Microsome-mediated reactions of phenols of polycyclic hydrocarbons with DNA

Phenolic metabolites of 7 polycyclic hydrocarbons were incubated with rat-liver microsomal fractions in the presence of DNA. Hydrocarbon-nucleoside adducts with chromatographic properties similar to those of diol-epoxide-deoxyribonucleoside adducts, were detected in hydrolysates of DNA that had been incubated with phenols of benzo[a]pyrene, benz[a]anthracene and chrysene. Adducts were not detected when phenols of phenanthrene, pyrene, dibenz[a,c]anthracene or dibenz[a,h]anthracene were further metabolised. The possible contribution of phenolic metabolites to the carcinogenic activity and DNA binding of polycyclic hydrocarbons is discussed.