Polycyclic Aromatic Compounds, 25: 371–391, 2005 Copyright c  2005 Taylor & Francis Inc. ISSN: 1040-6638 print / 1563-5333 online DOI: 10.1080/10406630500447019 SYNTHESES OF ADDUCTS OF ACTIVE METABOLITES OF CARCINOGENIC POLYCYCLIC AROMATIC HYDROCARBONS WITH 2 ′ -DEOXYRIBONUCLEOSIDES Ronald G. Harvey Qing Dai Chongzhao Ran Keunpoong Lim Ben May Institute for Cancer Research, The University of Chicago, Chicago, IL, USA Ian Blair Trevor M. Penning Department of Pharmacology, University of Pennsylvania, Philadelphia, PA, USA Syntheses are reported for: (1) adducts of the quinone metabolites of benzo[a]pyrene (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 benzo[a]pyrene anti-diol epoxide (with 13 C-atoms 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. Keywords PAH-2 ′ -deoxyribonucleoside adducts, benzo[a]pyrene-7,8- dione (BPQ), 15 N -labelled BPQ-guanosine adduct, 13 C -benzo[a]pyrene, 13 C -BPQ, 13 C -BP 7,8-diol, radical-cation adducts of benzo[a]pyrene Received 25 September 2005; accepted 31 October 2005. These investigations were supported by NIH program project grant (P01-CA-092537). Address correspondence to Ronald G. Harvey, The Ben May Institute for Cancer Research, University of Chicago, 5841 South Maryland Avenue, MC 6027, Chicago, IL 60637, USA. E-mail: rharvey@huggins.bsd.uchicago.edu 371