PMID: 2114214Jul 15, 1990Paper

Inhibition by 6-mercaptopurine of the binding of a benzo(a)pyrene diol-epoxide to DNA in Chinese hamster ovary cells

Cancer Research
M C MacLeodA Daylong

Abstract

The finding that 7r,8t-dihydroxy-9,10-t-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene (BPDE-I) is stabilized against hydrolysis by binding to cellular membranes suggested that nucleophilic compounds which would colocalize with BPDE-I in membranes might inhibit the deleterious biological effects of BPDE-I. We have explored the possibility that hydrophobic, sulfhydryl-containing compounds might provide such inhibition using the binding of BPDE-I to DNA in Chinese hamster ovary cells as a biological end point. Of several such compounds tested, 6-mercaptopurine (6-MP) was the most potent, exhibiting 50% inhibition of BPDE-I:DNA binding at about 30 microM and about 95% inhibition at 500 microM. 6-MP, at concentrations of 30 microM or greater, was also effective in preventing the induction of mutations by BPDE-I at the aprt locus. By varying the time of addition of the two compounds, it was shown that the action of 6-MP is intracellular. In vitro, 6-MP readily forms an adduct with BPDE-I, and the same adduct is found as a major metabolite in cells treated with BPDE-I and 6-MP. These findings are consistent with the hypothesis that 6-MP and BPDE-I colocalize in membranes of Chinese hamster ovary cells and form a covalent adduct, thus preventi...Continue Reading

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