Synthesis and kinetics of decomposition of 7-(2-cyanoethyl)guanine and O6-(2-cyanoethyl)guanine, markers for reaction of acrylonitrile and 3-(methylnitrosamino)propionitrile with DNA.
Acrylonitrile, a carcinogen in rodents, is used in the large-scale production of acrylic polymers. 3-(Methylnitrosamino)propionitrile, a potent carcinogen in Fisher rats, is an Areca-derived nitrosamine which has been found in the saliva of betel quid chewers. Upon metabolic activation, both of these carcinogens can react with DNA to form 7-(2-cyanoethyl)guanine and O6-(2-cyanoethyl)guanine. The latter has never been described. We have therefore synthesized this derivative by reacting 2-(N-carbethoxy-N-nitrosamino)propionitrile with deoxyguanosine.
Prokopczyk
B
B
American Health Foundation, Naylor Dana Institute for Disease Prevention, Valhalla, NY 10595.
Bertinato
P
P
Hoffmann
D
D
D000181:Acrylonitrile; D055598:Chemical Phenomena; D002621:Chemistry; D004249:DNA Damage; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009570:Nitriles; D009602:Nitrosamines; D013056:Spectrophotometry, Ultraviolet
D009570:Nitriles; D009602:Nitrosamines; C047692:7-(2-cyanoethyl)guanine; C057606:O(6)-(2-cyanoethyl)guanine; D006147:Guanine; C042162:3-(methylnitrosamino)propionitrile; D000181:Acrylonitrile