Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 19, 1989 - Issue 12
5
Views
0
CrossRef citations to date
0
Altmetric
Original Article

Studies on covalent binding of (-)trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene metabolites to cytochromes P-450 LM2 and LM4 and NADPH-cytochrome P-450 reductase

, , , &
Pages 1421-1435 | Received 02 Mar 1989, Accepted 30 Jul 1989, Published online: 30 Sep 2009

References

  • Atlas S. A., Boobis A. R., Felton J. S., Thorgeirsson S. S., Nebert D. W. Ontogenic expression of polycyclic aromatic compound-inducible monooxygenase activities and forms of cytochrome P-450 in rabbit: evidence for temporal control and organ specificity of two genetic regulatory systems. Journal of Biological Chemistry 1977; 252: 4712–4721
  • Belvedere G., Miller H., Vatsis K. P., Coon M. J., Gelboin H. V. Hydroxylation of benzo‘α’pyrene and binding of (-)trans-7,8-dihydroxy-7,8-dihydrobenzo‘α’pyrene metabolites to deoxyribonucleic acid catalyzed by purified forms of rabbit liver microsomal cytochrome P-450: effect of 7,8-benzoflavone, butylated hydroxytoluene, and ascorbic acid. Biochemical Pharmacology 1980; 29: 1693–1702
  • Bernhardt R., Makower A., Jánig G.-R., Ruckpaul K. Selective chemical modification of a functionally linked lysine in cytochrome P-450LM2. Biochimica et Biophysica Acta 1984; 785: 186–190
  • Black S. D., Coon M. J. Comparative structures of P-450 cytochromes. Cytochrome P-450: structure, mechanism, and biochemistry, P. R. Ortiz de Montellano. Plenum, New York 1986; 161–216
  • Black S. D., Coon M. J. P-450 cytochromes. structure and function. Advances in Enzymology and Related Areas of Molecular Biology 1987; 60: 35–87
  • Bonner W. M., Laskey R. A. A film detection method for tritium-labelled proteins and nucleic acids in polyacrylamide gels. European Journal of Biochemistry 1974; 46: 83–88
  • Boyd M. R. Toxicity mediated by reactive metabolites of furans. Biological Reactive Intermediates, R. Snyder, D. V. Parke, J. J. Kocsis, D. J. Jollow, G. G. Gibson, C. M. Witmer. Plenum, New York 1982; Vol. IIB: 865–879
  • Committee on Biological Effects of Atmospheric Pollutants. Particulate Polycyclic Organic Matter. National Academy of Sciences, Washington, DCUSA 1972; 1–361
  • Conney A. H. Pharmacological implications of microsomal enzyme induction. Pharmacological Reviews 1967; 19: 317–366
  • Coon M. J., van der Hoeven T. A., Dahl S. B., Haugen D. A. Two forms of liver microsomal cytochrome P-450, P-450LM2, P-450LM4 (rabbit liver). Methods in Enzymology 1978; 52: 109–117
  • Daily H. A., Strittmatter P. Characterization of the interaction of amphipathic cytochrome b5 with stearyl coenzyme A desaturase and NADPH-cytochrome P-450 reductase. Journal of Biological Chemistry 1980; 255: 5184–5189
  • Davies H. W., Britt S. G., Pohl L. R. Carbon tetrachloride and 2-isopropyl-4-pentenamide-induced inactivation of cytochrome P-450 leads to heme-derived protein adducts. Archives of Biochemistry and Biophysics 1986; 244: 387–392
  • Dean W. L., Coon M. J. Immunochemical studies on two electrophoretically homogeneous forms of rabbit liver microsomal cytochrome P-450: P-450LM2 and P-450LM4. Journal of Biological Chemistry 1977; 252: 3255–3261
  • Decker C., Sugiyama K., Underwood M., Correia M. A. Inactivation of rat hepatic cytochrome P-450 by spironolactone. Biochemical and Biophysical Research Communications 1986; 136: 1162–1169
  • De Matteis F. Loss of microsomal components in drug-induced liver damage, in cholestasis, and after administration of chemicals which stimulate heme catabolism. Hepatic Cytochrome P-450 Monooxygenase Systems, J. B. Schenkman, D. Kupfer. Pergamon Press, New York 1982; 307–340
  • 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‘α’pyrene and (-)trans-7,8-dihydroxy-7,8-dihydrobenzo‘α’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
  • Deutsch J., Vatsis K. P., Coon M. J., Leutz J. C., Gelboin H. V. Catalytic activity and stereoselectivity of purified forms of rabbit liver microsomal cytochrome P-450 in the oxygenation of the (-) and (+) enantiomers of trans7,8-dihydroxy-7,8-dihydrobenzo‘α’pyrene. Molecular Pharmacology 1979; 16: 1011–1018
  • Fasco M. J., Vatsis K. P., Kaminsky L. S., Coon M. J. Regioselective and stereoselective hydroxylation of R and S warfarin by different forms of purified cytochrome P-450 from rabbit liver. Journal of Biological Chemistry 1978; 253: 7813–7820
  • French J. S., Coon M. J. Properties of NADPH-cytochrome P-450 reductase purified from rabbit liver microsomes. Archives of Biochemistry and Biophysics 1979; 195: 565–577
  • Gelboin H. V. A microsome-dependent binding of benzo‘α’pyrene to DNA. Cancer Research 1969; 29: 1272–1276
  • Gillette J. R. Biochemistry of drug oxidation and reduction by enzymes in hepatic endoplasmic reticulum. Advances in Pharmacology 1966; 4: 219–261
  • 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 phenacetin and acetaminophen. Biological Reactive Intermediates, R. Snyder, D. V. Parke, J. J. Kocsis, D. J. Jollow, G. G. Gibson, C. M. Witmer. Plenum, New York 1982; Vol. IIB: 931–950
  • Gotoh O., Fujii-Kuriyama Y. Evolution, structure, and gene regulation of cytochrome P-450. Frontiers in Biotransformation, K. Ruckpaul. Akademie Verlag, Berlin 1989, (in press)
  • Gozukara E. M., Belvedere G., Robinson R. C., Deutsch J., Coon M. J., Guengerich F. P., Gelboin H. V. The effect of epoxide hydratase on benzo‘α’pyrene diol epoxide hydrolysis and binding to DNA and mixed-function oxidase proteins. Molecular Pharmacology 1981; 19: 53–161
  • Guengerich F. P. Covalent binding to apoprotein is a major fate of heme in a variety of reactions in which cytochrome P-450 is destroyed. Biochemical and Biophysical Research Communications 1986; 138: 193–198
  • Guengerich F. P. Cytochrome P-450 enzymes and drug metabolism. Progress in Drug Metabolism, J. W. Bridges, L. F. Chasseaud, G. G. Gibson. Taylor & Francis, London 1987; Vol. 10: 1–54
  • Gurtoo H. L., Marinello A. J., Struck R. F., Paul B., Dahms R. P. Studies on the mechanism of denaturation of cytochrome P-450 by cyclophosphamide and its metabolites. Journal of Biological Chemistry 1981; 256: 11691–11701
  • Halpert J. R., Miller N. E., Gorsky L. D. On the mechanism of inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. Journal of Biological Chemistry 1985; 260: 8397–8403
  • Haugen D. A., Coon M. J. Properties of electrophorectically homogeneous phenobarbital-inducible and β-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. Journal of Biological Chemistry 1976; 251: 7929–7939
  • Huberman E., Sachs L., Yang S. K., Gelboin H. V. Identification of mutagenic metabolites of benzo‘α’pyrene in mammalian cells. Proceedings of the National Academy of Sciences, USA 1976; 73: 607–611
  • Jeffrey A. M., Weinstein I. B., Jennette K. W., Grzeskowiak K., Nakanishi K., Harvfy R. G., Autrup H., Harris C. Structures of benzo(a)pyrene-nucleic acid adducts formed in human and bovine bronchial explants. Nature 1977; 269: 348–350
  • King H. W. S., Osborne M. R., Beland F. A., Harvey R. G., Brookes P. 7α 8β- dihydroxy-9β,10β-epoxy-7,8,9,10-tetrahydrobenzo‘α’pyrene is an intermediate in the metabol ism and binding to DNA of benzo‘α’pyrene. Proceedings of the National Academy of Sciences. USA 1976; 73: 2679–2681
  • Kirby K. S. A new method for the isolation of deoxyribonucleic acids: evidence on the nature of bonds between deoxyribonucleic acid and protein. Biochemical Journal 1957; 66: 495–504
  • Laemmli U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970; 227: 680–685
  • LeStourgeon W. M., Rusch H. P. Localization of nucleolar and chromatin residual acidic protein changes during differentiation in Physarum polycephalum. Archives of Biochemistry and Biophysics 1973; 155: 144–158
  • Lu A. Y. H., West S. B. Reconstituted mammalian mixed-function oxidases: requirements. specificities, and other properties. Hepatic Cytochrome P-450 Monooxygenase Systems, J. B. Schenkamn, K. Kupfer. Pergamon Press, New York 1982; 523–544
  • McCaustland D. J., Engel J. F. Metabolites of polycyclic aromatic hydrocarbons. II. Synthesis of 7,8-dihydrobenzo‘α’pyrene-7,8-diol and 7,8-dihydrobenzo‘α’pyrene-7,8-epoxide. Tetrahedron Letters 1975; 30: 2549–2552
  • McCaustland D. J., Duncan W. P., Engel J. F. Metabolites of polycyclic aromatic hydrocarbons. V. Trans-7,8-dihydrobenzo‘α’pyrene-7,8-diol-7-14C. Journal of Labelled Compounds and Radiopharmaceuticals 1976; 12: 443–448
  • Menard R. H., West D. M., Gelboin H. V., Vatsis K. P., Coon M. J. Benzo‘α’pyrene oxygenation by purified cytochromes P-450LM2 and P-450LM4 from rabbit liver. Fourth International Symposium on Microsomes and Drug Oxidations. University of Michigan, 1979, abstract No. P-714
  • Miller E. C., Miller J. A. Biochemical mechanism of chemical carcinogenesis. Molecular Biology of Cancer, H. Bush. Academic Press, New York 1974; 377–402
  • Miller E. C., Miller J. A. Some historical perspectives on the metabolism of xenobiotic chemicals to reactive electrophiles. Bioactivation of Foreign Compounds, M. W. Anders. Academic Press, New York 1985; 3–28
  • Neal R. A. Thiono-sulfur compounds. Bioactivation of Foreign Compounds, M. W. Anders. Academic Press, New York 1985; 519–540
  • Nebert D. W., Adesnik M., Coon M. J., Estabrook R. W., Gonzalez F. J., Guengerich F. P., Gunsalus I. C., Johnson E. F., Kemper B., Levin W., Phillips I. R., Sato R., Waterman M. R. The P-450 gene superfamily: recommended nomenclature. DNA 1987; 6: 1–11
  • Norman R. L., Johnson E. F., Muller-Eberhard U. Identification of the major cytochrome P-450 form transplacentally induced in neonatal rabbits by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Journal of Biological Chemistry 1978; 253: 8640–8647
  • Ortiz de Montellano P. R., Reich N. O. Inhibition of cytochrome P-450 enzymes. Cytochrome P-450: Structure, Mechanism, and Biochemistry, P. R. Ortiz de Montellano. Plenum, New York 1986; 273–314
  • Shack J. On the recognition and estimation of denatured deoxyribonucleate. Journal of Biological Chemistry 1958; 233: 677–680
  • Sims P. The metabolic activation of some polycyclic hydrocarbons: the role of dihydrodiols and diol-epoxides. Biological Reactive Intermediates, R. Snyder, D. V. Parke, J. J. Kocsis, D. J. Jollow, G. G. Gibson, C. M. Witmer. Plenum, New York 1982; Vol. IIA: 487–500
  • Sims P., Grover P. L. Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis. Advances in Cancer Research 1974; 20: 165–274
  • Sims P., Grover P. L., Swaisland A., Pal K., Hewer A. Metabolic activation of benzo‘α’pyrene proceeds by a diol epoxide. Nature 1974; 252: 326–328
  • Tamburini P. P., MacFarquhar S., Schenkman J. B. Evidence of binary complex formation between cytochrome P-450, cytochrome b5, and NADPH-cytochrome P-450 reductase of hepatic microsomes. Biochemical and Biophysical Research Communications 1986; 134: 519–526
  • Thakker D. R., Yagi H., Akagi H., Koreeda M., Lu A. Y. H., Levin W., Wood A. W., Conney A. H., Jerina D. M. Metabolism of benzo‘α’pyrene. VI. Stereoselective metabolism of benzo‘α’pyrene 7,8-dihydrodiol to diol epoxides. Chemico-Biological Interactions 1977; 16: 281–300
  • Thakker D. R., Yagi H., Levin W., Wood A. W., Conney A. H., Jerina D. M. Polycyclic aromatic hydrocarbons: metabolic activation to ultimate carcinogens. Bioactivation of Foreign Compounds, M. W. Anders. Academic Press, New York 1985; 177–242
  • Vatsis K. P., Deutsch J., Gelboin H. V., Coon M. J. Catalytic activity and stereospecificity of phenobarbital-inducible and 5,6-benzoflavone-inducible isozymes of liver microsomal cytochrome P-450 in the oxygenation of benzo‘α’pyrene and trans-7,8-dihydroxy-7,8-dihydrobenzo‘α’pyrene. Microsomes, Drug Oxidations, and Chemical Carcinogenesis, M. J. Coon, A. H. Conney, R. W. Estabrook, H. V. Gelboin, J. R. Gillette, P. J. O'Brien. Academic Press, New York 1980; Vol. 2: 1065–1077
  • Vatsis K. P., Theoharides A. D., Kupfer D., Coon M. J. Hydroxylation of prostaglandins by inducible isozymes of rabbit liver microsomal cytochrome P-450: participation of cytochrome b, 5. Journal of Biological Chemistry 1982; 257: 11221–11229
  • Vermilion J. L., Coon M. J. Purified liver microsomal NADPH-cytochrome P-450 reductase: spectral characterization of oxidation-reduction states. Journal of Biological Chemistry 1978; 253: 2694–2704
  • Weinstein I. B., Jeffrey A. M., Jennette K. W., Blobstein S. H., Harvey R. G., Harris C., Autrup H., Kasai H., Nakanishi K. Benzo‘α’pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Science 1976; 193: 592–595
  • Wiebel F. J., Leutz J. C., Diamond L., Gelboin H. V. Aryl hydrocarbon (benzo‘α’pyrene) hydroxylase in microsomes from rat tissues: differential inhibition and stimulation by benzoflavones and organic solvents. Archives of Biochemistry and Biophysics 1971; 144: 78–86
  • Wislocki P. G., Wood A. W., Chang R. L., Levin W., Yagi H., Hernandez O., Jerina D. M., Conney A. H. High mutagenicity and toxicity of a diol epoxide derived from benzo(a), pyrene. Biochemical and Biophysical Research Communications 1976; 68: 1006–1012
  • Wood A. W., Wislocki P. G., Chang R. L., Levin W., Lu A. Y. H., Yagi H., Hernandez O., Jerina D. M., Conney A. H. Mutagenicity and cytotoxicity of benzo(a), pyrene benzoring epoxides. Cancer Research 1976; 36: 3358–3366
  • Yang S. K., Gelboin H. V. Microsomal mixed-function oxidases and epoxide hydratase convert benzo‘α’pyrene stereospecifically to optically active dihydroxydihydrobenzo‘α’pyrenes. Biochemical Pharmacology 1976a; 25: 2221–2225
  • Yang S. K., Gelboin H. V. Nonenzymatic reduction of benzo‘α’pyrene diol-epoxides to trihydroxypentahydrobenzo‘α’pyrenes by reduced nicotinamide adenine dinucleotide phosphate. Cancer Research 1976b; 36: 4185–4189
  • Yang S. K., McCourt D. W., Roller P. P., Gelboin H. V. Enzymatic conversion of benzo‘α’pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-r-9,10-oxy-7,8,9,10-tetrahydrobenzo‘α’pyrene through a single enantiomer of r-7,i-8-dihydroxy-7,8-dihydrobenzo‘β’pyrene. Proceedings of the National Academy of Sciences, USA 1976; 73: 2594–2598
  • Yang S. K., Gelboin H. V., Trump B. F., Autrup H., Harris C. C. Metabolic activation of benzo‘α’pyrene and binding to DNA in cultured human bronchus. Cancer Research 1977a; 37: 1210–1215
  • Yang S. K., Gelboin H. V., Weber J. D., Sankaran V., Fischer D. L., Engel J. F. Resolution of optical isomers by high-pressure liquid chromatography: the separation of benzo‘α’pyrene trans-diol derivatives. Analytical Biochemistry 1977b; 78: 520–526
  • Yang S. K., McCourt D. W., Leutz J. C., Gelboin H. V. Benzo‘α’pyrene diol epoxides; mechanism of enzymatic formation and optically active intermediates. Science 1977c; 196: 1199–1201
  • Yang S. K., Deutsch J., Gelboin H. V. Benzo‘α’pyrene metabolism: activation and detoxification. Polycyclic Hydrocarbons and Cancer: Environment, Chemistry, and Metabolism, H. V. Gelboin, P. O. P. Ts'O. Academic Press, New York 1978; Vol. 1: 205–231

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.