Prostaglandin H synthase-mediated reaction of carcinogenic arylamines with tRNA and homopolyribonucleotides.
Prostaglandin H synthase mediates the reaction of an extensive series of carcinogenic arylamines with tRNA. Structure-activity relationships suggest that benzidine is especially reactive due to extended conjugation between the 4,4'-diamino groups. In trapping experiments with homopolyribonucleotides, benzidine reacts with polyguanylic acid but 4-aminobiphenyl reacts with polycytidylic acid. The nitrenium ion of 4-aminobiphenyl (formed by N,O-acyltransferase activation of N-hydroxy-4-acetylaminobiphenyl) reacts primarily with polyguanylic acid and to a lesser extent with polyadenylic acid. The results suggest that arylamine activation by prostaglandin H synthase does not involve nitrenium ion formation.
D000818:Animals; D001560:Benzidines / Q000378:metabolism; D002273:Carcinogens / Q000378:metabolism*; D008297:Male; D011131:Polyribonucleotides / Q000378:metabolism*; D011451:Prostaglandin-Endoperoxide Synthases / Q000378:metabolism*; D012343:RNA, Transfer / Q000378:metabolism*; D051381:Rats; D012756:Sheep; D013329:Structure-Activity Relationship
D001560:Benzidines; D002273:Carcinogens; D011131:Polyribonucleotides; C029876:benzidine; D012343:RNA, Transfer; D011451:Prostaglandin-Endoperoxide Synthases