Adducts between the carcinogen 2-acetamidophenanthrene and adenine and guanine of DNA.

The sulfate and acetate esters of the carcinogen N-hydroxy-2-acetamidophenanthrene attack calf thymus DNA in vitro to yield adducts of 2-acetamidophenanthrene with guanine and adenine in the DNA. These adducts were found to be 8-(N-2-phenanthrylacetamido)deoxyguanosine and N6-1-(2-acetamidophenanthryl)deoxyadenosine, respectively. These reactions, and the already known reactions of esters of N-hydroxy-2-acetamidofluorene, together with Hückel molecular orbital calculations, suggest that the relative tendencies of a series of N-aryl-N-acetylnitrenium ions to react with adenine and guanine may be predicted.