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High mutageniticity of metabolically activated chrysene 1,2 dihydrodiol: evidence for bay region activation of chrysene. |
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| Authors: | A W Wood W Levin D Ryan P E Thomas H Yagi H D Mah D R Thakker D M Jerina A H Conney |
| Institution: | 4. Department of Biochemistry and Drug Metabolism Hoffmann-La Roche Inc., Nutley, New Jersey 07110 USA |
| Abstract: | Chrysene and the 3 metabolically possible vicinal dihydrodiols of chrysene were tested for mutagenicity towards strain TA100 in the presence of hepatic microsomes or a highly purified hepatic microsomal monooxygenase system. The products formed during the metabolic activation of chrysene 1,2-dihydrodiol were more than 20 times as mutagenic to the bacteria than the metabolites formed from chrysene, chrysene 3,4-dihydrodiol or chrysene 5,6-dihydrodiol. When the double bond in the 3,4-position of chrysene 1,2-dihydrodiol was saturated, the resulting tetrahydrodiol could not be metabolically activated. These results, which strongly suggest that chrysene 1,2-dihydrodiol is activated by metabolism to either or both of the diastereomeric chrysene 1,2-diol-3,4-epoxides, provide additional support for the bay region theory of polycyclic hydrocarbon carcinogenicity. |
| Keywords: | Benzo[a]pyrene 7 8-dihydrodiol benzo[a]pyrene 7 8-diol-9 10-epoxide either or both diastereomers of 7 8-dihydroxy-9 10-epoxy-7 8 9 10-tetrahydrobenzo[a]pyrene derived from benzo[a]pyrene 7 8-dihydrodiol benz[a]anthracene 3 4-dihydrodiol benz[a]anthracene 3 4-diol-1 2-epoxide either or both diastereomers of 3 4-dihydroxy-1 2-epoxy-1 2 3 4-tetrahydrobenz[a]anthracene derived from benz[a]anthracene 3 4-dihydrodiol chrysene 1 2-dihydrodiol chrysene 3 4-dihydrodiols chrysene 5 6-dihydrodiols chrysene 1 2-diol-3 4-epoxide either or both diastereomers of 1 2-dihydroxy-3 4-epoxy-1 2 3 4-tetrahydrochrysene derived from chrysene 1 2-dihydrodiol |
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