The involvement of a ‘bay-region’ and a non-‘bay-region’ diol-epoxide in the metabolic activation of benz(a)anthracene in mouse skin and in hamster embryo cells

Abstract

The principal nucleoside-hydrocarbon adducts present in hydrolysates of DNA that had been isolated either from mouse skin or from hamster embryo cells treated with benz[a]anthracene have been examined by chromatography on Sephadex LH20 and by high pressure liquid chromatography on Spherisorb 5 ODS. The results show that one of the major adducts prepared from the DNA of mouse skin and of hamster embryo cells has chromatographic properties similar to those of an adduct formed when anti-BA-8,9-diol 10,11-oxide (r-8,t-9-dihydroxy-t-10,11-oxy-8,9,10,11-tetrahydrobenz[a]anthracene) reacts with DNA, whilst a second major adduct has chromatographic properties similar to those of an adduct prepared by reacting anti-BA-3,4-diol 1,2-oxide (t-3,r-4-dihydroxy-t-1,2-oxy-1,2,3,4-tetrahydrobenz[a]anthracene) with DNA. On the basis of this and other evidence, it appears that both of these diol-epoxides may contribute to the biological activity of benz[a]anthracene.