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.
D000081:Acetamides; D000225:Adenine; D002273:Carcinogens; D055598:Chemical Phenomena; D002621:Chemistry; D002850:Chromatography, Gel; D004247:DNA; D003839:Deoxyadenosines; D003853:Deoxyribonucleosides; D004952:Esters; D006147:Guanine; D006151:Guanosine; D006877:Hydroxamic Acids; D010616:Phenanthrenes; D013329:Structure-Activity Relationship; D013431:Sulfates
D000081:Acetamides; D002273:Carcinogens; D003839:Deoxyadenosines; D003853:Deoxyribonucleosides; D004952:Esters; D006877:Hydroxamic Acids; D010616:Phenanthrenes; D013431:Sulfates; D006151:Guanosine; C001366:N-hydroxy-2-acetylaminophenanthrene; D006147:Guanine; D004247:DNA; D000225:Adenine