Catechol-induced alterations in metabolic activation and binding of enantiomeric and racemic 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrenes to DNA in mouse skin

Carcinogenesis
A A MelikianD Hoffmann

Abstract

Catechol (1,2-dihydroxybenzene) is a potent co-carcinogen with benzo[a]pyrene (BaP) and with (+/-)-7,8-dihydroxy-7,8- dihydrobenzo[a]pyrene (BaP-7,8-diol) in mouse skin. The effects of catechol on the metabolic activation of (+)- and (-)-[3H]BaP-7,8-diols and on epidermal DNA adduct formation of racemic and enantiomeric [3H]BaP-7,8-diols were examined by applying the tritiated diols to mouse skin. The major metabolite of the (+)-[3H]BaP-7,8-diol was the hydrolysis product of (-)-[3H]-7 alpha, 8 beta-dihydroxy-9 beta, 10 beta-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (anti-BPDE). This suggests that a peroxyl radical-mediated pathway is predominantly responsible for the epoxidation of this diol. Formation of (-)-anti[3H]BPDE from (+)-[3H]BaP-7,8-diol was greater than that of (+)-anti-BPDE from (-)-[3H]BaP-7,8-diol. Co-application of catechol with [3H]BaP-7,8-diols inhibited epoxidation of the (+) enantiomer to a greater extent than that of the (-) enantiomer. Catechol decreased the total DNA-binding and the formation of the major adduct with (+)-[3H]BaP-7,8-diol metabolites but catechol had no significant effect on the binding and formation of (+)-anti-[3H]BPDE-deoxyguanosine, the major DNA adduct derived from (-)-[3H]BaP-7,8-diol....Continue Reading

Citations

Jan 1, 1992·Pharmacology & Therapeutics·J DiGiovanni
Jan 15, 2000·The Journal of Biological Chemistry·N GuoC Vaziri

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