PMID: 3756866Oct 1, 1986Paper

Metabolism of 7,8-dihydrobenzo(a)pyrene by rat liver microsomal enzymes and mutagenicity of metabolites

Cancer Research
P L Chiu, S K Yang

Abstract

7,8-Dihydrobenzo[a]pyrene (7,8-H2BaP) was metabolized by rat liver microsomes to form 7,8,9,10-tetrahydro-BaP trans-9,10-diol, 7,8,9,10-tetrahydro-BaP cis-9,10-diol, 7-hydroxy-7,8-H2BaP, 8-hydroxy-7,8-H2BaP, two phenolic products of 7,8-H2BaP [abbreviated as 7,8-H2BaP phenol 1 and phenol 2 according to their elution order on reversed-phase high-performance liquid chromatography (HPLC)], 4,5,7,8-tetrahydro-BaP trans-4,5-diol, BaP cis-7,8-dihydrodiol, BaP, and the metabolites known to be formed from the metabolism of BaP. Metabolites were isolated by reversed-phase and normal-phase HPLC and identified by ultraviolet-visible absorption and mass spectral analyses and by comparing their retention times with synthetic standards whenever available. The enantiomeric compositions of some mono-ol and diol metabolites were determined by chiral stationary phase HPLC. The optical purities of monool and diol metabolites formed were found to be dependent on the nature of cytochrome P-450 isozymes present in liver microsomes. Metabolites formed by liver microsomes from untreated, phenobarbital-treated, 3-methylcholanthrene-treated, and polychlorinated biphenyls (Aroclor 1254)-treated male Sprague-Dawley rats were quantified by using specifical...Continue Reading

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