SYNTHESES OF ADDUCTS OF ACTIVE METABOLITES OF CARCINOGENIC POLYCYCLIC AROMATIC HYDROCARBONS WITH 2'-DEOXYRIBONUCLEOSIDES

摘要

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