Structures of covalent adducts derived from the reactions of the 9,10-epoxides of 7,8,9,10-tetrahydrobenzo[a]pyrene and 9, 10, 11, 12-tetrahydrobenzo[e]pyrene with DNA
- 1 January 1982
- journal article
- research article
- Published by Oxford University Press (OUP) in Carcinogenesis: Integrative Cancer Research
- Vol. 3 (3) , 255-260
- https://doi.org/10.1093/carcin/3.3.255
Abstract
The reaction of a racemic mixture of 7β, 8α-dihydroxy-9α, 10α-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (B[a]PDE) and its enantiomer with DNA is highly stereoselective. About 90% of the adducts are derived from the former enantiomer reacting with the amino group of guanine residues. To investigate this stereoselectively we compared the reactions of 9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene and 9,10-epoxy-9,10,11,12-tetrahydrobenzo[e]pyrene with DNA. Most of the stereoselectivity seen with B[a]PDE is lost. Both epoxides give mainly adducts on the N 2 group of guanine by both cis and trans additions to the epoxide. Other adducts, tentatively identified as deoxyadenosine derivatives, were also detected.Keywords
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