doi: 10.1023/B:JOBP.0000035860.68226.22.
AM1 Study of N-2-Acetylaminofluorene bonded to Deoxyguanosine at the Minor Adduct Site
Affiliations
- PMID: 23345866
- PMCID: PMC3456492
- DOI: 10.1023/B:JOBP.0000035860.68226.22
Item in Clipboard
AM1 Study of N-2-Acetylaminofluorene bonded to Deoxyguanosine at the Minor Adduct Site
J Biol Phys.
2004 Jun.
Abstract
We have computed the total energy as a function of six important torsion angles of the carcinogen N-2-acetylaminofluorene (AAF) bonded to thenitrogen N2 of deoxyguanosine using the semiempirical quantum mechanical method AM1. One global minimum and one local minimum are found separated by a modest barrier. We have computed the normal-mode frequencies of the relevant torsional motions and have determined the rate of conversion betweenthe two minima.
Keywords: N-2-ac; deoxyguanosine.
Similar articles
-
Total energy of deoxyguanosine bonded to N-2-acetylaminofluorene by the semi-empirical modified-neglect of differential diatomic overlap method.Mutat Res. 2001 Feb 20;473(2):211-7. doi: 10.1016/s0027-5107(00)00151-2. Mutat Res. 2001. PMID: 11166038
-
AAF linked to the guanine amino group: a B-Z junction.Nucleic Acids Res. 1983 May 25;11(10):3241-54. doi: 10.1093/nar/11.10.3241. Nucleic Acids Res. 1983. PMID: 6856457 Free PMC article.
-
Mutagenic properties of 3-(deoxyguanosin-N2-yl)-2-acetylaminofluorene, a persistent acetylaminofluorene-derived DNA adduct in mammalian cells.Biochemistry. 2004 Nov 30;43(47):15005-13. doi: 10.1021/bi048279+. Biochemistry. 2004. PMID: 15554708
-
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.Chem Biol Interact. 1978 Sep;22(2-3):329-39. doi: 10.1016/0009-2797(78)90136-9. Chem Biol Interact. 1978. PMID: 699181
-
Interaction of nucleophiles with the enzymatically-activated carcinogen, N-hydroxy-2-acetylaminofluorene, and with the model ester, N-acetoxy-2-acetylaminofluorene.Carcinogenesis. 1985 Feb;6(2):271-7. doi: 10.1093/carcin/6.2.271. Carcinogenesis. 1985. PMID: 3971491
References
-
- Nesnow S., Argus M., Bergman H., Chu K., Frith C., Helmes T., McGaughy R., Ray V., Slaga T.J., Tennant R., Weisburger E. Chemical Carcinogens. A Review and Analysis of the Literature of Selected Chemicals and the Establishment of the Gene-Tox Carcinogen Data Base. The U.S. Environmental Protection Agency Gene-Tox Program. Mutat. Res. 1988;185:1–195. - PubMed
-
- Kriek E., Miller J.A., Juhl U., Miller E.C. 8-(N-2-fluorenylacetamido) Guanosine, an Arylamidation Reaction Product of Guanosine and the Carcinogen N-acetoxy-N-2-fluorenylacetamide in Neutral Solution. Biochemistry. 1967;6:177–182. - PubMed
-
- Kriek E. Persistent Binding of a New Reaction Product of the Carcinogen N-hydroxy-N-2-acetylaminofluorene with Guanine in Rat Liver DNA in vivo. Cancer Res. 1972;32:2042–2048. - PubMed
-
- Westra J.G., Kriek E., Hittenhausen H. Identification of the Persistently Bound Form of the Carcinogen N-acetyl-2-aminofluorene to Rat Liver DNA in vivo. Chem. Biol. Interactions. 1976;15:149–164. - PubMed
-
- Yamasaki H., Leffler S., Weinstein I.B. Effect of N-2-acetylaminofluorene Modification on the Structure and Template Activity of DNA and Reconstituted Chromatin. Cancer Res. 1977;37:684–691. - PubMed
LinkOut - more resources
Full Text Sources