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Metabolic Pathways of 7,12-dimethylbenz[a]anthracene in Hepatic Microsomes

Yang, Shen K. and Dower, William V. (1975) Metabolic Pathways of 7,12-dimethylbenz[a]anthracene in Hepatic Microsomes. Proceedings of the National Academy of Sciences of the United States of America, 72 (7). pp. 2601-2605. ISSN 0027-8424.

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High pressure liquid chromatography has enabled quantitative analysis of the in vitro metabolism of 7,12-dimethylbenz[a]anthracene, 7-methyl-12-hydroxymethylbenz[a]anthracene, 7-hydroxymethyl-12-methylbenz[a]anthracene, and 7,12-dihydroxymethylbenz[a]anthracene by 3-methylcholanthrene-induced and control rat liver microsomes. The following previously unrecognized metabolites have been tentatively identified: 5,6-dihydro-5,6-dihydroxy-7-methyl-12-hydroxymethylbenz[a]anthracene, 3-hydroxy-7,12-dihydrodihydroxymethylbenz[a]anthracene, 4-hydroxy-7,12-dihydrodihydroxymethylbenz[a]anthracene, and 8,9-dihydro-8,9-dihydroxy-7,12-dihydroxymethylbenz[a]anthracene. The epoxide hydratase inhibitor 1,2-epoxy-3,3,3-trichloropropane was found to eliminate all dihydrodiol formation and markedly inhibit the formation of several dimethylbenzanthracene metabolites. It is proposed that the tentatively identified 3-hydroxy and 4-hydroxy derivatives are formed by an enzymatic mechanism that does not involve epoxides as intermediates. The metabolic pathways of 7,12-dimethylbenz[a]anthracene in hepatic microsomal enzymes are proposed.

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Additional Information:Copyright © 1975 by the National Academy of Sciences. Communicated by John D. Baldeschwieler, April 24, 1975. The authors gratefully acknowledge helpful discussions with Drs. John D. Baldeschwieler and Harry V. Gelboin. This work was supported by the National Science Foundation under Grant no. 38855X, and the National Institutes of Health under Grant no. GM-21111-02. S.K.Y. is the recipient of a Postdoctoral Research Fellowship (1-F-22-CA 01474-01) from the National Cancer Institute. This is Contribution no. 5037 from the Arthur Amos Noyes Laboratory.
Subject Keywords:carcinogen; adrenocorticolytic agent; high pressure liquid chromatography
Issue or Number:7
Record Number:CaltechAUTHORS:YANpnas75
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:10641
Deposited By: Archive Administrator
Deposited On:22 May 2008
Last Modified:03 Oct 2019 00:11

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