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Xenobiotica
the fate of foreign compounds in biological systems
Volume 5, 1975 - Issue 4
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Research Article

Enzymic Reduction of Aromatic Hydrocarbon Epoxides by the Microsomal Fraction of Rat Liver

J. Booth Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, Fulham Road, London, SW3 6JB, UK
,
A. Hewer Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, Fulham Road, London, SW3 6JB, UK
,
C. R. Keysell Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, Fulham Road, London, SW3 6JB, UK
&
P. Sims Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, Fulham Road, London, SW3 6JB, UK
Pages 197-203 | Received 11 Sep 1974, Published online: 22 Sep 2008

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S. Kitamura, M. Mita, K. Matsuda, S. Ohta & K. Tatsumi. (2000) Reduction of stilbene oxide and styrene oxide to the corresponding alkenes by intestinal bacteria. Xenobiotica 30:4, pages 359-369.
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Kathryn E. McLane, Jed Fisher & K. Ramakrishnan. (1983) Reductive Drug Metabolism. Drug Metabolism Reviews 14:4, pages 741-799.
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N. P. E. Vermeulen, D. D. Breimer, J. Holthuis, C. Mol, B. H. Bakker & A. Van Der Gen. (1981) The metabolic fate of 1′,2′-epoxyhexobarbital in the rat. Xenobiotica 11:8, pages 547-557.
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Daniel W. Nebert, Nancy M. Jensen & Harry V. Gelboin. (1979) The Ah Locus: Genetic Regulation of the Metabolism of Carcinogens, Drugs, and Other Environmental Chemicals by Cytochrome P-450-Mediated Monooxygenase. CRC Critical Reviews in Biochemistry 6:4, pages 401-437.
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Peter Jenner & Bernard Testa. (1978) Novel Pathways in Drug Metabolism. Xenobiotica 8:1, pages 1-25.
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JayantiR. Patel, GaryW. Griffin & JohnL. Laseter. (1978) Determination of Arene Oxides by a Gas Chromatography-Mass Spectrometry System: Thermal Reactions of 9, 10-Epoxy-9, 10-Dihydrophenanthrene. Analytical Letters 11:3, pages 239-247.
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Natalia Guevara, Cecilia Maldonado, Manuel Uría, Raquel González, Manuel Ibarra, Silvana Alvariza, Antonella Carozzi, Carlos Azambuja, Pietro Fagiolino & Marta Vázquez. (2017) Role of CYP2C9, CYP2C19 and EPHX Polymorphism in the Pharmacokinetic of Phenytoin: A Study on Uruguayan Caucasian Subjects. Pharmaceuticals 10:4, pages 73.
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GR Keysell. (1981) The in Vitro Metabolism of Some Aromatic Polycyclic Hydrocarbon ‘K-Region’ Epoxides and Dihydrodiol Epoxide Derivatives by Rat Liver Preparations. Journal of Pharmacy and Pharmacology 33:Supplement_1, pages 89P-89P.
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Yong T. Lee & Jed F. Fisher. (2000) A Mechanistic Study of the Dihydroflavin Reductive Cleavage of the Dihydroflavin–Tetrahydronaphthalene Epoxide Adducts. Bioorganic Chemistry 28:3, pages 163-175.
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F. Peter Guengerich & Timothy L. Macdonald. 1993. Advances in Electron Transfer Chemistry. Advances in Electron Transfer Chemistry 191 241 .
Omar Elmalak, Mordecai Rabinovitz & Jochanan Blum. (2009) Alkali metal mediated conversion of arene oxides and arene imines into aromatic hydrocarbons. Journal of Heterocyclic Chemistry 30:1, pages 291-292.
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L. Webb. (1988) Studies on the apparent detoxification of sarcophytoxide by the prosobranch mollusc Ovula ovum. Comparative Biochemistry and Physiology Part C: Comparative Pharmacology 90:1, pages 155-160.
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Johan Meijer & Joseph W. Depierre. (1988) Cytosolic epoxide hydrolase. Chemico-Biological Interactions 64:3, pages 207-249.
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S. Ahmad, L. B. Brattsten, C. A. Mullin & S. J. Yu. 1987. Molecular Aspects of Insect-Plant Associations. Molecular Aspects of Insect-Plant Associations 73 151 .
Derek R. Boyd & Donald M. Jerina. 1985. Chemistry of Heterocyclic Compounds. Chemistry of Heterocyclic Compounds 197 282 .
Franz Oesch. (2016) Significance of Various Enzymes in the Control of Mutagenic and Carcinogenic Metabolites Derived from Aromatic Structures. Toxicologic Pathology 12:4, pages 391-396.
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B D Preston, J A Miller & E C Miller. (1983) Non-arene oxide aromatic ring hydroxylation of 2,2',5,5'-tetrachlorobiphenyl as the major metabolic pathway catalyzed by phenobarbital-induced rat liver microsomes.. Journal of Biological Chemistry 258:13, pages 8304-8311.
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Daniel Mansuy & Marc Fontecave. (1983) Reduction of benzyl halides by liver microsomes. Biochemical Pharmacology 32:12, pages 1871-1879.
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S.A. Wrighton, W.E. Fahl, F.L. ShinnickJr.Jr. & C.R. Jefcoate. (1982) Characteristics of microsomal reduction of benzo[a]pyrene 4,5-oxide. Chemico-Biological Interactions 40:3, pages 345-356.
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W. Nastainczyk, H.J. Ahr & V. Ullrich. (1982) The reductive metabolism of halogenated alkanes by liver microsomal cytochrome P450. Biochemical Pharmacology 31:3, pages 391-396.
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OSCAR HERNANDEZ & JOHN R. BEND. 1982. Metabolic Basis of Detoxication. Metabolic Basis of Detoxication 207 228 .
Wolfgang Nastainczyk, Hansjürgen Ahr & Volker Ulrich. 1982. Biological Reactive Intermediates—II. Biological Reactive Intermediates—II 799 808 .
Franz Oesch. 1982. Chemical Carcinogenesis. Chemical Carcinogenesis 1 24 .
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Edmond J. La Voie & Stephen S. Hecht. 1981. Hazard Assessment of Chemicals. Hazard Assessment of Chemicals 155 249 .
THOMAS M. GUENTHNER & FRANZ OESCH. 1981. Polycyclic Hydrocarbons and Cancer. Polycyclic Hydrocarbons and Cancer 183 212 .
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L.F. Chasseaud. 1979. 175 274 .
Yasushi Yamazoe, Masahiko Sugiura, Tetsuya Kamataki & Ryuichi Kato. (1978) Reconstitution of benzo[a] pyrene 4,5-oxide reductase activity by purified cytochrome P -450 . FEBS Letters 88:2, pages 337-340.
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DANIEL W. NEBERT, STEVEN A. ATLAS, THOMAS M. GUENTHNER & RICHARD E. KOURI. 1978. Molecular and Cell Biology. Molecular and Cell Biology 345 390 .
SHEN K. YANG, JOSEPH DEUTSCH & HARRY V. GELBOIN. 1978. Environment, Chemistry, and Metabolism. Environment, Chemistry, and Metabolism 205 231 .
Barney Kadis. (1978) Steroid epoxides in biologic systems: A review. Journal of Steroid Biochemistry 9:1, pages 75-81.
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S. Chaturapit & G.M. Holder. (1978) Studies on the hepatic microsomal metabolism of [14C]phenanthrene. Biochemical Pharmacology 27:14, pages 1865-1871.
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Daniel W. Nebert. 1978. Pharmacological Intervention in the Aging Process. Pharmacological Intervention in the Aging Process 55 83 .
William E. Fahl, Stephen Nesnow & Colin R. Jefcoate. (1977) Microsomal metabolism of benzo(a)pyrene. Archives of Biochemistry and Biophysics 181:2, pages 649-664.
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A. Bettencourt, G. Lhoest, M. Roberfroid & M. Mercier. (1977) Gas chromatographic and mass fragmentographic assays of carcinogenic polycyclic hydrocarbon epoxide hydratase activity. Journal of Chromatography A 134:2, pages 323-330.
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Leila Diamond & William M. Baird. 1977. Growth, Nutrition, and Metabolism of Cells in Culture. Growth, Nutrition, and Metabolism of Cells in Culture 421 470 .
Peter Sims. 1977. Biological Reactive Intermediates. Biological Reactive Intermediates 358 370 .
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Cary W. Griffin, Kiyoyasu Ishikawa & Shantilal K. Satra. (2009) Deoxygenations of arene oxides. Models for enzymatic deoxygenation. Journal of Heterocyclic Chemistry 13:6, pages 1369-1370.
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James W. Flesher, Ronald G. Harvey & Katherine L. Sydnor. (2006) Oncogenicity of k‐region epoxides of benzo( a )pyrene and 7,12‐dimethylbenz( a )anthracene . International Journal of Cancer 18:3, pages 351-353.
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R. Kato, K. Iwasaki, T. Shiraga & H. Noguchi. (1976) Evidence for the involvement of cytochrome P-450 in reduction of benzo(a)pyrene 4,5-oxide by rat liver microsomes. Biochemical and Biophysical Research Communications 70:3, pages 681-687.
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David Avnir & Jochanan Blum. (1976) A heterocyclic arene oxide. 5,6-Diphenylbenz[c]acridine 5,6-oxide. Journal of Heterocyclic Chemistry 13:3, pages 619-621.
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G. Wayne Ivie. (1976) Epoxide to Olefin: A Novel Biotransformation in the Rumen. Science 191:4230, pages 959-961.
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Donald C. Hobbs & Hugh M. Mcllhenny. 1976. Annual Reports in Medicinal Chemistry Volume 11. Annual Reports in Medicinal Chemistry Volume 11 190 199 .

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