Benzo[a]pyrene metabolism by purified cytochrome P-450 from 3-methylcholanthrene-treated rats

References

• Autrup H., Granftstrom R. C., Harris C. C. Metabolism of chemical carcinogens by tracheobronchial tissues. Organ and Species Specificity in Chemical Carcinogenesis, R. Langenbach, S. Nesnow, J. M. Rice. Plenum, New York 1983; 473–494
   Google Scholar
• Bentley P., Oesch F. Purification of rat liver epoxide hydratase to apparent homogeneity. FEES Letters 1975; 59: 291–295
   PubMed Web of Science ®Google Scholar
• Deutsch J., Leutz J. C., Yang S. K., Gelboin H. V., Chiang Y. L., Vatsis K. P., Coon M. J. Regio- and stereoselectivity of various forms of purified cytochrome P-450 in the metabolism of benzo(a)pyrene and (—)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene as shown by product formation and binding to DNA. Proceedings of the National Academy of Sciences of the United States of America 1978; 75: 3123–3127
   PubMed Web of Science ®Google Scholar
• Eastman A. E., Bresnick E. Persistent binding of 3-methylcholanthrene to mouse lung DNA and its correlation with susceptibility to pulmonary neoplasia. Cancer Research 1979; 39: 2400–2405
   PubMed Web of Science ®Google Scholar
• Gozukara E. M., Belvedere G., Robinson R. C., Deutsch J., Coon M. T., Guengerich F. P., Gelboin H. V. The effect of epoxide hydratase on benzo(a)pyrene diol epoxide hydrolysis and binding to DNA and mixed-function oxidases proteins. Molecular Pharmacology 1981; 19: 153–161
   PubMed Web of Science ®Google Scholar
• Gozukara E. M., Guengerich F. P., Miller F., Gelboin H. V. Different patterns of benzo(a)pyrene metabolism of purified cytochrome P-450 from methyloholanthrene, β-naphthoflavone and phenobarbital treated rats. Carcinogenesis 1982; 3: 129–133
   PubMedGoogle Scholar
• Guentkner T. M., Oesch F. The effects of modulation of microsomal epoxide hydrolase activity on microsome-catalyzed activation of benzo(a)pyrene and its covalent binding to DNA. Cancer Letters 1981; 11: 175–183
   PubMedGoogle Scholar
• Harada N., Omura T. Selective induction of two different molecular species of cytochrome P-450 by phenobarbital and 3-methylcholanthrene. Journal of Biochemistry 1981; 89: 237–248
   PubMed Web of Science ®Google Scholar
• Hesse S., Jernström B., Martinez M., Moldéus P., Christodouides L., Ketterer B. Inactivation of DNA-binding metabolites of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol by glutathione and glutathione-S-transferase. Carcinogenesis 1982; 3: 757–760
   PubMed Web of Science ®Google Scholar
• Holder G., Yagi H., Dansette P., Jerina D. M., Levin W., Lu A. Y. H., Conney A. H. Effects of inducers and epoxide hydrase on the metabolism of benzo(a)pyrene by liver microsomes and a reconstituted system: analysis by high pressure liquid chromatography. Proceedings of the National Academy of Sciences of the United States of America 1974; 71: 4356–4360
   PubMed Web of Science ®Google Scholar
• Hundley S. G., Freudenthal I. A comparison of benzo(a)pyrene metabolism by liver and lung microsomal enzymes from 3-methylcholanthrene-treated rhesus monkeys and rats. Cancer Research 1977; 37: 3120–3125
   PubMed Web of Science ®Google Scholar
• Ioannides C., Parkinson C., Parke D. V. Activation of benzo(a)pyrene and 2-acetamidofluorene to mutagens by microsomal preparations from different animal species: role of cytochrome P-450 and P-448. Xenobiotica 1981; 11: 701–708
   PubMed Web of Science ®Google Scholar
• Jerina D. M., Dansette P. M., Lu A. Y. H., Levin W. Hepatic microsomal epoxide hydrase: a sensitive radiometric assay for hydration of arene oxides of carcinogenic aromatic hydrocarbons. Molecular Pharmacology 1977; 13: 342–351
   PubMed Web of Science ®Google Scholar
• Levin W., Michaud D. P., Thomas P. E., Jerina D. M. Distinct rat hepatic microsomal epoxide hydrolases catalyzed the hydration of cholesterol 5,6α-oxide and certain xenobiotic alkene and arene oxide. Archives of Biochemistry and Biophysics 1983; 220: 485–495
   PubMed Web of Science ®Google Scholar
• Oesch F. Differential control of rat microsomal “aryl hydrocarbon” monooxygenase and epoxide hydratase. Journal of Biological Chemistry 1976; 251: 79–87
   PubMed Web of Science ®Google Scholar
• Oesch F., Guenthner T. M. Effects on the modulation of epoxide hydrolase activity on the binding of benzo(a)pyrene metabolites to DNA in the intact nuclei. Carcinogenesis 1983; 4: 57–65
   PubMed Web of Science ®Google Scholar
• Oesch F., Timms C. W., Walker C. H., Guenthner T. M., Sparrow A., Watabe T., Wolf C. R. Existence of multiple forms of microsomal epoxide hydrolases with radically different substrate specificities. Carcinogenesis 1984; 5: 7–9
   PubMedGoogle Scholar
• Okano P., Miller H. N., Robinson R. C., Gelboin H. V. Comparison of benzo(a)pyrene and (—)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene metabolism in human blood monocytes and lymphocytes. Cancer Research 1979; 39: 3184–3193
   PubMed Web of Science ®Google Scholar
• Sagami I., Watanabe M. Purification and characterization of pulmonary P-450 from 3-methylcholanthrene-treated rats. Journal of Biochemistry 1983; 93: 1499–1508
   PubMed Web of Science ®Google Scholar
• Seifried H. E., Birkett D. J., Levin W., Lu A. Y. H., Conney A. H., Jerina D. M. Metabolism of benzo(a)pyrene: effect of 3-methylcholanthrene pretreatment on metabolism by microsomes from lungs of genetically “responsive” and “nonresponsive” mice. Archives of Biochemistry and Biophysics 1977; 178: 256–263
   PubMed Web of Science ®Google Scholar
• Selkirk J. K., Groy R. G., Gelboin H. V. High-pressure liquid chromatographic separation of 10 benzo(a)pyrene phenols and the identification of 1-phenol and 7-phenol as new metabolites. Cancer Research 1976; 36: 922–926
   PubMedGoogle Scholar
• Serabjit-Singh C. J., Wolf C. R., Philpot R. M. The rabbit pulmonary monooxygenase system: immunochemical and biochemical characterization of enzyme components. Journal of Biological Chemistry 1979; 254: 9901–9907
   PubMed Web of Science ®Google Scholar
• Slaughter S. R., Wolf C. R., Marciniszn J. R., Philpot R. M. The rabbit pulmonary monooxygenase system: partial structural characterization of the cytochrome P-450 components and comparison to the hepatic cytochrome P-450. Journal of Biological Chemistry 1981; 256: 2499–2503
   PubMed Web of Science ®Google Scholar
• Smith B. R., Bend J. R. Metabolic interactions of hydrocarbons with mammalian lung. Reviews in Biochemical Toxicology, E. Hodgson, J. R. Bend, R. M. Philpot. Elsevier-North Holland, New York 1981; vol. 3: 77–122
   Google Scholar
• Smith B. R., Plummer J. L., Ball L. M., Bend J. R. Characterization of pulmonary arene oxide biotransformation using the perfused rabbit lung. Cancer Research 1980; 40: 101–106
   PubMed Web of Science ®Google Scholar
• Thakker D. R., Yagi H., Lu A. Y. H., Levin W., Conney A. H., Jerina D. M. Metabolism of benzo(a)pyrene. IV. Conversion of (±)-trans-7,8-dihydroxy-7,8- dihydrobenzo(a)pyrene to the highly mutagenic 7,8-diol-9,10-epoxides. Proceedings of the National Academy of Sciences of the United States of America 1976; 73: 3381–3385
   PubMed Web of Science ®Google Scholar
• Ueng T. -H., Alvares A. P. Pulmonary cytochromes P-450 from rabbits treated with 3-methylcholanthrene. Molecular Pharmacology 1982; 22: 221–228
   PubMed Web of Science ®Google Scholar
• Wolf C. R., Smith B. R., Ball L. M., Serabjit-Singh C., Bend J. R., Philpot R. M. The rabbit pulmonary monooxygenase system: catalytic differences between two purified forms of cytochrome P-450 in the metabolism of benzo(a)pyrene. Journal of Biological Chemistry 1979; 254: 3658–3663
   PubMed Web of Science ®Google Scholar
• Wood A. W., Levin W., Lu A. Y. H., Yagi H., Harnandez O., Jerina D. M., Conney A. H. Metabolism of benzo(a)pyrene and benzo(a)pyrene derivatives to mutagenic products by highly purified hepatic microsomal enzymes. Journal of Biological Chemistry 1976; 251: 4882–4890
   PubMed Web of Science ®Google Scholar
• Yang S. K., Selkirk J. K., Plotkin E. V., Gelboin H. V. Kinetic analysis of the metabolism of benzo(a)pyrene to phenols, dihydrodiols, and quinones by high-pressure liquid chromatography compared to analysis by aryl hydrocarbon hydroxylase assay, and the effect of enzyme induction. Cancer Research 1975; 35: 3642–3650
   PubMed Web of Science ®Google Scholar
• Yasukochi Y., Masters B. S. S. Some properties of a detergent-solubilized NADPH-cytochrome c reductase purified by biospecific affinity chromatography. Journal of Biological Chemistry 1976; 251: 5337–5344
   PubMed Web of Science ®Google Scholar