Synthesis and kinetics of decomposition of 7-(2-cyanoethyl)guanine and O-(2-cyanoethy)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 Fischer 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 -(2-cyanoethyl)guanine. The latter has never been described. We have therefore synthesized this derivative by reacting 2-(-carbethoxy--nitrosamino)propionitrile with deoxyguanosine. [ABSTRACT FROM PUBLISHER]