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
- 30 September 1978
- journal article
- Published by Elsevier BV in Chemico-Biological Interactions
- Vol. 22 (2-3), 329-339
- https://doi.org/10.1016/0009-2797(78)90136-9
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, 10β-(deoxyguanosin-N2-yl)-7β,8α,9α-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.Keywords
This publication has 14 references indexed in Scilit:
- Structures of benzo(a)pyrene–nucleic acid adducts formed in human and bovine bronchial explantsNature, 1977
- Visualization of drug-nucleic acid interactions at atomic resolution: III. Unifying structural concepts in understanding drug-DNA interactions and their broader implications in understanding protein-DNA interactionsJournal of Molecular Biology, 1977
- Conformation of DNA modified with a dihydrodiol epoxide derivative of benzo[a]pyreneBiochemistry, 1977
- Identification of the persistently bound form of the carcinogen N-acetyl-2-aminofluorene to rat liver DNA in vivoChemico-Biological Interactions, 1976
- Benzo[a]pyrene-nucleic acid derivative found in vivo: structure of a benzo[a]pyrenetetrahydrodiol epoxide-guanosine adductJournal of the American Chemical Society, 1976
- Benzo[ a ]pyrene Diol Epoxides as Intermediates in Nucleic Acid Binding in Vitro and in VivoScience, 1976
- Physical studies on deoxyribonucleic acid after covalent binding of a carcinogenBiochemistry, 1972
- Modification of ribonucleic acid by chemical carcinogens IV. Circular dichroism and proton magnetic resonance studies of oligonucleotides modified with N-2-acetylaminofluoreneJournal of Molecular Biology, 1971
- Changes of stability and conformation of DNA following the covalent binding of a carcinogenFEBS Letters, 1971
- The reaction of the carcinogen N-acetoxy-2-acetylaminofluorene with DNA and other polynucleotides and its stereochemical implicationsBiochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, 1971