Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 18, 1988 - Issue 5
19
Views
16
CrossRef citations to date
0
Altmetric
Original Article

Effects of chemical and enzymic probes on microsomal covalent binding of bromobenzene and derivatives. Evidence for quinones as reactive metabolites

, &
Pages 501-510 | Received 12 May 1987, Accepted 13 Dec 1987, Published online: 30 Sep 2009

References

  • Abul-Hajj Y. Estrogen 1,2-epoxide or estrogen quinones/semiquinones. Biochemical Biophysical Research Communications 1985; 133: 1078–1085
  • Bruice P. Y., Bruice T. C., Yagi H., Jerina D. M. Nucleophilic displacement of the arene oxides of phenanthrene. Journal of the American Chemical Society 1976; 98: 2973–2981
  • Burton G. W., Hughes L., Ingold K. U. Antioxidant activity of phenols related to vitamin E. Are there chain-breaking antioxidants better than α-tocopherol?. Journal of the American Chemical Society 1983; 105: 5950–5951
  • Capdevila F., Estabrook R. W., Prough R. A. The existence of a benzo‘a’pyrene-3,6-quinone reductase in rat liver microsomai fractions. Biochemical Biophysical Research Communications 1978; 83: 1291–1298
  • Capdevila J., Orrenius S. Metabolism of benzo‘a’pyrene-3,6-quinone by isolated hepatocytes. FEBS Letters 1980; 119: 33–37
  • Deamer D. W., Heikkila R. E., Panganamala R. V., Cohen G., Cornwell D. S. The alloxan-dialuric acid cycle and the generation of hydrogen peroxide. Physiological Chemistry and Physics 1971; 3: 426–430
  • Dodgson J. W. The reaction of p-benzoquinone with sulphurous acid and with alkali. Part I. Journal of the Chemical Society (London) 1914; 105: 2435–2443
  • Finley K. T. The addition-substitution chemistry of quinones. The Chemistry of Quinoid Compounds, S. Patai. John Wiley and Sons, New York 1974; 880–900
  • Gravela E., Albano E., Dianzani M. V., Poli G., Slater T. F. Effects of carbon tetrachloride on isolated rat hepatocytes: Inhibition of protein and lipoprotein secretion. Biochemical Journal 1979; 178: 509–512
  • Hernandez O., Gopinathan M. B. Synthesis of glutathione adducts of K-region epoxides. Journal of the Chemical Society Chemical Communications 1984; 1491–1492
  • Hesse S., Mezger M., Wolff T. Activation of ‘14C’-chlorobiphenyls to protein-binding metabolites by rat liver microsomes. Chemico-Biological Interactions 1978; 20: 355–365
  • Hesse S., Mezger M. Involvement of phenolic metabolites in the irreversible protein-binding of aromatic hydrocarbons: Reactive metabolites of ‘14C’ naphthalene and ‘14C’-1-naphthol formed by rat liver microsomes. Molecular Pharmacology 1979; 16: 667–675
  • Hesse S., Wolff T., Mezger M. Involvement of phenolic metabolites in the irreversible protein-binding of 14C-bromobenzene catalyzed by rat liver microsomes. Archives of Toxicology 1980, Supplement 4: 358–362
  • Jeffrey A. M., Yeh H. J. C., Jerina D. M., DeMarinis R. M., Foster D. E., Piccolo D. E., Berchtold G. A. Stereochemical course in reactions between nucleophiles and arene oxides. Journal of the American Chemistry Society 1974; 96: 6929–6937
  • Jerina D. M., Daly J. W., Witkop B., Zaltzman-Nirenberg P., Udenfriend S. Role of the arene oxide-oxepin system in the metabolism of aromatic substrates. I. In vitro conversion of benzene oxide to a premercapturic acid and a dihydrodiol. Archives of Biochemistry and Biophysics 1968; 128: 176–183
  • Johanssen I., Ingelman-Sundberg M. Hydroxyl radical mediated P-450 dependent metabolic activation of benzene in microsomes and reconstituted enzyme systems from rabbit liver. Journal of Biological Chemistry 1985; 258: 7311–7316
  • Jollow D. J., Mitchell J. R., Zampaglione N., Gillette J. R. Bromobenzene-induced liver necrosis, Protective role of glutathione and evidence for 3,4-bromobenzene oxide as the hepatotoxic metabolite. Pharmacology 1974; 11: 151–169, (1974)
  • Lau P. T. S., Gompf T. E. Reaction of quinones with thiourea: A novel route to 2-amino-6-hydroxybenzothiazoles and 2-amino-5-hydroxynaphtho ‘1,2-d’thiazoles. Journal of Organic Chemistry 1970; 35: 4103–4108
  • Lau S. S., Zannoni V. G. Brombenzene epoxidation leading to binding on macromolecular protein sites. Journal of Pharmacology and Experimental Therapeutics 1981; 219: 563–572
  • Lau S. S., Monks T. J., Gillette J. R. Multiple reactive metabolites derived from bromobenzene. Drug Metabolism and Disposition 1984a; 12: 291–296
  • Lau S. S., Monks T. J., Gillette J. R. Identification of 2-bromohydroquinone as a metabolite of bromobenzene and o-bromophenol: implications for bromobenzene-induced nephrotoxicity. The Journal of Pharmacology and Experimental Therapeutics 1984b; 230: 360–366
  • Lau S. S., Monks T. J., Greene L. E., Gillette J. R. Detection and half-life of bromobenzene-3,4-oxide in blood. Xenobiotica 1984c; 14: 539–543
  • Monks T. J., Pohl L. R., Gillette J. R., Hong M., Highet R. J., Ferretti J. A., Hinson J. A. Stereoselective formation of two bromobenzene-glutathione conjugates. Chemico-Biological Interactions 1982; 41: 203–216
  • Monks T. J., Lau S. S., Highet R. J. Formation of nontoxic reactive metabolites of p-bromophenol: Identification of a new glutathione conjugate. Drug Metabolism and Disposition 1984; 12: 432–437
  • Nakasimhan N., Weller P. E., Buben J. A., Wiley R. A., Hanzlik R. P. Microsomal metabolism and covalent binding of ‘3H/14C’-bromobenzene. Evidence for quinones as reactive metabolites. Xenobiotica 1988; 18: 491–499
  • Nishikimi M. Oxidation of ascorbic acid with superoxide an ion generated by the xanthine-xanthine oxidase system. Biochemical Biophysical Research Communications 1975; 63: 463–468
  • Reid W. D., Christie B., Krishna G., Mitchell J. R., Moskowitz J., Brodie B. B. Bromobenzene metabolism and hepatic necrosis. Pharmacology 1971; 6: 41–55
  • Reid W. D., Krishna G. Centrolobular hepatic necrosis related to covalent binding of metabolites of halogenated aromatic hydrocarbons. Experimental and Molecular Pathology 1973; 18: 90–99
  • Sawhata T., Neal R. A. Biotransformation of phenol to hydroquinone and catechol by rat liver microsomes. Molecular Pharmacology 1983; 23: 453–460
  • Selkirk J. K., Croy R. G., Roller P. P., Gelboin H. V. High-pressure liquid chromatographic analysis of benzo‘a’pyrene metabolism and covalent binding and the mechanism of action of 7,8-benzoflavone and 1,2-epoxy-3,3,3-trichloropropane. Cancer Research 1974; 34: 3474–3480
  • Shen A. L., Fahl W. E., Jefcoate C. R. Metabolism of benzo‘a’pyrene by isolated hepatocytes and factors affecting covalent binding of benzo‘a’pyrene metabolites to DNA in hepatocyte and microsomal systems. Archives of Biochemistry and Biophysics 1980; 204: 511–523
  • Sipes G., Krishna G., Brodie B. B. Mechanism of bromobenzene toxicity. II. Studies, in vitro. Federation Proceedings 1971; 30: 439
  • Smart R. C., Zannoni V. G. DT-diaphorase and peroxidase influence the covalent binding of the metabolites of phenol, the major metabolite of benzene. Molecular Pharmacology 1984; 26: 105–111
  • Toranzo E. G., Gillesse T., Mendenhall M., Traiger G. J., Riley P. G., Hanzlik R. P., Wiley R. A. Effect of substituents on arene oxide mediated liver toxicity among substituted bromobenzenes. Toxicology and Applied Pharmacology 1979; 40: 415–425
  • Thor H., Svensson S. A. Biotransformation of bromobenzene to reactive metabolites in isolated hepatocytes. Advances in Experimental Medicine and Biology 1981; 136A: 287–299
  • Tunek A., Platt K. L., Bentley P., Oesch F. Microsomal metabolism of benzene to species irreversibly binding to microsomal protein and effects of modifications of this metabolism. Molecular Pharmacology 1978; 14: 920–292
  • Van Bladeren P. J., Vyas K. P., Sayer J. M., Ryan D. E., Thomas P. E., Levin W., Jerina D. M. Stereoselectivity of cytochrome P-450 c in the formation of naphthaline and anthracene 1,2–oxides. Journal of Biological Chemistry 1984; 259: 8966–8973
  • Vogel E., Gunther H. Benzene oxide-oxepin valence tautomerism. Angewandte Chemie International Edition 1967; 6: 385–476
  • Wilkinson C. F., Hetnarski K., Cantwell G., Di Carlo F. Structure-activity relationships in the effects of 1-alkyl imidazoles on microsomal oxidation in vitro and in vivo. Biochemical Pharmacology 1974; 23: 2377–2386

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.