Computer-generated graphic models of the N2-substituted deoxyguanosine adducts of 2-acetylaminofluorene and benzo[a]pyrene and the O6-substituted deoxyguanosine adduct of 1-naphthylamine in the DNA double helix

Chemico-biological Interactions
F A Beland

Abstract

Computer models of three deoxyguanosine-carcinogen adducts in double-helical DNA are presented. The carcinogen moiety is rotated and the best fit within the double helix is evaluated. The 2-acetylaminofluorene (AAF) derivative, 3-(deoxyguanosin-N2-yl)-AAF, is found to be situated within the minor groove, has very little freedom of rotation and causes little helical distortion. The (+)-anti-benzo[a]-pyrene (BP)-diol epoxide-N2 adduct, 10beta-(deoxyguanosin-N2-yl)-7beta, 8alpha,9alpha-trihydroxy-7,8,9,10-tetrahydro-BP, has a similar fit with a greater degree of steric interaction, suggesting that this adduct could cause some local destabilization. The 1-naphthylamine (NA) derivative, N1-(deoxyguanosine-O6-yl)-1-NA, resides within the major groove, does not perturb the helix and has considerable freedom of movement.

References

Aug 1, 1976·Proceedings of the National Academy of Sciences of the United States of America·H W KingP Brookes

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Citations

Jul 1, 1980·Chemico-biological Interactions·F A BelandF E Evans
May 12, 1997·Mutation Research·S Shibutani, A P Grollman
Apr 1, 1980·Proceedings of the National Academy of Sciences of the United States of America·H B GamperJ C Bartholomew
May 25, 1983·Nucleic Acids Research·B Hingerty, S Broyde
Jan 1, 1985·Annals of the New York Academy of Sciences·K J MillerP J Kowalczyk
Jun 9, 1983·Nature·D H Phillips
May 22, 1986·Proceedings of the Royal Society of London. Series B, Containing Papers of a Biological Character·P J RidlerP Brookes
Sep 1, 1983·Environmental Health Perspectives·R E StephensJ R Millette
Jun 1, 1979·Journal of Chromatography·F A BelandD A Casciano
Jun 1, 1985·Chemico-biological Interactions·M C MacLeod, K Zachary

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