Cytochrome P450 dependent xenobiotic activation by physiological hydroperoxides in intact hepatocytes

European Journal of Drug Metabolism and Pharmacokinetics

Volumn 22, Issue 4, 1997, Pages 305-310

  Anari, M R ^a   Khan, S ^a   Jatoe, S D ^a   O'Brien, P J ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Amines; Carcinogens; Cytochrome P450; Hydrazines; Peroxidase

Indexed keywords

1 BENZYLIMIDAZOLE; 2 AMINO 3 METHYLIMIDAZO[4,5 F]QUINOLINE; 3 METHYLCHOLANTHRENE; CYTOCHROME P450; CYTOCHROME P450 INHIBITOR; DNA; ETHYLBENZENE; HYDROPEROXIDE; KYNURAMINE; LINOLEIC ACID; PHENELZINE; RESORUFIN DERIVATIVE; TYRAMINE; XENOBIOTIC AGENT;

ANIMAL CELL; CONFERENCE PAPER; CONTROLLED STUDY; CYTOTOXICITY; DEMETHYLATION; DNA ADDUCT; LIPID PEROXIDATION; LIVER CELL; MALE; METABOLIC ACTIVATION; NONHUMAN; OXIDATION; OXIDATIVE STRESS; RAT;

EID: 0031422710     PISSN: 03787966     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF03190961     Document Type: Conference Paper

References (23)

1. Anari M.R., Khan S., Liu Z.C., O'Brien P.J. (1995) : Cytochrome P450 peroxidase/peroxygenase mediated xenobiotic metabolic activation and cytotoxicity in isolated hepatocytes. Chem. Res. Toxicol., 8, 997-1004.
2. Anari M.R., Josephy P.D., Henrey T., O'Brien P.J. (1997) : Hydrogen peroxide supports human and rat cytochrome P450 1A2-catalyzed 2-amino-3-methyl imidazo [4,5-f] quinoline bioactivation to mutagenic metabolites: significance of cytochrome P450 peroxygenase. Chem. Res. Toxicol., 10, 528-534.
3. O'Brien P.J. (1978) : Hydroperoxides and superoxides in microsomal oxidations. Pharmacol. Ther., A2, 517-537.
4. Hycay E.G., O'Brien P.J. (1971) : Cytochrome P450 as a microsomal peroxidase utilizing a lipid peroxide substrate Arch. Biochem. Biophys., 147, 14-27.
5. Estabrook R.W., Martin-Wixtrom C., Saeki Y., Renneberg R., Hildebrandt A., Werringloer J. (1994) : The peroxidatic function of liver microsomal cytochrome P450: comparison of hydrogen peroxide and NADPH catalysed N-demethylation reactions. Xenobiotica, 14, 87-104.
6. LM compared with peroxidase catalysis. FEBS Lett, 96, 349-353.
7. Coon M.J., Vaz A.D.N., Bestervelt L.L. (1996) : Peroxidative reactions of diversozymes. FASEB J., 10, 428-434.
8. 2 biosynthesis. J. Biol. Chem., 264, 141-150.
9. Song W.C., Brash A.R. (1991) : Purification of an allene oxide synthase and identification of the enzyme as a cytochrome P450. Science, 253, 731-734.
10. Matsui K., Shibutari M., Hase T., Kajurara T. (1996) : Fatty acid hydroperoxide lyase is a cytochrome P450 (CYP74B). FEBS Lett, 394, 21-24.
11. Shimizu T., Murakami Y., Hatano T. (1994) : Gln and Thr mutation of cytochrome P450 1A2 remarkably enhance homolytic O-O cleavage of alkyl hydroperoxides. J. Biol. Chem., 269, 13296-13304.
12. Reed C.J., DeMatteis F. (1989) : Cumene hydroperoxide-dependent oxidation of tetramethyl phenylenediamine and 7-ethoxycoumarin by cytochrome P-450. Biochem. J., 261, 793-800.
13. Jatoe S.D., Khan S., O'Brien P.J. (1991) : Molecular cytotoxic mechanisms of carcinogenic arylamines. Prog. Pharmacol. Clin. Pharmacol., 8, 245-253.
14. Moldeus P., Hogberg J., Orrenius S. (1978) : Isolation and use of liver cells. Methods Enzymol., 52, 60-70.
15. Kreamer B.L., Staecker J.L., Saurada N., Sattler G.L., Hsia M.T.S., Pitot H.C. (1986) : Use of speed, isodensity Percoll centrifugation method to increase the viability of isolated rat hepatocyte preparations. In vitro cell. Dev. Biol., 22, 201-211.
16. Reed D.J., Balson J.R., Beaty B.W., Brodie N., Potter D.W. (1980) : High performance liquid chromatography analysis of nanomole levels of glutathione, glutathione disulfide, and related thiols and disulfides. Anal. Biochem., 106, 55-62.
17. Ortiz de Montellano P.R., Augusto O., Viola F., Kunze K.L. (1983) : Carbon radicals in the metabolism of alkyl hydrazines. J. Biol. Chem., 258, 8623-8629.
18. Hanioka N., Jinno H., Takahashi A., Nakano K., Yoda R., Nishimura T.M. (1995) : Interaction of tetrachloroethylene with rat hepatic microsomal P450-dependent monooxygenases. Xenobiotica, 25, 151-165.
19. Hammons G.J., Milton D., Stepps K. Guengerich F.P., Tukey R.H., Kadlubar F.F. (1997) : Metabolism of carcinogenic heterocyclic and aromatic amines by recombinant human cytochrome P450 enzymes. Carcinogenesis, 18, 851-854.
20. Albano E., Comoglio A., Clot P., Iannone A., Ingelman Sundberg M. (1995) : Activation of alkylhydrazines for free radical intermediates by ethanol-inducible cytochrome P-4502E1 (CYP2E1). Biochim. Biophys. Acta, 1243, 414-420.
21. Ortiz de Montellano P.R., Watanabe M.D. (1986) : Free radical pathways in the in vitro hepatic metabolism of phenelzine. Mol. Pharmacol., 31, 213-219.
22. Wener P., Cohen G. (1991) : Intramitochondrial formation of oxidised glutathione during the oxidation of benzylamine by monoamine oxidases. FEBS Lett., 280, 44-46.
23. 2. Arch. Biochem. Biophys., 210, 505-516.