Roles of electrophilic sulfuric acid ester metabolites in mutagenesis and carcinogenesis by some polynuclear aromatic hydrocarbons.

Hydroxylation of meso-methyl groups with subsequent formation of reactive benzylic esters bearing a good leaving group (e.g. sulfate) was proposed as a possible biochemical mechanism of activation and tumorigenicity of methyl-substituted polycyclic aromatic hydrocarbons (PAHs). In support of this postulation, recent studies have demonstrated the formation by rodent hepatic sulfotransferase activity of electrophilic, mutagenic, and carcinogenic sulfuric acid esters of several hydroxymethyl aromatic hydrocarbons including hydroxymethyl derivatives of benz[a]anthracene, 6-hydroxymethylbenzo[a]pyrene, 5-hydroxymethylchrysene, 9-hydroxymethyl-10-methylanthracene, and 1-hydroxymethylpyrene. Besides these hydroxymethyl PAHs containing a primary benzylic alcoholic group, some aromatic hydrocarbons with secondary benzylic hydroxyl functional group(s) are also metabolically activated through sulfuric acid esterification.