Effect of ring size on conformations of aromatic amine-DNA adducts: the aniline-C8 guanine adduct resides in the B-DNA major groove

Chemical Research in Toxicology
R ShapiroS Broyde

Abstract

While the one-ring amine aniline (AN) has only slight genetic activity, the polycyclic aromatic amines 2-aminofluorene (AF) and 1-aminopyrene (AP) are significant mutagens and carcinogens. Moreover, the bulkier AP is more mutagenic per adduct than AF in the tetracycline-resistance gene of plasmid pBR322 [Melchior et al. (1994) Carcinogenesis 15, 889]. To elucidate possible conformational origins of the differing mutagenic effects of these three adducts, which may stem from their differing ring sizes, we have examined their conformations in two mutation-susceptible sequences from the above gene: TTGAG*GCCG (sequence I) and GAATG*GTGC (sequence II), where G* = C8-modified guanine. No experimental high-resolution NMR data are yet available for the aniline adduct in a DNA duplex. Minimized potential energy calculations were carried out, using the molecular mechanics program DUPLEX to explore the conformation space of these adducts. In the case of AN, a relatively unperturbed B-DNA helix with the amine in the major groove was strongly favored in both sequences. In the case of AF- and AP-modified DNA, however, several differing conformations were competitive in energy. They included major groove structures, as well as conformations w...Continue Reading

References

May 12, 1997·Mutation Research·S Shibutani, A P Grollman

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Citations

Nov 18, 2005·Journal of Environmental Science and Health. Part C, Environmental Carcinogenesis & Ecotoxicology Reviews·Bongsup P Cho
Jan 15, 2011·Journal of Nucleic Acids·Bo Hang
Nov 20, 2002·Biomarkers : Biochemical Indicators of Exposure, Response, and Susceptibility to Chemicals·Gabriele Sabbioni, Christopher R Jones
Dec 8, 2015·Chemical Research in Toxicology·Dustin A PoliticaMichael P Stone
Nov 2, 2016·Chemical Research in Toxicology·Richard A Manderville, Stacey D Wetmore
Feb 9, 2006·Chemical Reviews·Ludovic C J Gillet, Orlando D Schärer
Aug 30, 2013·Chemical Research in Toxicology·Michael S KuskaStacey D Wetmore
Jun 19, 2014·Chemical Research in Toxicology·Katie A Wilson, Stacey D Wetmore
Sep 6, 2012·Chemical Research in Toxicology·Igor ShamovskyPeter Sjö
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Aug 24, 2017·Journal of Agricultural and Food Chemistry·Richard A Manderville, Stacey D Wetmore
Jun 21, 2018·Journal of Chemical Information and Modeling·Ryan W KungStacey D Wetmore

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