf2 level; induction of

Species or TestSystem (Pharmacological

antioxidant response element-reporter human mammary carcinoma MCF7 cells (AREc32 cells)


Data) Method (Pharmacological Data)

All trans-retinoic acid does not influence the stability of IVrf2In order establish the mechanism by which retinoic acid exerts its inhibitory effects, we investigated whether the nuclear concentration of Nrfl was changed in the presence of this compound. This, however, was found not to be the case (Figure 11). We therefore conclude that ATRA does not antagonise Nrf2-mediated induction of gene expression by either destabilizing the bZIP factor or by preventing its nuclear translocation.In order to establish whether retinoic acid inhibited the binding of Nrf2 to its enhancer, we carried out electrophoretic mobility shift assays using a core ARE binding sequence. Three complexes were observed to interact with this enhancer (Figure 12) and their binding was reduced in the presence of tBHQ and retinoic acid, indicating that retinoic acid does interfere with the activation of the ARE enhancer element (track 4 v. track 2). Using a further method for the loading of Nrf2 on the ARE enhancer, we were able to confirm that retinoic acid inhibited the binding of Nrf2 to the ARE in the presence of tBHQ (Figure 13). We therefore conclude that ATRA inhibits the ability of Nrf2 to transactivate gene expression by interfering with its recruitment onto AREs in gene promoters.

Results

10 μM title compound treatment significantly induced Nrf2 level as compared to control; figures are given

Location

Page/Page column 20; 36; 14/26

Reference

THE UNIVERSITY COURT OF THE UNIVERSITY OF DUNDEE

Patent: WO2008/12534 A2, 2008 ; Title/Abstract Full Text Show Details

139 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 1 - activity against P. acnes (MIC, MBC and (S)DDA assays)The following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compounds (a) t-butyl-p-hydroquinone (TBHQ), dissolved in ethanol, and (b) zinc pyrithione (ZP), dissolved in DMSO. Both test compounds were sourced from Sigma- Aldrich, UK.Mixtures of TBHQ and ZP were then subjected to SDDA assays as described above, including in the presence of salt and lipid (SL-(S)DDA measurements). Increases in zone diameter (mm) were measured with respect to the ZP in unsupplemented assays and the TBHQ in supplemented assays, these being the compounds showing the larger zones of inhibition during the previous individual disc diffusion assays.For the (S)DDA experiments, 200 μg of TBHQ or ZP was loaded onto each disc.All the (S)DDA experiments were conducted in triplicate.The MIC and MBC results are shown in Table 1 below and the (S)DDA results in Tables 2 (unsupplemented) and 3 (supplemented). All results are collated from a number of experiments.Table 1 Table 2 (unsupplemented (S)DDAs)Table 3 (supplemented (S)DDAs)(SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)These data show that both of the test compounds are active against P. acnes NCTC 737. When the TBHQ is combined with the pyrithione, however, the data demonstrate a synergistic antimicrobial interaction between the two test compounds, with a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in the presence of salt and lipid. Example 5 - activity against Propionibacterium spp (copper pyrithione)Copper (II) pyrithione (CuP) was tested against P. acnes NCTC 737 with a number of quinones, using the same procedure as in Example 3. The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc, with the exception of 2-t-butyl-pbenzoquinone which was used at 100 μg per disc. The TBHQ was dissolved in ethanol and the copper pyrithione, 2-methyl-p- benzoquinone and 2-chloro-pbenzoquinone in DMSO.Table 9 Table 10* Denotes data obtained in a separate series of experiments to those involving TBHQ and CuP.These data demonstrate a synergistic antimicrobial interaction when a quinone is combined with copper pyrithione, there being in nearly all cases a significant increase in zone diameter over that exhibited by either compound alone.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

MBC is 7.8 μg/ml, MIC/MBC is 1

Location

Page/Page column 22-24; 26-27; 33-34

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

140 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 1 - activity against P. acnes (MIC, MBC and (S)DDA assays)The following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compounds (a) t-butyl-p-hydroquinone (TBHQ), dissolved in ethanol, and (b) zinc pyrithione (ZP), dissolved in DMSO. Both test compounds were sourced from Sigma- Aldrich, UK.Mixtures of TBHQ and ZP were then subjected to SDDA assays as described above, including in the presence of salt and lipid (SL-(S)DDA measurements). Increases in zone diameter (mm) were measured with respect to the ZP in unsupplemented assays and the TBHQ in supplemented assays, these being the compounds showing the larger zones of inhibition during the previous individual disc diffusion assays.For the (S)DDA experiments, 200 μg of TBHQ or ZP was loaded onto each disc.All the (S)DDA experiments were conducted in triplicate.The MIC and MBC results are shown in Table 1 below and the (S)DDA results in Tables 2 (unsupplemented) and 3 (supplemented). All results are collated from a number of experiments.Table 1 Table 2 (unsupplemented (S)DDAs)Table 3 (supplemented (S)DDAs)(SL-(S)DDA = (S)DDA carried out in the presence of salt and lipid)These data show that both of the test compounds are active against P. acnes NCTC 737. When the TBHQ is combined with the pyrithione, however, the data demonstrate a synergistic antimicrobial interaction between the two test compounds, with a significant increase in zone diameter over that exhibited by either compound alone. This synergistic interaction is maintained in the presence of salt and lipid. Example 5 - activity against Propionibacterium spp (copper pyrithione)Copper (II) pyrithione (CuP) was tested against P. acnes NCTC 737 with a number of quinones, using the same procedure as in Example 3. The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a


number of experiments.For the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc, with the exception of 2-t-butyl-pbenzoquinone which was used at 100 μg per disc. The TBHQ was dissolved in ethanol and the copper pyrithione, 2-methyl-p- benzoquinone and 2-chloro-pbenzoquinone in DMSO.Table 9 Table 10* Denotes data obtained in a separate series of experiments to those involving TBHQ and CuP.These data demonstrate a synergistic antimicrobial interaction when a quinone is combined with copper pyrithione, there being in nearly all cases a significant increase in zone diameter over that exhibited by either compound alone. Results

unsupplemented disc diffusion assay value is 9.27 mm, 12.20 mm, supplemented (Triolein at 1percent v/v, sodium chloride, 100 mM) disc diffusion assay value is 57.64 mm

Location

Page/Page column 22-27; 33-34

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

141 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum NCTC 11865

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

142 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-002

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details


143 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-003

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

144 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-004

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

145 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-005

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from


the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

62.5 μg/ml

Results

MBC is 62.5 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

146 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-006

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

147 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-007

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ;


Title/Abstract Full Text Show Details

148 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-008

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

149 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-010

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 15.6 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

150 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-017

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA


assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

151 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-019

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

31.25 μg/ml

Results

MBC is 31.25 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

152 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-021

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Results

MBC is 31.25 μg/ml

Location

Page/Page column 22-24; 30-33


Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

153 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-023

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

154 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-026

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

155 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-039

Method

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC


(Pharmacological Data)

and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

156 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-043

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Results

MBC is 15.6 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

157 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-044

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml


Results

MBC is 31.25 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

158 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-046

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

159 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-053

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

160 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem

Propionibacterium granulosum PRP-055


(Pharmacological Data) Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

161 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-059

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

162 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

erythromycin resistant of Propionibacterium acnes PRP-068

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

163 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-101

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

MBC is 7.8 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

164 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-102

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

MBC is 15.6 μg/ml

Location

Page/Page column 22-24; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

165 of 549

Effect (Pharmacological

antimicrobial


Data) Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum NCTC 11865

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 11.50 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

166 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-002

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 18.12 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

167 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-003

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 18.12 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

168 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem

tetracycline resistant of Propionibacterium acnes PRP-004


(Pharmacological Data) Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 19.88 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

169 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-005

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 10.67 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

170 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-006

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 9.42 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

171 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-007

Method

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC


(Pharmacological Data)

and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 12.74 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

172 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-008

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 17.92 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

173 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-010

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 18.54 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

174 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-017

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA


assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Results

disc diffusion assay value is 13.98 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

175 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-019

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 10.36 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

176 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-021

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Location

Page/Page column 22-25; 30-33

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

177 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-023

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were


ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Results

disc diffusion assay value is 18.54 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

178 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-026

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 13.98 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

179 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-039

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 17.71 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

180 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-043

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of


antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Location

Page/Page column 22-25; 30-33

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

181 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-044

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Location

Page/Page column 22-25; 30-33

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

182 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-046

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 20.71 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

183 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-053

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from


the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance. Results

disc diffusion assay value is 17.09 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

184 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-055

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 18.02 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

185 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-059

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 19.88 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

186 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

erythromycin resistant of Propionibacterium acnes PRP-068

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 16.78 mm


Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

187 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-101

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 12.84 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

188 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline, macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-102

Method (Pharmacological Data)

Example 4 - activity aeainst other propionibacteriaThe activities of TBHQ and ZP against a panel of different propionibacteria were assessed using the MIC and MBC assays described above. The results are shown in Table 7, which also indicates the resistance phenotype for each of the test strains.Table 7 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK)](S)DDA assays were then conducted on the two test compounds individually and in combination, against the same panel of test organisms. The solvents used were ethanol for the TBHQ and DMSO for the ZP, and again 200 μg of each test compound was loaded onto each disc. The results are shown in Table 8.Table 8 These data show both TBHQ and ZP to be active against all of the propionibacterial strains tested. Combinations of the two actives, however, appear from the SDDA results to be acting synergistically against most of the test organisms, with significant increases in zone diameters and areas. This potentiation of antibacterial activity is observed against many of the antibiotic resistant strains, a fact likely to be of considerable clinical importance.

Results

disc diffusion assay value is 14.50 mm

Location

Page/Page column 22-25; 30-33

Reference

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

189 of 549

Effect (Pharmacological Data)

Nrf2; activation of

Species or TestSystem (Pharmacological Data)

neuroblastoma IMR-32 cells

Concentration (Pharmacological Data)

50 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells treated with title comp. for 5 h at 37 deg C; cells extracts prepared and after or without incubation with λ phosphatase (30 min at 30 deg C) activation of Nrf2 by phosphorylation determined using immunoblotting

Further Details (Pharmacological Data)

Nrf2: nuclear factor erythroid 2 related factor 2


190 of 549

191 of 549

Results

title comp. induced Nrf2 activation by phosphorylation

Reference

Apopa, Patrick L.; He, Xiaoqing; Ma, Qiang

Journal of Biochemical and Molecular Toxicology, 2008 , vol. 22, # 1 p. 63 - 76 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

Nrf2 content; increase of

Species or TestSystem (Pharmacological Data)

neuroblastoma IMR-32 cells

Concentration (Pharmacological Data)

50 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells treated with title comp. for 5 h at 37 deg C; Nrf2 content determined in cell extracts by immunoblotting

Further Details (Pharmacological Data)

Nrf2: nuclear factor erythroid 2 related factor 2

Results

title comp. increased Nrf2 content in cell extracts

Reference

Apopa, Patrick L.; He, Xiaoqing; Ma, Qiang

Journal of Biochemical and Molecular Toxicology, 2008 , vol. 22, # 1 p. 63 - 76 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml; MIC/MBC ratio = 1

Location

Page/Page column 27-30; 32-34

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ;


Title/Abstract Full Text Show Details

192 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms. (d) Disc diffusion assay (DDA)This is an internationally recognised standard method for qualitatively assessing the antimicrobial activity of a compound.A sterile paper disc was impregnated with a sample of the test compound in a suitable solvent and 30 minutes allowed for the solvents to evaporate (where possible). The disc was then placed on an agar plate onto which the test micro-organism had been inoculated. The plate was then incubated under the conditions described above, following which it was examined visually for signs of microbial growth. If the test compound had antimicrobial activity, a circular zone of no growth would be obtained around the disc. The diameter of this zone of "inhibition" was measured using a ProtoCOL.(TM). automated zone sizer (Synbiosis, Cambridge, UK). In general, a greater diameter and/or area of the zone of inhibition indicates a greater antimicrobial activity in the relevant test compound, although other factors such as test compound mobility through the agar gel may also influence the result.

Results

The diameter of zone of inhibition = 11.04 - 14.68 mm

Location

Page/Page column 27-28; 30-34

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

193 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum NCTC 11865

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml


Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

194 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-002

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

195 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-003

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the


microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

196 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-004

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

197 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-005


Data) Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

62.5 μg/ml

Results

Minimum bactericidal concentration (MBC) = 62.5 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

198 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-006

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type

7.8 μg/ml


(Pharmacological Data) Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

199 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-007

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

200 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-008

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a


standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

201 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-010

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 15.6 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

202 of 549

Effect (Pharmacological Data)

antimicrobial


Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-017

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

203 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-019

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological

MIC


Data) Value of Type (Pharmacological Data)

31.25 μg/ml

Results

Minimum bactericidal concentration (MBC) = 31.25 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

204 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-021

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Results

Minimum bactericidal concentration (MBC) = 31.25 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

205 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-023

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor


of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

206 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-026

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details


207 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-039

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

208 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-043

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then


individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Results

Minimum bactericidal concentration (MBC) = 15.6 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

209 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-044

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Results

Minimum bactericidal concentration (MBC) = 31.25 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

210 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-046

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gram-


negative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

211 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-053

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ;


Title/Abstract Full Text Show Details

212 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-055

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

213 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-059

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth


as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

214 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

erythromycin resistant of Propionibacterium acnes PRP-068

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

215 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-101

Method (Pharmacological

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved


Data)

in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Results

Minimum bactericidal concentration (MBC) = 7.8 μg/ml

Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

216 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-102

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Results

Minimum bactericidal concentration (MBC) = 15.6 μg/ml


Location

Page/Page column 27-30; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

217 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum NCTC 11865

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 11.50 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

218 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-002

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then


individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 18.12 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

219 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-003

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 18.12 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

220 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline resistant of Propionibacterium acnes PRP-004

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the


test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 19.88 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

Show next 20

221 of 549

Hide facts Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-005

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 10.67 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

222 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-006

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was


recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 9.42 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

223 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-007

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 12.74 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

224 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

clindamycin resistant of Propionibacterium acnes PRP-008

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the


relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 17.92 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

225 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-010

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 18.54 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

226 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-017

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7


days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 13.98 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

227 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium granulosum PRP-019

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 10.36 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

228 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-021

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the


roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 0.00 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

229 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin-ketolide resistant of Propionibacterium acnes PRP-023

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 18.54 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

230 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-026

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gram-


negative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 13.98 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

231 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-039

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 17.71 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

232 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-043

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the


chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above. Results

The diameter of zone of inhibition = 0.00 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

233 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium granulosum PRP-044

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 0.00 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

234 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-046


Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 20.71 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

235 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-053

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 17.09 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

236 of 549

Effect (Pharmacological Data)

antimicrobial

Species or Test-

Propionibacterium granulosum PRP-055


System (Pharmacological Data) Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 18.02 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

237 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-059

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 19.88 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

238 of 549

Effect

antimicrobial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

erythromycin resistant of Propionibacterium acnes PRP-068

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 16.78 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

239 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-101

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 12.84 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ;


Title/Abstract Full Text Show Details

240 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

tetracycline/macrolide-lincosamide-streptogramin resistant of Propionibacterium acnes PRP-102

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Results

The diameter of zone of inhibition = 14.50 mm

Location

Page/Page column 27-31; 36-39

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

241 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

black pigmented gram-negative anaerobic of Porphyromonas gingivalis NCTC 11834

Method (Pharmacological Data)

Test micro-organismsThe principal test micro-organism used was Propionibacterium acnes NCTC 737. Other propionibacterial strains, including some P. granulosum strains and including some having antibiotic resistance, were also used as test organisms in Example 4.Propionibacteria are known to be involved in acne, which is a complex, multi-factorial skin disease in which P. acnes and other Propionibacterium spp. play key roles. Activity observed against the chosen test organisms is therefore expected to be a reasonable qualitative predictor of activity against micro-organisms responsible for skin and skin structure infections, in particular acne.All the propionibacteria were cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 6.0; all cultures were incubated anaerobically at 37 °C for 72 hours. Also tested was Porphyromonas gingivalis NCTC 11834 - this is a black pigmented gramnegative anaerobic bacterium belonging to the genus Porphyromonas. Porphyromonas are a human commensal bacterium, predominantly associated with the oral cavity. Clinically, Por. gingivalis is associated with periodontal lesions, infections and adult periodontal disease. Gingivitis (inflammation of the gums that causes bleeding and exposes the base of the teeth) can be a precursor to periodontal disease by allowing Por. gingivalis to infect the areas near the roots of the teeth and thus cause tooth decay and infection.Activity observed against this micro-organism is expected to be a reasonable qualitative predictor of antimicrobial activity, in particular against micro-organisms responsible for periodontal lesions, infections, and periodontal disease.Por. gingivalis was cultured and maintained on Wilkins-Chalgren Anaerobe Medium (agar and broth) at pH 7.0; all cultures were incubated anaerobically at 37 0C for 5-7 days.The following tests were carried out to assess antimicrobial activity against the test organisms.(a) Minimum inhibitory concentration (MIC) assayThis is a standard international method for quantitatively assessing the antimicrobial activity of a compound in a liquid medium. The method used a sterile 96-well microtitre plate, capable of holding about 200 μl of liquid per well. The wells contained liquid culture medium and ranges of decreasing concentrations of the relevant test compound in doubling dilutions (e.g. 1000, 500, 250, 125...μg/ml, etc.. down to 0.49 μg/ml). The culture medium was as described above.The wells were inoculated with a liquid suspension of freshly grown micro-organism and incubated under the conditions described above. After incubation, the microtitre plate was examined visually (with the aid of a light box) for cloudiness in each well, which would indicate microbial growth. The MIC value was recorded as the lowest concentration of test compound required to inhibit microbial growth, i.e., the lowest concentration for which the liquid in the well remained clear. The assays were conducted in duplicate (minimum) and included both negative (culture medium with no micro-organisms) and positive (culture medium plus diluting solvent plus micro-organism) controls.Since inhibition does not necessarily indicate killing of microbial cells, merely that growth as visible to the naked eye has been inhibited, it is desirable to conduct a further test (the MBC assay described below) to establish the concentration of the test compound needed to kill the test organism.(b) Minimum bactericidal concentration (MBC) assayThis assay, normally carried out after an MIC assay, determines the minimum concentration of a compound that is lethal to the micro-organism being tested.Following an MIC assay, a 5 μl sample was withdrawn from the first microtitre well that showed positive growth and from all the subsequent wells that showed no growth. These samples were then individually sub-cultured on antibiotic-free agar medium, under the incubation conditions described above.

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

< 0.49 μg/ml

Results

Minimum bactericidal concentration (MBC) = 0.49 μg/ml; MIC/MBC ratio = <1

Location

Page/Page column 27-30; 40

Reference

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

242 of 549

243 of 549

244 of 549

Effect (Pharmacological Data)

antioxidative

Species or TestSystem (Pharmacological Data)

2,2-diphenyl-1-picrylhydrazyl

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

PDP value is concentration-dependent

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

83.2 percent

Reference

El-Ghorab, Ahmed; Shaaban, Hamdy A.; El-Massry, Khaled F.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2008 , vol. 56, # 13 p. 5021 - 5025 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antioxidative

Species or TestSystem (Pharmacological Data)

linoleic acid

Concentration (Pharmacological Data)

100 μg/ml

Further Details (Pharmacological Data)

PDP value is concentration-dependent

Type (Pharmacological Data)

percent inhibition

Value of Type (Pharmacological Data)

89.9 percent

Reference

El-Ghorab, Ahmed; Shaaban, Hamdy A.; El-Massry, Khaled F.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2008 , vol. 56, # 13 p. 5021 - 5025 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antioxidative

Species or TestSystem (Pharmacological Data)

2,2-diphenyl-1-picrylhydrazyl

Concentration (Pharmacological Data)

100 μg/ml

Type (Pharmacological Data)

percent inhibition


245 of 549

Value of Type (Pharmacological Data)

83.2 percent

Reference

El-Ghorab, Ahmed; Shaaban, Hamdy A.; El-Massry, Khaled F.; Shibamoto, Takayuki

Journal of Agricultural and Food Chemistry, 2008 , vol. 56, # 13 p. 5021 - 5025 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxic

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Location

Page/Page column 25; 99; 70/91

Comment (Pharmacological Data)

No effect

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

246 of 549

Effect (Pharmacological Data)

tert-butyl hydroperoxide (t-BuOOH)-induced cell death; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM abolished the decrease in cell viability induced by t-BuOOH; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

247 of 549

Effect (Pharmacological Data)

NMDA-induced cell death; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM abolished the decrease in cell viability induced by NMDA; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY


Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

248 of 549

Effect (Pharmacological Data)

glutamate-induced cell death; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM abolished the decrease in cell viability induced by glutamate; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

249 of 549

Effect (Pharmacological Data)

caspase-3 activity; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Location

Page/Page column 25; 99; 70/91

Comment (Pharmacological Data)

No effect

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

250 of 549

Effect (Pharmacological Data)

tert-butyl hydroperoxide (t-BuOOH)-induced increase in caspase-3 activity; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM was able to prevent the increase in caspase-3 activity evoked by tBuOOH; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details


251 of 549

Effect (Pharmacological Data)

NMDA-induced increase in caspase-3 activity; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM was able to prevent the increase in caspase-3 activity evoked by NMDA; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

252 of 549

Effect (Pharmacological Data)

glutamate-induced increase in caspase-3 activity; effect on

Species or TestSystem (Pharmacological Data)

neurons

Method (Pharmacological Data)

Example 26: Effect of the Nrf2 Inducer fert-butylhydroquinone (f-BHQ)on Cell Death Induced by f-BuOOH, NMDA, and GlutamateApplication of t-BuOOH (60 μM), NMDA (100 μM), and glutamate (300 μM) each significantly decreased the number of viable neurons after 24 hours, compared to the number of untreated control neurons (Figure 42 A). This decrease was abolished by 20 μM t-BHQ (tert- butylhydroquinone). Furthermore, t-BHQ alone had no effect on neuronal viability.To substantiate the protection observed by t-BHQ treatment, the activity of caspase-3 was examined. Caspase-3 has been described as a terminal effector of the apoptotic-like cell death pathway. t-BuOOH, NMDA and glutamate each induced an increase in caspase-3 activity (Figure 42 B). tBHQ had no effect on basal levels of caspase-3 activity, but was able to prevent the increase evoked by all three stressors (Figure 42 B).Taken together, the above data suggests that 1) Nr.pound.2 translocation mediated by oxidative stress-induced injury is protective in cultured neurons, and 2) nuclear Nr.pound.2 increases in response to t-BuOOH-mediated oxidative stress, but not in response to NMDA/glutamate-mediated excitotoxicity.

Results

title compound at 20 μM was able to prevent the increase in caspase-3 activity evoked by glutamate; figure is given

Location

Page/Page column 25; 99; 70/91

Reference

THE JOHNS HOPKINS UNIVERSITY

Patent: WO2007/5879 A2, 2007 ; Title/Abstract Full Text Show Details

253 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 1 - activity against Propionibacterium spy (disc diffusion assays)The following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compounds t-butylhydroquinone (TBHQ, an alkyl-substituted hydroquinone) and aqueous copper (II) sulphate (both sourced from Sigma- Aldrich).The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and lipid (SL SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the copper sulphate (ie, the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 1 below.Table 1 (SL (S)DDA = (S)DDA with salt and lipid (1percent (v/v) Tween 80) supplementsThese data show that both TBHQ and copper sulphate alone are active against P. acnes. When the quinone and the copper salt are combined, however, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone. This synergy is maintained under the supplemented conditions.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 32-33

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;


Title/Abstract Full Text Show Details

254 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 1 - activity against Propionibacterium spy (disc diffusion assays)The following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compounds t-butylhydroquinone (TBHQ, an alkyl-substituted hydroquinone) and aqueous copper (II) sulphate (both sourced from Sigma- Aldrich).The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and lipid (SL SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the copper sulphate (ie, the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 1 below.Table 1 (SL (S)DDA = (S)DDA with salt and lipid (1percent (v/v) Tween 80) supplementsThese data show that both TBHQ and copper sulphate alone are active against P. acnes. When the quinone and the copper salt are combined, however, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone. This synergy is maintained under the supplemented conditions.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 32-33

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

255 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Staphylococcus aureus ATCC 29213

Method (Pharmacological Data)

Example 3 - activity asainst S. aureus (disc diffusion assays)The following experiments all used S. aureus ATCC 29213 as the test organism. MIC, MBC and DDA assays, as described above, were carried out using the test compounds TBHQ and aqueous copper (II) sulphate, as in Example 1.The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and serum (SS SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the TBHQ (the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 2 below.Table 2(SS (S)DDA = (S)DDA with salt and serum supplements) These data show that TBHQ alone is active against S. aureus. Copper sulphate alone however does not appear to be as active as the quinone, and appears to be inactive against the organism in the disc diffusion assays, at the concentration tested.Surprisingly, when the quinone and the copper salt are combined, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

256 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Staphylococcus aureus ATCC 29213

Method (Pharmacological Data)

Example 3 - activity asainst S. aureus (disc diffusion assays)The following experiments all used S. aureus ATCC 29213 as the test organism. MIC, MBC and DDA assays, as described above, were carried out using the test compounds TBHQ and aqueous copper (II) sulphate, as in Example 1.The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and serum (SS SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the TBHQ (the compound showing the larger zone diameters during the previous disc


diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 2 below.Table 2(SS (S)DDA = (S)DDA with salt and serum supplements) These data show that TBHQ alone is active against S. aureus. Copper sulphate alone however does not appear to be as active as the quinone, and appears to be inactive against the organism in the disc diffusion assays, at the concentration tested.Surprisingly, when the quinone and the copper salt are combined, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

257 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum NCTC 11865

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 10.45 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

258 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-002

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 10.56 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details


259 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-003

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 18.61 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

260 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-004

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 13.80 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

261 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-005

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P.


granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel. Results

title compound demonstrated a DDA zone of 15.05 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

262 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-006

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 9.93 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

263 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-007

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 8.78 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

264 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-008


Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 13.90 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

265 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-010

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 8.68 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

266 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-017

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 9.93 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;


Title/Abstract Full Text Show Details

267 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-019

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Location

Page/Page column 44-47

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

268 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-021

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 8.57 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

269 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-023

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel


Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel. Results

title compound demonstrated a DDA zone of 11.92 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

270 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-026

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 11.29 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

271 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-039

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 17.04 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

272 of 549

Effect (Pharmacological Data)

antimicrobial

Species or Test-

Propionibacterium granulosum PRP-043


System (Pharmacological Data) Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 10.77 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

273 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-044

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Location

Page/Page column 44-47

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

274 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-046

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 14.22 mm


Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

275 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-053

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 9.93 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

276 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium granulosum PRP-055

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 10.04 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

277 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-059

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown


in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel. Results

title compound demonstrated a DDA zone of 10.87 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

278 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-068

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 12.55 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

279 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-101

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 14.01 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

280 of 549

Effect

antimicrobial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

Propionibacterium acnes PRP-102

Method (Pharmacological Data)

Example 7 - activity against other Propionibacterium sppThe activity (MIC by agar dilution and DDA) of copper (II) sulphate pentahydrate (CSPH) alone and in combination with TBHQ was determined against a panel of different propionibacterium strains. For (S)DDA experiments 200 μg of each test compound was added per disc. The TBHQ was dissolved in ethanol and the copper (II) sulphate pentahydrate in deionised water. MIC experiments were performed in duplicate, DDA experiments as single replicates only. SDDA experiments were conducted in triplicate.The MIC and DDA results for the copper salt are shown in Table 11, and SDDA results with TBHQ in Table 12. The tables indicate the resistance phenotype for each of the test species/strains.Table 11 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK).]f lpercent (v/v) trioleinTable 12 [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-Streptogramin (MLS), Macroliode- LincosamideStreptogramin-Ketolide (MLSK).]These data indicate that copper (II) sulphate pentahydrate demonstrates an excellent level of activity against all propionibacterium strains tested. This activity appears to be maintained even under the supplemented (salt and lipid) conditions. However, the majority of P. granulosum strains appear to exhibit a degree of resistance to the copper salt as demonstrated by increased MIC levels and smaller DDA zones of inhibition.When the copper salt and the quinone are combined, however, the synergistic interaction initially observed with P. acnes NCTC 737 was similarly observed with all of the propionibacterium strains tested as part of this panel.

Results

title compound demonstrated a DDA zone of 9.01 mm

Location

Page/Page column 44-47

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

281 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Propionibacterium acnes NCTC 737

Method (Pharmacological Data)

Example 1 - activity against Propionibacterium spy (disc diffusion assays)The following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compounds t-butylhydroquinone (TBHQ, an alkyl-substituted hydroquinone) and aqueous copper (II) sulphate (both sourced from Sigma- Aldrich).The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and lipid (SL SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the copper sulphate (ie, the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 1 below.Table 1 (SL (S)DDA = (S)DDA with salt and lipid (1percent (v/v) Tween 80) supplementsThese data show that both TBHQ and copper sulphate alone are active against P. acnes. When the quinone and the copper salt are combined, however, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone. This synergy is maintained under the supplemented conditions.

Results

title compound gave an antimicrobial activity with zone diameter (S)DDA of 12.20 mm

Location

Page/Page column 32-33

Reference

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

282 of 549

Effect (Pharmacological Data)

antimicrobial

Species or TestSystem (Pharmacological Data)

Staphylococcus aureus ATCC 29213

Method (Pharmacological Data)

Example 3 - activity asainst S. aureus (disc diffusion assays)The following experiments all used S. aureus ATCC 29213 as the test organism. MIC, MBC and DDA assays, as described above, were carried out using the test compounds TBHQ and aqueous copper (II) sulphate, as in Example 1.The two compounds were then subjected in combination to the SDDA assay described above, including in the presence of salt and serum (SS SDDA measurement). Increases in zone diameter (mm) were measured with respect to those observed for the TBHQ (the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds).For all the (S)DDA experiments, 200 μg of each test compound was loaded onto each disc. The TBHQ was dissolved in ethanol and the copper sulphate in deionised water.MIC/MBC experiments were performed in duplicate and (S)DDA experiments in triplicate.The results of the tests on both TBHQ and copper sulphate alone, together with those for the combination, are shown in Table 2 below.Table 2(SS (S)DDA = (S)DDA with salt and serum supplements) These data show that TBHQ alone is active against S. aureus. Copper sulphate alone however does not appear to be as active as the quinone, and appears to be inactive against the organism in the disc diffusion assays, at the concentration tested.Surprisingly, when the quinone and the copper salt are combined, the data demonstrate a synergistic antimicrobial interaction between the two, with a significant increase in zone diameter over that exhibited by either compound alone.

Results

title compound gave an antimicrobial activity with zone diameter of (S)DDA of 40.42 mm and SS (S)DDA of 43.68 mm

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED


Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

283 of 549

284 of 549

285 of 549

Effect (Pharmacological Data)

antiprotozoal

Species or TestSystem (Pharmacological Data)

Leishmania tarentolae

Kind of Dosing (Pharmacological Data)

title comp. dissolved in 100 percent dimethyl sulfoxide at either 1 or 10 mmol/l

Method (Pharmacological Data)

1E6 cells/ml added in 96-well microtiter plates; serial dilutions of title comp. added; plates incubated at 25 deg C for 3 days; inhibition of growth was detd. visually

Further Details (Pharmacological Data)

controls: medium only, cells with medium with or without DMSO

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

0.2 mg/l

Reference

St. George, Stephanie; Bishop, Jeanette V.; Titus, Richard G.; Selitrennikoff, Claude P.

Antimicrobial Agents and Chemotherapy, 2006 , vol. 50, # 2 p. 474 - 479 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antiprotozoal

Species or TestSystem (Pharmacological Data)

Leishmania major LV39

Kind of Dosing (Pharmacological Data)

title comp. dissolved in 100 percent dimethyl sulfoxide at either 1 or 10 mmol/l

Method (Pharmacological Data)

1E6 promastigotes/ml added in 96-well microtiter plates; serial dilutions of title comp. added; plates incubated at 25 deg C for 3 days; inhibition of growth was detd. visually

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1 mg/l

Reference

St. George, Stephanie; Bishop, Jeanette V.; Titus, Richard G.; Selitrennikoff, Claude P.

Antimicrobial Agents and Chemotherapy, 2006 , vol. 50, # 2 p. 474 - 479 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antiprotozoal

Species or TestSystem (Pharmacological Data)

Leishmania major LV39

Concentration (Pharmacological Data)

0.4 mg/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in 100 percent dimethyl sulfoxide at either 1 or 10 mmol/l

Method (Pharmacological Data)

2E5 peritoneal exudate cell macrophages, 1.25E6 amastigotes added per well; treated with title comp.; 3 days later, stained and counterstained; no. of amastigotes/100 macrophages and no. of macrophages with at least one amastigote detd. microscopically


286 of 549

287 of 549

288 of 549

Further Details (Pharmacological Data)

ref.: pentostam; control: medium with or without DMSO

Comment (Pharmacological Data)

No effect

Reference

St. George, Stephanie; Bishop, Jeanette V.; Titus, Richard G.; Selitrennikoff, Claude P.

Antimicrobial Agents and Chemotherapy, 2006 , vol. 50, # 2 p. 474 - 479 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hepatocytes

Concentration (Pharmacological Data)

5 - 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with various concentrations of title comp. for 0.5 to 24 h; lysed; expression of HO-1, NQO1 and Nrf2 proteins measured by Western blotting

Further Details (Pharmacological Data)

controls: untreated cells and β-actin (loading control); HO: heme oxygenase; NQO: NAD<P>H:quinone oxidoreductase; Nrf2: NF-E2-related factor 2; induction of these enzymes represents primary cellular defensive mechanism

Results

title comp. treatment up-regulated HO-1 (200 μmol/l), NQO1 (5-200 μmol/l) and Nrf2 (20-500 μmol/l) in a time-dependent manner; diagram

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

C57BL/6 wild-type neonatal mouse fibroblasts

Concentration (Pharmacological Data)

200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; expression of heme oxygenase-1 (HO) protein measured by Western blotting

Further Details (Pharmacological Data)

controls: untreated cells and β-actin (loading control); induction of HO-1 enzyme represents primary cellular defensive mechanism

Results

title comp. treatment strongly induced HO-1 protein (diagram), but caused a weak induction of NQO1 protein

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

Nrf2 knock-out C57BL/6 neonatal mouse fibroblasts

Concentration (Pharmacological

200 μmol/l


Data)

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290 of 549

291 of 549

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; expression of heme oxygenase-1 (HO-1) and NAD<P>H:quinone oxidoreductase-1 (NQO1) protein measured by Western blotting

Further Details (Pharmacological Data)

controls: untreated cells and β-actin (loading control); induction of these enzymes represents primary cellular defensive mechanism

Results

title comp. failed to induce HO-1 protein (diagram) but caused a weak induction of NQO1

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hepatocytes

Concentration (Pharmacological Data)

200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; total RNA extracted; semi-quantitative RT-PCR analysis of HO-1, NQO1 and Nrf2 performed

Further Details (Pharmacological Data)

controls: untreated cells and β-actin (loading control); HO: heme oxygenase; NQO: NAD<P>H:quinone oxidoreductase; Nrf2: NF-E2-related factor 2

Results

title comp. treatment increased HO-1 and NQO1 mRNA levels; maximal transcriptional activation of enzymes observed at 4 h and then decreased gradually; diagram

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

C57BL/6 wild-type neonatal mouse fibroblasts

Concentration (Pharmacological Data)

200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; phosphorylation changes of ERK1/2, JNK1/2 and Akt analyzed using phospho-specific antibodies

Further Details (Pharmacological Data)

controls: untreated cells; loading control: β-actin

Results

title comp. treatment activated phosphorylation of ERK1/2 (sustained up to 12 h) but not activated JNK1/2; diagram

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological

enzyme; induction of


Data)

292 of 549

293 of 549

Species or TestSystem (Pharmacological Data)

human hepatocytes

Concentration (Pharmacological Data)

200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; phosphorylation changes of ERK1/2, JNK1/2 and Akt analyzed using phospho-specific antibodies

Further Details (Pharmacological Data)

controls: untreated cells; loading control: β-actin

Results

title comp. treatment strongly activated phosphorylation of ERK1/2 and JNK1/2, but failed to activate p85; title comp. did not affect phosphorylation of Akt; diagram

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat hepatocytes

Concentration (Pharmacological Data)

200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells incubated with title comp. for 0.5 to 24 h; lysed; phosphorylation changes of ERK1/2, JNK1/2 and Akt analyzed using phospho-specific antibodies

Further Details (Pharmacological Data)

controls: untreated cells; loading control: β-actin

Results

title comp. treatment strongly activated phosphorylation of ERK1/2 and JNK1/2, but failed to activate p85; title comp. inhibited phosphorylation of Akt; diagram

Reference

Keum, Young-Sam; Han, Yong-Hae; Liew, Celine; Kim, Jung-Hwan; Xu, Changjiang; Yuan, Xiaoling; Shakarjian, Michael P.; Chong, Saeho; Kong, Ah-Ng

Pharmaceutical Research, 2006 , vol. 23, # 11 p. 2586 - 2594 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as

described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The

solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active


against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 33-35; 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

294 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The

solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

295 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 1 - activity against S. aureus -MIC, MBC (S)DDA assaysThe following experiments all used S. aureus ATCC 29213 as the test organism.MIC, MBC and DDA assays, as

described above, were carried out using the test compound benzoyl peroxide (BP) and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt, lipid and blood, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For most (S)DDA assays, 200 μg of each compound was loaded onto each disc. The exceptions were the thymoquinone assays, in which only 50 μg of the benzoquinone was used. The

solvents used were DMSO (for benzoyl peroxide, 2-methyl-p- hydroquinone, 2,3-dimethyl-jy-hydroquinone and 2-ethyl-&jp-hydroquinone) and ethanol (for TBHQ, thymoquinone, p-hydroquinone, .pound.>-benzoquinone and thymohydroquinone).The MIC, MBC and DDA results are shown in Table 1 below and the SDDA results in Table 2. All results are collated from a number of experiments.Table 1* Data variable: synergy observed in some tests and not in othersTable 2 EPO The data in Tables 1 and 2 show that each of the benzo/hydroquinones alone is active against S. aureus ATCC 29213, some strongly so - in particular the substituted benzo/hydroquinones appear to be more active than their unsubstituted counterparts, as indicated by the MIC/MBC results. Activity is maintained, at least to some extent, in the presence of salt, lipid and serum. BP alone is much less, if at all, active against the organism.When BP is combined with a benzo/hydroquinone however, the SDDA data indicate a potential synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and blood, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 12.34 mm and the area increase 186.0 percent. EPO Thus in the presence of a suitable benzo/hydroquinone, the otherwise relatively inactive peroxide can be made very active against 5. aureus. Moreover this synergy is also likely to be retained on topical application to the skin.

Results

title compound resulted in a 41.77 mm disc diffusion assay (DDA); title compound resulted in a 54.16 mm disc diffusion assay (DDA) in the presence of salt; title compound resulted in a 31.44 mm disc diffusion assay (DDA) in the presence of a lipid; title compound resulted in a 10.89 mm disc diffusion assay (DDA) in the presence of blood


Location

Page/Page column 33-35

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

296 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 3 - activity against S. aureus - TTK assaysTTK assays were then conducted, as described above, on samples of BP, TBHQ and a BP/TBHQ mixture, using S. aureus ATCC 29213 as the test organism. The solvents used were DMSO for the BP and ethanol for the TBHQ. The results are shown in Table 3. cfu values were measured at time 0, 0.5 hours and 1 hour.Table 3 EPO These data show that a combination of peroxide and hydroquinone can kill the S. aureus bacteria more quickly than either compound alone when used at the same concentration as in the mixture This provides further evidence of antimicrobial synergy between the two agents

Results

15.6 μg/ml of title compound resulted in a 7.63E5 - 8.47E5 CFU/ml t=0-1.0 wherein time to kill was >1 h

Location

Page/Page column 36-37

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

297 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29213 of Staphylococcus aureus

Method (Pharmacological Data)

Example 4 - activity against S aureus - MTTK assaysSamples containing BP, TBHQ and BP/TBHQ mixtures were also subjected to MTTK assays as described above, using S. aureus ATCC 29213 as the test organism The BP was dissolved in DMSO and the TBHQ in ethanolThe results, after 24 hours, are shown in Table 4 below (The initial starting inoculum contained 3 25 x 107 cfu/ml, 1 x 103 cfu/ml represented the lower detection limit )Table 4Benzoyl Peroxide2 3 4 5O x 0 0.25 x 0.5 x 1 x 2 x 4 x μg/mi 31.3 μg/ml 62.5 μg/ml 125 μg/ml 250 μg/ml 500 μg/mlO x0 μg/ml0.125 xB 0.98 μg/ml0.25 x1.95 μg/mlTBHQ0.5 x 3.9 μg/ml1 x7.8 μg/mt2 x15.6 μg/ml Table 4 identifies three synergistic mixtures of BP and TBHQ, as highlighted in bold on a dark grey background The light grey cells indicate the lowest concentration of EPO each individual active which is sufficient to kill on its own (ie, the MBC). For the synergistic mixtures, the reduction in microbial activity was greater (after 24 hours) than that obtained using either BP or TBHQ alone at the same concentrations as in the mixture.The three synergistic BP/TBHQ combinations were those containing:a) 0.25 x MBC of BP (31.25 μg/ml) + 0.5 x MBC of TBHQ (3.9 μg/ml)b) 0.5 x MBC of BP (62.5 μg/ml) + 0.25 x MBC of TBHQ (1.95 μg/ml)c) 0.5 x MBC of BP (62.5 μg/ml) + 0.5 x MBC of TBHQ (3.9 μg/ml).This further confirms that the peroxide and the hydroquinone may be used together, each at a concentration lower than its individual MBC, to counter staphylococci.This further confirms that the peroxide and the hydroquinone may be used together, each at a concentration lower than its individual MBC, to counter staphylococci. It is likely that mixtures containing higher concentrations of either test compound will also act synergistically against S. aureus ATCC 29213.

Results

mixture of BP and TBHQ showed reduction in microbial activity greater (after 24 hours) than that obtained using title compound alone

Location

Page/Page column 37-38

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

298 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27848 of Staphylococcus simulans

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological

MIC


Data) Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

299 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29971 of Staphylococcus xylosus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

300 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29974 of Staphylococcus cohnii

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details


301 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29970 of Staphylococcus haemolyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

302 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27836 of Staphylococcus warneri

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

303 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27840 of Staphylococcus capitis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used


National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.9 - 3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

304 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27844 of Staphylococcus hominis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

305 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 33753 of Staphylococcus auricularis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

0.98 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

306 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

307 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600-U of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

308 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATCC 12602 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

309 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12604 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

310 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12605 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

311 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12606 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

312 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12607 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

313 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 25923 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

314 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 15 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

315 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

CPHL EMRSA 16 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

316 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 17 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

317 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu3 of Staphylococcus aureus vancomycin (Van)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

318 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu50 of Staphylococcus aureus vancomycin (Van)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

319 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL GISA HO41340156 of Staphylococcus aureus vancomycin (Van)/teicoplanin (Tec)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

320 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 7292 of Staphylococcus saprophyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

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Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

321 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 11047 of Staphylococcus epidermidis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

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322 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATCC 12601 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

323 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27848 of Staphylococcus simulans

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

31.25 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

324 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29971 of Staphylococcus xylosus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.62 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

325 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29971 of Staphylococcus xylosus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

326 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29974 of Staphylococcus cohnii

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC


Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

327 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29970 of Staphylococcus haemolyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

328 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27836 of Staphylococcus warneri

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

329 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATCC 27840 of Staphylococcus capitis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

330 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27844 of Staphylococcus hominis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

1.95 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

331 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27844 of Staphylococcus hominis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

332 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 33753 of Staphylococcus auricularis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

333 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC


Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

334 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600-U of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

335 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12601 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

336 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATCC 12602 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

337 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12604 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

338 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12605 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

339 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12606 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

340 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12607 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC


Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

341 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 25923 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

342 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 15 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

343 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

CPHL EMRSA 16 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

344 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 17 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

345 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu3 of Staphylococcus aureus vancomycin (Van)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

National Collection of Type Cultures (NCTC),.


Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

346 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu50 of Staphylococcus aureus vancomycin (Van)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

347 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL GISA HO42340156 of Staphylococcus aureus vancomycin (Van)/teicoplanin (Tec)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC


Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

348 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 7292 of Staphylococcus saprophyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

349 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 11047 of Staphylococcus epidermidis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

350 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATCC 27848 of Staphylococcus simulans

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 53.07 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

351 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29971 of Staphylococcus xylosus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 49.72 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

352 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29974 of Staphylococcus cohnii

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 60.40 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41


Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

353 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29970 of Staphylococcus haemolyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 51.08 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

354 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27836 of Staphylococcus warneri

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 54.43 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

355 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27848 of Staphylococcus capitis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3


appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Results

title compound resulted in a 73.90 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

356 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 27848 of Staphylococcus hominis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 64.59 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

357 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 33753 of Staphylococcus auricularis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 80.18 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

358 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600 of Staphylococcus aureus

Method (Pharmacological

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of


Data)

each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used

National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 49.24 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

359 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600-U of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 51.24 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

360 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12600-U of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 57.34 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

361 of 549

Effect (Pharmacological Data)

antibacterial


Species or TestSystem (Pharmacological Data)

ATCC 12601 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 57.34 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

362 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12602 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 57.66 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

363 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12604 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 55.03 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ;


Title/Abstract Full Text Show Details

364 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12605 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 59.55 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

365 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12606 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 53.34 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

366 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 12607 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3


Results

title compound resulted in a 54.50 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

367 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 25923 of Staphylococcus aureus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 44.70 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

368 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 15 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 55.14 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

369 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 16 of Staphylococcus aureus methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3


aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains. Results

title compound resulted in a 67.72 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

370 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL EMRSA 17 of Staphylococcus simulans methicillin (Met)/β-lactams resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 51.05 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

371 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu3 of Staphylococcus aureus vancomycin (Van)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 50.73 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

372 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL VISA Mu50 of Staphylococcus aureus vancomycin (Van)-resistant


Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 50.11 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

373 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

CPHL GISA HO41340156 of Staphylococcus aureus vancomycin (Van)/teicoplanin (Tec)-resistant

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 75.37 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

374 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 7292 of Staphylococcus saprophyticus

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 41.67 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

375 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

NCTC 11047 of Staphylococcus epidermidis

Method (Pharmacological Data)

Example 5 - activity against other staphylococci -MIC, MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other staphylococcal bacterial strains, including some with known antibiotic resistance. MIC, MBC and (S)DJDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 5 below and the (S)DDA results in Table 6. All results are collated from a number of experiments. Table 5 indicates the EPO resistance phenotype for each of the test strains, some of which are resistant to many commonly used National Collection of Type Cultures (NCTC),. Methicillin (Met), Vancomycin (Van), Teicoplanin (Tec), not determined (ND)3 epidemic methicillin resistant S. aureus (EMRSA)3 vancomycin intermediate S. aureus (VISA)3 glycopeptide resistant S. aureus (GISA).]* Other uncharacterised antibiotic resistances may be present.Table 6 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the staphylococcal strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. Even in cases where the SDDA zone increase is less than 5 mm, the interaction appears to be indifferent rather than strongly antagonistic, thus providing the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity. These results are likely to be of particular clinical value for the antibiotic resistant test strains.

antibiotics.Table 5 EPO [Abbreviations: American Type Culture Collection (ATCC). Central Public Health Laboratory UK (CPHL)&3

Results

title compound resulted in a 57.34 mm disc diffusion assay (DDA)

Location

Page/Page column 38-41

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

376 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 6 - activity against P. acnes -MIC, MBC (S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each

compound was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, phydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

377 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 6 - activity against P. acnes -MIC, MBC (S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each

compound was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, phydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important


constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

378 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 6 - activity against P. acnes -MIC, MBC (S)DDA assaysThe following experiments all used P. acnes NCTC 737 as the test organism.MIC, MBC and DDA assays, as described above, were carried out using BP and a range of different benzoquinones and hydroquinones. Supplemented DDA assays, in the presence of salt and lipid, were also conducted.Each of the quinones was then subjected, in combination with BP, to the SDDA assay described above. In each case, increases in zone diameter (mm) and area (percent) were measured with respect to those observed for the compound showing the larger zone diameters during the previous disc diffusion assays on the individual compounds. EPO For all (S)DDA assays, 200 μg of each

compound was loaded onto each disc. The solvents used were DMSO (for BP, 2,3-dimethyl-&jp-hydroquinone and hydroquinone) and ethanol (for TBHQ, thymoquinone, phydroquinone axidp- benzoquinone).The MC, MBC and DDA results are shown in Table 7 below and the SDDA results in Table 8. All results are collated from a number of experiments.Table 7Table 8 EPO The data in Tables 7 and 8 show that each of the quinones alone is active against P. acnes ΗCC 737, some (in particular TBHQ, 2,3-dimethyl-p-hydroquinone and 2- ethyl-p-hydroquinone) strongly so. BP is also active against the organism, although less strongly than the more active quinones. In most cases quinone activity is maintained, at least to some extent, in the presence of salt and lipid, which are important constituents of the human skin environment. In some cases quinone activity appears to be potentiated by one or both of the supplements.Again when BP is combined with a benzo/hydroquinone, the SDDA data imply a potentially synergistic antimicrobial interaction between the two, in each case with a significant increase in zone diameter over that exhibited by either compound alone.The BP/TBHQ SDDA assay was repeated in the presence of salt and lipid, as described above. Antibacterial synergy appeared to be retained under these supplemented conditions, the zone diameter increase being 18.34 mm and the area increase 419.8 percent.

Results

title compound resulted in a 9.95 mm disc diffusion assay (DDA); title compound resulted in a 19.48 mm disc diffusion assay (DDA) in the presence of salt; title compound resulted in a 10.37 mm disc diffusion assay (DDA) in the presence of a lipid

Location

Page/Page column 41-43

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

379 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ;


Title/Abstract Full Text Show Details

380 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 11865 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

381 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-002 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

382 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-003 of Propionibacterium acnes tetracycline (Tet)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table


9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

383 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-004 of Propionibacterium acnes tetracycline (Tet)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

384 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-005 of Propionibacterium granulosum macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

62.5 μg/ml


Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

385 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-007 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

386 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-008 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

387 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-010 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant


Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

388 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-017 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

389 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-023 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC


Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

390 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-026 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

391 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-043 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

392 of 549

Effect (Pharmacological Data)

antibacterial


Species or TestSystem (Pharmacological Data)

PRP-044 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

393 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-046 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

1.95 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

394 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-053 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant


peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

395 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-055 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

396 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-059 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details


397 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-068 of Propionibacterium acnes erythromycin (Ery)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

398 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-101 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

399 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-102 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-


Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

400 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 25577 of Propionibacterium avidum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

401 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46


Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

402 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 11865 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

403 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-002 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

404 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-003 of Propionibacterium acnes tetracycline (Tet)-resistant

Method

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against


(Pharmacological Data)

other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

405 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-004 of Propionibacterium acnes tetracycline (Tet)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

406 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-005 of Propionibacterium granulosum macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type

62.5 μg/ml


(Pharmacological Data) Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

407 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-007 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

408 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-008 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

409 of 549

Effect (Pharmacological Data)

antibacterial

Species or Test-

PRP-010 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant


System (Pharmacological Data) Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

410 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-017 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

411 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-023 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.


Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

412 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-026 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

413 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-043 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details


414 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-044 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

31.25 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

415 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-046 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

416 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-053 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an


indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

417 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-055 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

418 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-059 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED


Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

419 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-068 of Propionibacterium acnes erythromycin (Ery)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

420 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-101 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

7.8 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

Show next 20

421 of 549

Hide facts Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-102 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against


(Pharmacological Data)

other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

422 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATC 25577 of Propionibacterium avidum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Type (Pharmacological Data)

MBC

Value of Type (Pharmacological Data)

3.9 μg/ml

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

423 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 737 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 8.65 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED


Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

424 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

NCTC 11865 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 11.00 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

425 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-002 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 28.42 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

426 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-003 of Propionibacterium acnes tetracycline (Tet)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 38.01 mm in disc diffusion assay (DDA)


Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

427 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-004 of Propionibacterium acnes tetracycline (Tet)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 30.32 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

428 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-005 of Propionibacterium granulosum macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Location

Page/Page column 44-46

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

429 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-007 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction


between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Results

title compound resulted in 13.43 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

430 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-008 of Propionibacterium acnes clindamycin (Clin)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 14.47 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

431 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-010 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 18.71 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

432 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-017 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-Lincosamide-


Streptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Results

title compound resulted in 18.40 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

433 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-023 of Propionibacterium acnes macrolide-lincosamide-streptogramin-ketolide (MLSK)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 23.90 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

434 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-026 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 8.18 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

435 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-043 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the


TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains. Results

title compound resulted in 10.56 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

436 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-044 of Propionibacterium granulosum macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 10.70 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

437 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-046 of Propionibacterium acnes

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 17.46 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

438 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-053 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant


Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 23.49 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

439 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-055 of Propionibacterium granulosum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 13.07 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

440 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-059 of Propionibacterium acnes macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 17.56 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

441 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem

PRP-068 of Propionibacterium acnes erythromycin (Ery)-resistant


(Pharmacological Data) Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 20.89 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

442 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-101 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Location

Page/Page column 44-46

Comment (Pharmacological Data)

No effect

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

443 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

PRP-102 of Propionibacterium acnes tetracycline (Tet)/macrolide-lincosamide-streptogramin (MLS)-resistant

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 23.80 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

444 of 549

Effect

antibacterial


(Pharmacological Data) Species or TestSystem (Pharmacological Data)

ATC 25577 of Propionibacterium avidum

Method (Pharmacological Data)

Example 8 - activity against other propionibacteria - MIC MBC (S)DDA assaysThe activities of BP, TBHQ and combinations of the two were tested against other Propionibacteriiim spp strains, including some with known antibiotic resistance. MIC, MBC and (S)DDA assays were carried out as described above for each of the strains.For all (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 9 below and the (S)DDA results in Table 10. All results are collated from a number of experiments. Table 9 indicates the resistance phenotype for each of the test strains.Table 9 EPO [Abbreviations: American Type Culture Collection (ATCC), National Collection of Type Cultures (NCTC), Propionibacterium Panel Number (PRP), Tetracycline (Tet), Erythromycin (Ery), Clindamycin (Clin), Macrolide-LincosamideStreptogramin (MLS), Macroliode- Lincosamide-Streptogramin-Ketolide (MLSK) .]Table 10 EPO Taking an increase in zone size of greater than 5 mm as an indicator of potential synergy, for most of the propionibacterial strains tested the combination of peroxide and hydroquinone exhibits a potentially synergistic antibacterial interaction. In some cases only a small increase in zone diameter is seen in the SDDA tests, potentially indicative of an indifferent interaction between the two test compounds - this could still provide the opportunity to prepare antimicrobial formulations with reduced levels of the potentially irritant peroxide yet without undue loss of antimicrobial activity.These results are likely to be of particular clinical value for the antibiotic resistant test strains.

Results

title compound resulted in 9.16 mm in disc diffusion assay (DDA)

Location

Page/Page column 44-46

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

445 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29212 of Enterococcus faecalis

Method (Pharmacological Data)

Example 10 - activity against E. faecalisThe activities of BP, TBHQ and combinations of the two were tested against E. faecalis ATCC 29212, using MIC, MBC and (S)DDA assays as described above.For the (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 12 below and the (S)DDA results in Table 13. All results are collated from a number of experiments. EPO Table 12Table 13Tables 12 and 13 show that formulations according to the invention have activity against E.faecalis as well as against a range of different staphylococcal and propionibacterial strains as shown in Examples 5 and 8. Again, although the peroxide alone has relatively low activity against this organism, when combined with the hydroquinone a significant level of antibacterial synergy is observed.BP/TBHQ combinations were also subjected to DDA and SDDA tests againstAcimtobacter bavmanni ATCC 19606, Escherichia coli ATCC 25922, Haemophilus influenzae ATCC 49247, Klebsiella pneumoniae ATCC 700603, Pseudomonas aeruginosa ATCC 27853 and Streptococcus pyogenes ATCC 12344. Both test compounds were used at 200 μg per disc, the BP in DMSO and the TBHQ in ethanol. In these cases the SDDA data failed to give a clear indication of a synergistic interaction.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological Data)

15.6 μg/ml

Location

Page/Page column 47-48

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

446 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29212 of Enterococcus faecalis

Method (Pharmacological Data)

Example 10 - activity against E. faecalisThe activities of BP, TBHQ and combinations of the two were tested against E. faecalis ATCC 29212, using MIC, MBC and (S)DDA assays as described above.For the (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 12 below and the (S)DDA results in Table 13. All results are collated from a number of experiments. EPO Table 12Table 13Tables 12 and 13 show that formulations according to the invention have activity against E.faecalis as well as against a range of different staphylococcal and propionibacterial strains as shown in Examples 5 and 8. Again, although the peroxide alone has relatively low activity against this organism, when combined with the hydroquinone a significant level of antibacterial synergy is observed.BP/TBHQ combinations were also subjected to DDA and SDDA tests againstAcimtobacter bavmanni ATCC 19606, Escherichia coli ATCC 25922, Haemophilus influenzae ATCC 49247, Klebsiella pneumoniae ATCC 700603, Pseudomonas aeruginosa ATCC 27853 and Streptococcus pyogenes ATCC 12344. Both test compounds were used at 200 μg per disc, the BP in DMSO and the TBHQ in ethanol. In these cases the SDDA data failed to give a clear indication of a synergistic interaction.

Type (Pharmacological Data)

MIC

Value of Type (Pharmacological

31.25 μg/ml


Data) Location

Page/Page column 47-48

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

447 of 549

Effect (Pharmacological Data)

antibacterial

Species or TestSystem (Pharmacological Data)

ATCC 29212 of Enterococcus faecalis

Method (Pharmacological Data)

Example 10 - activity against E. faecalisThe activities of BP, TBHQ and combinations of the two were tested against E. faecalis ATCC 29212, using MIC, MBC and (S)DDA assays as described above.For the (S)DDA assays, 200 μg of each compound was loaded onto each disc. The solvents used were DMSO for the BP and ethanol for the TBHQ.The MIC and MBC results are shown in Table 12 below and the (S)DDA results in Table 13. All results are collated from a number of experiments. EPO Table 12Table 13Tables 12 and 13 show that formulations according to the invention have activity against E.faecalis as well as against a range of different staphylococcal and propionibacterial strains as shown in Examples 5 and 8. Again, although the peroxide alone has relatively low activity against this organism, when combined with the hydroquinone a significant level of antibacterial synergy is observed.BP/TBHQ combinations were also subjected to DDA and SDDA tests againstAcimtobacter bavmanni ATCC 19606, Escherichia coli ATCC 25922, Haemophilus influenzae ATCC 49247, Klebsiella pneumoniae ATCC 700603, Pseudomonas aeruginosa ATCC 27853 and Streptococcus pyogenes ATCC 12344. Both test compounds were used at 200 μg per disc, the BP in DMSO and the TBHQ in ethanol. In these cases the SDDA data failed to give a clear indication of a synergistic interaction.

Results

title compound resulted in a 33.67 mm in a disc diffusion assay (DDA)

Location

Page/Page column 47-48

Reference

SYNTOPIX LIMITED

Patent: WO2006/100495 A1, 2006 ; Title/Abstract Full Text Show Details

448 of 549

449 of 549

Effect (Pharmacological Data)

gene expression; induction of

Species or TestSystem (Pharmacological Data)

HepG2 cells

Concentration (Pharmacological Data)

80 μmol/l

Kind of Dosing (Pharmacological Data)

400x stock in dimethylsulfoxide

Method (Pharmacological Data)

cells treated with title comp. for 24 h; total RNA isolated, cDNA prepared, subjected to quantitative real-time PCR using ABI GeneAmp; level of UDPglucuronosyltransferase (UGT) 1A1, cytochrome P450 (CYP1A1), AhR, PXR determined

Further Details (Pharmacological Data)

control: vehicle; AhR: aryl hydrocarbon receptor; PXR: pregnane X receptor; mRNA levels normalized against β-actin mRNA

Results

title comp. significantly induced mRNA level (folds) of UGT1A1 (1.97), CYP1A1 (6.38), PXR (2.00), AhR (2.23)

Reference

Sugatani, Junko; Yamakawa, Kasumi; Tonda, Eri; Nishitani, Shinichi; Yoshinari, Kouichi; Degawa, Masakuni; Abe, Ikuro; Noguchi, Hiroshi; Miwa, Masao

Biochemical Pharmacology, 2004 , vol. 67, # 5 p. 989 - 1000 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; induction of

Species or TestSystem (Pharmacological Data)

HepG2 cells

Concentration (Pharmacological Data)

80 μmol/l

Kind of Dosing (Pharmacological Data)

400x stock in dimethylsulfoxide

Method

cells transfected with UDP-glucuronosyltransferase (UGT) 1A1 290 bp enhancer module-tk-luciferase construct and pRL-SV40 plasmid; treated with title


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(Pharmacological Data)

comp. for 0-72 h; luciferase reporter assay

Further Details (Pharmacological Data)

control: vehicle; fold activation calculated by dividing activity with title comp. by that without title comp.

Results

title comp. time-dependently elevated reporter activity reaching near plateau at 48 h (226 percent elevation) (figure)

Reference

Sugatani, Junko; Yamakawa, Kasumi; Tonda, Eri; Nishitani, Shinichi; Yoshinari, Kouichi; Degawa, Masakuni; Abe, Ikuro; Noguchi, Hiroshi; Miwa, Masao

Biochemical Pharmacology, 2004 , vol. 67, # 5 p. 989 - 1000 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

dermal fibroblasts

Concentration (Pharmacological Data)

3 - 3000 μmol/l

Kind of Dosing (Pharmacological Data)

at 3-fold conc. increments

Method (Pharmacological Data)

cells exposed to title comp.; conversion of (3-<4,5-dimethyl thiazol-2-yl>-2,5-diphenyl tetrazolium bromide to formazan by mitochondrial dehydrogenase by viable cells determined spectrophotometrically

Results

title inhibited cell viability by 20 percent at 15 μmol/l

Reference

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological Data)

dermal fibroblasts

Concentration (Pharmacological Data)

15 μmol/l

Method (Pharmacological Data)

cells exposed to title comp.; apoptosis determined by measuring caspase 3 protease activity by using fluorometry

Further Details (Pharmacological Data)

reference comp.: H2O2 (13.6 μmol/l)

Results

title comp. induced apoptosis (increased caspase 3 activity to 203 percent of control)

Reference

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidant

Species or TestSystem (Pharmacological Data)

dermal fibroblasts

Concentration (Pharmacological Data)

15 μmol/l

Method (Pharmacological Data)

cells exposed to title comp.; lipid peroxidation assayed by means reaction of lipid hydroperoxides with methylene blue derivative in presense of hemoglobin to yield methylene blue, color change determined spectrophotometrically

Further Details (Pharmacological

reference comp.: H2O2 (13.6 μmol/l)


Data)

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Results

title comp. stimulated lipid peroxidation (to 183 percent of control)

Reference

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

protein expression; effect on

Species or TestSystem (Pharmacological Data)

dermal fibroblasts

Concentration (Pharmacological Data)

15 μmol/l

Method (Pharmacological Data)

cells treated with title comp.; matrix metalloproteinase 1 levels determined by indirect ELISA

Further Details (Pharmacological Data)

reference comp.: H2O2 (13.6 μmol/l)

Comment (Pharmacological Data)

No effect

Reference

Philips; Burchill; O'Donoghue; Keller; Gonzalez

Skin Pharmacology and Physiology, 2004 , vol. 17, # 3 p. 147 - 152 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells grown in DMEM with 5 percent FBS; transfected with TLRP; 48 h later, treated with title comp. for 1 h, followed by LPS (1 μg/ml) for 5 h; luciferase activity measured; effect on TNFα enhancer/promoter activity determined

Further Details (Pharmacological Data)

controls: DMSO, LPS, and title comp. alone; DMEM: Dulbecco's modified Eagle's medium; LPS: lipopolysaccharide; FBS: fetal bovine serum; TLRP: TNFα luciferase reporter plasmid

Results

title comp. completely blocked LPS-induced luciferase activity in both transient and stable transfection modes; diagram

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological

cells transfected with TNFα-luciferase reporter plasmid grown in 48-well plates; treated with title comp. for 1 h followed by LPS stimulation for 5 h; cell lysate analyzed for luciferase activity and effect on TNFα transcription measured


Data)

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Further Details (Pharmacological Data)

control: vehicle; TNFα: tumor necrosis factor α; LPS: lipopolysaccharide

Results

title comp. strongly inhibited LPS-induced TNFα transcription in both 6 and 24 h treatments times; diagram

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells nuclear extracts

Concentration (Pharmacological Data)

100 - 400 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

in vitro assay; nuclear extracts prepared from DMSO- or LPS- (1 μg/ml, 3 h) stimulated cells; incubated with title comp. for 30 min at RT; analyzed for NF-κB DNA binding activity and specificity by EMSA (electrophoretic mobility shift assay)

Further Details (Pharmacological Data)

controls: DMSO, LPS, and title comp. alone; DMSO: dimethyl sulfoxide; NF-κB: nuclear factor-κB; LPS: lipopolysaccharide; RT: room temperature

Comment (Pharmacological Data)

No effect

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells treated with title comp. for 1 h, followed by LPS (1 μg/ml) for 30-120 min; nuclear extracts prepared, analyzed for NF-κB by immunoblotting; effect on NFκB nuclear translocation and accumulation of NF-κB p65 subunit studied

Further Details (Pharmacological Data)

control: vehicle; LPS: lipopolysaccharide; further, effect on nuclear accumulation of NF-κB p65 subunit studied, using YO-PRO stained nucleus, by immunofluorescent microscopy

Comment (Pharmacological Data)

No effect

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells


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Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells transfected with pIKKβ-FLAG; 24 h later, treated with title comp. for 1-3 h, followed by stimulation with LPS (10 μg/ml) for 30 min; lysate collected, IKK complex immunoprecipitated; effect on IKK activity studied using IκBα as substrate

Further Details (Pharmacological Data)

controls: vehicle, LPS; LPS: lipopolysaccharide; IKK: IκBα kinase complex; signaling pathway analyzed

Comment (Pharmacological Data)

No effect

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

anti-inflammatory

Species or TestSystem (Pharmacological Data)

mouse macrophage RAW 264.7 cells

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

cells grown to confluence; incubated in DMEM without serum for 18 h; treated with title comp. for 1 h, followed by LPS (1 μg/ml) for 5-120 min; cell lysate analyzed by IB with antibodies specific for IκBα; effect on IκBα degradation studied

Further Details (Pharmacological Data)

control: vehicle; IκBα is kinase enzyme complex; DMEM: Dulbecco's modified Eagle's medium; LPS: lipopolysaccharide; IB: immunoblotting; signaling pathway analyzed

Comment (Pharmacological Data)

No effect

Reference

Ma, Qiang; Kinneer, Krista; Ye, Jianping; Chen, Bruce J.

Molecular Pharmacology, 2003 , vol. 64, # 2 p. 211 - 219 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mRNA expression; induction of

Species or TestSystem (Pharmacological Data)

human colon carcinoma HCA-7 cells

Concentration (Pharmacological Data)

25 - 50 μmol/l

Method (Pharmacological Data)

cells starved overnight in serum-free medium; title comp. added for 6 h; total RNA isolated; cyclooxygenase-2 (COX-2) and microsomal glutathione Stransferase 1-like 1 (MGST1-L1) mRNA estimated using real-time polymerase chain reaction

Further Details (Pharmacological Data)

mRNA: messenger ribonucleic acid; further invest.: 5 h incubation with interleukin-1β (IL-1β, 5 ng/ml, 1 h after title comp.) with or without indolo<3,2b>carbazole (ICZ)

Results

title comp. at 20 and 50 μmol/l increased COX-2 mRNA level 2 and 3-fold, resp.; further increased COX-2 mRNA above IL-1β-induced, but not IL-1β/ICZinduced level; antagonized IL-1β-stimulated MGST1-L1 expression

Reference

Sherratt, Philip J.; McLellan, Lesley I.; Hayes, John D.

Biochemical Pharmacology, 2003 , vol. 66, # 1 p. 51 - 61 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological

transmitter release; inhibition of


Data)

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Species or TestSystem (Pharmacological Data)

human colon carcinoma HCA-7 cells

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

cells starved overnight in serum-free medium; stimulated with AA for 15 min, 37 deg C, simultaneously with title comp. treatment or after 24 h title comp. incubation; prostaglandin E2 (PGE2) release measured in culture medium by enzyme immunoassay

Further Details (Pharmacological Data)

AA: arachidonic acid; further invest.: 23 h incubation with interleukin-1β (IL-1β, 5 ng/ml, 1 h after title comp.)

Results

title comp. decreased PGE2 production to 44 percent of control after 24 h incubation, to 18 percent of control with simultaneous stimulation; IL-1β-induced PGE2 production was reduced by 24 h incubation with title comp. below that of untreated cells

Reference

Sherratt, Philip J.; McLellan, Lesley I.; Hayes, John D.

Biochemical Pharmacology, 2003 , vol. 66, # 1 p. 51 - 61 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transcriptional activity; induction of

Species or TestSystem (Pharmacological Data)

human hepatoma Hep-G2 cells

Concentration (Pharmacological Data)

25 - 50 μmol/l

Method (Pharmacological Data)

cells transfected with COX-2 gene promoter CAT reporter construct; recovered overnight in serum-free medium; treated with title comp.; reporter gene activity assayed by measuring CAT activity

Further Details (Pharmacological Data)

CAT: chloramphenicol acetyltransferase; further invest.: co-transfection with mouse Nrf2 transcription factor coding sequence

Results

title comp. increased CAT activity dose-dependently; effect was enhanced by Nrf2 co-transfection (figure)

Reference

Sherratt, Philip J.; McLellan, Lesley I.; Hayes, John D.

Biochemical Pharmacology, 2003 , vol. 66, # 1 p. 51 - 61 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

Ca. 1E-07 - 0.005 mol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in ethanol:dodecane (98:2, v/v)

Method (Pharmacological Data)

cells treated with title comp. for 24 h; medium replaced with RPMI 1640 medium containing neutral red for 3 h; cytotoxicity determined by uptake of neutral red; absorbance read at 540 nm

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. showed concentration-dependent inhibition of neutral red uptake; inhibition was detected at higher than 1E-5 mol/l title comp. concentration and almost complete inhibition was observed at 1E-3 mol/l title comp. concentration; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological

cell morphology; effect on


Data)

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Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 or 6 h; stained with 4',6-diamidino-2-phenylindole dihydrochloride and examined under fluorescence microscopy

Further Details (Pharmacological Data)

control: cells treated with ethanol/dodecane (98:2, v/v)

Results

at 1 or 2 h, title comp.-treated cells did not show frequent nuclear condensation which became distinct at 3 and 6 h; time-dependent increase in nuclear condensation and fragmentation were observed; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cell morphology; effect on

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 h and replaced with PBS (pH 7.4); stained with 2percent (w/v) aqueous uranyl acetate for 2 h and examined under electron microscopy

Further Details (Pharmacological Data)

control: untreated cells; VLS: vacuole-like structure

Results

title comp. caused disruption in mitochondrial structure as compared with control; degradation of cristae and intramitochondrial structure, defects in mitochondrial bilayer and VLS were frequently obsd.; ultrastructure of cells was also similar; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mitochondrial transmembrane potential; effect on

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 1 h; stained with 5,5',6,6'-tetrachloro-1,1',3,3'-tetraethylbenzimidazolcarbocyanine at room temperature for 20 min; mitochondrial membrane potential was analyzed by FACScalibur flow cytometer

Further Details (Pharmacological Data)

control: untreated cells

Results

title comp. treatment caused disruption in mitochondrial transmembrane potential; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological

human monocytic leukemia U937 cells


Data)

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Concentration (Pharmacological Data)

0.5 - 2 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 h or 2-4 h; lysed; centrifuged; supernatant collected; DEVDase (caspase-3 or -9) activity determined using Ac-DEVD-7amino-4-methylcoumarin as substrate

Further Details (Pharmacological Data)

control: ethanol:dodecane (98:2, v/v) treated cells; further study with glutathione (GSH) and N-acetylcysteine (NAC); caspase cascade plays an essential role in internucleosomal DNA laddering that typifies apoptotic cell death

Results

title comp. increased DEVDase activity conc. and time-dependently; with 1.5 mmol/l, highest activity were obsd. at 3 h which drastically decreased at 4 h; GSH completely inhibited DEVDase; NAC slightly affected title comp. induced effect; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 h; lysed; centrifuged; supernatant collected; caspase-6, -9, -8, and -1/-4 activity determined using VEID, LHED, IETD and YVAD, respectively as substrate

Further Details (Pharmacological Data)

control: cells treated with ethanol:dodecane (98:2, v/v); caspase cascade plays an essential role in internucleosomal DNA laddering that typifies apoptotic cell death

Results

title comp. induced caspase-9 and -6, though increase of activity was not great; title comp. induced caspase-8 activity; induction of caspase-1 and -4 activity was barely detected; table

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. in presence of poly(ADP-ribose) polymerase (PARP) for 1.5 to 6 h; lysed; cell lysates separated on 7.5percent SDSpolyacrylamide gels and PARP cleavage determined by Western blotting

Further Details (Pharmacological Data)

PARP which contains DEVD peptide sequence is one of the target of DEVDase (caspase-3, -7); caspase cascade plays an essential role in internucleosomal DNA laddering that typifies apoptotic cell death

Results

title comp. treated cells showed PARP cleavage at 1.5 h and almost all 116-kDa peptide was cleaved at 4.5 h; in cells treated with title comp., an 89-kDa peptide was detected in addition to original 116-kDa PARP peptide; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological

1.5 mmol/l


Data)

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Method (Pharmacological Data)

cells treated with title comp. for 3 to 6 h; lysed; cell lysates separated on 14percent SDS-polyacrylamide gel and active caspase-3 and -7 detected by Western blotting

Further Details (Pharmacological Data)

caspase cascade plays an essential role in internucleosomal DNA laddering that typifies apoptotic cell death

Results

title comp. apparently processed procaspase-3 and -7 to active forms in cells; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione levels; decrease of

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

0.5 - 2 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 h; washed; glutathione was extracted with perchloric acid; after addition of o-phthalaldehyde, fluorescence with excitation at 350 nm and emission at 420 nm; reduced glutathione level determined

Further Details (Pharmacological Data)

control: cells treated with ethanol:dodecane (98:2, v/v)

Results

title comp. decreased glutathione levels dose-dependently and showed maximal effect at 1.5 mmol/l title comp. concentration; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

apoptosis induction

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

1.5 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 3 h; cytosolic extracts prepared; cytosolic protein was separated on 15percent SDS-polyacrylamide gel; release of cytochrome c detected by Western blotting

Further Details (Pharmacological Data)

control: cells treated with ethanol:dodecane (98:2, v/v); release of cytochrome c from mitochondria to cytosol has been implicated as an important step in apoptosis

Results

title comp. showed denser bands of cytochrome c than control; title comp. treatment caused release of cytochrome c from mitochondria to cytosol; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

intracellular ATP levels; effect on

Species or TestSystem (Pharmacological Data)

human monocytic leukemia U937 cells

Concentration (Pharmacological Data)

0.5 - 2 mmol/l

Method (Pharmacological Data)

cells treated with title comp. for 1 h in presence or absence of glucose (GLU); lysed; centrifuged; supernatant collected; intracellular ATP concentration was determined using luminometer control: cells treated with ethanol:dodecane (98:2, v/v)


Further Details (Pharmacological Data)

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Results

in the absence of GLU, title comp. caused drastic conc.-dependent decrease in ATP at 15 min; at 1.0, 1.5 mmol/l, ATP decrease was about 10, 50percent of control in absence/presence of GLU, respectively; in presence of GLU, ATP decrease was moderate; fig.

Reference

Okubo; Yokoyama; Kano

Food and Chemical Toxicology, 2003 , vol. 41, # 5 p. 679 - 688 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; expression of

Species or TestSystem (Pharmacological Data)

rat hepatoma H4IIE cells

Concentration (Pharmacological Data)

500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in DMSO

Method (Pharmacological Data)

cells were maint. in monolayer cult.; treated with title comp. for 12 h (with or without pretreatment with CHX (1 μmol/l) for 1 h); mRNA isolated; Northern blot analysis using rCYP1A1 cDNA probes performed

Further Details (Pharmacological Data)

CHX: cycloheximide; CYP1A1: cytochrome P450 1A1; further investigation on mechanism of action by using actinomycin-D and PD98059; control: DMSO (0.1 percent)

Results

title comp. induced expression of CYP1A1 mRNA; no synergistic effect of title comp. with cycloheximide

Reference

Lamb, John G.; Franklin, Michael R.

Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; expression of

Species or TestSystem (Pharmacological Data)

rat hepatoma H4IIE cells

Concentration (Pharmacological Data)

1 - 500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in DMSO

Method (Pharmacological Data)

cells were maint. in monolayer cultures; treated with title comp. for 12 h; mRNA isolated; Northern blot analysis using rGSTA2 cDNA probes performed

Further Details (Pharmacological Data)

GSTA2: glutathione S-transferase A2; control: DMSO (0.1 percent)

Results

title comp. dose-dep. induced expression of GSTA2 mRNA from ca. 1.5 to 8.5 rGSTA2 mRNA; linear dose-response curve, (fig.)

Reference

Lamb, John G.; Franklin, Michael R.

Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; expression of

Species or TestSystem (Pharmacological Data)

rat hepatoma H4IIE cells

Concentration (Pharmacological Data)

500 μmol/l

Kind of Dosing (Pharmacological

title comp. was dissolved in DMSO


Data)

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Method (Pharmacological Data)

cells were maint. in monolayer cultures; 60-80 percent confluent cells transfected with luciferase expression plasmid; incub. overnight; treated with title comp. for 24 h; whole cell extracts prep.; luciferase activ. determ. for assessment of GSTA2 expression

Further Details (Pharmacological Data)

GSTA2: glutathione S-transferase A2; luciferase reporter constracts contained various region of the rGSTA gene promotor region; controls: naive cells (received no chemical treatment), DMSO (0.1 percent)

Results

title comp. sign. induced expression of GSTA2, results depended on vector type; the highest degree of expression was observed in case of 1.72 kb constract (42824 in respect to control naive cells 176 units luciferase activity), (tab.)

Reference

Lamb, John G.; Franklin, Michael R.

Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

rat hepatoma H4IIE cells

Concentration (Pharmacological Data)

500 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. was dissolved in DMSO

Method (Pharmacological Data)

cells were maintained in monolayer cultures; near-confluent cells in 6-well plates were treated with title comp. for 24 h; medium replaced; WST-8 reagent added (30 μl); after further 3 h incubation absorbance at 460 nm measured

Further Details (Pharmacological Data)

controls: naive cells (received no chemical treatment), DMSO (0.1 percent)

Results

title comp. induced 32 percent decrease in cell viability (fig.)

Reference

Lamb, John G.; Franklin, Michael R.

Journal of Biochemical and Molecular Toxicology, 2002 , vol. 16, # 4 p. 154 - 161 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

RNA; examination of

Species or TestSystem (Pharmacological Data)

mouse Hepa-1c1c7 hepatoma cell culture

Concentration (Pharmacological Data)

0.4 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO

Method (Pharmacological Data)

cells cultured in Dulbecco's modified Eagle's medium+fetal bovine serum; in logarithmic growth phase treated with title comp.; RNA extracted; sizeseparated; Northern blotted; transcripts semi-quantified

Further Details (Pharmacological Data)

effect on induction of subunits of GCL studied; GCL: glutamate-cysteine ligase; GCLM and GCLC: modifier and catalytic subunit of GCL, respectively; mechanism of increase studied

Results

dose-dependent increase of GCLM RNA; 50 μmol/l title comp. induced maximum increase: ca. 10-fold; moderated increase of GCLC RNA: ca. 2-fold; no cell toxicity after 24 h treatment with 50 μmol/l; diagrams given

Reference

Solis, Willy A.; Dalton, Timothy P.; Dieter, Matthew Z.; Freshwater, Sarah; Harrer, Judy M.; He, Lei; Shertzer, Howard G.; Nebert, Daniel W. Biochemical Pharmacology, 2002 , vol. 63, # 9 p. 1739 - 1754 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

genotoxic

Species or TestSystem (Pharmacological

supercoiled φX-174 RF I double-stranded plasmid DNA


Data)

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Concentration (Pharmacological Data)

1 - 100 μmol/l

Method (Pharmacological Data)

DNA incub. in presence of title comp. with/without Cu(2+) (1-10 μmol/l) for 30 min at 37 deg C in PBS; electrophoresed and stained with ethidium bromide; DNA strand breaks determined by measuring formation of open circular and linear DNA forms

Further Details (Pharmacological Data)

PBS: phosphate buffered saline; additional experiment performed with Cu(2+) (10 μmol/l; induced no genotoxicity); control: untreated DNA

Results

title comp. alone induced no genotoxicity; in presence of Cu(2+) dose-depend. induced DNA strand breaks; complete supercoiled double-stranded DNA degradation observed at title comp. conc. of 100 μmol/l in presence of Cu(2+) (1-10 μmol/l); figs.

Reference

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genotoxic

Species or TestSystem (Pharmacological Data)

supercoiled φX-174 RF I double-stranded plasmid DNA

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

DNA incub. in presence of title comp. with Cu(2+) (10 μmol/l) and various additives for 30 min at 37 deg C in PBS; electrophoresed and stained with ethidium bromide; genotoxicity assessed by measuring formation of open circular and linear DNA forms

Further Details (Pharmacological Data)

additives: BCS, GSH, catalase, NaN3, 2,2,6,6-tetramethyl-4-piperidone; BCS: bathocuproinedisulfonic acid; GSH: reduced glutathione; PBS: phosphate buffered saline; negative control: untreated DNA; positive control: title comp. with Cu(2+) (10 μmol/l)

Results

addition of BCS (40 μmol/l), GSH (1 mmol/l), catalase (200 U/ml), NaN3 (100 mmol/l) and 2,2,6,6-tetramethyl-4-piperidone (100 mmol/l) inhibited title comp./Cu(2+)-induced genotoxicity; fig.

Reference

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genotoxic

Species or TestSystem (Pharmacological Data)

supercoiled φX-174 RF I double-stranded plasmid DNA

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

DNA incub. in presence of title comp. with Cu(2+) (10 μmol/l) and various additives for 30 min at 37 deg C in PBS; electrophoresed and stained with ethidium bromide; genotoxicity assessed by measuring formation of open circular and linear DNA forms

Further Details (Pharmacological Data)

additives: superoxide dismutase, heat-inactivated superoxide dismutase and catalase, 5,5-dimethyl-1-pyrroline-N-oxide, mannitol; PBS: phosphate buffered saline; negative control: untreated DNA; positive control: title comp. with Cu(2+) (10 mmol/l)

Results

addition of superoxide dismutase (200 U/ml), heat-inactivated superoxide dismutase and catalase, 5,5-dimethyl-1-pyrroline-N-oxide (100 mmol/l) and mannitol (100 mmol/l) showed no effect on title comp./Cu(2+)-induced genotoxicity; figs.

Reference

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genotoxic

Species or TestSystem (Pharmacological Data)

hepatocytes of rat

Concentration (Pharmacological

10 - 50 μmol/l


Data)

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Method (Pharmacological Data)

cells pretreated/untreated with various additives for 30 min and incub. in presence of title comp. for further 60 min at 37 deg C in PBS; nuclear DNA isolated and hydrolyzed; genotoxicity assessed by measuring 8-OHdG formation using HPLC/ECD method

Further Details (Pharmacological Data)

cells isolated from female F-344 rats; additives: bathocuproine and neocuproine (both at conc. of 50 μmol/l); 8-OHdG: 8-hydroxy-2'-deoxyguanosine; HPLC/ECD: high-performance liquid chromatography with electrochemical detection; control: untreated cells

Results

title comp. alone dose-depend. induced 8-OHdG formation; addition of bathocuproine and neocuproine inhibited title comp. induced genotoxicity; fig.

Reference

Li, Yunbo; Seacat, Andrew; Kuppusamy, Periannan; Zweier, Jay L; Yager, James D; Trush, Michael A

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2002 , vol. 518, # 2 p. 123 - 133 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

metabolic

Endpoint of Effect (Pharmacological Data)

MRP1 mRNA and protein expression

Species or TestSystem (Pharmacological Data)

MCF-7 cells

Concentration (Pharmacological Data)

50 - 200 μmol/l

Kind of Dosing (Pharmacological Data)

50, 100, and 200 μmol/l

Method (Pharmacological Data)

cells were cultivated in suppl. RPMI 1640 medium in the pres. of title comp. for 48 h; total RNA was isolated; plasma membrane fraction was prepared; Northern and Western blot analysis

Further Details (Pharmacological Data)

multidrug resistance protein (MRP)

Results

title comp. induced MRP1 mRNA and protein levels ca. 2-fold

Reference

Schrenk, Dieter; Baus, Petra R.; Ermel, Nadine; Klein, Christopher; Vorderstemann, Birgit; Kauffmann, Hans-Martin

Toxicology Letters, 2001 , vol. 120, # 1-3 p. 51 - 57 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer HCT116 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing wild-type p53 were treated with title comp. for various lengths of time; total cellular RNA was prepared, levels of γglutamylcysteine synthetase (γ-GCSh) and MRP1 were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on γ-GCSh and multidrug-resistance protein 1 (MRP1) expression

Results

modestly but singif. increased γ-GCSh and MRP1 levels, max. induction (after 10 h) 2.78- and 1.52-fold (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer SW480 cell line

100 μmol/l


Concentration (Pharmacological Data)

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Method (Pharmacological Data)

in vitro; cells containing p53 mutant status were treated with title comp. for various lengths of time; total cellular RNA was prepared, levels of γglutamylcysteine synthetase (γ-GCSh) and MRP1 were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on γ-GCSH and multidrug-resistance protein 1 (MRP1) expression

Results

modestly increased γ-GCSh and MRP1 levels, max. induction (after 6 h) 1.77- and 1.25-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer HT29 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing p53 mutant status were treated with title comp. for various lengths of time; total cellular RNA was prepared, levels of γglutamylcysteine synthetase (γ-GCSh) and MRP1 were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on γ-GCSh and multidrug-resistance protein 1 (MRP1) expression

Results

signif. increased γ-GCSh levels and modestly increased MRP1 levels, max. induction (after 24 h) 7.07- and 1.61-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer Caco2 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing p53 mutant status were treated with title comp. for various lengths of time; total cellular RNA was prepared, levels of γ-GCSh and multidrug-resistance protein 1 (MRP1) were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on γ-glutamylcysteine synthetase (γ-GCSh) and MRP1 expression

Results

signif. increased γ-GCSh and MRP1 levels, max. induction (after 24 h) 4.51- and 2.49-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer 4016 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological

in vitro; cells with p53 mutant status, one p53 allele replaced with a drug-resistance marker (neomycin), were treated with title comp. for various lengths of time; total cellul. RNA was prepared, γ-GCSh and MRP1 levels deter. by RNase protection assay


Data)

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Further Details (Pharmacological Data)

effect of title comp. on γ-glutamylcysteine synthetase (γ-GCSh) and multidrug-resistance protein 1 (MRP1) expression

Results

signif. increased γ-GCSh levels and only modest increased MRP1 levels, max. induction (after 10 h) 2.76- and 1.14-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer 379.2 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells with p53 mutant status, both p53 alleles replaced with a drug-resistance marker (neomycin), were treated with title comp. for various lengths of time; total cellul. RNA was prepared, γ-GCSh and MRP1 levels deter. by RNase protect. assay

Further Details (Pharmacological Data)

effect of title comp. on γ-glutamylcysteine synthetase (γ-GCSh) and multidrug-resistance protein 1 (MRP1) expression

Results

signif. increased γ-GCSh and MRP1 levels, max. induction (after 10 h) 5.01- and 2.32-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer 8054 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells with wild-type p53, both p21 alleles have been knocked out, were treated with title comp. for various lengths of time; total cellular RNA was prepared, γ-GCSh and MRP1 levels determined by RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on γ-glutamylcysteine synthetase (γ-GCSh) and multidrug-resistance protein 1 (MRP1) expression

Results

only modestly increased γ-GCSh and MRP1 levels, max. induction (after 6 h) 2.14- and 1.44-fold, respectively (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer HCT116 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing wild-type p53 were treated with title comp. for various lengths of time (2-24 h); total cellular RNA was prepared, levels of multidrug-resistance protein (MPR) members were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on MRP2, MRP3, MRP4, MRP5 and MRP6 expression

title comp. induced expression of MRP2 and MRP3, expression of MRP4 and MRP5 was induced only marginally; expression of MRP6 was not detected in


Results

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this cells (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme expression

Species or TestSystem (Pharmacological Data)

colorectal cancer 379.2 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells contain. mutant p53 status (both p53 replaced with drug-resistance marker (neomycin)) were treated with title comp. for 2-24 h; total cellular RNA was prepared, levels of MPR members were determined by the RNase protection assay

Further Details (Pharmacological Data)

effect of title comp. on multidrug-resistnace protein (MRP) members (MRP2, MRP3, MRP4, MRP5 and MRP6) expression

Results

title comp. induced expression of MRP2 and MRP3, expression of MRP4 and MRP5 was induced only marginally; expression of MRP6 was not detected in this cells (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem (Pharmacological Data)

colorectal cancer HCT116 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing wild-type p53 were treated with title comp. for 0-24 h; total cellular glutathione measured

Results

treatment with title comp. significantly increased intracellular glutathione levels (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem (Pharmacological Data)

colorectal cancer HT29 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing mutant p53 status were treated with title comp. for 0-24 h; total cellular glutathione measured

Results

treatment with title comp. significantly increased intracellular glutathione levels (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem

colorectal cancer 8054 cell line


(Pharmacological Data)

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Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing wild-type p53 (and both p21 alleles have been knocked out) were treated with title comp. for 0-24 h; total cellular glutathione measured

Results

treatment with title comp. significantly increased intracellular glutathione levels (diagram)

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem (Pharmacological Data)

colorectal cancer Caco2 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing mutant p53status were treated with title comp. for 0-24 h; total cellular glutathione measured

Comment (Pharmacological Data)

No effect

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem (Pharmacological Data)

colorectal cancer 397.2 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing mutant p53status, both p53 alleles were replaced by a drug-resistance marker (neomycin), were treated with title comp. for 0-24 h; total cellular glutathione measured

Comment (Pharmacological Data)

No effect

Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

glutathione; induction of

Species or TestSystem (Pharmacological Data)

colorectal cancer 4016 cell line

Concentration (Pharmacological Data)

100 μmol/l

Method (Pharmacological Data)

in vitro; cells containing mutant p53status, one p53 allele was replaced by a drug-resistance marker (neomycin), were treated with title comp. for 0-24 h; total cellular glutathione measured

Comment (Pharmacological Data)

No effect


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Reference

Lin-Lee, Yen-Chiu; Tatebe, Shigeru; Savaraj, Niramol; Ishikawa, Toshihisa; Tien Kuo

Biochemical Pharmacology, 2001 , vol. 61, # 5 p. 555 - 563 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or TestSystem (Pharmacological Data)

Escherichia coli IC204

Concentration (Pharmacological Data)

150 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. dissolved in water

Method (Pharmacological Data)

in vitro; plate incorporation assay; Difco agar; minimal ET4 plates; 37 deg C; 2 d; number of revertants per plates counted

Further Details (Pharmacological Data)

mut+ WP2 uvrA/pKM101 bacterial strain

Comment (Pharmacological Data)

No effect

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or TestSystem (Pharmacological Data)

Escherichia coli IC206

Concentration (Pharmacological Data)

150 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. dissolved in water

Method (Pharmacological Data)

in vitro; plate incorporation assay; Difco agar; minimal ET4 plates; 37 deg C; 2 d; number of revertants per plates counted

Further Details (Pharmacological Data)

mutY WP2 uvrA/pKM101 bacterial strain

Comment (Pharmacological Data)

No effect

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or TestSystem (Pharmacological Data)

Escherichia coli IC208

Concentration (Pharmacological Data)

150 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. dissolved in water


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Method (Pharmacological Data)

in vitro; plate incorporation assay; Difco agar; minimal ET4 plates; 37 deg C; 2 d; number of revertants per plates counted

Further Details (Pharmacological Data)

mutY oxyR WP2 uvrA/pKM101 bacterial strain

Comment (Pharmacological Data)

No effect

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Endpoint of Effect (Pharmacological Data)

growth

Species or TestSystem (Pharmacological Data)

Escherichia coli IC203

Concentration (Pharmacological Data)

1000 μg/disc

Kind of Dosing (Pharmacological Data)

paper discs (6 mm in diameter) impregnated with title comp. dissolved in water

Method (Pharmacological Data)

in vitro; LA plates; paper discs impregnated with title comp. placed on solidified top agar; in the pres. and abs. of S9 mix; inhibition zone determined

Further Details (Pharmacological Data)

WP2 uvrA/pKM101 bacterial strain deficient in OxyR

Results

diameter of inhibition zone 7-13 mm; cytotoxicity of title comp. inhibited by S9

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Endpoint of Effect (Pharmacological Data)

growth

Species or TestSystem (Pharmacological Data)

Escherichia coli IC188

Concentration (Pharmacological Data)

1000 μg/disc

Kind of Dosing (Pharmacological Data)

paper discs (6 mm in diameter) impregnated with title comp. dissolved in water

Method (Pharmacological Data)

in vitro; LA plates; paper discs impregnated with title comp. placed on solidified top agar; incubated overnight; diameter of inhibition zone determined

Further Details (Pharmacological Data)

parent WP2 uvrA/pKM101 bacterial strain

Results

diameter of inhibition zone 7 mm

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect

mutagenic (microorganism)


(Pharmacological Data)

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Species or TestSystem (Pharmacological Data)

Escherichia coli IC203

Concentration (Pharmacological Data)

50 - 150 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. dissolved in water

Method (Pharmacological Data)

in vitro; plate incorporation assay; Difco agar; minimal ET4 plates; 37 deg C; 2 d; with and without metabolic activation with S9 mix; number of revertants per plates counted

Further Details (Pharmacological Data)

WP2 uvrA/pKM101 bacterial strain deficient in OxyR

Results

oxidative mutagenesis in the abs. of S9 mix; mutagenesis inhibited by S9

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

mutagenic (microorganism)

Species or TestSystem (Pharmacological Data)

Escherichia coli IC188

Concentration (Pharmacological Data)

50 - 150 μg/plate

Kind of Dosing (Pharmacological Data)

title comp. dissolved in water

Method (Pharmacological Data)

in vitro; plate incorporation assay; Difco agar; minimal ET4 plates; 37 deg C; 2 d; number of revertants per plates counted

Further Details (Pharmacological Data)

parent WP2 uvrA/pKM101 bacterial strain

Comment (Pharmacological Data)

No effect

Reference

Martinez, Alicia; Urios, Amparo; Blanco, Manuel

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 2000 , vol. 467, # 1 p. 41 - 53 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antidiabetic

Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

peroral

Kind of Dosing (Pharmacological Data)

title comp. mixed with AIN-76 diet at dose of 0.028 g/kg diet; admin. for 7 d before and after administration of streptozotocin

Method (Pharmacological Data)

5-wks old rats; diabetes induced by admin. of streptozotocin; rats killed 7 d after admin. of streptozotocin; islets isol.; glucose-stimulated insulin release exam.

Further Details (Pharmacological Data)

rats kept at 23 deg C; 12:12 h light:dark cycle


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Results

body weight gain increased ; serum glucose conc. decreased; glucose-stimul. insulin secretion from pancreatic islet increased compared to control; diabetogenic action of streptozotocin prevented

Reference

Nishizono; Hayami; Ikeda; Imaizumi

Bioscience, biotechnology, and biochemistry, 2000 , vol. 64, # 6 p. 1153 - 1158 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antimutagenic

Species or TestSystem (Pharmacological Data)

Salmonella typhimurium TA98

Method (Pharmacological Data)

in vitro; bacterial suspension containing title comp. and N-OH-Trp-P2; incub. for 20 min; poured on agar medium of minimal glucose; His+-revertant colonies count. after 2-d culture

Further Details (Pharmacological Data)

N-OH-Trp-P-2 = N-hydroxy-3-amino-1-methyl-5H-pyrido<4,3-b>indole; scavenging activity of title comp. eval. from suppression of mutation induced ny NOH-Trp-P-2; IC50 = conc. required for 50 percent scavenging of N-OH-Trp-P-2 radicals before damage to DNA

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.70 mmol/l

Reference

Sun, Mingzhou; Sakakibara, Hiroyuki; Ashida, Hitoshi; Danno, Gen-Ichi; Kanazawa, Kazuki

Bioscience, Biotechnology and Biochemistry, 2000 , vol. 64, # 11 p. 2395 - 2401 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genotoxic

Species or TestSystem (Pharmacological Data)

pUC18 DNA

Concentration (Pharmacological Data)

0.001 mol/l

Method (Pharmacological Data)

DNA (0.3 μg) incubated with title comp. in tris-HCl (pH 8.0) at 37 deg C for 60 min; electrophoresis of 0.7 percent agarose gel; DNA bands were stained and visialized under irradiation with UV light at 312 nm; gel was scanned with densitometer

Further Details (Pharmacological Data)

control: without title comp.

Results

title comp. increased cleavage of DNA to about 17.6 percent (figure, diagram)

Reference

Okubo, Tomoko; Nagai, Fumiko; Seto, Takako; Satoh, Kanako; Ushiyama, Keiko; Kano, Itsu

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 2 p. 199 - 203 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

protein; induction of

Species or TestSystem (Pharmacological Data)

Caco-2 cells

Concentration (Pharmacological Data)

80 μmol/l

Method (Pharmacological Data)

preconfluent Caco-2 clone TC-7 cells incubated for 72 h with title comp.; homogenate proteins separated, blotted and reacted with rabbit anti-sheep antibodies for UGT1A6 and goat anti-rabbit antibodies for MRP2 (multidrug resistance protein 2)

Further Details (Pharmacological Data)

imaging, and quantitative analysis performed as described previously; quantification is based on mg cell protein; 100 percent represents protein levels in solvent controls contg. DMSO

Results

title comp. induced protein levels of UDP-glucuronosyltransferase UGT1A6 to 303 percent and of the apical conjugate export pump MRP2 to 186 percent over the control; coordinate induction of UGT1A6 and MRP2 by title comp.

Reference

Bock, Karl Walter; Eckle, Tilman; Ouzzine, Mohamed; Fournel-Gigleux, Sylvie


Biochemical Pharmacology, 2000 , vol. 59, # 5 p. 467 - 470 Title/Abstract Full Text View citing articles Show Details

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Effect (Pharmacological Data)

genetic toxicity in vitro

Endpoint of Effect (Pharmacological Data)

chromosome damage

Species or TestSystem (Pharmacological Data)

Chinese hamster ovary (CHO) cells

Concentration (Pharmacological Data)

15 - 125 μmol/l

Kind of Dosing (Pharmacological Data)

15, 31, 62 and 125 μM

Method (Pharmacological Data)

in vitro; chromosome damages induced in CHO cells treated with title comp. in the presence of washed rat liver microsomes were evaluated; mitotic index, cells with aberrations and aberrations per 100 cells were recorded

Results

sign. dose-dependent chromosome damaging effect: decrease in mitotic index from 6.5 percent in control to 0 percent at 125 μM, increase in cells with aberrations from 3 to 47 percent at 62 μM, increase in total number of aberrations per 100 cells from 3 to 114 at 125 μM

Reference

Anderson; Phillips

Food and Chemical Toxicology, 1999 , vol. 37, # 9-10 p. 1015 - 1025 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

ryanodine receptor complex; modification of

Species or TestSystem (Pharmacological Data)

New Zealand White rabbit skeletal muscle SR membranes

Concentration (Pharmacological Data)

<= 100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in dimethyl sulfoxide

Method (Pharmacological Data)

SR vesicles (50 μg/ml) placed in solution A at 37 deg C for 3 min; title comp. added for 30 min; CPM added; CPM fluorescence monitored by spectrofluorometer; SDS-PAGE of CPM-labeled SR protein performed

Further Details (Pharmacological Data)

SR: sarcoplasmic reticulum; CPM: 7-diethylamino-3-(4'-maleimidylphenyl)-4-methylcoumarin; SDS-PAGE: SDS-polyacrylamide gel electrophoresis; solution A contained KCl, MOPS (pH 7.0) and 1 mmol/l MgCl2; solvent control

Comment (Pharmacological Data)

No effect

Reference

Feng, Wei; Liu, Guohua; Xia, Ruohong; Abramson, Jonathan J.; Pessah, Isaac N.

Molecular Pharmacology, 1999 , vol. 55, # 5 p. 821 - 831 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

100 - 200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO to prepare high strength stock solutions, which were diluted with medium to obtain desired concentrations

Method (Pharmacological

cells treated for 4-16 h with title comp.; total RNA extracted; treated with DNase; separated on agarose gel and Northern blotted to determine expression of c-jun gene and that of detoxifying enxyme NAD(P)H:quinone oxidoreductase (NQO1)


Data)

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Further Details (Pharmacological Data)

control: vehicle

Results

title comp. treatment led to 2- to 3-fold increase in expression of c-jun and NQO1 genes; an increase in concentration from 100 to 200 μmol/l led to further increase in expression of c-jun gene, but NQO1 gene expression remained unchanged; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

100 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO to prepare high strength stock solutions, which were diluted with medium to obtain desired concentrations

Method (Pharmacological Data)

cells treated for 4-16 h with title comp.; total RNA extracted; treated with DNase; separated on agarose gel and Northern blotted to determine expression of c-jun gene and that of detoxifying enzyme NAD(P)H:quinone oxidoreductase (NQO1)

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. caused maximum expression of c-jun and NQO1 genes at 4 h and it remained unchanged at 8 h of treatment; increase in time of exposure to 16 h resulted in substantial decrease in expression of c-jun and NQO1 genes; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

10 - 200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO to prepare high strength stock solutions, which were diluted with medium to obtain desired concentrations

Method (Pharmacological Data)

cells treated for 16 h with title comp.; total RNA extracted; treated with DNase; separated on agarose gel and Northern blotted to determine expression cjun gene and that of detoxifying enzyme NAD(P)H-quinone oxidoreductase (NQO1)

Further Details (Pharmacological Data)

control: vehicle

Results

title comp. treatment resulted in concentration-dependent increase in expression of c-jun and NQO1 genes; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

100 - 200 μmol/l


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Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO to prepare high strength stock solutions, which were diluted with medium to obtain desired concentrations

Method (Pharmacological Data)

cells treated for 16 h with title comp.; total RNA extracted; treated with DNase; separated on agarose gel and Northern blotted to determine gene expression of detoxifying enzyme NRH:quinone oxidoreductase (NQO2)

Further Details (Pharmacological Data)

control: vehicle

Results

NQO2 gene expression was slightly higher with 200 μmol/l title comp. than with 100 μmol/l title comp.; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

100 - 200 μmol/l

Kind of Dosing (Pharmacological Data)

title comp. dissolved in DMSO to prepare high strength stock solutions, which were diluted with medium to obtain desired concentrations

Method (Pharmacological Data)

cells co-transfected with plasmids pCJ4.5-CAT, pCJ1.7-CAT and pCJ-ARE-tk-CAT and pRSV-β-galactosidase; after 32 h, treated with title comp. for 16 h; analyzed for β-galactosidase and chloramphenicol acetyl transferase (CAT) activity

Further Details (Pharmacological Data)

pCJ-tk-CAT contain antioxidant responsive element (ARE) from c-jun genes attached to CAT gene; pCJ4.5-CAT, pCJ1.7-CAT contain 4.5, 1.7 kb of c-jun promoter regulating the CAT gene, resp.

Results

title comp. treatment resulted in increased expression of ARE-mediated CAT gene as well as the expression of CAT gene mediated by 4.5 and 1.7 kb of cjun promoter but the fold induction was signif. lower than that of endogenous c-jun gene; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

gene expression; increase of

Species or TestSystem (Pharmacological Data)

human hepatoblastoma Hep-G2 cells

Concentration (Pharmacological Data)

100 - 200 μmol/l

Method (Pharmacological Data)

cells co-transfected with plasmids hARE-tk-CAT, GST Ya ARE-tk-CAT and pRSV-β-galactosidase; after 32 h, treated with title comp. for 16 h; analyzed for βgalactosidase and chloramphenicol acetyl transferase (CAT) activity

Further Details (Pharmacological Data)

hARE-tk-CAT, GST YA ARE-tk-CAT contain antioxidant responsive element (ARE) from NAD(P)H:quinone oxidoreductase (NQO1, human), glutathione Stransferase (GST) Ya (rat) attached to CAT gene

Results

both NQO1 and GST Ya gene AREs mediated high levels of CAT gene expression, which were induced several fold in response to title comp.; fig.

Reference

Radjendirane, Venugopal; Jaiswal, Anil K.

Biochemical Pharmacology, 1999 , vol. 58, # 4 p. 597 - 603 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

antioxidant activity in light-sensitized oxidation of stripped soybean oil

Reference

Hall III, Clifford A.; Cuppett, Susan L.; Dussault, Pat

Journal of Agricultural and Food Chemistry, 1998 , vol. 46, # 4 p. 1303 - 1310 Title/Abstract Full Text View citing articles Show Details

Comment

in vitro antifungal activity against Saccharomyces cerevisiae: minimum inhibitory concentration, MIC=1600 μg/mL; minimum fungicidal concentration,


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(Pharmacological Data)

MFC=1600 μg/mL

Reference

Kubo, Isao; Lee, Sang Hwa

Journal of Agricultural and Food Chemistry, 1998 , vol. 46, # 10 p. 4052 - 4055 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

rat basophilic leukemia (RBL-2H3) cells

Concentration (Pharmacological Data)

1 - 30 μmol/l

Method (Pharmacological Data)

cells were incubated with title comp. in the presence of 16 nmol/l 12-O-tetradecanoylphorbol-13-acetate (TPA) for 3 h at 37 deg C; the lactate dehydrogenase (LDH) release measured by LDH assay

Results

LDH release activity was less than 5 percent

Reference

Teshima; Onose; Ikebuchi; Sawada

Inflammation Research, 1998 , vol. 47, # 8 p. 328 - 333 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

transmitter releasing

Species or TestSystem (Pharmacological Data)

rat basophilic leukemia (RBL-2H3) cells

Concentration (Pharmacological Data)

Ca. 1 - 30 μmol/l

Method (Pharmacological Data)

cells were incubated with title comp. in the presence or absence of 16 nmol/l 12-O-tetradecanoylphorbol-13-acetate (TPA) for 3 h at 37 deg C; the TNF-α release measured by EIA

Results

title comp. did not induce release of TNF-α in the presence or absence of TPA (diagram)

Reference

Teshima; Onose; Ikebuchi; Sawada

Inflammation Research, 1998 , vol. 47, # 8 p. 328 - 333 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

HepG2 cells

Method (Pharmacological Data)

cells treated with title comp. for 24 h; luciferase activity determined in luminometer; β-gal activity determined spectrophotometrically at 595 nm after incubation with CRG at 37 deg C for 1 h

Further Details (Pharmacological Data)

cells transfected with p1.62YaLUC and expression plasmids for pCMVβ and pRSVGR; β-gal: β-galactosidase; CRG: chlorophenol red β-galactopyranoside

Results

title comp. caused induction in reporter expression

Reference

Falkner, K. Cameron; Rushmore, Thomas H.; Linder, Mark W.; Prough, Russell A.

Molecular Pharmacology, 1998 , vol. 53, # 6 p. 1016 - 1026 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

DNA; examination of

Species or TestSystem (Pharmacological Data)

pUC18 supercoiled plasmid DNA

Concentration

0 - 10E-2 M


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Exposure Period (Pharmacological Data)

60 min

Method (Pharmacological Data)

in vitro; estimation of DNA cleavage

Further Details (Pharmacological Data)

37 deg C

Results

increase of linear form (concentration-dependent)

Reference

Okubo, Tomoko; Nagai, Fumiko; Ushiyama, Keiko; Kano, Itsu

Toxicology Letters, 1997 , vol. 90, # 1 p. 11 - 18 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genetic toxicity in vitro

Species or TestSystem (Pharmacological Data)

Syrian hamster embryo (SHE) cells

Concentration (Pharmacological Data)

0.625 - 5 mg/l

Exposure Period (Pharmacological Data)

24 h

Method (Pharmacological Data)

micronucleus test performed; the percentage of binucleated cells ( percent BN)-500 cells analyzed and micronucleated cells ( percent MNBC)-1000 cells analyzed, determined

Further Details (Pharmacological Data)

relative cell number (number of live cells in treated/number of live cells in the solvent control*100) determined

Results

dose-dependent increase of relative cell number; percent BN: 22, 24, 14 and 5 percent at the dose 0.625, 1.25, 2.5 and 5 μg/ml, resp.; percent MNBC: 0.9, 1.2 and 0.9 percent at the dose 0.625, 1.25 and 2.5 μg/ml, resp.

Reference

Gibson, David P.; Brauninger, Roger; Shaffi, Hussain S.; Kerckaert, Gary A.; LeBoeuf, Robert A.; Isfort, Robert J.; Aardema, Marilyn J.

Mutation Research - Genetic Toxicology and Environmental Mutagenesis, 1997 , vol. 392, # 1-2 p. 61 - 70 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

rat lung epithelial L2 cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

cells were pretreated with title comp. for 16 h and treated with tBOOH (up to 200 μmol/l) in the presence of 100 μmol/l ADP; intracellular Ca(2+) conc. was monitored by fluorescence spectrophotometry up to 15 min

Further Details (Pharmacological Data)

tBOOH: tert-butyl hydroperoxide; control: 0.1 percent DMSO

Results

title comp. alleviated inhibition of ADP - mediated Ca(2+) signaling by tBOOH (diagram)

Reference

Choi, Jinah; Liu, Rui-Ming; Forman, Henry Jay

Biochemical Pharmacology, 1997 , vol. 53, # 7 p. 987 - 993 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytoprotective

Species or TestSystem (Pharmacological Data)

rat lung epithelial L2 cells


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Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

cells were pretreated with title comp. for 16 h before incubation with tBOOH (50 - 200 μmol/l) for 2 - 4 h; ATP level was monitored by the firefly luciferin luciferase reaction; phosphorescence mode

Further Details (Pharmacological Data)

tBOOH: tert-butyl hydroperoxide; control: 0.1 percent DMSO; further investigation on mechanism of title comp. cytoprotection with BSO (irreversive inhibitor of γ-glutamylcysteine synthetase); GSH: glutathione

Results

title comp. prevented the decrease of ATP level caused by tBOOH treatment (diagram); this potency appeared to depend on alteration of the intracellular GSH pool

Reference

Choi, Jinah; Liu, Rui-Ming; Forman, Henry Jay

Biochemical Pharmacology, 1997 , vol. 53, # 7 p. 987 - 993 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

Fischer-344 rat

Sex

male

Concentration (Pharmacological Data)

0.5 mM

Exposure Period (Pharmacological Data)

0 - 3 h

Method (Pharmacological Data)

freshly isolated hepatocytes; biochemical assays

Further Details (Pharmacological Data)

37 deg C

Results

time-dependent cell death accompanied by depletion of intracellular ATP, glutathione, and protein thiols

Reference

Nakagawa, Yoshio

Toxicology Letters, 1996 , vol. 84, # 2 p. 63 - 68 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative stress

Species or TestSystem (Pharmacological Data)

calf thymus DNA

Concentration (Pharmacological Data)

1E-06 - 0.01 mol/l

Exposure Period (Pharmacological Data)

60 min

Method (Pharmacological Data)

calf thymus DNA, 1 mg/ml incubated, 37 deg C with the presence or absence of CuCl2, 1E-6 M or FeCl2, 1E-5 M; formation of 8-hydroxydeoxyguanosine (8OHdG) determination

Results

content of 8OHdG in DNA 10.1 mol/1E5 mol dG; formation of 8OHdG greatly increased by title compound in conc.-dependent manner

Reference

Nagai, Fumiko; Okubo, Tomoko; Ushiyama, Keiko; Satoh, Kanako; Kano, Itsu

Toxicology Letters, 1996 , vol. 89, # 2 p. 163 - 167 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

metabolic

Species or TestSystem (Pharmacological Data)

Fischer 344 rat


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Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mmol/kg

Kind of Dosing (Pharmacological Data)

single dose

Exposure Period (Pharmacological Data)

4 - 19 h

Method (Pharmacological Data)

in vivo; bile duct-cannulated; (160-200 g) rats housed individually in metabolic cages; food and water ad libitum; urine collected for 19 h; bile samples collected at hourly intervals for 4 h; urinary and biliary metabolites of drug assessed by HPLC

Results

drug underwent oxidation and GSH conjugation; conjugates were excreted into bile and underwent further metabolism prior to excretion in urine

Reference

Peters, Melanie M. C. G.; Lau, Serrine S.; Dulik, Deanne; Murphy, Darlene; Van Ommen, Ben; Van Bladeren, Peter J.; Monks, Terrence J.

Chemical Research in Toxicology, 1996 , vol. 9, # 1 p. 133 - 139 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

degranulation

Species or TestSystem (Pharmacological Data)

RBL-2H3 cells

Concentration (Pharmacological Data)

Ca. 0.1 - 50 μmol/l

Method (Pharmacological Data)

2E5 cells/well incubated with title comp., buffer, antigen (dinitrophenylated BSA, DNP7-BSA, 10 μg/ml) or TPA (phorbol 12-myristate 13-acetate, 10 ng/ml); activity of released hexosaminidase (indication of degranulation) determined

Further Details (Pharmacological Data)

compared with effect of 2,5-di(tert-butyl)-1,4-hydroquinone

Results

title comp. did not affect antigen induced and in the presence of TPA did not induce β-hexosaminidase secretion (diagram)

Reference

Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

intracellular Ca2+ level

Species or TestSystem (Pharmacological Data)

RBL-2H3 cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

6E5 cells/ml loaded with Fura-2 AM (6 μmol/l); antigen, dinitrophenylated BSA (DNP7-BSA, 10 μg) and title comp. added; fluorescence measured 100 s after addition of the title comp. at 37 deg C

Further Details (Pharmacological Data)

compared with effect of 2,5-di(tert-butyl)-1,4-hydroquinone

Results

title comp. did not affect intracellular Ca2+ (data not shown)

Reference

Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

intracellular Ca2+ level

Species or TestSystem (Pharmacological

RBL-2H3 cells


Data)

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Concentration (Pharmacological Data)

10 - 50 μmol/l

Method (Pharmacological Data)

6E5 cells/ml loaded with Fura-2 AM (6 μmol/l); title comp. added 150 s after or before 2,5-di(tert-butyl)-1,4-hydroquinone (DTBHQ); fluorescence measured 100 s after addition of the title comp. at 37 deg C

Results

title comp. was not antagonistic with DTBHQ (diagram)

Reference

Akasaka, Reiko; Teshima, Reiko; Kitajima, Satoshi; Momma, Junko; Inoue, Tohru; Kurokawa, Yuji; Ikebuchi, Hideharu; Sawada, Jun-ichi

Biochemical Pharmacology, 1996 , vol. 51, # 11 p. 1513 - 1519 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

leukotriene LTC4 release

Species or TestSystem (Pharmacological Data)

rat basophilic leukemia cells

Concentration (Pharmacological Data)

10 μmol/l

Method (Pharmacological Data)

cells incubated alone or in the presence of anti-DNP IgE (1 h) at 37 deg C; PIPES buffer; then incub. with title comp. in the presence of 12-Otetradecanoylphorbol-13-acetate (10 ng/ml) or buffer alone (30 min); DNP7-BSA added to antigen stimul. cells

Further Details (Pharmacological Data)

leukotriene LTC4 amount determined by LTC4/D4/E4 enzymeimmunoassay; cross reactivity with LTB4 and prostaglandin D2 given

Results

title comp. inhibited the release of LTC4 only in the cause of antigen stimulation; in the presence of 12-O-tetradecanolylphorbol-13-acetate and without additive - no effect (table)

Reference

Akasaka; Teshima; Ikebuchi; Sawada

Inflammation Research, 1996 , vol. 45, # 12 p. 583 - 589 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

Ah receptor nuclear translocation-defective (c4) cells

Method (Pharmacological Data)

cultured cells incubated with title comp. dissolved in DMSO, different enzyme activities and GSH level measured after 24 h of incubation by known methods; pure DMSO as control

Results

GSH level 220 percent, γ-glutamylcysteine synthetase, NAD(P)H:menadione oxidoreductase, cytosolic aldehyde dehydrogenase class 3, UDPglucuronosyltransferase, GSH S-transferase and CYP1A1 activ. 220, 210, 7500, 270, 95 and 100 percent of the control, resp.

Reference

Shertzer, Howard G.; Vasiliou, Vasilis; Liu, Rui-Ming; Tabor, M. Wilson; Nebert, Daniel W.

Chemical Research in Toxicology, 1995 , vol. 8, # 3 p. 431 - 436 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

mouse hepatoma Hepa-1c1c7 cells

Method (Pharmacological Data)

cultured cells incubated with title comp. dissolved in DMSO, different enzyme activities and GSH level measured after 24 h of incubation by known methods; pure DMSO as control

Results

GSH level 260 percent, γ-glutamylcysteine synthetase, NAD(P)H:menadione oxidoreductase, cytosolic aldehyde dehydrogenase class 3, UDPglucuronosyltransferase, GSH S-transferase and CYP1A1 activ. 240, 340, 330, 170, 200 and 86 percent of the control, resp.

Reference

Shertzer, Howard G.; Vasiliou, Vasilis; Liu, Rui-Ming; Tabor, M. Wilson; Nebert, Daniel W.

Chemical Research in Toxicology, 1995 , vol. 8, # 3 p. 431 - 436 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of


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Species or TestSystem (Pharmacological Data)

human breast adenocarcinoma MCF-7/0 cells

Concentration (Pharmacological Data)

30 μmol/l

Exposure Period (Pharmacological Data)

5 d

Method (Pharmacological Data)

cells (1E5) cultured in the presence of title comp.; cell homogenates; assayed for aldehyde dehydrogenase activity

Further Details (Pharmacological Data)

induction of class-3 aldehyde dehydrogenase (ALDH-3) activity

Results

NAD(P)-dependent ALDH-3 activity was elevated > 50-fold

Reference

Sreerama, Lakshmaiah; Rekha, Ganaganur K.; Sladek, Norman E.

Biochemical Pharmacology, 1995 , vol. 49, # 5 p. 669 - 676 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

mouse hepatoma Hepa-1c7c7 cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

in vitro; effect on NMO1, ALDH3c, UGT1*06 and CYP1A1 activities and mRNA levels assayed; modified Eagle's α-medium; 5 percent FCS; incub. for 6-24 h; cells homogenized; Northern blot

Further Details (Pharmacological Data)

FCS: fetal calf serum; NMO1: NAD(P)H:menadione oxidoreductase; ALDH3c: cytosolic aldehyde dehydrogenase class 3; UGT1*06: UDPglucuronosyltransferase form 1*06; CYP1A1: cytochrome P450 1A1

Results

title comp. increased ALDH3c, NMO1 and UGT1*06 but not CYP1A1 activities and its mRNA levels

Reference

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

mouse hepatoma c4 cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

in vitro; effect on NMO1, ALDH3c, UGT1*06 and CYP1A1 activities and mRNA levels assayed; modified Eagle's α-medium; 5 percent FCS; incub. for 6-24 h; cells homogenized; Northern blot

Further Details (Pharmacological Data)

FCS: fetal calf serum; NMO1: NAD(P)H:menadione oxidoreductase; ALDH3c: cytosolic aldehyde dehydrogenase class 3; UGT1*06: UDPglucuronosyltransferase form 1*06; CYP1A1: cytochrome P450 1A1

Results

title comp. increased ALDH3c, NMO1 and UGT1*06 mRNA levels

Reference

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem

mouse hepatoma c2 cells


(Pharmacological Data)

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Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

in vitro; effect on NMO1, ALDH3c, UGT1*06 and CYP1A1 activities and mRNA levels assayed; modified Eagle's α-medium; 5 percent FCS; incub. for 6-24 h; cells homogenized; Northern blot

Further Details (Pharmacological Data)

FCS: fetal calf serum; NMO1: NAD(P)H:menadione oxidoreductase; ALDH3c: cytosolic aldehyde dehydrogenase class 3; UGT1*06: UDPglucuronosyltransferase form 1*06; CYP1A1: cytochrome P450 1A1

Results

title comp. increased ALDH3c, NMO1 and UGT1*06 mRNA levels

Reference

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; induction of

Species or TestSystem (Pharmacological Data)

mouse hepatoma c37 cells

Concentration (Pharmacological Data)

50 μmol/l

Method (Pharmacological Data)

in vitro; effect on NMO1, ALDH3c, UGT1*06 and CYP1A1 activities and mRNA levels assayed; modified Eagle's α-medium; 5 percent FCS; incub. for 6-24 h; cells homogenized; Northern blot

Further Details (Pharmacological Data)

FCS: fetal calf serum; NMO1: NAD(P)H:menadione oxidoreductase; ALDH3c: cytosolic aldehyde dehydrogenase class 3; UGT1*06: UDPglucuronosyltransferase form 1*06; CYP1A1: cytochrome P450 1A1

Results

title comp. increased ALDH3c, NMO1 and UGT1*06 mRNA levels

Reference

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

antagonist

Species or TestSystem (Pharmacological Data)

mouse hepatoma Hepa-1c7c7 cells

Concentration (Pharmacological Data)

25 μmol/l

Kind of Dosing (Pharmacological Data)

added in DMSO

Method (Pharmacological Data)

in vitro; effect on menadione-induced cytotoxicity assayed; modified Eagle's α-medium; 5 percent FCS; pretreated with title comp. for 24 h; exposed to 20100 μM menadione; cell viability assessed 2 h latter

Further Details (Pharmacological Data)

FCS: fetal calf serum; DMSO: dimethylsulfoxide

Results

title comp. protected against subsequent exposure to menadione; DMSO alone had no protective activity; graphical representation

Reference

Vasiliou, Vasilis; Shertzer, Howard G.; Liu, Rui-Ming; Sainsbury, Malcolm; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 11 p. 1885 - 1892 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative stress

Species or TestSystem (Pharmacological Data)

mouse ch/ch cells


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Method (Pharmacological Data)

in vitro; effect on Nmo1, Ahd4 and Ugtl*06 gene expression assayed; DMEM with 5 percent FBS and NaHCO3; 95 percent air-5 percent CO2; 34 deg C; incubated for 12 h; RNA extracted; NMO1, ALDH3c and UGT1*06 mRNAs level determined; Northern blot

Further Details (Pharmacological Data)

NMO1: TCDD-inducible NAD(P)H:menadione oxidoreductase; Nmo1: NMO1 gene; ALDH3c: TCDD-inducible cytosolic aldehyde dehydrogenase; Ahd4: ALDH3c gene; UGT1*06: TCDD-inducible glucuronosyltransferase; Ugtl*06: UGT11*06 gene

Results

increased NMO1 mRNA level but had no effect on ALDH3c and UGT1*06 mRNAs levels

Reference

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

oxidative stress

Species or TestSystem (Pharmacological Data)

mouse 14CoS/14CoS cells

Concentration (Pharmacological Data)

25 μmol/l

Method (Pharmacological Data)

in vitro; effect on Nmo1, Ahd4 and Ugtl*06 gene expression assayed; DMEM with 5 percent FBS and NaHCO3; 95 percent air-5 percent CO2; 34 deg C; incubated for 12 h; RNA extracted; NMO1, ALDH3c and UGT1*06 mRNAs level determined; Northern blot

Further Details (Pharmacological Data)

NMO1: TCDD-inducible NAD(P)H:menadione oxidoreductase; Nmo1: NMO1 gene; ALDH3c: TCDD-inducible cytosolic aldehyde dehydrogenase; Ahd4: ALDH3c gene; UGT1*06: TCDD-inducible glucuronosyltransferase; Ugtl*06: UGT11*06 gene

Results

increased NMO1 mRNA level but had no effect on ALDH3c and UGT1*06 mRNAs levels

Reference

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

mouse ch/ch cells

Concentration (Pharmacological Data)

1E-09 - 0.005 mol/l

Method (Pharmacological Data)

in vitro; effect on cell injury assayed; DMEM supplemented with 5 percent FBS and NaHCO3; 95 percent air-5 percent CO2; 34 deg C; incubated for 6-24 h; amount of toxicity assessed by light microscopy, cell counts and trypan blue dye exclusion

Further Details (Pharmacological Data)

FBS: fetal bovine serum

Results

produced about >90 cell death

Reference

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

cytotoxicity

Species or TestSystem (Pharmacological Data)

mouse 14CoS/14CoS cells

Concentration (Pharmacological Data)

1E-09 - 0.005 mol/l

Method (Pharmacological Data)

in vitro; effect on cell injury assayed; DMEM supplemented with 5 percent FBS and NaHCO3; 95 percent air-5 percent CO2; 34 deg C; incubated for 6-24 h; amount of toxicity assessed by light microscopy, cell counts and trypan blue dye exclusion

Further Details (Pharmacological

FBS: fetal bovine serum


Data)

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Results

produced about < 5 percent cell death

Reference

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

mouse hepatoma Hepa-1 cells nuclear extracts

Concentration (Pharmacological Data)

25 - 50 μmol/l

Method (Pharmacological Data)

in vitro; effect on EpRE probe binding to DNA assayed; 10 μg of nuclear extracts from title comp. treated cells for 6-12 h; 0.1 ng of labeled EpRE probe; binding buffer; room temp.; incubation time 20 min; gel mobility shift analysis

Further Details (Pharmacological Data)

EpRE: electrophile response element

Results

title comp. increased EpRE probe binding

Reference

Vasiliou, Vasilis; Puga, Alvaro; Chang, Ching-Yi; Tabor, M. Wilson; Nebert, Daniel W.

Biochemical Pharmacology, 1995 , vol. 50, # 12 p. 2057 - 2068 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

genetic toxicity in vitro

Species or TestSystem (Pharmacological Data)

chinese hamster V79 cells

Concentration (Pharmacological Data)

120 - 720 μmol/l

Exposure Period (Pharmacological Data)

1 h

Method (Pharmacological Data)

in DMSO; DPBS; 37 deg C; CREST labeling procedure; arachidonic acid supplemented (+AA) and nonsupplemented V79 cells; induction of micronucleated (MN) cells; effects of catalase and glutathione

Further Details (Pharmacological Data)

Cochran-Armitage binomial trend test; one-tailed Fisher exact test

Results

total MN cells per 1000: 15-79 (28) (+AA), 19-80 (29); CREST-positive: 7-50 (14) (+AA), 10-36 (21); CREST-negative: 8-36 (12) (+AA), 9-44 (8); binucleated cells counted 2000-2678 (4119) (+AA), 2000 (2000); inhibition effect of catalase and GSH

Reference

Dobo; Eastmond

Environmental and Molecular Mutagenesis, 1994 , vol. 24, # 4 p. 293 - 300 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

ED50 in KB Cells 17.50 μg/mL

Reference

Lam; Garg; Swanson; Pezzuto

Journal of Pharmaceutical Sciences, 1988 , vol. 77, # 5 p. 393 - 395 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

ED50 in P-388 Cells 1.20 μg/mL

Reference

Lam; Garg; Swanson; Pezzuto

Journal of Pharmaceutical Sciences, 1988 , vol. 77, # 5 p. 393 - 395 Title/Abstract Full Text View citing articles Show Details

Ecotoxicology (10) 1 of 10

Effect (Ecotoxicology)

antifungal


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Species or TestSystem (Ecotoxicology)

Gloeophyllum trabeum ATCC 11539

Concentration (Ecotoxicology)

25 - 500 ppm

Method (Ecotoxicology)

agar-plate test; five replicates; radial fungal growth normalized to fungal growth on control plates; solvent: water or acetone; IC50 value calculated by regression of relative growth versus log of concentration

Further Details (Ecotoxicology)

brown-rot fungus

Type (Ecotoxicology)

IC50

Value of Type (Ecotoxicology)

< 200 ppm

Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

antifungal

Species or TestSystem (Ecotoxicology)

Postia placenta ATCC 11538

Concentration (Ecotoxicology)

25 - 500 ppm

Method (Ecotoxicology)

agar-plate test; five replicates; radial fungal growth normalized to fungal growth on control plates; solvent: water or acetone; IC50 value calculated by regression of relative growth versus log of concentration

Further Details (Ecotoxicology)

brown-rot fungus

Type (Ecotoxicology)

IC50

Value of Type (Ecotoxicology)

< 200 ppm

Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

antifungal

Species or TestSystem (Ecotoxicology)

Irpex lacteus ATCC 11245

Concentration (Ecotoxicology)

25 - 500 ppm

Method (Ecotoxicology)

agar-plate test; five replicates; radial fungal growth normalized to fungal growth on control plates; solvent: water or acetone; IC50 value calculated by regression of relative growth versus log of concentration

Further Details (Ecotoxicology)

white-rot fungus

Type (Ecotoxicology)

IC50

Value of Type (Ecotoxicology)

< 200 ppm

Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

antifungal

Species or TestSystem (Ecotoxicology)

Trametes versicolor ATCC 12679

Concentration (Ecotoxicology)

25 - 500 ppm

Method (Ecotoxicology)

agar-plate test; five replicates; radial fungal growth normalized to fungal growth on control plates; solvent: water or acetone; IC50 value calculated by regression of relative growth versus log of concentration

Further Details (Ecotoxicology)

white-rot fungus

Type (Ecotoxicology)

IC50

Value of Type

< 200 ppm


(Ecotoxicology)

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Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

antifungal

Species or TestSystem (Ecotoxicology)

Trametes versicolor ATCC 12679

Kind of Dosing (Ecotoxicology)

treatment with conc. of 5 percent

Method (Ecotoxicology)

laboratory decay test; agar-block test; aspen (Populus spp.) sapwood wafers treated with title comp. and exposed to the white-rot fungus for 6 weeks; extent of degradation measured by compression strength loss in radial direction; five replicates

Comment (Ecotoxicology)

No effect

Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

antifungal

Species or TestSystem (Ecotoxicology)

Gloeophyllum trabeum ATCC 11539

Kind of Dosing (Ecotoxicology)

treatment with conc. of 5 percent

Method (Ecotoxicology)

laboratory decay test; soil-block test; SYP sapwood wafers treated with title comp. and exposed to the brown-rot fungus for 5 weeks; extent of degradation measured by compression strength loss in radial direction; five replicates

Further Details (Ecotoxicology)

SYP, southern yellow pine (Pinus spp.)

Results

average percent strength loss: 9.2 in treatment compared to 83.0-99.1 in control

Reference

Schultz, Tor P; Nicholas, Darrel D

Phytochemistry, 2002 , vol. 61, # 5 p. 555 - 560 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

toxicity to fish (acute)

Species or TestSystem (Ecotoxicology)

Ictalurus punctatus, channel catfish

Exposure Period (Ecotoxicology)

48 h

Method (Ecotoxicology)

static toxicity tests according to ASTM standard methods for fish; 17 deg C; fish were not fed during exper.; 20-l glass jar; 15 l well water; mortality meas. at 1, 3, 6, 24, 48 hd

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

0.37 mg/l

Results

mean values

Reference

Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

Environmental Toxicology and Chemistry, 1997 , vol. 16, # 9 p. 1930 - 1934 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

toxicity to fish (acute)

Species or TestSystem (Ecotoxicology)

Lepomis macrochirus, bluegill

Exposure Period (Ecotoxicology)

48 h

Method (Ecotoxicology)

static toxicity tests according to ASTM standard methods for fish; 17 deg C; fish were not fed during exper.; 20-l glass jar; 15 l well water; mortality meas. at 1, 3, 6, 24, 48 hd

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

0.15 mg/l

Results

mean values


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10 of 10

Reference

Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

Environmental Toxicology and Chemistry, 1997 , vol. 16, # 9 p. 1930 - 1934 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

toxicity to fish (acute)

Species or TestSystem (Ecotoxicology)

Oncorhynchus mykiss, rainbow trout

Exposure Period (Ecotoxicology)

48 h

Method (Ecotoxicology)

static toxicity tests according to ASTM standard methods for fish; 17 deg C; fish were not fed during exper.; 20-l glass jar; 15 l well water; mortality meas. at 1, 3, 6, 24, 48 hd

Type (Ecotoxicology)

LC50

Value of Type (Ecotoxicology)

0.37 mg/l

Results

mean values

Reference

Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

Environmental Toxicology and Chemistry, 1997 , vol. 16, # 9 p. 1930 - 1934 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

toxicity to aquatic invertebrates (acute)

Endpoint of Effect (Ecotoxicology)

reattachment inhibition

Species or TestSystem (Ecotoxicology)

Dreissena polymorpha, zebra mussel

Exposure Period (Ecotoxicology)

48 h

Method (Ecotoxicology)

15 mussels (5-8-mm shell length); well water; 17 deg C; pH 8.0; satic tox. tests according to standard ASTM methods; petri dishes; righting response; reattach. and mortality; 48-h postexpos. period; 48-h EC90 also

Further Details (Ecotoxicology)

mussels collect. by divers from relativl nonindustrialized areas of Lake Michigan or Lake Erie; 48-h EC50 and EC90=effect. conc. of test comp. required to inhibit reattachment of 50 and 90 percent, resp.

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

1.0 mg/l

Results

48-h EC90: 1.9 mg/l; mean values

Reference

Cope, W. Gregory; Bartsch, Michelle R.; Marking, Leif L.

Environmental Toxicology and Chemistry, 1997 , vol. 16, # 9 p. 1930 - 1934 Title/Abstract Full Text View citing articles Show Details

Other Data Abiotic Degradation, Hydrolysis (1) 1 of 1

Type (Abiotic Degradation, Hydrolysis)

oxidation

Concentration (Abiotic Degradation, Hydrolysis)

0.1 mmol/l

Rate Constant

2.68 - 4.77 min-1

pH-Value (Abiotic Degradation, Hydrolysis)

3 - 11

Method, Remarks (Abiotic Degradation, Hydrolysis)

alkaline catalytic hydrolysis in the presence of potassium peroxydisulfate

Reference

Lau, Tim K.; Chu, Wei; Graham, Nigel J. D.

Environmental Science and Technology, 2007 , vol. 41, # 2 p. 613 - 619 Title/Abstract Full Text View citing articles Show Details

Use (91) Use Pattern

Location

Reference


Pharmaceuticals

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Osaka University; HAYASHI, Ryuhei; NISHIDA, Kohji; KATORI, Ryosuke

Patent: EP2878197 A1, 2015 ; Title/Abstract Full Text Show Details

tissue preservation solution

Page/Page column 11

Osaka University; HAYASHI, Ryuhei; NISHIDA, Kohji; KATORI, Ryosuke

Patent: EP2878197 A1, 2015 ; Title/Abstract Full Text Show Details

Personal care composition in combination with 2-methyl-4-isothiazolin-3-one

Antioxidant for prevention of siloxanes polymerization

Page/Page column title page; 1; 2

Tran, Thu-Ba Thi; Younathan, Janet Nadya

Patent: US2010/22606 A1, 2010 ;

Air Products and Chemicals, Inc.

Patent: EP2050753 A1, 2009 ;

Title/Abstract Full Text Show Details

Title/Abstract Full Text Show Details

skin treatment composition comprisingcalcium glycerophosphate and a fatty acid source derived from an animal or a vegetable suitable for enhancing skin cell growth, proliferation and repair

antioxidant

AKPHARMA INC.

Patent: US2008/107743 A1, 2008 ; Title/Abstract Full Text Show Details

RANBAXY LABORATORIES LIMITED

Patent: WO2005/87706 A1, 2005 ; Title/Abstract Full Text Show Details

GPC BIOTECH AG

Patent: WO2005/120479 A1, 2005 ; Title/Abstract Full Text Show Details

Glinski, Jan

Patent: US2006/93571 A1, 2006 ; Title/Abstract Full Text Show Details

E.I. DU PONT DE NEMOURS AND COMPANY

Patent: US2007/59344 A1, 2007 ; Title/Abstract Full Text Show Details

Giner, Victor Casana

Patent: US2007/77308 A1, 2007 ; Title/Abstract Full Text Show Details

AKPHARMA INC.

Patent: US2008/107743 A1, 2008 ; Title/Abstract Full Text Show Details

Lipid-based anti-oxidant of a coating composition for protecting core material from oxidative damage

National Starch and Chemical Investment Holding Corporation

Patent: US2008/112987 A1, 2008 ; Title/Abstract Full Text Show Details

Lipid-based anti-oxidant of a coating composition for protecting core material from hydrolytic damage

National Starch and Chemical Investment Holding Corporation

Patent: US2008/112987 A1, 2008 ; Title/Abstract Full Text Show Details

Lipid-based anti-oxidant of a coating composition for ensuring long-term stability

National Starch and Chemical Investment Holding Corporation

Patent: US2008/112987 A1, 2008 ; Title/Abstract Full Text Show Details

complexing agent in a nanoparticulate formulation for epilepsy-related disorders

MARINUS PHARMACEUTICALS

Patent: WO2008/66899 A2, 2008 ; Title/Abstract Full Text Show Details

complexing agent in a nanoparticulate formulation for central nervous system disorders

MARINUS PHARMACEUTICALS

Patent: WO2008/66899 A2, 2008 ; Title/Abstract Full Text Show Details


antimicrobial formulation

SYNTOPIX LIMITED

Patent: WO2008/35078 A1, 2008 ; Title/Abstract Full Text Show Details

SYNTOPIX LIMITED

Patent: WO2008/35085 A1, 2008 ; Title/Abstract Full Text Show Details

Increases nutrient digestion

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Improves rumen fermentation

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Improves microbial growth

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Improves microbial efficiency

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Increase milk production

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Increase milk fat

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Reduce the formation of free radicals in the diet

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Prevents oxidation of different types of fats utilized in a ruminant diet

NOVUS INTERNATIONAL, INC.

Patent: US2008/15217 A1, 2008 ; Title/Abstract Full Text Show Details

Show next 20

Laboratory Use and Handling

Hide facts Use Pattern

Location

Reference

Antioxidant for agricultural compositions

VALENT BIOSCIENCES CORPORATION

Patent: WO2008/143961 A1, 2008 ; Title/Abstract Full Text Show Details

Antioxidant for agrochemical formulations

VALENT BIOSCIENCES CORPORATION

Patent: WO2008/143969 A1, 2008 ; Title/Abstract Full Text Show Details

Antioxidant

SUNTORY LIMITED

Patent: WO2007/4689 A1, 2007 ; Title/Abstract Full Text Show Details

whitening skin

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details

Bleach dark or blotchy areas

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details


Hyperpigmentation caused by child bearing (chloasma gravidarum

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details

hyperpigmentation caused by birth control (chloasma pillularae)

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details

Post-inflammatory hyperpigmentation following trauma

L'Oreal S.A.

Patent: US2007/25939 A1, 2007 ; Title/Abstract Full Text Show Details

improving oxidative stability in meat

E.I. DU PONT DE NEMOURS AND COMPANY

Patent: US2007/59344 A1, 2007 ; Title/Abstract Full Text Show Details

foodstuff

Giner, Victor Casana

Patent: US2007/77308 A1, 2007 ; Title/Abstract Full Text Show Details

biologically active material beneficial for the human or other animals' health

Giner, Victor Casana

Patent: US2007/77308 A1, 2007 ; Title/Abstract Full Text Show Details

Thermal polymerization inhibitor in a one-part self etching, self-priming dental adhesive

DENTSPLY DETREY GmbH

Patent: EP1776943 A1, 2007 ; Title/Abstract Full Text Show Details

tyrosine kinase inhibitor

BRAIN N' BEYOND BIOTECH PVT. LTD.

Patent: WO2007/54977 A2, 2007 ; Title/Abstract Full Text Show Details

ganaxolone formulation having enhanced stability and pharmacokinetic properties useful for the treatment of epilepsy-related and other cenral nervous system diorders

complexing agent

MARINUS PHARMACEUTICALS

Patent: WO2007/62266 A2, 2007 ; Title/Abstract Full Text Show Details

MARINUS PHARMACEUTICALS

Patent: WO2007/62266 A2, 2007 ; Title/Abstract Full Text Show Details

Antimicrobial

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin structure conditions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Eczema

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Superficial infected traumatic lesions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

wounds

SYNTOPIX LIMITED


Patent: WO2007/96601 A2, 2007 ;

Title/Abstract Full Text Show Details

Burns

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

ulcers

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Folliculitis

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Mycoses

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne lesions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Bacteria associated with acne

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Skin conditions

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Staphylococcal infection

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Atopic dermatitis

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Primary skin infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Secondary skin infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Primary skin structure infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Secondary skin structure infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Acne-related scarring

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

methicillin resistant S. aureus (MRSA)-associated infections

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ;


Title/Abstract Full Text Show Details

Skin care

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Hair care

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Cosmeceutical preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Toiletry product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Laundry product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Fabric treatment product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Bath additive

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Shower additive

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Cleansing preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Agricultural product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

Horticultural product

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

veterinary preparation

SYNTOPIX LIMITED

Patent: WO2007/96601 A2, 2007 ; Title/Abstract Full Text Show Details

monomer for the synthesis of polimeric antioxidant

Page/Page column 6

Cholli, Ashok L.; Kumar, Vijayendra; Kumar, Javant; Parmar, Virinder Singh; Samuelson, Lynne Ann; Bruno, Ferdinando F.

Patent: US2007/154430 A1, 2007 ; Title/Abstract Full Text Show Details

personal care composition

Glinski, Jan

Patent: US2006/93571 A1, 2006 ; Title/Abstract Full Text Show Details

Antioxidant for pesticidal composition

VALENT BIOSCIENCES CORPORATION

Patent: WO2006/107905 A1, 2006 ; Title/Abstract Full Text Show Details


antioxidant response element

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

neurodegenerative disease

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

Alzheimer's disease

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

Huntington's disease

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

Parkinson's disease

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

ALS disease

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

Friedreich's Ataxia

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

AIDS dementia

Johnson, Jeffrey A.; Calkins, Marcus J.

Patent: US2006/121014 A1, 2006 ; Title/Abstract Full Text Show Details

Skin benefit agent for cosmetic composition

Unilever Home and Personal Care USA, Division Of Conopco, Inc.

Patent: US2006/110341 A1, 2006 ; Title/Abstract Full Text Show Details

Sinthetic antioxidant for investigation of inhibition of lipid peroxidation

Board of Trustees of Michigan State University

Patent: US2005/59727 A1, 2005 ; Title/Abstract Full Text Show Details

diabetic retinopathy

Alcon, Inc.

Patent: US2005/137147 A1, 2005 ; Title/Abstract Full Text Show Details

drusen formation in age-related macular degeneration

Alcon, Inc.

Patent: US2005/137147 A1, 2005 ; Title/Abstract Full Text Show Details

glaucomatous retinopathy

Alcon, Inc.

Patent: US2005/137146 A1, 2005 ; Title/Abstract Full Text Show Details

optic neuropathy

Alcon, Inc.

Patent: US2005/137146 A1, 2005 ; Title/Abstract Full Text Show Details

anti-oxidant in solid stick insecticidal composition

RECKITT BENCKISER (AUSTRALIA) PTY LIMITED; RECKITT BENCKISER (UK) LIMITED

Patent: WO2005/20686 A1, 2005 ; Title/Abstract Full Text Show Details


modulating component of fungicidal compositions

ISAGRO S.P.A.

Patent: WO2005/94580 A1, 2005 ; Title/Abstract Full Text Show Details

deodorant agent

Hu, Jinlian; Zeng, Fang; Li, Pei

Patent: US2005/232880 A1, 2005 ; Title/Abstract Full Text Show Details

antioxidants and/or free-radical scavengers for composition for treating a keratinous material

stabilizer of a pharmaceutical composition

L'OREAL S.A.

Patent: US2004/253283 A1, 2004 ; Title/Abstract Full Text Show Details

Oshlack, Benjamin; Huang, Hua-Pin; Goliber, Philip; Mannion, Richard

Patent: US2003/229111 A1, 2003 ; Title/Abstract Full Text Show Details

antioxidant

Yamamura; Nishiwaki; Tanigaki; Terauchi; Tomiyama; Nishiyama Bulletin of the Chemical Society of Japan, 1995 , vol. 68, # 10 p. 2955 - 2960 Title/Abstract Full Text View citing articles Show Details

Isolation from Natural Product (1) Isolation from Natural Product

Reference

Moutan Cortex (root cortex of Paeonia suffruticosa Andrews)

Okubo, Tomoko; Nagai, Fumiko; Seto, Takako; Satoh, Kanako; Ushiyama, Keiko; Kano, Itsu

Biological and Pharmaceutical Bulletin, 2000 , vol. 23, # 2 p. 199 - 203 Title/Abstract Full Text View citing articles Show Details

Quantum Chemical Calculations (1) Calculated Properties

Method (Quantum Chemical Calculations)

Reference

Dissociation energy, bonding energy

Ab initio calcns. (LCAO, GO SCF, DIM, SAMO, X-à, HartreeFock)

Guitard, Romain; Paul, Jean-François; Nardello-Rataj, Véronique; Aubry, Jean-Marie Food Chemistry, 2016 , vol. 213, p. 284 - 295 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-<Butyl-(2)>-hydrochinon

6

Reaxys Registry Number: 1938906

CAS Registry Number: 4197-81-3 Type of Substance: isocyclic Molecular Formula: C10H14O2

Linear Structure Formula: C10H14O2

Molecular Weight: 166.22

InChI Key: FVUAMBRGAQSGFR-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-<Butyl-(2)>-hydrochinon, 2-sec.-Butyl-hydrochinon, 2-sek.Butylhydrochinon, Butyl-2-hydrochinon Identification Substance Label (1) Label

Reference

Id

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

1 prep out of 2 reactions.

Identification Physical Data (3)

4


Derivative (1) Comment (Derivative)

Reference

Dibenzoat: F: 92-93grad

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

Physical Data Melting Point (2) Melting Point

Solvent (Melting Point)

Reference

100 - 101 °C

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

99 - 100 °C

H2O

Bogoljubskii

Journal of Organic Chemistry USSR (English Translation), 1966 , vol. 2, p. 1420 Zhurnal Organicheskoi Khimii, 1966 , vol. 2, p. 1433 Full Text Show Details

Further Information (1) Description (Further Information)

Reference

Further information

Hawthorne; Reintjes

Journal of the American Chemical Society, 1965 , vol. 87, p. 4585,4586 Full Text Show Details

Chemical Name: 4-(2,5-dihydroxyphenyl)butane

7

Reaxys Registry Number: 2046151

CAS Registry Number: 4197-69-7 Type of Substance: isocyclic Molecular Formula: C10H14O2

Linear Structure Formula: C10H14O2

Molecular Weight: 166.22

InChI Key: XRCRJFOGPCJKPF-UHFFFAOYSA-N

12 prep out of 17 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-(2,5-dihydroxyphenyl)butane, 2-n-Butylhydroquinone, butylhydroquinone, 1-n-butyl-1,4-hydroquinone, 3-butylhydroquinone, 2-butylhydroquinone, 2.5-Dihydroxy-1-butyl-benzol Identification Substance Label (6) Label

Reference

3c

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

2c

Shahidzadeh, Mansour; Ghandi, Mehdi

Journal of Organometallic Chemistry, 2001 , vol. 625, # 1 p. 108 - 111 Title/Abstract Full Text View citing articles Show Details

16

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899

Identification Physical Data (16) Spectra (8)

16


Title/Abstract Full Text View citing articles Show Details

(H2Q-n-C4H9)

Clemmer et al.

Inorganic Chemistry, 1979 , vol. 18, p. 2567,2570, 2571 Full Text View citing articles Show Details

Ic

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Patent-Specific Data (1) Location in Patent

Reference

Claim

Chemex Pharmaceuticals, Inc.

Patent: US4954659 A1, 1990 ; Title/Abstract Full Text Show Details

L'Oreal

Patent: US4931467 A1, 1990 ; Title/Abstract Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Dibenzoat: F: 97-98grad

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

Physical Data Melting Point (11) Melting Point

Solvent (Melting Point)

Reference

79 - 80.5 °C

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

88 - 88.5 °C

Pilar,J. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3599 - 3606 Full Text View citing articles Show Details

87 - 88 °C

benzene hexane

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

87 - 87.5 °C

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

86.5 - 87 °C

Eastman Kodak Co.

Patent: US2533203 , 1948 ; Full Text Show Details

CCl4

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

benzene

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details


H2O

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

84 - 85 °C

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

87 °C

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

89 °C

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

180 - 185 °C

20 Torr

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

Crystal Property Description (2) Colour & Other Properties

Reference

light-yellow

Ghandi, Mehdi; Shahidzadeh, Mansour

Journal of Organometallic Chemistry, 2006 , vol. 691, # 23 p. 4918 - 4925 Title/Abstract Full Text View citing articles Show Details

Nadeln

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Gulland

Biochemical Journal, 1932 , vol. 26, p. 32,43 Full Text Show Details

Dissociation Exponent (1) Comment (Dissociation Exponent)

Reference

(pk')pK(a)

Clemmer et al.

Inorganic Chemistry, 1979 , vol. 18, p. 2567,2570, 2571 Full Text View citing articles Show Details

Further Information (1) Description (Further Information)

Reference

Further information

Hawthorne; Reintjes

Journal of the American Chemical Society, 1965 , vol. 87, p. 4585,4586 Full Text Show Details

Spectra NMR Spectroscopy (5) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts Spectrum

1H

hexadeuterioacetone

300 MHz

supporting information

Kim, Ikyon; Kim, Kyungsun; Choi, Jungeun

Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8492 - 8495 Title/Abstract Full Text View citing articles Show Details

Chemical shifts Spectrum

13C

hexadeuterioacetone

75 MHz

supporting information

Kim, Ikyon; Kim, Kyungsun; Choi, Jungeun

Journal of Organic Chemistry, 2009 , vol. 74, #

Location

Comment (NMR Spectroscopy)

Reference


21 p. 8492 - 8495 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

CDCl3

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Reference

Spectrum

CHCl3

3604 - 3360 cm**(-1)

Gayo, Leah M.; Winters, Michael P.; Moore, Harold W.

Journal of Organic Chemistry, 1992 , vol. 57, # 25 p. 6896 - 6899 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (2) Description (Mass Spectrometry)

Location

Reference

HRMS (High resolution mass spectrometry) EI (Electron impact) Spectrum

supporting information

Kim, Ikyon; Kim, Kyungsun; Choi, Jungeun

Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8492 - 8495 Title/Abstract Full Text View citing articles Show Details

EI (Electron impact) Spectrum

supporting information

Kim, Ikyon; Kim, Kyungsun; Choi, Jungeun

Journal of Organic Chemistry, 2009 , vol. 74, # 21 p. 8492 - 8495 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-(2-Methyl-propyl)-hydrochinon

8

Reaxys Registry Number: 2087604

CAS Registry Number: 4197-78-8 Type of Substance: isocyclic Molecular Formula: C10H14O2

Linear Structure Formula: C10H14O2

Molecular Weight: 166.22

InChI Key: SVQYCWCFQLUSIL-UHFFFAOYSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(2-Methyl-propyl)-hydrochinon, 2-Methyl-propyl-hydrochinon, tert-Butylhydrochinon, Isobutylhydrochinon Identification Derivative (1) Comment (Derivative)

Reference

Dibenzoat: F: 120.5-121grad

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951

2 prep out of 2 reactions.

Identification Physical Data (4) Spectra (2)

4


Full Text View citing articles Show Details

Physical Data Melting Point (3) Melting Point

Solvent (Melting Point)

Reference

105 - 106 °C

hexane

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

111.5 - 112 °C

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

123 - 126 °C

Ethyl Corp.

Patent: US3075832 , 1958 ; Chem.Abstr., 1963 , vol. 59, # 12706 Full Text Show Details

Further Information (1) Description (Further Information)

Reference

Further information

Hawthorne; Reintjes

Journal of the American Chemical Society, 1965 , vol. 87, p. 4585,4586 Full Text Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Reference

Chemical shifts

1H

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Reference

Bands

Florjanczyk,Z. et al.

Journal of Organometallic Chemistry, 1976 , vol. 112, p. 21 - 28 Full Text View citing articles Show Details

Chemical Name: 2-n-pentyl-1,4-dihydroxybenzene

9

Reaxys Registry Number: 1947681

CAS Registry Number: 4693-32-7 Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: ZFMFIBDSZCASNS-UHFFFAOYSA-N

19 prep out of 36 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-n-pentyl-1,4-dihydroxybenzene, n-pentylhydroquinone, 2-pentyl-hydroquinone, 2.5-Dihydroxy-1-pentyl-benzol, 2-Pentyl-hydrochinon, nPentylhydroquinone Identification Substance Label (3)

Identification Physical Data (9) Spectra (3)

10


Label

Reference

21

The University of Chicago; MRKSICH, Milan; HODNELAND, Christian

Patent: US2015/369816 A1, 2015 ; Title/Abstract Full Text Show Details

5

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Physical Data Melting Point (6) Melting Point

Solvent (Melting Point)

Reference

81 - 82 °C

benzene

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

86 °C

benzene hexane

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

benzene

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

86 °C

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

87 °C

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647 Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

85 - 86 °C

Stoughton; Baltzly; Bass

Journal of the American Chemical Society, 1934 , vol. 56, p. 2007 Full Text View citing articles Show Details

Lamson; Brown; Ward

Journal of Pharmacology and Experimental Therapeutics, 1935 , vol. 53, p. 198,201 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

176 - 180 °C

3 Torr

Stoughton; Baltzly; Bass

Journal of the American Chemical Society, 1934 , vol. 56, p. 2007 Full Text View citing articles Show Details

Crystal Property Description (2) Colour & Other Properties

Location

Reference

white

Paragraph 0201

The University of Chicago; MRKSICH, Milan; HODNELAND, Christian

Patent: US2015/369816 A1, 2015 ; Title/Abstract Full Text Show Details

Nadeln

Cruickshank; Robinson

Journal of the Chemical Society, 1938 , p. 2064,2066 Full Text Show Details

Asahina; Yasue

Chemische Berichte, 1936 , vol. 69, p. 643,647


Yakugaku Zasshi, 1936 , vol. 56, p. 549,554 Full Text Show Details

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Chemical shifts

1H

CDCl3

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

Reference

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Bands

KBr

3310 cm**(-1)

Reference Tandon, V. K.; Vaish, Meenu; Jain, P. K.

Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995 , vol. 34, # 2 p. 93 - 96 Title/Abstract Full Text Show Details

Chemical Name: (1-Methylbutyl)-hydrochinon Reaxys Registry Number: 2360976

Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: ACAFGTOPCUFNBP-UHFFFAOYSA-N

10

1 prep out of 2 reactions.

1

4 prep out of 9 reactions.

Identification Physical Data (3) Spectra (2)

2

Synthesize | Hide Details Find similar Chemical Names and Synonyms (1-Methylbutyl)-hydrochinon Chemical Name: 2-(2,2-Dimethyl-propyl)-hydrochinon Reaxys Registry Number: 2518750

CAS Registry Number: 39868-20-7 Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: IZRKOTZTHHSHEF-UHFFFAOYSA-N

11

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(2,2-Dimethyl-propyl)-hydrochinon, 2-Neopentylhydrochinon


Identification Substance Label (3) Label

Reference

VII

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

Ib

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

IIb

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

Physical Data Melting Point (2) Melting Point

Solvent (Melting Point)

Reference

142 - 144 °C

cyclohexane

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

107.5 - 108 °C

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

Electrochemical Characteristics (1) Description (Electrochemical Characteristics)

Reference

polarographic half-wave potential

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Reference

Chemical shifts

1H

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Reference

Bands

Lisa,E. et al.

Collection of Czechoslovak Chemical Communications, 1972 , vol. 37, p. 3307 - 3312 Full Text View citing articles Show Details

Chemical Name: (3-Methyl-butyl-2)-hydrochinon

12

Reaxys Registry Number: 2522734

Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: CGESVEGXWXLTTN-UHFFFAOYSA-N

no reactions.

Physical Data (1)

1


Synthesize | Hide Details Find similar Chemical Names and Synonyms (3-Methyl-butyl-2)-hydrochinon Physical Data Further Information (1) Description (Further Information)

Reference

Further information

Hawthorne; Reintjes

Journal of the American Chemical Society, 1965 , vol. 87, p. 4585,4586 Full Text Show Details

Chemical Name: 2-isopentyl-hydroquinone Reaxys Registry Number: 2556709

CAS Registry Number: 22296-58-8 Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: NOENSGSCMXILBW-UHFFFAOYSA-N

13

7 prep out of 8 reactions.

Identification Physical Data (2) Spectra (3) Bioactivity (1)

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-isopentyl-hydroquinone, 2-Isopentyl-hydrochinon, 2.5-Dihydroxy-1-isopentyl-benzol Identification Substance Label (2) Label

Reference

1;R1=i-C5H11,R3=OH,

Casiraghi, Giovanni; Casnati, Giuseppe; Puglia, Giuseppe; Sartori, Giovanni

Synthesis, 1980 , # 2 p. 124 - 125 Title/Abstract Full Text Show Details

VI

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

Physical Data Melting Point (2) Melting Point

Solvent (Melting Point)

Reference

103 - 105 °C

CCl4

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

101 °C

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Spectra

6


NMR Spectroscopy (1) Description (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Reference

NMR

In CDCl3

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Reference

IR

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

UV/VIS Spectroscopy (1)

Description (UV/VIS Spectroscopy)

Reference

Spectrum

John; Dietzel; Guenther

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1938 , vol. 252, p. 208,220 Full Text Show Details

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Quilico et al.

Gazzetta Chimica Italiana, 1950 , vol. 80, p. 325,331, 342 Full Text Show Details

John; Dietzel; Guenther

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1938 , vol. 252, p. 208,220 Full Text Show Details

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Chari et al.

Indian Journal of Chemistry, 1969 , vol. 7, p. 40,41 Full Text Show Details

Casiraghi, Giovanni; Casnati, Giuseppe; Puglia, Giuseppe; Sartori, Giovanni

Synthesis, 1980 , # 2 p. 124 - 125 Title/Abstract Full Text Show Details

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Chemical Name: 2-tert.-Pentyl-hydrochinon Reaxys Registry Number: 2557231

CAS Registry Number: 2349-72-6 Type of Substance: isocyclic Molecular Formula: C11H16O2

Linear Structure Formula: C11H16O2

Molecular Weight: 180.247

InChI Key: FKWOGPPGVRDIRZ-UHFFFAOYSA-N

14

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-tert.-Pentyl-hydrochinon, tert.-Pentyl-hydrochinon Identification

2 prep out of 2 reactions.

Identification Physical Data (3)

3


Substance Label (2) Label

Reference

VI

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

6

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Physical Data Melting Point (2)

Melting Point

Solvent (Melting Point)

Reference

107.5 - 108 °C

toluene

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

106 - 107 °C

H2O

Perrotti; Castelfranchi

Chimica e l'Industria (Milan, Italy), 1960 , vol. 42, p. 1333,1338 Full Text Show Details

Electrochemical Characteristics (1) Description (Electrochemical Characteristics)

Reference

polarographic half-wave potential

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Chemical Name: 2-hexyl-hydroquinone Reaxys Registry Number: 1950697

CAS Registry Number: 4197-72-2 Type of Substance: isocyclic Molecular Formula: C12H18O2

Linear Structure Formula: C12H18O2

Molecular Weight: 194.274

InChI Key: NOUJHHZNUIXAEX-UHFFFAOYSA-N

15

14 prep out of 22 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-hexyl-hydroquinone, 2-Hexyl-hydrochinon, 2.5-Dihydroxy-1-hexyl-benzol, 2-hexyl-benzene-1,4-diol, 2-n-hexyl-hydroquinone, 1-hexylhydroquinone, Hexyl-hydrochinon Identification Substance Label (3) Label

Reference

3, R=(CH2)4CH3

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

n=6

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Identification Physical Data (11) Spectra (5)

10


Patent-Specific Data (1) Related Markush Structure (RN)

Reference

11716937

SAN DIEGO STATE UNIVERSITY FOUNDATION

Patent: WO2006/102007 A2, 2006 ; Title/Abstract Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Dibenzoat: F: 53-54grad

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

Physical Data Melting Point (6) Melting Point

Solvent (Melting Point)

Location

Reference

81.5 - 82.7 °C

hexane ethyl acetate

supporting information

Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

85 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

78 °C

benzene

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

84 - 84.5 °C

Hawthorne; Reintjes

Journal of the American Chemical Society, 1964 , vol. 86, p. 951 Full Text View citing articles Show Details

88 °C

petroleum ether benzene

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

79 - 80 °C

benzene petroleum ether

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

152 °C

1 Torr

Lowe et al.

Journal of the Chemical Society, 1951 , p. 3286,3291 Full Text Show Details

Crystal Property Description (3) Colour & Other Properties

Location

Reference

white

supporting information

Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

white

SAN DIEGO STATE UNIVERSITY FOUNDATION

Patent: WO2006/102007 A2, 2006 ; Title/Abstract Full Text Show Details

Nadeln

Renz

Helvetica Chimica Acta, 1947 , vol. 30, p. 124,136 Full Text Show Details


Further Information (1) Description (Further Information)

Reference

Further information

Hawthorne; Reintjes

Journal of the American Chemical Society, 1965 , vol. 87, p. 4585,4586 Full Text Show Details

Spectra NMR Spectroscopy (4) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts Spectrum

1H

chloroform-d1

500 MHz

supporting information

Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

Chemical shifts Spectrum

13C

chloroform-d1

125 MHz

supporting information

Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

1H

chloroform-d1

1H

Signals given

SAN DIEGO STATE UNIVERSITY FOUNDATION

Patent: WO2006/102007 A2, 2006 ;

13C

chloroform-d1

Original Text (NMR Spectroscopy)

Location

NMR (CDCl3): δ 6.64 (m, 2H),

6.55 (dd, J= 8.5, 3 Hz, IH), 4.46 (s, IH), 4.40 (s, IH), 2.55 (t, J= 7.5 Hz, 2H), 1.60 (m, 2H), 1.33 (m, 6H), 0.90 (t, J= 7 Hz, 3H); 13C

NMR (CDCl3): 5 149.4, 147.5,

130.1, 116.9, 116.1, 113.3, 31.7, 30.0, 29.6, 29.1, 22.5, 14.0.

Comment (NMR Spectroscopy)

Reference

Title/Abstract Full Text Show Details

Signals given

SAN DIEGO STATE UNIVERSITY FOUNDATION

Patent: WO2006/102007 A2, 2006 ; Title/Abstract Full Text Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Location

Reference

Bands

potassium bromide

supporting information

Zillman, David J.; Hincapie, Gloria C.; Reza Savari; Mizori, Farhad G.; Cole, Thomas E.

Tetrahedron Letters, 2010 , vol. 51, # 23 p. 3033 - 3036 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-isohexyl-hydroquinone Reaxys Registry Number: 3254597

CAS Registry Number: 37966-30-6 Type of Substance: isocyclic Molecular Formula: C12H18O2

Linear Structure Formula: C12H18O2

Molecular Weight: 194.274

InChI Key: ZPGHSIFTYOUSFG-UHFFFAOYSA-N

16

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-isohexyl-hydroquinone, 2.5-Dihydroxy-1-isohexyl-benzol, 2-Isohexyl-hydrochinon Physical Data Melting Point (2)

2 prep out of 2 reactions.

Physical Data (3)

2


Melting Point

Solvent (Melting Point)

Reference

94 °C

Brockmann; Mueller

Justus Liebigs Annalen der Chemie, 1939 , vol. 540, p. 51,62 Full Text Show Details

100 °C

benzene

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Kuroda; Wada

Scientific Papers of the Institute of Physical and Chemical Research (Japan), 1938 , vol. 34, p. 1740,1756,1758 Chem. Zentralbl., 1939 , vol. 110, # I p. 2792 Full Text Show Details

Chemical Name: 2-(2,3-dimethylbutan-2-yl)benzene-1,4-diol Reaxys Registry Number: 10532952

Type of Substance: isocyclic Molecular Formula: C12H18O2

Linear Structure Formula: C12H18O2

Molecular Weight: 194.274

InChI Key: HEQLCAFIYZVZCM-UHFFFAOYSA-N

17

1 prep out of 1 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(2,3-dimethylbutan-2-yl)benzene-1,4-diol, 2-(1,1,2-trimethylpropyl)benzene-1,4-diol Identification Substance Label (1) Label

Reference

3f

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Reference

112 - 115 °C

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Crystal Property Description (1) Colour & Other Properties

Location

Reference

white

supporting information

Luethy, Monique; Darmency, Vincent; Renaud, Philippe

European Journal of Organic Chemistry, 2011 , # 3 p. 547 - 552 Title/Abstract Full Text View citing articles Show Details

Spectra

Identification Physical Data (2) Spectra (9)

2


NMR Spectroscopy (6) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

chloroform-d1

25 °C

Chemical shifts

13C

CDCl3

Spectrum

13C

Spectrum

1H

Chemical shifts

Location

Reference

300 MHz

supporting information

Luethy, Monique; Darmency, Vincent; Renaud, Philippe

European Journal of Organic Chemistry, 2011 , # 3 p. 547 - 552 Title/Abstract Full Text View citing articles Show Details

20 °C

75 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

CDCl3

20 °C

75 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

1H

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

1H

1H

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (2) Description (IR Spectroscopy)

Reference

Reflection spectrum

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Bands

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Chemical Name: n-octylhydroquinone

18

Reaxys Registry Number: 1958200

CAS Registry Number: 1706-69-0 Type of Substance: isocyclic Molecular Formula: C14H22O2

Linear Structure Formula: C14H22O2

Molecular Weight: 222.327

InChI Key: ZZXILYOBAFPJNS-UHFFFAOYSA-N

12 prep out of 23 reactions.

Identification Physical Data (10) Spectra (10)

14


Synthesize | Hide Details Find similar Chemical Names and Synonyms n-octylhydroquinone, octylhydroquinone, 2-octylbenzene-1,4-diol, 2-octyl-hydroquinone, 2-Octyl-hydrochinon, 2.5-Dihydroxy-1-octyl-benzol, 2,5Dihydroxy-octyl-benzol Identification Substance Label (5) Label

Reference

3a

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

7-8

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

5a

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Tab. II

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

Patent-Specific Data (1) Location in Patent

Reference

Claim

Seiko Kagaku Kabushiki Kaisha

Patent: EP812816 A1, 1997 ; Title/Abstract Full Text Show Details

Fuji Photo Film Co., Ltd.

Patent: US3979412 A1, 1976 ; Title/Abstract Full Text Show Details

Daihachi Chemical Industry Co., Ltd.

Patent: US6127464 A1, 2000 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (8) Melting Point

Solvent (Melting Point)

Comment (Melting Point)

Reference

92 - 94 °C

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details


96 - 97 °C

ethanol

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

94 - 95 °C

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

96 - 97 °C

Fuji Photo Film Co.

Patent: JP461464 , 1961 ; Chem.Abstr., 1965 , vol. 63, # 1736c Full Text Show Details

96.5 - 98 °C

acetic acid petroleum ether

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

96 - 97 °C

hexane

Williams

Journal of Organic Chemistry, 1957 , vol. 22, p. 772 Full Text View citing articles Show Details

96.5 - 98 °C

nach Sintern bei 94grad.

Eastman Kodak Co.

Patent: US2728659 , 1953 ; Full Text Show Details

94 - 94.5 °C

petroleum ether

Quilico; Panizzi; Muganaini

Gazzetta Chimica Italiana, 1949 , vol. 79, p. 89,104 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

186 - 190 °C

0.1 Torr

Fuji Photo Film Co.

Patent: JP461464 , 1961 ; Chem.Abstr., 1965 , vol. 63, # 1736c Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Quilico; Panizzi; Muganaini

Gazzetta Chimica Italiana, 1949 , vol. 79, p. 89,104 Full Text Show Details

Spectra NMR Spectroscopy (7) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Comment (NMR Spectroscopy)

1H

1H

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

Spectrum

1H

CDCl3

20 °C

400 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

Reference


Spectrum

13C

CDCl3

20 °C

100 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

CDCl3

20 °C

100 MHz

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 5864 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (2) Description (IR Spectroscopy)

Reference

Bands

Ozawa; Momose; Machida; Natori; Yoshihira

Chemical and pharmaceutical bulletin, 1968 , vol. 16, # 5 p. 853 - 862 Title/Abstract Full Text View citing articles Show Details

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Reflection spectrum

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Kumli, Eveline; Montermini, Florian; Renaud, Philippe

Organic Letters, 2006 , vol. 8, # 25 p. 5861 - 5864 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-(1',1',3',3'-tetramethylbutyl)hydroquinone Reaxys Registry Number: 1966347

CAS Registry Number: 719-03-9 Type of Substance: isocyclic Molecular Formula: C14H22O2

Linear Structure Formula: C14H22O2

Molecular Weight: 222.327

InChI Key: RDMIJQCFPQDYQN-UHFFFAOYSA-N

19

4 prep out of 15 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(1',1',3',3'-tetramethylbutyl)hydroquinone, 2-(1,1,3,3-tetramethyl-butyl)-hydroquinone, 2.5-Dihydroxy-1-(1.1.3.3-tetramethyl-butyl)-benzol, 2(1,1,3,3-Tetramethyl-butyl)-hydrochinon, 2-(1,1,3,3-tetramethylbutyl)hydroquinone, 2-<1,1,3,3-Tetramethyl-butyl>-hydrochinon, 2-tert. octylhydrochinon

Identification Physical Data (7)

13


Identification Substance Label (2) Label

Reference

IIc

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

7

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Physical Data Melting Point (5)

Melting Point

Solvent (Melting Point)

Reference

142 - 144 °C

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

142.5 - 143 °C

Pospisil,J. et al.

Collection of Czechoslovak Chemical Communications, 1966 , vol. 31, p. 98 - 105 Full Text View citing articles Show Details

Pospisil; Taimr

Patent: CS111292 , 1963 ; Chem.Abstr., 1965 , vol. 62, # 6434 Full Text Show Details

142.5 - 143 °C

toluene

Pospisil,J.; Taimr,L.

Collection of Czechoslovak Chemical Communications, 1964 , vol. 29, p. 381 - 389 Full Text View citing articles Show Details

142 °C

petroleum ether

Niederl; Natelson; Beekman

Journal of the American Chemical Society, 1933 , vol. 55, p. 2571,2574 Full Text Show Details

Roehm and Haas Co.

Patent: US2008032 , 1933 ; Full Text Show Details

Roehm and Haas Co.

Patent: DE657724 , 1934 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 24, p. 172 Full Text Show Details

128 °C

Roehm and Haas Co.

Patent: US2008337 , 1932 ;

Full Text Show Details

Roehm and Haas Co.

Patent: DE666134 , 1933 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 137 Full Text Show Details

Crystal Phase (1) Description (Crystal Phase)

Comment (Crystal Phase)

Reference

Crystal morphology

Bildung von Mischkrystallen mit 4-<1.1.3.3-Tetramethyl-butyl>-brenzcatechin.

Niederl; Natelson; Beekman

Journal of the American Chemical Society, 1933 , vol. 55, p. 2571,2574 Full Text Show Details

Electrochemical Characteristics (1) Description (Electrochemical Characteristics)

Reference

polarographic half-wave potential

Ryba,O. et al.

Collection of Czechoslovak Chemical Communications, 1965 , vol. 30, p. 843 - 852 Full Text View citing articles Show Details

Reaxys Registry Number: 4424411

Type of Substance: isocyclic Molecular Formula: C14H22O2

0 prep out of 1 reactions.

Identification

1


Linear Structure Formula: C14H22O2

Molecular Weight: 222.327

InChI Key: JWUNLNNCUQLSNK-UHFFFAOYSA-N

20

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Identification Substance Label (1) Label

Reference

1d

Ishii, Fumio; Kishi, Ken-ichi

Synthesis, 1980 , # 9 p. 706 - 708 Title/Abstract Full Text Show Details

Chemical Name: 4-hydroxy-2-(1-methylheptyl)phenol

1 prep out of 1 reactions.

Reaxys Registry Number: 19693596

CAS Registry Number: 155758-80-8 Molecular Formula: C14H22O2

Linear Structure Formula: C14H22O2

Molecular Weight: 222.327

InChI Key: BANSWHXXYJGPAP-UHFFFAOYSA-N

21

Spectra (2)

1

Synthesize | Hide Details Find similar Chemical Names and Synonyms 4-hydroxy-2-(1-methylheptyl)phenol Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

chloroform-d1

Chemical shifts

13C

chloroform-d1

Location

Reference

400 MHz

supporting information

Kuninobu, Yoichiro; Matsuki, Takashi; Takai, Kazuhiko

Journal of the American Chemical Society, 2009 , vol. 131, # 29 p. 9914 - 9915 Title/Abstract Full Text View citing articles Show Details

100 MHz

supporting information

Kuninobu, Yoichiro; Matsuki, Takashi; Takai, Kazuhiko

Journal of the American Chemical Society, 2009 , vol. 131, # 29 p. 9914 - 9915 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 6506980

Type of Substance: isocyclic Molecular Formula: C16H26O2

Linear Structure Formula: C16H26O2

1 prep out of 1 reactions.

Identification Physical Data (1)

2


Molecular Weight: 250.381

InChI Key: BXUOVJDNORSWHO-UHFFFAOYSA-N

22

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Identification Substance Label (2) Label

Reference

3, R=(CH2)8CH3

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

n=10

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

104 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Reaxys Registry Number: 25075068

Molecular Formula: C16H26O2

Linear Structure Formula: C16H26O2

Molecular Weight: 250.381

InChI Key: BQIIWUDZCOLYDK-UHFFFAOYSA-N

23

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

no reactions.

Bioactivity (1)

1


Chemical Name: 2-(1-methyl-decyl)-hydroquinone Reaxys Registry Number: 3289690

Type of Substance: isocyclic Molecular Formula: C17H28O2

Linear Structure Formula: C17H28O2

Molecular Weight: 264.408

InChI Key: NRFYGJCKDSMUFZ-UHFFFAOYSA-N

24

1 prep out of 1 reactions.

Physical Data (1)

1

Identification Physical Data (3)

2

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(1-methyl-decyl)-hydroquinone, 2-(1-Methyl-decyl)-hydrochinon Physical Data Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

163 - 166 °C

0.5 Torr

Eastman Kodak Co.

Patent: US2701197 , 1951 ; Full Text Show Details

Chemical Name: 2-undecyl-hydroquinone Reaxys Registry Number: 3302775

CAS Registry Number: 89118-49-0 Type of Substance: isocyclic Molecular Formula: C17H28O2

Linear Structure Formula: C17H28O2

Molecular Weight: 264.408

InChI Key: ZQVFLVKRECCNSE-UHFFFAOYSA-N

25

1 prep out of 2 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-undecyl-hydroquinone, 2.5-Dihydroxy-1-undecyl-benzol, 2-Undecyl-hydrochinon Identification Substance Label (1) Label

Reference

n=11

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Physical Data Melting Point (2) Melting Point

Solvent (Melting Point)

Reference

98 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details


100 - 101.5 °C

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

benzene

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Chemical Name: 2-dodecylbenzene-1,4-diol Reaxys Registry Number: 1974428

CAS Registry Number: 4595-23-7 Type of Substance: isocyclic Molecular Formula: C18H30O2

Linear Structure Formula: C18H30O2

Molecular Weight: 278.435

InChI Key: ZNQOWAYHQGMKBF-UHFFFAOYSA-N

26

12 prep out of 20 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-dodecylbenzene-1,4-diol, 2-dodecyl-hydroquinone, 2-Dodecyl-hydrochinon, 2.5-Dihydroxy-1-dodecyl-benzol Identification Substance Label (5) Label

Reference

A

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details

3, R=(CH2)10CH3

Ozaki, Yutaka; Hosoya, Ayako; Okamura, Kyouko; Kim, Sang-Won

Synlett, 1997 , vol. 1997, # 4 p. 365 - 366 Title/Abstract Full Text View citing articles Show Details

7-12

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

n=12

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Physical Data Melting Point (7) Melting Point

Solvent (Melting Point)

Reference

107 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124

Identification Physical Data (8) Spectra (5)

9


Title/Abstract Full Text Show Details

105 - 106 °C

methanol H2O

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

106.5 - 108 °C

Eastman Kodak Co.

Patent: US2728659 , 1953 ; Full Text Show Details

105 °C

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

109 - 111 °C

benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

109 - 111 °C

petroleum ether

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

109 °C

Hasan; Stedman

Journal of the Chemical Society, 1931 , p. 2112,2120 Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Location

Reference

white

supporting information

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (3) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

1H

chloroform-d1

400 MHz

supporting information

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 9646,6 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Location

Comment (NMR Spectroscopy)

Reference

Mass Spectrometry (2) Description (Mass Spectrometry)

Location

Reference

electrospray ionisation (ESI) spectrum

supporting information

Pulsipher, Abigail; Dutta, Debjit; Luo, Wei; Yousaf, Muhammad N.

Angewandte Chemie, International Edition, 2014 , vol. 53, # 36 p. 9487 - 9492,6 Angewandte Chemie, 2014 , vol. 126, # 36 p. 9641 - 9646,6 Title/Abstract Full Text View citing articles Show Details


spectrum electron impact (EI)

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-(1,1,3,3,5,5-Hexamethyl-hexyl)-hydrochinon Reaxys Registry Number: 3058015

CAS Registry Number: 23491-04-5 Type of Substance: isocyclic Molecular Formula: C18H30O2

Linear Structure Formula: C18H30O2

Molecular Weight: 278.435

InChI Key: VQHUOHBXLHZHAW-UHFFFAOYSA-N

27

1 prep out of 2 reactions.

Identification Physical Data (1)

1

Identification Physical Data (4)

3

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-(1,1,3,3,5,5-Hexamethyl-hexyl)-hydrochinon Identification Substance Label (1) Label

Reference

IId

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

106 - 108 °C

hexane

Buben,I.; Pospisil,J.

Collection of Czechoslovak Chemical Communications, 1969 , vol. 34, p. 1991 - 2001 Full Text View citing articles Show Details

Chemical Name: 2-tetradecyl-hydroquinone Reaxys Registry Number: 3332425

CAS Registry Number: 50677-17-3 Type of Substance: isocyclic Molecular Formula: C20H34O2

Linear Structure Formula: C20H34O2

Molecular Weight: 306.489

InChI Key: XSOIFQUPZMOPBW-UHFFFAOYSA-N

28

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3 prep out of 6 reactions.


Label

Reference

n=14

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Physical Data Melting Point (3) Melting Point

Solvent (Melting Point)

Reference

107 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

110 °C

petroleum ether

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

110 - 112 °C

benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Chemical Name: 2-n-pentadecylhydroquinone Reaxys Registry Number: 3350551

CAS Registry Number: 53918-51-7 Type of Substance: isocyclic Molecular Formula: C21H36O2

Linear Structure Formula: C21H36O2

Molecular Weight: 320.516

InChI Key: IFTCIJGLDWOLSB-UHFFFAOYSA-N

29

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Reference

4

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (4)

Melting Point

Solvent (Melting Point)

Comment (Melting Point)

Reference

10 prep out of 11 reactions.

Identification Physical Data (4) Spectra (3) Bioactivity (2)

5


104 - 105 °C

ethyl acetate hexane

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

107.6 - 108 °C

Sublimation.im Vakuum.

Loev; Dawson

Journal of the American Chemical Society, 1956 , vol. 78, p. 4083,4086 Full Text View citing articles Show Details

105.5 - 106.5 °C

petroleum ether

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

105.5 - 106.5 °C

CHCl3

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Chemical shifts

1H

pyridine-d5

Reference ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Bands

KBr

3270 - 1193 cm**(-1)

Reference ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

spectrum

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Matsushita Electric Industrial Co., Ltd.

Patent: US4758381 A1, 1988 ; Title/Abstract Full Text Show Details

Loev; Dawson

Journal of the American Chemical Society, 1956 , vol. 78, p. 4083,4086 Full Text View citing articles Show Details

Wasserman; Dawson

Journal of the American Chemical Society, 1950 , vol. 72, p. 4994,4996 Full Text Show Details

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

ElSohly; Adawadkar; Benigni; Watson; Little Jr.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text Show Details

2 of 2

Comment (Pharmacological Data)

lack of ability to cross-react with poison ivy urushiol in sensitized guinea pigs

Reference

ElSohly, Mahmoud A.; Adawadkar, Prakash D.; Benigni, Daniel A.; Watson, Edna S.; Little, Thomas L.


Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 606 - 611 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 25075069

Molecular Formula: C21H36O2

Linear Structure Formula: C21H36O2

Molecular Weight: 320.516

InChI Key: JUXSWZJTJGFKMP-UHFFFAOYSA-N

no reactions.

Bioactivity (1)

1

8 prep out of 13 reactions.

Identification Physical Data (8) Spectra (8) Bioactivity (2)

9

30

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Chemical Name: 2-hexadecyl-hydroquinone Reaxys Registry Number: 2057070

CAS Registry Number: 4595-26-0 Type of Substance: isocyclic Molecular Formula: C22H38O2

Linear Structure Formula: C22H38O2

Molecular Weight: 334.543

InChI Key: MKJMXPFTCHYBRV-UHFFFAOYSA-N

31

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-hexadecyl-hydroquinone, 2.5-Dihydroxy-1-hexadecyl-benzol, 2-Hexadecyl-hydrochinon, 2-hexadecylbenzene-1,4-diol, Hexadecylhydroquinone Identification Patent-Specific Data (1) Related Markush Structure (RN)

Reference

12759913

Meiji Dairies Corporation

Patent: EP1854777 A1, 2007 ; Title/Abstract Full Text Show Details

Physical Data Melting Point (6) Melting Point

Solvent (Melting Point)

Reference

114 °C

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121


Title/Abstract Full Text View citing articles Show Details

110 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

110 - 111 °C

benzene petroleum ether

Neiland; Trybatscha

Patent: SU371196 , 1973 ; Ref. Zh., Khim., 1974 , vol. 8, # N121P Full Text Show Details

112.5 - 113.5 °C

petroleum ether benzene

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

112 °C

petroleum ether

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

110 - 111 °C

benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Crystal Property Description (2) Colour & Other Properties

Reference

white

Meiji Dairies Corporation

Patent: EP1854777 A1, 2007 ; Title/Abstract Full Text Show Details

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Nadeln

Spectra NMR Spectroscopy (7) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

1H

methanol-d4

300 MHz

13C

methanol-d4

75 MHz

Original Text (NMR Spectroscopy) 1H-NMR:

(300MHz, CD3OD) δ: 0.88 (t, 3H,

J=6.7Hz, -CH3); 1.27 (s large, 26H, (CH2)13-); 1.50 (qt, 2H, J=6.6Hz, -CH2-); 2.49 (t, 2H, J=7.6Hz, -CH2-Ar); 4.83 (s, 2H, -OH); 6.43 (dd, 1H, J3=8.5Hz, J5=3.3Hz, aromatic-CH); 6.51 (d, 1H, J5=3.3Hz, aromatic-CH); 6.56 (d, 1H, J3=8.5Hz, aromatic-CH) 13C-NMR:

(75MHz, CD3OD) δ: 13.18; 22.36;

22.93; 29.09-29.67; 29.89; 31.68; 112.45; 115.26; 116.21; 130.04; 147.62; 149.48

Comment (NMR Spectroscopy)

Reference

Signals given

Meiji Dairies Corporation

Patent: EP1854777 A1, 2007 ; Title/Abstract Full Text Show Details

Signals given

Meiji Dairies Corporation

Patent: EP1854777 A1, 2007 ; Title/Abstract Full Text Show Details

Spectrum

1H

CDCl3 tetradeuteriomethanol

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

CDCl3 tetradeuteriomethanol

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121 Title/Abstract Full Text View citing articles


Show Details

Spin-spin coupling constants

CDCl3 tetradeuteriomethanol

1H-1H.

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

1H

CDCl3

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Spin-spin coupling constants

CDCl3

1H-1H

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Meiji Dairies Corporation

Patent: EP1854777 A1, 2007 ; Title/Abstract Full Text Show Details

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Neiland; Trybatscha

Patent: SU371196 , 1973 ; Ref. Zh., Khim., 1974 , vol. 8, # N121P Full Text Show Details

Armstrong et al.

Journal of the American Chemical Society, 1960 , vol. 82, p. 1928,1932 Full Text Show Details

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Shi, Ji-Liang; Chen, Xin; Jiang, Xi-Kui

Journal of Organic Chemistry, 1996 , vol. 61, # 14 p. 4698 - 4702 Title/Abstract Full Text View citing articles Show Details

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121 Title/Abstract Full Text View citing articles Show Details

Rhodia Chimie

Patent: US6049015 A1, 2000 ; Title/Abstract Full Text Show Details

2 of 2

Comment (Pharmacological Data)

in vitro significant differential cytotoxicity against the NCI panel of human tumor cell lines

Reference

Groweiss, Amiram; Cardellina II, John H.; Pannell, Lewis K.; Uyakul, Duangchan; Kashman, Yoel; Boyd, Michael R.

Journal of Natural Products, 1997 , vol. 60, # 2 p. 116 - 121 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 6517964

4 prep

Identification

2


Type of Substance: isocyclic Molecular Formula: C23H40O2

Linear Structure Formula: C23H40O2

Molecular Weight: 348.569

InChI Key: YFUNSXVYSZPKHH-UHFFFAOYSA-N

out of 4 reactions.

Physical Data (2) Spectra (3) Bioactivity (2)

32

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Identification Substance Label (2) Label

Reference

8d

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details

n=17

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Physical Data Melting Point (2) Melting Point

Reference

111.9 - 113.1 °C

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details

107 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectroscopy)

Chemical shifts

1H

1H

dimethylsulfoxide-d6

Reference Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 1694 Title/Abstract Full Text View citing articles Show Details

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Comment (IR Spectroscopy)

Reference

Bands

KBr

3280 - 1459 1/cm

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (1) Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details


Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

antioxidative activity (tert-butylhydroperoxide-initiated lipid peroxidation of rabbit erythrocyte ghost membrane, IC50 = 12.66 μM)

Reference

Jinno, Shuji; Okita, Takaaki

Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 11 p. 1688 - 1694 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 2-octadecyl-hydroquinone Reaxys Registry Number: 2058595

CAS Registry Number: 1706-70-3 Type of Substance: isocyclic Molecular Formula: C24H42O2

Linear Structure Formula: C24H42O2

Molecular Weight: 362.596

InChI Key: GDOYYIKTCYJSRI-UHFFFAOYSA-N

33

7 prep out of 9 reactions.

Synthesize | Hide Details Find similar Chemical Names and Synonyms 2-octadecyl-hydroquinone, 2-Octadecyl-hydrochinon, 2.5-Dihydroxy-1-octadecyl-benzol, 2-Octadecylhydrochinon Identification Substance Label (2) Label

Reference

n=18

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

Tab.II

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

Physical Data Melting Point (7) Melting Point

Solvent (Melting Point)

Reference

111 °C

Berger, K.; Ballauf, M.

Molecular Crystals and Liquid Crystals (1969-1991), 1988 , vol. 157, p. 109 - 124 Title/Abstract Full Text Show Details

112 - 113 °C

acetic acid petroleum ether

Neiland; Trybatscha

Patent: SU371196 , 1973 ; Ref. Zh., Khim., 1974 , vol. 8, # N121P Full Text Show Details

Identification Physical Data (8)

7


112 °C

methylcyclohexane

Vandenberghe,A.; Willems,J.F.

Bulletin des Societes Chimiques Belges, 1965 , vol. 74, p. 397 - 406 Full Text View citing articles Show Details

112 - 114 °C

Fuji Photo Film Co.

Patent: JP461464 , 1961 ; Chem.Abstr., 1965 , vol. 63, # 1736c Full Text Show Details

114 - 115 °C

Eastman Kodak Co.

Patent: US2728659 , 1953 ; Full Text Show Details

100.5 °C

petroleum ether

Cook; Heilbron; Lewis

Journal of the Chemical Society, 1942 , p. 659 Full Text Show Details

112 - 114 °C

benzene

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Crystal Property Description (1) Colour & Other Properties

Reference

Nadeln

Asano; Hase

Yakugaku Zasshi, 1940 , vol. 60, p. 650,658 Yakugaku Zasshi, 1941 , vol. 61, p. engl. Ref. S. 1, 5 Chem.Abstr., 1942 , p. 83 Full Text Show Details

Reaxys Registry Number: 25075070

Molecular Formula: C26H46O2

Linear Structure Formula: C26H46O2

Molecular Weight: 390.65

InChI Key: QBNNFBSVSBMOLB-UHFFFAOYSA-N

no reactions.

Bioactivity (1)

1

1 prep out of 1 reactions.

1

34

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Reaxys Registry Number: 7716832

Type of Substance: isocyclic Molecular Formula: C28H50O2

Linear Structure Formula: C28H50O2

Molecular Weight: 418.704

InChI Key: DYWXLHVEDQVTAB-UHFFFAOYSA-N

35


Synthesize Find similar Reaxys Registry Number: 25075071

Molecular Formula: C36H66O2

Linear Structure Formula: C36H66O2

Molecular Weight: 530.919

InChI Key: GXXQXHYUOSYOLY-UHFFFAOYSA-N

no reactions.

Bioactivity (1)

1

no reactions.

Bioactivity (1)

1

36

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Reaxys Registry Number: 25075072

Molecular Formula: C41H76O2

Linear Structure Formula: C41H76O2

Molecular Weight: 601.053

InChI Key: FVSNTTJDBAWJOJ-UHFFFAOYSA-N

37

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present


Reference

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Reaxys Registry Number: 9107531

Type of Substance: isocyclic Molecular Formula: C46H86O2

Linear Structure Formula: C46H86O2

Molecular Weight: 671.188

InChI Key: ATLDLHAWYWIAEE-UHFFFAOYSA-N

1 prep out of 1 reactions.

38

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Identification Substance Label (1) Label

Reference

5

Tziveleka, Leto-A; Kourounakis, Angeliki P; Kourounakis, Panos N; Roussis, Vassilios; Vagias, Constantinos

Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 4 p. 935 - 939 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Tziveleka, Leto-A; Kourounakis, Angeliki P; Kourounakis, Panos N; Roussis, Vassilios; Vagias, Constantinos

Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 4 p. 935 - 939 Title/Abstract Full Text View citing articles Show Details

De Rosa; De Giulio; Iodice

Journal of Natural Products (Lloydia), 1994 , vol. 57, # 12 p. 1711 - 1716 Title/Abstract Full Text Show Details

Effect (Pharmacological Data)

antioxidant

Species or TestSystem (Pharmacological Data)

hepatic microsomal fraction from female Fischer-344 rats

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data) Reference

> 1 mmol/l

Tziveleka, Leto-A; Kourounakis, Angeliki P; Kourounakis, Panos N; Roussis, Vassilios; Vagias, Constantinos

Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 4 p. 935 - 939 Title/Abstract Full Text View citing articles Show Details

Identification Bioactivity (2)

2


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