Biological formation of the 1,3-butadiene DNA adducts 7-N-(2-hydroxy-3-buten-1-yl)guanine, 7-N-(1-hydroxy-3-buten-2-yl)guanine and 7-N-(2,3,4-trihydroxy-butyl)guanine

Male mice (B6C3F(1)) and male Wistar rats were exposed to [1,4-C-14]butadiene in a closed all-glass desiccator jar system, and liver DNA was obtained. After acid hydrolysis and HPLC chromatography radioactive 7-N-(1-hydroxy-3-buten-2-yl)guanine and 7-N-(2,3,4-trihydroxybutyl)guanine were identified as radioactive DNA adducts. The same DNA adducts were identified upon incubation of calf thymus DNA, rat liver microsomes, [1,4-C-14]butadiene and an NADPH-regenerating system. In this system, a third radioactive adduct was found which was identified as 7-N-(2-hydroxy-3-buten-yl)guanine.