Deprotonation and hydride shifts in nitrenium and iminium forms of aminoimidazole-azaarene mutagens

Chemico-Biological Interactions

Volumn 108, Issue 1-2, 1997, Pages 39-66

  Colvin, Michael E ^a   Seidl, Edward T ^b   Nielsen, Ida M B ^c   Le Bui, Loan ^d   Hatch, Frederick T ^e  

^a LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^b SANDIA NATIONAL LABORATORIES   (United States)

^c AARHUS UNIVERSITY   (Denmark)

^d 2600 Mission B   (United States)

^e 27 Pease Rd ^*  (United States)

Author keywords

2 Aminoimidazole azaarenes; Food mutagens; Quantum chemistry

Indexed keywords

5 AMINO 4 IMIDAZOLECARBOXAMIDE;

ARTICLE; CATALYSIS; CELL TRANSFORMATION; DNA BINDING; METHYLATION; MOLECULAR INTERACTION; MUTAGENESIS; MUTAGENICITY; NONHUMAN; PROTON TRANSPORT; QUANTUM CHEMISTRY; SOLVATION;

EID: 84962339352     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(97)00094-X     Document Type: Article

References (40)

1. Hatch F.T., Knize M.G., Felton J.S. Quantitative structure-activity relationships of heterocyclic amine mutagens formed during the cooking of food. Environ. Mol. Mutagen. 17:1991;4-19.
2. Novak M., Kahley M.J., Eiger E., Helmick J.S., Peters H.E. Reactivity and selectivity of nitrenium ions derived from ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid. J. Am. Chem. Soc. 115:1993;9453-9460.
3. Sabbioni G., Wild D. Quantitative structure-activity relationships of mutagenic aromatic and heteroaromatic azides and amines. Carcinogenesis. 13:1992;709-713.
4. Hartman G.D., Schlegel H.B. The relationship of the carcinogenic/mutagenic potential of arylamines to their singlet-triplet nitrenium ion energies. Chem.-Biol. Interact. 36:1981;319-330.
5. Ford G.F., Herman P.S. Relative stabilities of nitrenium ions derived from polycyclic aromatic amines. Relationship to mutagenicity. Chem.-Biol. Interact. 81:1992;1-18.
6. Ford G.F., Griffin G.R. Relative stabilities of nitrenium ions derived from heterocyclic amine food carcinogens. Relationship to mutagenicity. Chem.-Biol. Interact. 81:1992;19-33.
7. Hatch F.T., Colvin M.E., Seidl E.T. Structural and quantum chemical factors affecting mutagenic potency of aminoimidazo-azaarenes. Environ. Mol. Mutagen. 27:1996;314-330.
8. Nagao M., Wakabayashi K., Kasai H., Nishimura S., Sugimura T. Effect of methyl substitution on mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline, isolated from broiled sardine. Carcinogenesis. 2(11):1981;1147-1149.
9. Kaiser G., Harnasch D., King M.-T., Wild D. Chemical structure and mutagenic activity of aminoimidazoquinolines and aminonaphthimidazoles related to 2-amino-3-methylimidazo[4,5-f]quinoline. Chem.-Biol. Interact. 57:1986;97-106.
10. K.C. Chu, Quantitative structure-activity relationships in chemical carcinogenesis: Mechanistic schemes for polycyclic aromatic hydrocarbons and aromatic amines, in: D.B. Walters (Ed.), Safe Handling of Chemical Carcinogens, Mutagens, Teratogens and Highly Toxic Substances, vol. 2, Ann Arbor Science, Ann Arbor, MI, 1980, pp. 493-505.
11. Wallin H., Holme J.A., Becher G., Alexander J. Metabolism of the food carcinogen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in isolated rat liver cells. Carcinogenesis. 10:1989;1277-1283.
12. Vance W.A., Okamoto H.S., Wang Y.Y. Structure-activity relationships of nitro and methyl-nitro derivatives of indoline, indole, indazole and benzimidazole in Salmonella typhimurium. Mutat. Res. 173:1986;169-176.
13. Bolton J.L., McClelland R.A. Kinetics and mechanism of decomposition in aqueous solutions of 2-(hydroxyamino)imidazoles. J. Am. Chem. Soc. 111:1989;8172-8181.
14. T.H. Lowry, K.S. Richardson, Mechanism and Theory in Organic Chemistry, Harper and Row, New York, 1987.
15. Anderson G.B., Yang L.L.-N., Falvey D.E. Photogenerated arylnitrenium ions: photoisomerization of the N-tert-butyl-2-methylanthranilium ion and spin-selective reactivity of the isomeric arylnitrenium ion. J. Am. Chem. Soc. 115:1993;7254-7262.
16. Robbins R.J., Yang L.L.-N., Anderson G.B., Falvey D.E. Photogenerated arylnitrenium ions: reactions of N-tert-butyl (2-acetyl-4-substituted)phenyl nitrenium ions with alcohols and water studied by laser flash photolysis. J. Am. Chem. Soc. 117:1995;6544-6552.
17. Srivastava S., Falvey D.E. Reactions of a triplet arylnitrenium ion: laser flash photolysis and product studies of N-tert-butyl(2-acetyl-4-nitrophenyl)nitrenium ion. J. Am. Chem. Soc. 117:1995;10186-10193.
18. Fishbein J.C., McClelland R.A. Azide trapping of the intermediate in the Bamberger rearrangement. lifetime of a free nitrenium ion in aqueous solution. J. Am. Chem. Soc. 109:1987;2824-2825.
19. Eldin S., Jencks W.P. Lifetimes of iminium ions in aqueous solution. J. Am. Chem. Soc. 117:1995;4851-4857.
20. Colvin M.E., Janssen C.L., Whiteside R.A., Tong C.H. Parallel direct SCF for large-scale calculations. Theor. Chim. Acta. 84:1993;301-314.
21. C.L. Janssen, E.T. Seidl, M.E. Colvin, Object-oriented implementation of parallel ab initio programs, in: T. Mattson (Ed.), ACS Symposium Series 592, Parallel Computing in Computational Chemistry, American Chemical Society, Washington, DC, 1995, pp. 47-61.
22. M.J. Frisch, G.W. Trucks, M. Head-Gordon, P.M.W. Gill, M.W. Wong, J.B. Foresman, B.G. Johnson, H.B. Schlegel, M.A. Robb, E.S. Replogle, R. Gomperts, J.L. Andres, K. Raghavachari, J.S. Binkley, C. Gonzalez, R.L. Martin, D.J. Fox, D.J. Defrees, J. Baker, J.J.P. Stewart, J.A. Pople, Gaussian 92, Gaussian Inc., Pittsburg, PA, 1992.
23. Becke A.D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98:1993;5648-5652.
24. M.J. Frisch, G.W. Trucks, H.B. Schlegel, P.M.W. Gill, B.G. Johnson, M.A. Robb, J.R. Cheeseman, T. Keith, G.A. Petersson, J.A. Montgomery, K. Raghavachari, M.A. Al-Laham, V.G. Zakrzewski, J.V. Ortiz, J.B. Foresman, J. Cioslowski, B.B. Stefanov, A. Nanayakkara, M. Challacombe, C.Y. Peng, P.Y. Ayala, W. Chen, M.W. Wong, J.L. Andres, E.S. Replogle, R. Gomperts, R.L. Martin, D.J. Fox, J.S. Binkley, D.J. Defrees, J. Baker, J.P. Stewart, M. Head-Gordon, C. Gonzalez, J.A. Pople, Gaussian 94, Gaussian Inc., Pittsburg, PA, 1995.
25. Reed A.E., Weinstock R.B., Weinhold F. Natural population analysis. J. Chem. Phys. 83:1985;735-746.
26. Miertus S., Scrocco E., Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 55:1981;117-129.
27. Cramer C.J., Truhlar D.G. AM1-SM2 and PM3-SM3 parameterized SCF solvation models for free energies in aqueous solution. J. Computer-Aided Mol. Des. 6:1992;629-666.
28. Evleth E., Akacem Y., Colvin M.E. Comparison of ab initio and AMSOL semiempirical free energies of solvation of third-row species. Chem. Phys. Lett. 227:1994;412-418.
29. MacSpartan 1.1, Wavefunction, Inc., Irvine, CA, 1996.
30. C.L. Janssen, E.T. Seidl, G.E. Scuseria, T.P. Hamilton, Y. Yamaguchi, R.B. Remington, Y. Xie, G. Vacek, C.D. Sherrill, T.D. Crawford, J.T. Fermann, W.D. Allen, B.R. Brooks, G.B. Fitzgerald, D.J. Fox, J.F. Gaw, N.C. Handy, W.D. Laidig, T.J. Lee, R.M. Pizter, J.E. Rice, P. Saxe, A.C. Scheiner, H.F. Schaefer, PSI, 2.0 ed., PSITECH, Inc., Watkinsville, GA, 1994.
31. R.J. Bartlett, J.F. Stanton, Applications of Post-Hartree-Fock methods: A tutorial, in: K.B. Lipkowitz, D.B. Boyd (Eds.), Reviews in Computational Chemistry, vol. 5, VCH, New York, 1994, pp. 65-170.
32. Hout R.F. Jr., Levi B.A., Hehre W.J. Effect of electron correlation on theoretical vibrational frequencies. J. Comput. Chem. 3:1982;234-250.
33. M.E. Colvin, C.F. Melius, Continuum Solvent Models for Computational Chemistry, Sand Report 93-8239, Sandia National Laboratories, 1993.
34. Zhang Q., Bell R., Truong T.N. Ab initio and density functional theory studies of proton transfer reactions in multiple hydrogen bond systems. J. Phys. Chem. 99:1995;592-599.
35. C.J. Cramer, D.G. Truhlar, Continuum solvation methods: classical and quantum mechanical implementations, in: K.B. Lipkowitz, D.B. Boyd (Eds.), Reviews in Computational Chemistry, vol. 6, VCH, New York, 1995, pp. 1-72.
36. Tomasi J., Persico M. Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent. Chem. Rev. 94:1994;2027-2094.
37. Gibson S.T., Green J.P., Berkowitz J. Photoionization of the amidogen radical. J. Chem. Phys. 83(9):1985;4319-4328.
38. Ford G.P., Herman P.S. Energetics of the singlet and triplet states of alkylnitrenium ions: ab initio molecular orbital calculations. J. Am. Chem. Soc. 111:1989;3987-3996.
39. Smith D.A., Bitar J. Aromatic nitrenium ions based on 1-H-azepine. 1. Ab initio studies at the RHF, UHF, and CASSCF levels. J. Org. Chem. 58:1993;6-8.
40. Hashimoto Y., Shudo K. Chemical modification of DNA with muta-carcinogens. I. 3-Amino-1-methyl-5H-pyrido[4,3-b]indole and 2-amino-6-methyldipyrido[1,2-a;3′,2′-d]imidazole: Metabolic activation and structure of the DNA adducts. Environ. Health Perspect. 62:1985;209-214.