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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Nesnow, S., Argus, M., Bergman, H., Chu, K., Frith, C., Helmes, T., McGaughy, R., Ray, V., Slaga, T.J., Tennant, R. and 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. 185(1988), 1–195.
Kriek, E., Miller, J.A., Juhl, U. and 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 6(1967), 177–182.
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. 32(1972), 2042–2048.
Westra, J.G., Kriek, E. and Hittenhausen, H.: Identification of the Persistently Bound Form of the Carcinogen N-acetyl-2-aminofluorene to Rat Liver DNA in vivo, Chem. Biol. Interactions 15(1976), 149–164.
Yamasaki, H., Leffler, S. and Weinstein, I.B.: Effect of N-2-acetylaminofluorene Modification on the Structure and Template Activity of DNA and Reconstituted Chromatin, Cancer Res. 37(1977), 684–691.
Yamasaki, H., Pulkrabek, P., Grunberger, D. and Weinstein, I.B.: Differential Excision from DNA of the C8 and N2 Guanosine Adducts of N-acetyl-2-aminofluorene by Single Strand-Specific Endonucleases, Cancer Res. 37(1977), 3756–3760.
Santella, R.M., Grunberger, D., Weinstein, I.B. and Rich, A.: Induction of the Z Conformation in poly(dG-dC).poly(dG-dC) by Binding of N-2-acetylaminofluorene to Guanine Residues, Proc. Natl. Acad. Sci. USA 78(1981), 1451–1455.
Burnouf, D., Koehl, P. and Fuchs, R.P.P.: Single Adduct Mutagenesis: Strong Effect of the Position of a Single Acetylaminofluorene Adduct within aMutation Hot Spot, Proc. Natl. Acad. Sci. USA 86(1989), 4147–4151.
Gupta, P.K., Pandrangi, R.G., Lee, M.S. and King, C.M.: Induction of Mutations by N-acetoxy-N-acetyl-2-aminofluorene modified M13 Viral DNA, Carcinogenesis 12(1991), 819–824.
Shibutani, S., Suzuki, N. and Grollman, A.P.: Mutagenic Specificity of (acetylamino) Fluorenederived DNA Adducts in Mammalian Cells, Biochemistry 37(1998), 12034–12041.
Irving, C.C. and Veazey, R.A.: Persistent Binding of 2-acetylaminofluorene to Rat Liver DNA in vivoand Consideration of the Mechanism of Binding of N-hydroxy-2-acetylaminofluorene to Rat Liver Nucleic Acids, Cancer Res. 29(1969), 1799–1804.
Kriek, E.: Carcinogenesis by Aromatic Amines, Biochim. Biophys. Acta 355(1974), 177–203.
Kriek, E. and Westra, J.G.: Structural Identification of the Pyrimidine Derivatives formed from N-(deoxyguanosin-8-yl)-2-aminofluorene in Aqueous Solution at Alkaline pH, Carcinogenesis 1(1980), 459–468.
Fuchs, R.P.P. and Daune, M.P.: Physical Studies on Deoxyribonucleic Acid after Covalent Binding of a Carcinogen, Biochemistry 11(1972), 2659–2666.
Fuchs, R.P.P. and Daune, M.P.: Dynamic Structure of DNA modified with the Carcinogen Nacetoxy-N-2-acetylaminofluorene, Biochemistry 13(1974), 4435–4440.
Fuchs, R.P.P.: In VitroRecognition of Carcinogen-Induced Local Denaturation Sites Native DNA by S1 Endonuclease from Aspergillus oryzae, Nature 257(1975), 151–152.
Fuchs, R.P.P., Lefevre, J.F., Pouyet, J. and Daune, M.P.: Comparative Orientation of the Fluorene Residue in Native DNA modified by N-acetoxy-N-2-acetylaminofluorene and two 7-halogeno Derivatives, Biochemistry 15(1976), 3347–3351.
Hingerty, B. and Broyde, S.: Conformation of the Deoxydinucleoside Monophosphate dCpdG modified at Carbon 8 of Guanine with 2-(acetylamino) Fluorene, Biochemistry 21(1982), 3243–3252.
Broyde, S. and Hingerty, B.: Conformation of 2-aminofluorene-modified DNA, Biopolymers 22(1983), 2423–2441.
Hingerty, B.E. and Broyde, S.: Energy minimized Structures of Carcinogen-DNA Adducts: 2-acetylaminofluorene and 2-aminofluorene, J. Biomol. Struct. Dyn. 4(1986), 365–372.
Shapiro, R., Hingerty, B.E. and Broyde, S.: Minor-groove Binding Models for Acetylamino-fluorene modified DNA, J. Biomol. Struct. Dyn. 7(1989), 493–513.
Fritsch, V. and Westhof, E.: Minimization and Molecular Dynamics Studies of Guanosine and Z-DNA modified by N-2-acetylaminofluorene, J. Comp. Chem. 12(1991), 147–166.
Besson, M. and Mihalek, C.L.: Total Energy of Deoxyguanosine bonded to N-2-acetylaminofluorene by the Semi-Empirical Modified-Neglect of Differential Diatomic Overlap Method, Mutat. Res. 473(2001), 211–217.
Grad, R., Shapiro, R., Hingerty, B.E. and Broyde, S.: A Molecular Mechanics and Dynamics Study of the Minor Adduct between DNA and the Carcinogen 2-(acetylamino) Fluorene (dGN2-AAF), Chem. Res. Toxicol. 10(1997), 1123–1132.
Mitchell, A.D. and Cross, L.C. (eds.): Tables of Interatomic Distances and Configuration in Molecules and Ions,Special Pub. No. 11, Chemical Society, London, 1958, p. M237.
Neidle, S., Kuroda, R., Broyde, S., Hingerty, B.E., Levine, R.A., Miller, D.W. and Evans, F.E.: Studies on the Conformation and Dynamics of the C8-substituted Guanine Adduct of the Carcinogen Acetylaminofluorene; Model for a Possible Z-DNA modified Structure, Nucleic Acids Res. 12(1984), 8219–8233.
Dewar, M.J.S., Zoebisch, E.G., Healy, E.F. and Stewart, J.P.P.: AM1: A New General Purpose Quantum Mechanical Molecular Model, J. Am. Chem. Soc. 107(1985), 3902–3909.
Stewart, J.J.P.: MOPAC: A Semiempirical Molecular Orbital Program, J. Computer-Aided Molecular Design 4(1990), 1–105.
Dewar, M.J.S. and Thiel, W.: Ground States of Molecules. 38. The MNDO Method. Applications and Parameters, J. Am. Chem. Soc. 99(1977), 4899–4907.
Fletcher, R. and Powell, M.J.D.: A Rapidly Convergent Descent Method for Minimization, Comp. J. 6(1963), 163–168.
Davidon, W.C.: Variance Algorithm for Minimization, Comp. J. 10(1968), 406–410.
Press, W.H., Flannery, B.P., Teukolsky, S.A. and Vetterling, W.T.: Numerical Recipes, Cambridge University Press, Cambridge, 1986.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Besson, M., Batchelor, E. AM1 Study of N-2-Acetylaminofluorene bonded to Deoxyguanosine at the Minor Adduct Site. Journal of Biological Physics 30, 161–169 (2004). https://doi.org/10.1023/B:JOBP.0000035860.68226.22
Issue Date:
DOI: https://doi.org/10.1023/B:JOBP.0000035860.68226.22