Central role of radical cations in metabolic activation of polycyclic aromatic hydrocarbons

References

• Arcos J. C., Argus M. F. Chemical Induction of Cancer. Academic, New York 1974; vol. IIA: 15–41
   Google Scholar
• Buhler D. R., Unlü F., Thakker D. R., Slaga T. J., Conney A. H., Wood A. W., Chang R. L., Levin W., Jerina D. M. Effect of a 6-fluoro substitutent on the metabolism and biological activity of benzo[a]pyrene. Cancer Research 1983; 43: 1541–1549
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Auerbach R. Reactions between activated benzo[a]pyrene and nucleophilic compounds, with possible implications on the mechanism of tumor initiation. Journal of National Cancer Institute 1974; 53: 393–397
   PubMedGoogle Scholar
• Cavalieri E., Calvin M. Photochemical coupling of benzo[a]pyrene with 1-methylcytosine; photoenhancement of carcinogenicity. Photochemistry and Photobiology 1971; 14: 641–653
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Devanesan P., Mulder P., RamaKrishna N. V. S., Rogan E. Metabolism of 1- and 3-fluoro-benzo[a]pyrene by cytochrome P450 and horseradish peroxidase. Polycyclic Aromatic Compounds 1994; 7: 129–136
   Google Scholar
• Cafvalieri E., Devanesan P., Rogan E. Radical cations in the horseradish peroxidase and prostaglandin H synthase mediated metabolism and binding of benzo[a]pyrene to DNA. Biochemical Pharmacology 1988a; 37: 2183–2188
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Rogan E. Role of radical cations in aromatic hydrocarbon carcinogenesis. Environmental Health Perspectives 1985; 64: 69–84
   PubMed Web of Science ®Google Scholar
• Cavalieri E. L., Rogan E. G. The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacology and Therapeutics 1992; 55: 183–199
   PubMed Web of Science ®Google Scholar
• Cavalieri E. L., Rogan E. G., Cremonesi P., Davanesan P. D. Radical cations as precursors in the metabolic formation of quinones from benzo[a]pyrene and 6-fluorobenzo[a]pyrene. Fluoro substitution as a probe for one-electron oxidation in aromatic substrates. Biochemical Pharmacology 1988b; 37: 2173–2182
   PubMed Web of Science ®Google Scholar
• Cavalieri E. L., Rogan E. G., Devanesan P. D., Cremonesi P., Cerny R. L., Gross M. L., Bodell W. J. Binding of benzo[a]pyrene to DNA by cytochrome P-450-catalyzed one-electron oxidation in rat liver microsomes and nuclei. Biochemistry 1990a; 29: 4820–4827
   PubMed Web of Science ®Google Scholar
• Cavalieri E. L., Rogan E. G., Higginbotham S., Cremonesi P., Salmasi S. Tumorigenicity of 7,12-dimethylbenz[a]anthracene, some of its fluorinated derivatives, and 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthracene in mouse skin and rat mammary gland. Polycyclic Aromatic Compounds 1990b; 1: 59–70
   Google Scholar
• Cavalieri E., Rogan E., Roth R. W., Saugier R. K., Hakam A. The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA. Chemical-Biological Interactions 1983; 47: 87–109
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Roth R. Reaction of methylbenzanthracenes and pyridine by one-electron oxidation: a model for metabolic activation and binding of carcinogenic aromatic hydrocarbons. Journal of Organic Chemistry 1976; 41: 2679–2684
   PubMed Web of Science ®Google Scholar
• Cavalieri E., Roth R., Rogan E. Metabolic activation of aromatic hydrocarbons by one-electron oxidation in relation to the mechanism of tumor initiation. Polynuclear Aromatic Hydrocarbons: Chemistry, Metabolism and Carcinogenesis, R. I. Freudenthal, P. W. Jones. Raven, New York 1976; vol. 1: 181–190
   Google Scholar
• Chakravarti D., Pelling J. C., Cavalieri E. L., Rogan E. G. Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: The role of apurinic sites. Proceedings of the National Academy of Sciences, USA 1995, (in press)
   Web of Science ®Google Scholar
• Conney A. H. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons. G. H. A. Clowes Memorial Lecture. Cancer Research 1982; 42: 4875–4917
   PubMed Web of Science ®Google Scholar
• Cremonesi P., Cavalieri E., Rogan E. One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate. A model for metabolic activation. Journal of Organic Chemistry 1989; 54: 3561–3570
   Web of Science ®Google Scholar
• Cremonesi P., Hietbrink B., Rogan E. G., Cavalieri E. L. One-electron oxidation and dibenzo[a]pyrenes by manganic acetate. Journal of Organic Chemistry 1992a; 57: 3309–3312
   Web of Science ®Google Scholar
• Cremonesi P., Rogan E., Cavalieri E. Correlation studies of anodic peak potentials and ionization potentials for polycylic aromatic hydrocarbons. Chemical Research in Toxicology 1992b; 5: 346–355
   PubMed Web of Science ®Google Scholar
• Devanesan P. D., RamaKrishna N. V. S., Padmavathi N. S., Higginbotham S., Rogan E. G., Cavalieri E. L., Marsch G. A., Jankowiak R., Small G. J. Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin. Chemical Research in Toxicology 1993; 6: 364–371
   PubMed Web of Science ®Google Scholar
• Devanesan P. D., RamaKrishna N. V. S., Todorovic R., Rogan E. G., Cavalieri E. L., Jeong H., Jankowiak R., Small G. J. Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro. Chemical Research in Toxicology 1992; 5: 302–309
   PubMed Web of Science ®Google Scholar
• Devanesan P., Rogan E., Cavalieri E. The relationship between ionization potential and prostaglandin H synthase-catalyzed binding of aromatic hydrocarbons to DNA. Chemical-Biological Interactions 1987; 61: 89–95
   PubMed Web of Science ®Google Scholar
• Dunford H. B. One-electron oxidations by peroxidases. Xenobiotica 1995; 25: 725–733
   PubMed Web of Science ®Google Scholar
• Fried J. One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons. Chemical Carcinogens part A, P. O. P. Ts'o, J. DiPaolo. Marcel Dekker, New York 1974; 197–215
   Google Scholar
• Fried J., Schumm D. E. One electron transfer oxidation of 7,12-dimethylbenz[a]anthracene, a model for the metabolic activation of carcinogenic hydrocarbons. Journal of the American Chemical Society 1967; 89: 5508–5509
   PubMed Web of Science ®Google Scholar
• Hoffmann H. D., Lesko S. A., Jr, Ts'o P. O. P. Chemical linkage of polycyclic hydrocarbons to deoxyribonucleic acids and polynucleotides in aqueous solution and in a buffer-ethanol solvent system. Biochemistry 1970; 9: 2594–2604
   PubMed Web of Science ®Google Scholar
• Jeftic L., Adams R. N. Electrochemical oxidation pathways of benzo[a]pyrene. Journal of the American Chemical Society 1970; 92: 1332–1337
   PubMedGoogle Scholar
• Kasper C. B. Biochemical distinctions between the nuclear and microsomal membranes from rat hepatocytes. Journal of Biological Chemistry 1971; 246: 577–581
   PubMed Web of Science ®Google Scholar
• Khandwala A. S., Kasper C. B. Preferential induction of aryl hydroxylase activity in rat liver nuclear envelope by 3-methylcholanthrene. Biochemical and Biophysical Research Communications 1973; 54: 1241–1246
   PubMed Web of Science ®Google Scholar
• Lesko S. A., Jr, Smith A., Ts'o P. O. P., Umans R. S. Interaction of nucleic acids. IV. The physical binding of 3,4-benzpyrene to nucleosides, nucleotides, nucleic acids and nucleoprotein. Biochemistry 1968; 7: 434–447
   PubMed Web of Science ®Google Scholar
• Lesko S. A., Jr, Ts'o P. O. P., Umans R. S. Interaction of nucleic acids. V. Chemical linkage of 3,4-benzpyrene to deoxyribonucleic acid in aqueous solution. Biochemistry 1969; 8: 2291–2298
   PubMed Web of Science ®Google Scholar
• Li K.-M., Todorovic R., Rogan E. G., Cavalieri E. L., Ariese F., Suh M., Jankowiak R., Small G. J. Identification and quantitation of dibenzo[a, l]pyrene-DNA adducts formed by rat liver microsomes in vitro: Preponderance of depurinating adducts. Biochemistry 1995, (in press)
   Web of Science ®Google Scholar
• Marcoux L. S., Fritsch J. M., Adams R. N. One-electron oxidation of aromatic hydrocarbons. Journal of the American Chemical Society 1967; 89: 5766–5769
   Web of Science ®Google Scholar
• Miller J. A. Carcinogenesis by chemicals: an overview—G. H. A. Clowes Memorial Lecture. Cancer Research 1970; 30: 559–576
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 1981; 47: 2237–2345
   Web of Science ®Google Scholar
• Pataki J., Balick R. Relative carcinogenicity of some diethylbenz[a]anthracenes. Journal of Medical Chemistry 1972; 15: 905–909
   PubMed Web of Science ®Google Scholar
• RamaKrishna N. V. S., Cavalieri E. L., Rogan E. G., Dolnikowski G., Cerny R. L., Gross M. L., Jeong H., Jankowiak R., Small G. J. Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: Models for metabolic activation by one-electron oxidation. Journal of the American Chemical Society 1992a; 114: 1863–1874
   Web of Science ®Google Scholar
• RamaKrishna N. V. S., Devanesan P. D., Rogan E. G., Cavalieri E. L., Jeong H., Jankowiak R., Small G. J. Mechanism of metabolic activation of the potent carcinogen 7,12-dimethylbenz[a]anthracene. Chemical Research in Toxicology 1992b; 5: 220–226
   PubMed Web of Science ®Google Scholar
• RamaKrishna N. V. S., Gao F., Padmavathi N. S., Cavalieri E. L., Rogan E. G., Cerny R. L., Gross M. L. Model adducts of benzo[a]pyrene and nucleosides formed from its radical cation and diol epoxide. Chemical Research in Toxicology 1992c; 5: 293–302
   PubMed Web of Science ®Google Scholar
• RamaKrishna N. V. S., Li K.-M., Rogan E. G., Cavalieri E. L., George M., Cerny R. L., Gross M. L. Adducts of 6-methylbenzo[a]pyrene and 6-fluorobenzo[a]pyrene formed by electrochemical oxidation in the presence of deoxyribonucleosides. Chemical Research in Toxicology 1993a; 6: 837–845
   PubMed Web of Science ®Google Scholar
• RamaKrishna N. V. S., Padmavathi N. S., Cavalieri E. L., Rogan E. G., Cerny R. L., Gross M. L. Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[a, l]pyrene in the presence of nucleosides. Chemical Research in Toxicology 1993b; 6: 554–560
   PubMed Web of Science ®Google Scholar
• Rochlitz J. Neue Reaktionen der carcinogenen Kohlenwasserstoffe-II. Tetrahedron 1967; 23: 3043–3048
   PubMed Web of Science ®Google Scholar
• Rogan E. G., Cavalieri E. 3-Methylcholanthrene-inducible binding of aromatic hydrocarbons to DNA in purified rat liver nuclei. Biochemical and Biophysical Research Communications 1974; 58: 1119–1126
   PubMed Web of Science ®Google Scholar
• Rogan E. G., Cavalieri E. L., Tibbels S. R., Cremonesi P., Warner C. D., Nagel D. L., Tomer K. B., Cerny R. L., Gross M. L. Synthesis and identification of benzo[a]pyrene-guanine nucleoside adducts formed by electrochemical oxidation and by horseradish peroxidase catalyzed reaction of benzo[a]pyrene with DNA. Journal of the American Chemical Society 1988; 110: 4023–4029
   Web of Science ®Google Scholar
• Rogan E. G., Devanesan P. D., RamaKrishna N. V. S., Higginbotham S., Padmavathi N. S., Chapman K., Cavalieri E. L., Jeong H., Jankowiak R., Small G. J. Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin. Chemical Research in Toxicology 1993; 6: 356–363
   PubMed Web of Science ®Google Scholar
• Rogan E. G., Mailander P., Cavalieri E. Metabolic activation of aromatic hydrocarbons in purified rat liver nuclei: induction of enzyme activities and binding to DNA with and without monooxygenase-catalyzed formation of active oxygen. Proceedings of the National Academy of Sciences, USA 1976; 73: 457–461
   PubMed Web of Science ®Google Scholar
• Sims P., Grover P. L. Involvement of dihydrodiols and diol epoxides in the metabolic activation of polycyclic hydrocarbons other than benzo[a]pyrene. Polycyclic Hydrocarbons and Cancer, H. V. Gelboin, P. O. P. Ts'o. Academic, New York 1981; vol. 3: 117–181
   Google Scholar
• Tolbert L. M., Khanna R. K., Popp A. E., Gelbaum L., Bottomley L. A. Stereoelectronic effects in the deprotonation of arylalkyl radical cations: meso-ethylanthracenes. Journal of the American Chemical Society 1990; 112: 2373–2378
   Web of Science ®Google Scholar
• Wilk M., Bez W., Rochlitz J. Neue Reaktionen der carcinogenen Kohlenwasserstoffe 3,4-Benzpyren, 9,10-Dimethyl-1,2-Benzanthracen und 20-Methylcholanthren. Tetrahedron 1966; 22: 2599–2608
   Web of Science ®Google Scholar
• Wilk M., Girke W. Reactions between benzo[a]pyrene and nucleobases by one-electron oxidation. Journal of the National Cancer Institute 1972; 49: 1585–1597
   PubMedGoogle Scholar