Solution structure and 5{prime}-intercalation of the polynuclear aromatic BP residue in a (+)-cis-anti-[BP]-N{sup 6}-dA adduct opposite dT in a DNA duplex
Conference
·
OSTI ID:538958
- Memorial Sloan-Kettering Cancer Center, New York, NY (United States)
- New York Univ., New York, NY (United States); and others
The covalent binding of anti-benzo[a]pyrene-7,8-dihydroxy-9,10-epoxide (BPDE) to cellular DNA gives rise predominantly to WAG and N6-dA adducts. While the latter are formed in minor proportions, the mutagenic potential of these BPDE-N6-dA lesions could be important and dependent on the adduct structure. We have applied a combined NMR-molecular mechanics approach to determine the solution conformation of the minor (+)-cis-anti-[BP]dA adduct positioned opposite dT in the duplex d(C1-T2-C3-T4-C5-[BP-A6]-C7-T8-T9-C10- C11).d(G22-A21-G20-A19-G18-T17-G16-A15-A14-G14-G13-G12). The BP ring system is intercalated to the 5{prime}-side of the [BP]dA6 lesion site without disrupting the flanking Watson-Crick dC5.dG18 and [BP]dA6.dT17 base pairs. This is achieved in part by a buckling and propeller-twisting of the Watson-Crick [BP]dA6.dT17 base pair, as observed in the (+)-trans-anti-[BcPh-dA6.dT17] adduct (BcPh=benzo[c]phenanthrenyl) in the same sequence context, and which is stereochemically similar at the linkage site.
- OSTI ID:
- 538958
- Report Number(s):
- CONF-960807--
- Country of Publication:
- United States
- Language:
- English
Similar Records
Solution conformation of the (-)-trans-anti-benzo[c]phenanthrene-dA ([BPh]dA) adduct opposite dT in a DNA duplex: Intercalation of the covalently attached benzo[c]phenanthrenyl ring to the 3{prime}-side of the adduct site and comparison with the (+)-trans-anti-[BPh]dA opposite dT stereoisomer
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Journal Article
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Mon Jan 30 23:00:00 EST 1995
· Biochemistry (Eaton)
·
OSTI ID:469831
Solution conformation of the (-)-cis-anti-benzo[a]-pyrenyl-dG adduct opposite dC in a DNA duplex: Intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove
Journal Article
·
Tue Jul 30 00:00:00 EDT 1996
· Biochemistry (Eaton)
·
OSTI ID:490280
Solution conformation of (+)-trans-anti-benzo[a]pyrene-dG adduct positioned at a DNA replication fork junction
Conference
·
Mon Dec 30 23:00:00 EST 1996
·
OSTI ID:538956