DNA adducts formed by the fjord-region dihydrodiol epoxide of benzo[S]picene

Anti benzo[s]picene 9,10-dihydrodiol 11,12-epoxide was reacted with calf th ymus DNA and with its constituent deoxyribonucleotides. The origin of DNA a dducts was established by comparison of their HPLC retention times and UV s pectra with those of the nucleotide-derived adduct-markers. The low binding of the dihydrodiol epoxide to DNA (2%) and to deoxyguanylic and deoxyadeny lic acids precluded an NMR study, and assignment of cis or trans epoxide ri ng opening was made by analogy to other anti dihydrodiol epoxide adducts. T he adduct ratio for dGuo/dAdo in DNA was 24/76 and the ratios of dGuo cis/d Guo trans and dAdo cis/dAdo trans were 40/60 and 6/94, respectively.