PMID: 6411894Jul 1, 1983Paper

Transition-state alkylation geometries of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene enantiomeric isomers with nucleic acid dimers

Journal of Pharmaceutical Sciences
O KikuchiD R Bickers

Abstract

The steric contact spaces associated with the reaction of the enantiomeric isomers of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (I) with the exocyclic amino group of guanine of dinucleoside dimer structures were examined for a fixed transition-state geometry. This reaction is sterically prohibited for the B form DNA conformation. If, however, the nucleic acid structure is deformed, such that the distance between two adjacent base pairs (one containing guanine and cytosine) is maximized, sterically allowed transition-state geometries can be identified. It was not possible to uniquely identify the preferred transition-state complex with respect to nucleic acid structure or isomer of I. However, two types of general transition-state geometries were observed. In one, I was located "outside" the nucleic acid structure; in the other geometry, I was intercalated between adjacent base pairs in the transition state. The intercalation process might serve as a physical catalyst for the alkylation of NH2-guanine by I.

References

Sep 14, 1973·Journal of Theoretical Biology·H J Weintraub, A J Hopfinger
Aug 16, 1974·Science·D M Jerina, J W Daly
Sep 15, 1980·International Journal of Cancer. Journal International Du Cancer·E K Parkinson, R F Newbold

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