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Xenobiotica
the fate of foreign compounds in biological systems
Volume 23, 1993 - Issue 6
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Research Article

Generalized cytochrome P450-mediated oxidation and oxygenation reactions in aromatic substrates with activated N-H, O-H, C-H, or S-H substituents

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Pages 633-648 | Received 02 Sep 1992, Accepted 20 Mar 1993, Published online: 22 Sep 2008

References

  • Åström A., De Pierre J. W. Metabolism of 2-acetylaminofluorine by eight different forms of cytochrome P-450 isolated from rat liver. Carcinogenesis 1985; 6: 113–120
  • Augusto O., Beilan H. S., Oritz De Montellano P. R. The catalytic mechanism of cytochrome P-450. Spin-trapping evidence for one-electron substrate oxidation. Journal of Biological Chemistry 1982; 257: 11288–11295
  • Cavalieri E. L., Rogan E. G. Radical cations in aromatic hydrogen carcinogenesis. Free Radical Research Communication 1990; 11: 77–87
  • Gillette J. R., Nelson S. D., Mulder G. J., Jollow D. J., Mitchell J. R., Pohl L. R., Hinson J. A. Formation of chemically reactive metabolites of phenacetine and acetaminophen. Biological Reactive Intermediates-II: Chemical Mechanisms and Biological Effects, R. Snyder, D. V. Parke, J. J. Korsis, D. J. Jollow, G. G. Gibson, C. M. Witmer. Plenum, New York 1982; 931–950
  • Goldstein J. A., Weaver R., Sundheimer D. W. Metabolism of 2-acetylaminofluorene by two 3-methylcholantrene-inducible forms of rat liver cytochromes P-450. Cancer Research 1984; 44: 3768–3775
  • Gonzales F. J. The molecular biology of cytochrome P450s. Pharmacological Reviews 1989; 40: 243–288
  • Groves J. T., McClusky G. A. Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate. Biochemical and Biophysical Research Communications 1978; 81: 154–160
  • Guengerich F. P., Macdonald T. L. Mechanisms of cytochrome P-450 catalysis. FASEB Journal 1990; 4: 2453–2459
  • Hammons G. J., Guengerich F. P., Weis C. C., Beland F. A., Kadlubar F. F. Metabolic oxidation of carcinogenic arylamines by rat, dog, and human hepatic microsomes and by purified flavin-containing and cytochrome P-450 monooxygenases. Cancer Research 1985; 45: 3578–3585
  • Hanzlik R. P., Hogberg K., Judson C. M. Microsomal hydroxylation of specifically deuterated monosubstituted benzenes. Evidence for direct aromatic hydroxylation. Biochemistry 1984; 23: 3048–3055
  • Hanzlik Schaefer R. P. A. R., Moon J. B., Judson C. M. Primary and secondary kinetic deuterium isotope effects and transition-state structures foe benzylic chlorination and bromination of toluene. Journal of the American Chemical Society 1987; 109: 4926–4930
  • Harvison P. J., Forte A. J., Nelson S. D. Comparative toxicities and analgesic activities of three mono-methylated analogues of acetaminophen. Journal of Medicinal Chemistry 1986; 29: 1737–1743
  • Hinson J. A. Reactive metabolites of phenacetin and acetaminophen: a review. Environmental Health Perspectives 1983; 49: 71–79
  • Hinson J. A., Mitchell J. R., Jollow D. J. MicrosomalN-hydroxylation ofp-chloro-acetanilide. Molecular Pharmacology 1975; 11: 462–469
  • Hinson J. A., Nelson S. D., Gillette J. R. Metabolism of [p-18O]-phenacetin: the mechanism of activation of phenacetin to reactive metabolites in hamsters. Molecular Pharmacology 1979; 15: 419–427
  • Hinson J., Nelson S. D., Mitchel J. R. Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin. Molecular Pharmacology 1977; 13: 625–633
  • Hinson J. A., Pohl L. R., Monks T. J., Gillette J. R., Guengerich F. P. 3-Hydroxyacetaminophen: a microsomal metabolite of acetaminophen. Evidence against an epoxide as the reactive metabolite of acetaminophen. Drug Metabolism and Disposition 1980; 8: 289–294
  • Hoffmann K.-J., Axworthy D. B., Baillie T. A. Mechanistic studies on the metabolic activation of acetaminophen, in vivo. Chemical Research in Toxicology 1990; 3: 204–211
  • Hongslo J. K., BjØRnstad C., Schwarze P. E., Holme J. A. Inhibition of replicative DNA-synthesis by paracetamol in V79 Chinese hamster cells. Toxicology in Vitro 1989; 3: 13–20
  • Hyslop R. M., Jardine I. Metabolism of 6-thiopurines. 1. Irreversible binding of a metabolite of 6-thiopurine to mammalian hepatic protein. in vitro. Journal of Pharmacology and Experimental Therapeutics 1981; 218: 621–628
  • Kao J., Faulkner J., Bridges J. W. Metabolism of aniline in rats, pigs and sheep. Drug Metabolism and Disposition 1978; 6: 549–555
  • Korzekwa K. R., Jones J. P., Gillette J. R. Theoretical studies on cytochrome P450-mediated hydroxylation: a predictive model for hydrogen atom abstractions. Journal of the American Chemical Society 1990; 112: 7042–7046
  • Koymans L., Van Lenthe J. H., DonnÉ-Op Den Kelder G. M., Vermeulen N. P. E. Mechanisms of activation of phenacetin to reactive metabolites by cytochrome P450: a theoretical study involving radical intermediates. Molecular Pharmacology 1990; 37: 452–460
  • Koymans L., Van Lenthe J. H., Van De Straat R., DonnÉ-Op Den Kelder G. M., Vermeulen N. P. E. A theoretical study on the metabolic activation of paracetamol by cytochrome P-450: indications for a uniform oxidation mechanism. Chemical Research in Toxicology 1989; 2: 60–66
  • Koymans L., Menge W. M. P. B., Van Lenthe J. H., DonnÉ-Op Den Kelder G. M., Koppele Te J. M., Vermeulen N. P. E. A theoretical study on the oxidative metabolism of 4-chloro-acetanilide by cytochrome P450: alternative mechanisms for migration of 4-substituents during enzymatic oxidation. Recueil des Travaux Chimiques des Pays-Bas 1993; 112: 186–190
  • Lee J. S., Jacobsen N. E., Ortiz De Montallano P. R. 4-Alkyl radical extrusion in the cytochrome P-450 catalyzed oxidation of 4-alkyl-1,4-dihydropyridines. Biochemistry 1988; 27: 7703–7710
  • Letteron P., Fouin-Fortunet H., Tinel M., Danan G., Belghiti J., Pessayre D. Mechanism for isaxonine hepatitis. 1. Metabolic activation by mouse and human cytochrome P450. Journal of Pharmacology and Experimental Therapeutics 1984; 229: 845–850
  • Ling K.-H. J., Hanzlik R. P. Deuterium isotope effects on toluene metabolism. Product release as rate limiting step in cytochrome P450-catalysis. Biochemical and Biophysical Research Communications 1989; 160: 844–849
  • Malkinson A. M. Prevention of butylated hydroxytoluene-induced lung damage in mice by cedar terpene administration. Toxicology and Applied Pharmacology 1979; 49: 551–560
  • McMahon R. E., Turner J. C., Whitaker G. W. TheN-hydroxylation and ring-hydroxylation of 4-aminobiphenylin vitro by hepatic monooxygenases from rat, mouse, hamster, rabbit and guinea pig. Xenobiotica 1980; 10: 469–481
  • Moore M., Thor H., Moore Nelson G. S., MoldÉUs P., Orrenius S. The toxicity of acetaminophen andN-acetylp-benzoquinone imine in isolated hepatocytes is associated with thiol depletion and increased cytosolic Ca2+. Journal of Biological Chemistry 1985; 260: 13035–13040
  • Nebert D. W., Nelson D. R., Adesnik M., Coon M., Estabrook R. W., Gonzales F. J., Guengerich F. P., Gunsalus I. C., Johnson E. F., Kemper B., Levin W., Phillips I. R., Sato R., Waterman M. R. P450-superfamily: updated listing of all genes and recommended nomenclature for the chromosomal loci. DNA 1989; 8: 1–13
  • Nebert D. W., Nelson D. R., Coon M. J., Estabrook R., Feyereisen R., Fujii-Kuriyama Y., Gonzales F. J., Guengerich F. P., Gunsalus I. C., Johnson E. F., Loper J. C., Sato R., Waterman M. R., Waxman D. J. The P450 superfamily: update on new sequences, gene mapping, and recommended nomenclature. DNA and Cell Biology 1991a; 10: 1–14
  • Nebert D. W., Nelson D. R., Coon M. J., Estabrook R. W., Feyerisen R., Fujii-Kuriuama Y., Gonzales F. J., Guengerich F. P., Gunsalus I. C., Johnson E. F., Loper J. C., Sato R., Waterman M. R., Waxman D. J. Corrigendum. The P450 superfamily: update on new sequences, gene mapping, and recommended nomenclature. DNA and Cell Biology 1991b; 10: 397–398
  • Nelson S. D., Forte A. J., McMurtry R. J. Decreased toxicity of theN-methyl analogue of acetaminophen and phenacetine. Research Communications in Chemical Pathology and Pharmacology 1978; 22: 61–71
  • Nelson S. D., Forte A. J., Vaishnav Y., Mitchell J. R., Gillette J. R., Hinson J. A. The formation of arylating and alkylating metabolites of phenacetin in hamsters and hamster microsomes. Molecular Pharmacology 1981; 19: 140–145
  • Nelson S. D., Harvison P. J. Roles of cytochromes P-450 in chemically induced cytotoxicity. Mammalian Cytochromes P-450, F. P. Guengerich. CRC Press, Boca Raton, FL 1987; Vol. II: 19–79
  • Nelson D. R., Strobel H. W. Evolution of cytochrome P-450 proteins. Molecular Biology and Evolution 1987; 4: 572–593
  • Ortiz De Montellano P. R. Cytochrome P450 catalysis: radical intermediates and dehydrogenation reactions. Trends in Pharmacological Sciences 1989; 10: 354–359
  • Persson J. O., Terelius Y., Ingelman-Sundberg M. Cytochrome P450-dependent formation of reactive oxygen radicals; isoenzyme-specific inhibition of P450-mediated reduction of oxygen radicals; isoenzyme-specific inhibition of P450-mediated reduction of oxygen and carbon tetrachloride. Xenobiotica 1990; 20: 887–901
  • Rashed M. S., Nelson S. D. Characterization of glutathione conjugates of reactive metabolites of 3′-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen. Chemical Research in Toxicology 1989; 2: 41–45
  • Rietjens I. M. C. M., Tyrakowska B., Veeger C., Vervoort J. Reaction pathways for biodehalogenation of fluorinated anilines. European Journal of Biochemistry 1990; 194: 945–954
  • Sahawata T., Neal R. A. Biotransformation of phenol to hydroquinone and catechol by rat liver microsomes. Molecular Pharmacology 1983; 23: 453–460
  • Shoemaker D. D., Cysyk R. L., Gormely P. E., De Souza J. J. V., Malspeis L. Metabolism of 4′-(9-acridinylamino)methanesulfon-m-aniside by rat liver microsomes. Cancer Research 1984; 44: 1939–1945
  • Smith B. R., Plummer J. L., Wolf C. R., Philpot R. M., Bend J. R. p-Xylene metabolism by rabbit lung and liver and its relationship to the selective destruction of pulmonary cytochrome P-450. Journal of Pharmacology and Experimental Therepaeutics 1982; 223: 736–743
  • Streeter Bjorge A. J. S. M., Axworthy D. B., Nelson S. D., Baillie T. A. The microsomal metabolism and site of covalent binding to protein of 3′-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen. Drug Metabolism and Disposition 1984; 12: 565–576
  • Thompson J. A., Malkinson A. M., Wand M. D., Mastovich S. L., Mead E. W., Schullek K. M., Laudenschlager W. G. Oxidative metabolism of butylated hydroxytoluene by hepatic and pulmonary microsomes from rats and mice. Drug Metabolism and Disposition 1987; 5: 833–840
  • Uetrecht J. P., Sweetman B. J., Woosley R. L., Oates J. A. Metabolism of procainamide to a hydroxylamine by rat and human hepatic microsomes. Drug Metabolism and Disposition 1984; 12: 77–81
  • Uetrecht J. P., Woosley R. L., Freeman R. W., Sweetman B. J., Oates J. A. Metabolism of procainamide in the perfused rat liver. Drug Metabolism and Disposition 1981; 9: 183–187
  • Ullrich V., Wolf J., Amadori E., Standinger H. Mixed-function oxygenation of 4-halogeno-acetanilides in rat liver microsomes and model systems. Hoppe Seyler's Zeitschrift für physiologischen Chemie 1968; 349: 85–94
  • Van De Straat R., De Vries J., Groot E. J., Zijl R., Vermeulen N. P. E. Paracetamol, 3-monoalkyl- and 3,5-dialkyl derivatives: comparison of theirin vivo hepatotoxicity in mice. Toxicology and Applied Pharmacology 1987; 89: 183–189
  • Van Ommen B., Adang A., Müller F., Van Bladeren P. J. The microsomal metabolism of pentachlorophenol and its covalent binding to protein and DNA. Chemico-Biological Interactions 1986; 60: 1–11
  • White R. E. The involvement of free radicals in the mechanisms of monooxygenases. Pharmacology and Therapeutics 1991; 49: 21–42
  • White R. E., Miller J. P., Favreau L. V., Bhattacharyya A. Stereochemical dynamics of aliphatic hydroxylation by cytochrome P-450. Journal of the American Chemical Society 1986; 108: 6024–6031

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