Syntheses of adducts of active metabolites of carcinogenic polycyclic aromatic hydrocarbons with 2′-deoxyribonucleosides

Syntheses are reported for: (1) adducts of the quitione metabolites of benzo[a]pyrene (BPQ) and benz[a]anthracene (BAQ) with 2'-deoxyadenosine and 2'-deoxyguanosine; (2) N-15-labelled analogs of these adducts (four or five nitrogen atoms N-15-labelled); (3) depurinated adducts of BPQ and BAQ with adenine or guanine covalently linked to the N7 or N9 positions of the purine bases; (4) C-13-labetled derivatives of benzo[a]pyrene, BPQ, benzo[a]pyrene trans-7,8-dihydrodiol, and the benzo[a]pyrene anti-diol epoxide (with C-13-atoins at the 5- and 11-positions); and (5) depurinated adducts formed by reactions of the benzo[a]pyrene radical-cation at the C-8-, N-7-, and N-9-positions of adenine and guanine.