Metabolic activation and inactivation of chemical carcinogens

References

• Aitio , A. 1973 . “ Extrahepatic microsomal drug metabolism with special reference to glucuronide synthesis ” . Turku : Monistepalvelu . Thesis
   Google Scholar
• Bartsch , H. , Margison , G. P. , Malaveille , C. , Camus , A. M. , Brun , G. , Margison , J. M. , Kolar , G. F. and Wiessler , M. 1977 . Some aspects of metabolic activation of chemical carcinogens in relation to their organ specificity . Arch. Toxicol. , 39 : 51 – 63 .
   PubMed Web of Science ®Google Scholar
• Caldwell , J. 1979 . The significance of phase II (conjugation) reactions in drug disposition and toxicity . Life Sci. , 24 : 571 – 578 .
   PubMed Web of Science ®Google Scholar
• Capdevila , J. , Jacobsson , S. W. , Jernström , B. , Helia , O. and Orrenius , S. 1975 . Characterization of a rat lung microsomal fraction obtained by Sepharose 2B ultrafiltration . Cancer Res. , 35 : 2820 – 2829 .
   PubMed Web of Science ®Google Scholar
• Chouroulinkov , I. , Gentil , A. , Tierney , B. , Grover , P. and Sims , P. 1977 . The metabolic activation of 7‐methylbenz(a)anthracene in mouse skin: High tumour‐initiating activity of the 3,4‐dihydrodiol . Cancer Lett. , 3 : 247 – 253 .
   Web of Science ®Google Scholar
• Cohen , G. M. , Haws , S. M. , Moore , B. P. and Bridges , J. W. 1976 . Benzo(a)pyrene‐3‐yl hydrogen sulphate, a major ethyl acetate‐extractable metabolite of benzo(a)pyrene in human, hamster and rat lung cultures . Biochem. Pharmacol. , 25 : 2561 – 2570 .
   PubMed Web of Science ®Google Scholar
• De Pierre , J. W. and Ernster , L. 1978 . The metabolism of polycylic hydrocarbons and its relationship to cancer . Biochim. Biophys. Acta , 473 : 149 – 186 .
   PubMed Web of Science ®Google Scholar
• Estabrook , R. W. and Lindenlaub , E. , eds. 1979 . The Induction of Drug Metabolism , Stuttgart : Schattauer Verlag .
   Google Scholar
• Fahl , W. E. , Shen , A. L. and Jefcoate , C. R. 1979 . UDP‐glucuronosyl transferase and the conjugation of benzo(a)pyrene metabolites to DNA . Biochem. Biophys. Res. Commun. , 85 : 891 – 899 .
   Google Scholar
• Fahmy , M. J. , Fahmy , O. G. and Swenson , D. H. 1978 . Aflatoxin B,‐2,3‐dichloride as a model of the active metabolite of aflatoxin B1 in mutagenesis and carcinogenesis . Cancer Res. , 38 : 2608 – 2616 .
   PubMedGoogle Scholar
• Glatt , H. R. and Oesch , F. 1976 . Phenolic benzo(a)pyrene metabolites are mutagens . Mutat. Res. , 36 : 379 – 384 .
   PubMed Web of Science ®Google Scholar
• Goldstein , A. , Aronow , L. and Kalman , S. M. 1974 . Principles of Drug Action , New York : Harper & Row .
   Google Scholar
• Guenthner , T. M. , Fysh , J. M. and Nebert , D. W. 1979 . 2,3,7,8‐Tetrachlorodibenzo‐p‐dioxin: Covalent binding of reactive metabolic intermediates principally to protein in vitro . Pharmacology , 19 : 12 – 22 .
   PubMed Web of Science ®Google Scholar
• Heidelberger , C. 1973 . Current trends in chemical carcinogenesis . Fed. Proc. , 32 : 2154 – 2161 .
   PubMedGoogle Scholar
• Heidelberger , C. 1975 . Chemical carcinogenesis . Annu. Rev. Biochem. , 44 : 79 – 121 .
   PubMed Web of Science ®Google Scholar
• Hsu , W. T. , Sagher , D. , Lin , E. J. , Harvey , R. G. , Fu , P. P. and Weiss , S. B. 1979 . Benzo(a)pyrene‐7,8‐dihydrodiol: Selective binding to single stranded DNA and inactivation of ⊘X 174 DNA infectivity . Biochem. Biophys. Res. Commun. , 87 : 416 – 423 .
   PubMedGoogle Scholar
• Jerina , D. M. and Lehr , R. E. 1977 . “ The bay‐region theory: A quantum mechanical approach to aromatic hydrocarbon‐induced carcinogenicity ” . In Microsomes and Drug Oxidations , Edited by: Ullrich , V. , Roots , I. , Hildebrandt , A. , Estabrook , R. W. and Conney , A. H. 709 – 720 . Oxford : Pergamon .
   Google Scholar
• Kahl , G. F. , Klaus , E. , Legraverend , C. , Nebert , D. W. and Pelkonen , O. 1979 . Formation of benzo(a)pyrene metabolite‐nucleoside adducts in perfused rat and mouse liver and in mouse lung slices . Biochem. Pharmacol. , 28 : 1051 – 1056 .
   PubMed Web of Science ®Google Scholar
• Khandwala , A. S. and Kasper , C. B. 1973 . Preferential induction of aryl hydroxylase activity in rat liver nuclear envelope by 3‐methylcholanthrene . Biochem. Biophys. Res. Commun. , 54 : 1241 – 1246 .
   PubMed Web of Science ®Google Scholar
• Kinoshita , N. and Gelboin , H. V. 1978 . β‐Glucuronidase catalyzed hydrolysis of benzo(a)pyrene‐3‐glucuronide and binding to DNA . Science , 199 : 307 – 309 .
   PubMed Web of Science ®Google Scholar
• Kodama , M. , Ioki , Y. and Nagata , C. 1977 . Binding of benzo(a)pyrene‐semiquinone radicals with DNA and polynucleotides . Gann , 68 : 253 – 254 .
   PubMedGoogle Scholar
• Kriek , E. 1969/70 . On the mechanism of action of carcinogenic aromatic amines. I. Binding of 2‐acetylaminofluorene and N‐hydroxy‐2‐acetylaminofluorene to rat‐liver nucleic acids in vivo . Chem.‐Biol. Interact. , 1 : 3 – 17 .
   PubMedGoogle Scholar
• Levin , W. , Thakker , D. R. , Wood , A. W. , Chang , R. L. , Lehr , R. E. , Jerina , D. M. and Conney , A. H. 1978a . Evidence that benzo(a)anthracene 3,4‐diol‐1,2‐epoxide is an ultimate carcinogen on mouse skin . Cancer Res. , 38 : 1705 – 1710 .
   PubMed Web of Science ®Google Scholar
• Levin , W. , Wood , A. W. , Chang , R. L. , Yogi , H. , Mah , H. D. , Jerina , D. M. and Conney , A. H. 1978b . Evidence for bay region activation of chrysens 1,2‐dihydrodiol to an ultimate carcinogen . Cancer Res. , 38 : 1831 – 1834 .
   PubMed Web of Science ®Google Scholar
• Malaveille , C. , Tierney , B. , Grover , P. L. , Sims , P. and Bartsch , H. 1977 . High microsome‐mediated mutagenicity of the 3,4‐dihydrodiol of 7‐methylbenz(a)anthracene in S. typhimurium TA 98 . Biochem. Biophys. Res. Commun. , 75 : 427 – 433 .
   PubMed Web of Science ®Google Scholar
• Malaveille , C. , Bartsch , H. , Tierney , B. , Grover , P. L. and Sims , P. 1978 . Microsome‐mediated mutagenicities of the dihydrodiols of 7,12‐dimethylbenz(a,h)anthracene . Biochem. Biophys. Res. Commun. , 83 : 1468 – 1473 .
   PubMed Web of Science ®Google Scholar
• Miller , J. A. 1970 . Carcinogenesis by chemicals: An overview. G.H.A. Clowes memorial lecture . Cancer Res. , 30 : 559 – 576 .
   PubMed Web of Science ®Google Scholar
• Olajos , E. J. 1977 . Biological interactions of N‐nitroso compounds: A review . Ecotoxicol. Environ. Safety , 1 : 175 – 196 .
   PubMedGoogle Scholar
• Owens , I. S. , Koteen , G. M. , Pelkonen , O. and Legraverend , C. 1978 . “ Activation of certain benzo(a)‐pyrene phenols and the effect of some conjugating enzyme activities ” . In Conjugation Reactions in Drug Biotransformation , Edited by: Aitio , A. 39 – 51 . Amsterdam : Elsevier/North‐Holland .
   Google Scholar
• Parke , D. V. 1972 . Metabolism of drugs . Chem. Br. , 8 : 102 – 108 .
   PubMedGoogle Scholar
• Pelkonen , O. , Boobis , A. R. , Yagi , H. Jerina and Nebert , D. W. 1978 . The tentative identification of benzo(a)pyrene metabolite‐nucleoside complexes produced in vitro by mouse liver microsomes . Mol. Pharmacol. , 14 : 306 – 322 .
   PubMed Web of Science ®Google Scholar
• Pezzuto , J. M. , Lea , M. A. and Yang , C. S. 1976 . Binding of metabolically activated benzo(a)pyrene to nuclear macromolecules . Cancer Res. , 36 : 3647 – 3653 .
   PubMed Web of Science ®Google Scholar
• Pezzuto , J. M. , Lea , M. A. and Yang , C. S. 1977 . The role of microsomes and nuclear envelope in the metabolic activation of benzo(a)pyrene leading to binding with nuclear macromolecules . Cancer Res. , 37 : 3427 – 3433 .
   PubMed Web of Science ®Google Scholar
• Rogan , E. G. and Cavalieri , E. 1974 . 3‐Methylcholanthrene‐inducible binding of aromatic hydrocarbons to DNA in purified rat liver nuclei . Biochem. Biophys. Res. Commun. , 58 : 1119 – 1125 .
   PubMed Web of Science ®Google Scholar
• Sims , P. , Grover , P. L. , Swaisland , A. , Pal , K. and Hewe , A. 1974 . Metabolic activation of benzo(a)pyrene proceeds by a diol‐epoxide . Nature (Lond.) , 252 : 326 – 328 .
   PubMed Web of Science ®Google Scholar
• Sloane , N. H. , Chen , H. , Diwan , B. , Bedigian , R. and Meier , H. 1976 . “ The biosynthesis and biological properties of 6‐hydroxymethylbenzo(a)pyrene ” . In Carcinogenesis. A Comprehensive Survey vol. 1 Polynudear Aromatic Hydrocarbons: Chemistry Metabolism and Carcinogenesis , Edited by: Freudenthal , R. I. and Jones , P. W. vol. 1 , 171 – 180 . New York : Raven .
   Google Scholar
• Snyder , R. and Kocsis , J. J. 1975 . Current concepts of chronic benzene toxicity . Crit. Rev. Toxicol. , 3 : 265 – 288 .
   Google Scholar
• Sotaniemi , E. A. , Pelkonen , R. O. , Ahokas , J. T. , Pirttiaho , H. I. and Ahlqvist , J. 1978 . Relationship between in vivo and in vitro drug metabolism in man . Eur. J. Drug Metab. Pharmacokinet. , 1 : 39 – 45 .
   Google Scholar
• Testa , B. and Jenner , P. 1976 . Drug Metabolism: Chemical and Biochemical Aspects , New York : Dekker .
   Google Scholar
• Testa , B. and Jenner , P. 1978 . Novel drug metabolites produced by functionalization reactions: Chemistry and toxicology . Drug. Metab. Rev. , 7 : 325 – 369 .
   PubMed Web of Science ®Google Scholar
• Thakker , D. R. , Yagi , H. , Lu , A. Y. H. , Levin , W. , Conney , A. H. and Jerina , D. M. 1976 . Metabolism of benzo(a)pyrene–conversion of (+/–)‐trans‐7,8‐dihydroxy‐7,8‐dihydrobenzo(a)pyrene to highly mutagenic 7,8‐diol‐9,10‐epoxides . Proc. Natl. Acad. Sci. U.S.A. , 73 : 3381 – 3385 .
   PubMed Web of Science ®Google Scholar
• Thorgeirsson , S. S. and Nebert , D. W. 1977 . The Ah locus and metabolism of chemical carcinogens and other foreign compounds . Adv. Cancer Res. , 25 : 149 – 193 .
   PubMedGoogle Scholar
• Tierney , B. , Hewer , A. , Waslshe , C. , Grover , P. L. and Sims , P. 1977 . The metabolic activation of 7‐methyl‐ben(a)anthracene in mouse skin . Chem.‐Biol. Interact. , 18 : 179 – 193 .
   PubMed Web of Science ®Google Scholar
• Ullrich , V. , Roots , I. , Hildebrandt , A. G. , Estabrook , R. W. and Conney , A. H. , eds. 1977 . Microsomes and Drug Oxidations , Oxford : Pergamon .
   Google Scholar
• Vähäkangas , K. 1979 . The distribution of benzo(a)pyrene and its metabolites in an isolated perfused lung compared to an isolated perfused liver . Toxicol. Lett. , 4 : 413 – 418 .
   Google Scholar
• Vähäkangas , K. , Nevasaari , K. , Pelkonen , O. and Kärki , N. T. 1977 . The metabolism of benzo(a)pyrene in isolated perfused lungs from variously‐treated rats . Acta Pharmacol. Toxicol. , 41 : 129 – 140 .
   PubMedGoogle Scholar
• Viviani , A. and Lutz , W. K. 1978 . Modulation of the binding of the carcinogen benzo(a)pyrene to rat liver DNA in vivo by selective induction of microsomal and nuclear aryl hydrocarbon hydroxylase activity . Cancer Res. , 38 : 4640 – 4644 .
   PubMed Web of Science ®Google Scholar
• Warren , P. M. and Bellward , G. D. 1978 . Induction of aryl hydrocarbon hydroxylase by 3‐methylcholanthrene in liver, lung and kidney . Biochem. Pharmacol. , 27 : 2537 – 2541 .
   PubMedGoogle Scholar
• Wislocki , P. G. , Chang , R. L. , Wood , A. W. , Levin , W. , Yogi , H. , Hernandez , O. , Mah , H. D. , Dansette , P. M. , Jerina , D. M. and Conney , A. H. 1977 . High carcinogenicity of 2‐hydroxybenzo(a)pyrene on mouse skin . Cancer Res. , 37 : 2608 – 2611 .
   PubMed Web of Science ®Google Scholar
• Wislocki , P. G. , Kapitulnik , J. , Levin , W. , Lehr , R. , Schaefer‐Ridder , M. , Karle , J. M. , Jerina , D. M. and Conney , A. H. 1978 . Exceptional carcinogenic activity of benzo(a)anthracene 3,4‐dihydrodiol in the newborn mouse and the bay region theory . Cancer Res. , 38 : 693 – 696 .
   PubMed Web of Science ®Google Scholar
• Wood , A. W. , Wislocki , P. G. , Chang , R. L. , Levin , W. , Lu , A. Y. H. , Yagi , H. , Hernandez , O. , Jerina , D. M. and Conney , A. H. 1976 . Mutagenicity and cytotoxicity of benzo(a)pyrene benzo‐ring epoxides . Cancer Res. , 36 : 3358 – 3366 .
   PubMed Web of Science ®Google Scholar
• Wood , A. W. , Levin , W. , Ryan , D. , Thomas , P. E. , Yagi , H. , Mah , H. D. , Thakker , D. R. , Jerina , D. M. and Conney , A. H. 1977 . High mutagenicity of metabolically activated chrysene 1,2‐dihydrodiol: Evidence for bay region activation of chrysene . Biochem. Biophys. Res. Commun. , 78 : 847 – 854 .
   PubMed Web of Science ®Google Scholar
• Wood , A. W. , Chang , R. L. , Levin , W. , Thomas , P. E. , Ryan , D. , Stoming , T. A. , Thakker , D. R. , Jerina , D. M. and Conney , A. H. 1978a . Metabolic activation of 3‐methylcholanthrene and its metabolites to products mutagenic to bacterial and mammalian cells . Cancer Res. , 38 : 3398 – 3404 .
   PubMed Web of Science ®Google Scholar
• Wood , A. W. , Levin , W. , Thomas , P. E. , Ryan , D. , Karle , J. M. , Yagi , H. , Jerina , D. M. and Conney , A. H. 1978b . Metabolic activation of dibenzo(a,h)anthracene and its dihydrodiols to bacterial mutagens . Cancer Res. , 38 : 1967 – 1973 .
   PubMed Web of Science ®Google Scholar
• Zytkovicz , T. H. Moses and Spelsberg , T. C. 1978 . Competitive binding and metabolism of several carcinogenic polycyclic aromatic hydrocarbons by AKR mouse embryo cells in culture . Cancer Res. , 38 : 2307 – 2313 .
   PubMedGoogle Scholar