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© 1982 Oxford University Press

research-article

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

T. Kinoshita 1, H.M. Lee 2, R.G. Harvey 2 and A.M. Jeffrey 1

1Division of Environmental Sciences and Cancer Center/Institute of Cancer Research, Columbia University College of Physicians and Surgeons New York, NY 10032
2The Ben May Laboratory for Cancer Research, The University of Chicago 950 East 59 Street, Chicago, IL 60637, USA.

The reaction of a racemic mixture of 7ß, 8{alpha}-dihydroxy-9{alpha}, 10{alpha}-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 N2 group of guanine by both cis and trans additions to the epoxide. Other adducts, tentatively identified as deoxyadenosine derivatives, were also detected.


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