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Bioactivation of chemicals by cytochromes P450

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Języki publikacji
EN
Abstrakty
EN
Most chemical carcinogens require metabolism to generate highly reactive intermediates that manifest their carcinogenicity following covalent interaction with DNA. This bioactivation process is catalysed chiefly by cytochromes P450, a superfamily of enzymes localised primarily in the liver. The carcinogenic activity of a chemical is largely dependent on the profile and concentration of cytochromes P450 at the time of exposure.
Rocznik
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1--9
Opis fizyczny
Bibliogr. 70 poz., rys., tab.
Twórcy
autor
  • Molecular Toxicology Group, School of Biomedical and Molecular Sciences, University of Surrey, Guildford, Surrey, GU2 7XH, UK, Tel.: +44 1483 689709, Fax: +44 1483 686401, c.ioannides@surrey.ac.uk
Bibliografia
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  • Astrom, A., J.W. De Pierre. 1985. Metabolism of 2-acetylaminofluorene by eight different forms of cytochrome P-450 isolated from rat liver. Carcinogenesis 6: 113-120.
  • Ayrton, A.D., M. McFarlane, R. Walker, S. Neville, C. Ioannides. 1990a. The induction of P450 I proteins by aromatic amines may be related to their carcinogenic potential. Carcinogenesis 11: 803-809.
  • Ayrton, A.D., M. McFarlane, R. Walker, S. Neville, M.M. Coombs, C. Ioannides. 1990b. Induction of the P450 I family of proteins by polycyclic aromatic hydrocarbons. Possible relationship to their carcinogenicity. Toxicology 60: 173-186.
  • Bartsch, H., M. Castegnaro, M. Rojas, A-M. Camus, K. Alexandrov, M. Lang. 1992. Expression of pulmonary cytochrome P4501A1 and carcinogen adduct formation in high risk subjects for tobacco--related lung cancer. Toxicology Letters 64/65: 477-483.
  • Bhattacharyya, K.K., P.B. Brake, S.E. Eltom, S.A. Otto, C.R. Jefcoate. 1995. Identification of a rat adrenal cytochrome P450 active in polycyclic-hydrocarbon metabolism as rat CYP1B1- demonstration of a unique tissue-specific pattern on hormonal and aryl-hydrocarbon receptor-linked regulation. Journal of Biological Chemistry 270: 11595-11602.
  • Buters, J.T.M., S. Sakai, T. Richter, T. Pineau, D.L. Alexander, U. Savas, J. Doehmer, J.M. Ward, C.R. Jefcoate, F.J. Gonzalez. 1999. Cytochrome P450 CYP1B1 determines susceptibility to 7,12-dimethylbenz[a]anthracene-induced lymphomas. Proceedings of the National Academy of Sciences USA 96: 1977-1982.
  • Cheung, Y-L., S.M. Puddicombe, T.J.B. Gray, C. Ioannides. 1994. Mutagenicity and CYP1A induction by azobenzenes correlates with their carcinogenicity. Carcinogenesis 15: 1257-1263.
  • Cheung, Y-L., J. Snelling, N.N.D. Mohammed, T.J.B. Gray, C. Ioannides. 1996. Interaction with the aromatic hydrocarbon receptor, CYP1A induction, and mutagenicity of a series of diaminotoluenes: implications for their carcinogenicity. Toxicology and Applied Pharmacology 139: 203-211.
  • Cheung, Y-L., D.F.V. Lewis, T.I. Ridd, T.J.B. Gray, C. Ioannides. 1997. Diaminonaphthalenes and related aminocompounds: Mutagenicity, CYP1A induction and interaction with the Ah receptor. Toxicology 118: 115-127.
  • Christou, M., U. Savas, S. Schroeder, X. Shen, T. Thompson, M.N. Gould, C.R. Jefcoate. 1995. Cytochromes CYP1A1 and CYP1B1 in the rat mammary gland: Cell-specific expression and regulation by polycyclic aromatic hydrocarbons and hormones. Molecular and Cellular Endocrinology 115: 41-50.
  • Code, E.L., C.L. Crespi, B.W. Penman, F.J. Gonzalez, T.K.H. Chang, D.J. Waxman. 1997. Human cytochrome P4502B6 - Interindividual hepatic expression, substrate specificity, and role in procarcinogen activation. Drug Metabolism and Disposition 25: 985-993.
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  • Ioannides, C. 1999. Effect of diet and nutrition on the expression of cytochromes P450. Xenobiotica 29: 109-154.
  • Ioannides, C. (ed). 2002a. Enzyme Systems that Metabolise Drugs and Other Xenobiotics. 578 p. John Wiley & Sons, Chichester, UK.
  • Ioannides, C. 2002b. Pharmacokinetic interactions between herbal remedies and medicinal drugs. Xenobiotica 32: 451-478.
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  • Ioannides, C., D.V. Parke, 1990. The cytochrome P450 I gene family of microsomal haemoproteins and their role in the metabolic activation of chemicals. Drug Metabolism Reviews 22: 1-85.
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  • Ioannides, C., Y-L. Cheung, J. Wilson, D.F.V. Lewis, T.J.G. Gray. 1993. The mutagenicity and interactions of 2- and 4-(acetylamino)fluorene with cytochrome P450 and the aromatic hydrocarbon receptor may explain the difference in their carcinogenic potency. Chemical Research in Toxicology 6: 535-541.
  • Ioannides, C., C.R. Barnett, A. Irizar, P.R. Flatt. 1996. Expression of cytochrome P450 proteins in disease. In: Cytochromes P450: Metabolic and Toxicological Aspects (ed. C. Ioannides), pp. 301-327. CRC Press Inc, Boca Raton, USA.
  • Kamataki, T., K-I. Fujita, K. Nakayama, Y. Yamazaki, M. Miyamoto, N. Ariyoshi. 2002. Role of human cytochrome P450 (CYP) in the metabolic activation of nitrosamine derivatives: application of genetically engineered Salmonella expressing human CYP. Drug Metabolism Reviews 34: 667-676.
  • Kim, J.H., K.G. Stansbury, N.J. Walker, M.A. Trush, P.T. Strickland, T.R. Sutter. 1998. Metabolism of benzo[a]pyrene and benzo-[a]pyrene-7,8-diol by human cytochrome P450 1B1. Carcinogenesis 19: 1847-1853.
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  • Lewis, D.F.V., C. Ioannides, D.V. Parke. 1993. Validation of a novel molecular orbital approach (COMPACT) for the prospective safety evaluation of chemicals by comparison with rodent carcinogenicity and Salmonella mutagenicity data evaluated by the US NCI/NTP.Mutation Research 291: 61-77.
  • Liu, C., X. Zhuo, F.J. Gonzalez, X.X. Ding. 1996. Baculovirus-mediated expression and characterization of rat CYP2A3 and human CYP2A6: role in metabolic activation of nasal toxicants. Molecular Pharmacology 50: 781-788.
  • McKinnon, R.A., W.M. Burgess, M.P. Hall, S.J. Roberts-Thomson, F.J. Gonzalez, M.E. McManus. 1995. Characterization of CYP3A gene subfamily expression in human gastrointestinal tissues. Gut 36: 259-267.
  • Murray, G.I., M.C. Taylor, M.C.E. McFadyen, J.A. McKay, W.F. Greenlee, M.D. Burke, T.W. Melvin. 1997. Tumor-specific expression of cytochrome P-450 CYP1B1. Cancer Research. 57: 3026-3031.
  • Nebert, D.W. 1989. The Ah locus: genetic differences in toxicity, cancer, mutation and birth defects. CRC Critical Reviews in Toxicology 20: 153-174.
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  • Rendic, S., F. Di Carlo. 1997. Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metabolism Reviews 29: 413-580.
  • Ronis, M.J.J., K.O. Lindros, M. Ingelman-Sundberg. 1996. The CYP2E subfamily. In: Cytochromes P450: Metabolic and Toxicological Aspects (ed. C. Ioannides), pp. 211-239. CRC Press Inc, Boca Raton, USA.
  • Roy, D., A. Bernhardt, H.W. Strobel, J.G. Liehr. 1992. Catalysis of the oxidation of steroid and stilbene estrogens to estrogen quinone metabolites by the -naphthoflavone-inducible cytochrome P450IA family. Archives of Biochemistry and Biophysics 296: 450-456.
  • Ryan, D.E., W. Levin. 1990. Purification and characterization of hepatic cytochrome P-450. Pharmacology Therapeutics 45: 153-239.
  • Seeff, L.B., B.A. Cuccherini, H.J. Zimmerman, E. Adler, S.B. Benjamin, 1986. Acetaminophen toxicity in the alcoholic. A therapeutic misadventure. Annals of Internal Medicine 104: 399-404.
  • Shimada, T., S-I. Nakamura, S. Imaoka, Y. Funae. 1987. Genotoxic and mutagenic activation of aflatoxin B1 by constitutive forms of cytochrome P-450 in rat liver microsomes. Toxicology and Applied Pharmacology 91: 13-21.
  • Shimada, T., M. Iwasaki, M.V. Martin, F.P. Guengerich. 1989. Human liver microsomal cytochrome P-450 enzymes involved in the bioactivation of procarcinogens detected by umu gene response in Salmonella typhimurium TA1535/pSK1002. Cancer Research 49: 3218-3228.
  • Shimada, T., C.L. Hayes, H. Yamazaki, S. Amin, S.S. Hecht, F.P. Guengerich, T.R. Sutter, 1996. Activation of chemically diverse procarcinogens by human cytochrome P-450 1B1. Cancer Research 56: 2979-2984.
  • Shimada, T., K. Inoue, Y. Suzuki, T. Kawai, E. Azuma, T. Nakajima, M. Shindo, K. Kurose, A. Sugie, Y. Yamagishi, Y. Fujii-Kuriyama, M. Hashimoto. 2002. Arylhydrocarbon receptor-dependent induction of liver and lung cytochromes P450 1A1, 1A2, and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in genetically engineered C57BL/6J mice. Carcinogenesis 23: 1199-1207.
  • Shimizu, Y., Nakatsuru, M. Ichinose, Y. Takahashi, H. Kume, J. Mimura, Y. Fujii-Kuriyama, T. Ishikawa. 2000. Benzo[a]pyrene carcinogenicity is lost in mice lacking the aryl hydrocarbon receptor. Proceedings of the National Academy of Sciences USA 97: 779-782.
  • Shou, M., K.W. Krausz, F.J. Gonzalez, H.V. Gelboin. 1996. Metabolic activation of the potent carcinogen dibenzo[a]anthracene by cDNA-expressed human cytochromes P450. Archives of Biochemistry and Biophysics 328: 201-207.
  • Shu, L., P.F. Hollenberg. 1997. Alkylation of cellular macromolecules and target specificity of carcinogenic nitrosodialkylamines: metabolic activation by cytochromes P450 2B1 and 2E1. Carcinogenesis 18: 801-810.
  • Smith, T.J., Z. Guo, F.J. Gonzalez, F.P. Guengerich, G.D. Stoner, C.S. Yang. 1992. Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in human lung and liver microsomes and in human cells containing cDNA-expressed cytochromes P-450. Cancer Research 52: 1757-1763.
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  • Sohn, O.S., E.S. Fiala, S.P. Requeijo, J.H. Weisburger, F.J. Gonzalez. 2001. Differential effects of CYP2E1 status on the metabolic activation of the colon carcinogens azoxymethane and methylazoxymethanol. Cancer Research 61: 8435-8440.
  • Su, T., Z. Bao, Q-Y. Zhang, T.J. Smith, J-Y. Hong, X. Ding. 2000. Human cytochrome P450 CYP2A3: Predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Research 60: 5074-5079.
  • Valentine, J.L., S.S.T. Lee, M.J. Seaton, B. Asgharian, G. Farris, J.C. Corton, F.J. Gonzalez, M. Medinsky. 1996. Reduction of benzene metabolism and toxicity in mice that lack CYP2E1 expression. Toxicology Applied Pharmacology 14: 205-213.
  • Wall, K.L., W. Gao, J.M. TeKoppele, G.Y. Kwei, F.C. Kauffman, R.G. Thurman. 1991. The liver plays a central role in the mechanism of chemical carcinogenesis due to polycyclic aromatic hydrocarbons. Carcinogenesis 12: 783-786.
  • Wong, F.W-Y., W-Y. Chan, S.S-T. Lee. 1998. Resistance to carbon tetrachloride-induced hepatotoxicity in mice which lack CYP2E1 expression. Toxicology Applied Pharmacology 153: 109-118.
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Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAR0-0062-0094
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