Regiochemistry of nucleophilic attack by the guanine 2-amino group at the ring positions of nitrenium ions derived from carcinogenic polycyclic arylamines and nitroarenes: Molecular orbital calculations and simple models

Chemical Research in Toxicology

Volumn 12, Issue 1, 1999, Pages 53-59

  Ford, George P ^a   Thompson, Jon W ^a  

^a SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; CARCINOGEN; POLYCYCLIC AROMATIC COMPOUND;

ARTICLE; CHEMICAL CARCINOGENESIS; CHEMICAL MUTAGENESIS; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR RECOGNITION; REACTION ANALYSIS;

ALKYLATION; CARCINOGENS; CATIONS; DNA; GUANINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; POLYCYCLIC HYDROCARBONS, AROMATIC; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 0032913756     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9801460     Document Type: Article

References (44)

1. Lewtas, J., and Nishioka, M. C. (1990) Nitroarenes: their detection, mutagenicity and occurrence in the environment. In Nitroarenes, Occurrence, Metabolism, and Biological Impact (Howard, P. C., Hecht, S. S., and Beland, F. A., Eds.) pp 61-72, Plenum, New York.
2. Hecht, S. S., and El-Bayoumy, K. (1990) The possible role of nitroarenes in human cancer. In Nitroarenes, Occurrence, Metabolism, and Biological Impact (Howard, P. C., Hecht, S. S., and Beland, F. A., Eds.) pp 309-316, Plenum, New York.
3. Crabtree, H. C., Hart, D., Thomas, M. C., Witham, B. H., McKenzie, I. G., and Smith, C. P. (1991) Carcinogenic ranking of aromatic amines and nitrocompounds. Mutat. Res. 264, 155-162.
4. Later, D. W., Pelroy, R. A., Stewart, D. L., McFall, T., Both, G. M., Lee, M. L., Tedjamulia, M., and Castle, R. N. (1984) Microbial mutagenicity of isomeric two-, three-, and four-ring amino polycyclic aromatic hydrocarbons. Environ. Mutagen. 6, 497-515.
5. Miller, J. A., and Miller, E. C. (1983) Some historical aspects of N-aryl carcinogens and their metabolic activation. Environ. Health Perspect. 49, 3-12.
6. Kadlubar, F. F., and Beland, F. A. (1985) Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. In Polycylic Hydrocarbons and Carcinogenesis (Harvey, R. G., Ed.) ACS Symposium Series 283, pp 341-370, American Chemical Society, Washington, DC.
7. Fu, P. P., Herreno-Saenz, D., Von Tungeln, L. S., Lay, J. O., Wu, Y.-S., Lai, J.-S., and Evans, F. E. (1994) DNA adducts and carcinogenicity of nitro-polycyclic aromatic hydrocarbons. Environ. Health Perspect. 102 (Suppl. 6), 177-183.
8. Beland, F. A., and Kadlubar, F. F. (1990) Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Handbook of Experimental Pharmacology (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 267-325, Springer-Verlag, Berlin.
9. Kadlubar, F. F. (1994) DNA adducts of carcinogenic aromatic amines. In DNA Adducts. Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publication 125, pp 199-216, IARC, Lyon, France.
10. Delclos, K. B., and Kadlubar, F. F. (1997) Carcinogenic aromatic amines and amides, In Comprehensive Toxicology, Volume 12: Chemical Carcinogens and Anticarcinogens (Bowen, G. T., and Fischer, S. M., Eds.) pp 141-170, Elsevier, Oxford, U.K.
11. Kadlubar, F. F., Anson, J. F., Dooley, K. L., and Beland, F. A. (1981) Formation of urothelial and hepatic DNA adducts from the carcinogen 2-naphthylamine. Carcinogenesis 2, 467-470.
12. Beland, F. A., Beraneck, D. T., Dooley, K. L., Heflich, R. H., and Kadlubar, F. F. (1983) Arylamine-DNA adducts in vitro and in vivo: their role in bacterial mutagenesis and urinary bladder carcinogenesis. Environ. Health Perspect. 49, 125-134.
13. 6 atom of adenine. Carcinogenesis 1, 139-150.
14. Famulok, M., Bosold, F., and Boche, G. (1989) Synthesis of N-acetoxy-2-aminonaphthaline, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its in vitro reactions with (bio)nucleophiles. Tetrahedron Lett. 30, 321-324.
15. Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H. (1994) in DNA Adducts. Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) IARC Scientific Publication 125, IARC, Lyon, France.
16. Dipple, A. (1995) DNA adducts of chemical carcinogens. Carcinogenesis 16, 437-441.
17. Dipple, A., and Moschel, R. C. (1990) Chemistry of DNA alkylation and aralkylation. Prog. Clin. Biol. Res. 340A, 71-80.
18. Ford, G. P. (1997) Semiempirical molecular orbital theory in carcinogenesis research. J. Mol. Struct. (THEOCHEM) 401, 253-266.
19. Ford, G. P., and Scribner, J. D. (1990) Prediction of nucleoside-carcinogen reactivity. Alkylation of adenine, cytosine, guanine, and thymine and their deoxynucleosides by alkane diazonium ions. Chem. Res. Toxicol. 3, 219-230.
20. Singer, B. (1975) The chemical effects of nucleic acid alkylation and their relation to mutagenesis. Prog. Nucleic Acid Res. 15, 219-284.
21. Kennedy, S. A., Novak, M., and Kolb, B. A. (1997) Reactions of ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides. J. Am. Chem. Soc. 119, 7654-7664.
22. Ford, G. P., and Scribner, J. D. (1981) MNDO Molecular orbital study of nitrenium ions derived from carcinogenic aromatic amines and amides. J. Am. Chem. Soc. 103, 4281-4291.
23. Dewar, M. J. S., and Dougherty, R. C. (1975) The PMO Theory of Organic Chemistry, pp 78-140, Plenum, New York.
24. Herreno-Saenz, D., Evans, F. E., Beland, F. A., and Fu, P. P. (1995) Identification of two N2-deoxyguanosinyl DNA adducts upon nitroreduction of the environmental mutagen 1-nitropyrene. Chem. Res. Toxicol. 8, 269-277.
25. 2-deoxyguanosinyl adducts through long-range migration.Chem. Res. Toxicol. 7, 806-814.
26. Herreno-Saenz, D., Evans, F. E., and Fu, P. P. (1993) Formation of the adduct 6-(deoxyguanosin-N2-yl)-3-ammobenzo[a]pyrene from the mutagenic environmental contaminant 3-nitrobenzo[a]-pyrene. Carcinogenesis 14, 1065-1067.
27. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P. (1985) AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
28. Spartan, version 5.0 (1997) Wavefunction, Inc., Suite 370, 18401 Von Karman Ave., Irvine, CA 92612.
29. Baker, J. (1986) An algorithm for the location of transition states. J. Comput. Chem, 7, 385-395.
30. Wissner, A. (1990) HMO version 1.1: A Huckel molecular orbital program for the Macintosh. Tetrahedron Comput. Methodol. 3, 63-71 (version 2.0.3 at http://mwn.net/infomac2/science/hmo-plus-203.html).
31. Streitwieser, A. J., Jr. (1961) Molecular Orbital Theory for Organic Chemists, John Wiley & Sons, New York.
32. Srivastava, S., Toscano, J. P., Moran, R. J., and Falvey, D. E. (1997) Experimental confirmation of the iminocyclohexadienyl cation-like structure of arylnitrenium ions: Time-resolved IR studies of diphenylnitrenium ion. J. Am. Chem. Soc. 119, 11552-11553.
33. Ford, G. P., Herman, P. S., and Thompson, J. W. (1999) Syn and anti aryl nitrenium ions. J. Comput. Chem. (in press).
34. Cramer, C. J., Dulles, F. J., and Falvey, D. E. (1994) Ab initio characterization of phenylnitrenium and phenylcarbene: Remarkably different properties for isoelectronic species. J. Am. Chem. Soc. 116, 9787-9788.
35. Haberfield, P., and DeRosa, M. (1985) σ- and π-nitrenium ions. Chem. Commun., 1716-1717.
36. Ford, G. P., and Herman, P. S. (1991) Conformational preferences and energetics of N-O heterolyses in aryl nitrenium ion precursors: ab initio and semiempirical molecular orbital calculations. J. Chem. Soc., Perkin Trans. 2, 607-616.
37. 6-arylation of DNA by the carcinogen N-hydroxy-1-naphthylamine. Cancer Res. 38, 3628-3638.
38. Yu, S., Herreno-Saenz, D., Miller, D. W., Kadlubar, F. F., and Fu, P. P. (1992) Mutagenicity of nitro-polycyclic aromatic hydrocarbons with the nitro substituent situated at the longest molecular axis. Mutat. Res. 283, 45-52.
39. Garner, R. C., Stanton, C. A., Martin, C. N., Harris, C. C., and Grafstrom, R. C. (1985) Rat and human explant metabolism, binding studies, and DNA adduct analysis of benzo[a]pyrene and its 6-nitroderivative. Cancer Res. 45, 6225-6231.
40. Kaneko, M., and Nagata, C. (1983) Covalent binding of 6-nitrobenzo[a]pyrene to DNA in vitro. Gann 74, 5-7.
41. Brown, R. D. (1951) Molecular orbitals and organic reactions. Q. Rev., Chem. Soc., 63-99.
42. Gupta, R. C., Early, L., Fullerton, N. F., and Beland, F. (1989) Formation and removal of DNA adducts in target and nontarget tissues of rats administered multiple doses of 2-acetylami-nophenanthrene. Carcinogenesis 10, 2025-2033.
43. 2- and C8-modified deoxyguanosine as major products of the in vitro reaction of N-hydroxy-6-aminochrysene with DNA and the formation of these adducts in isolated rat hepatocytes treated with 6-nitrochrysene and 6-aminochrysene. Carcinogenesis 8, 1703-1709.
44. Ford, G. P., and Herman, P. S. (1991) Comparison of the relative stabilities of polycyclic aryl nitrenium ions and arylmethyl cations: ab initio and semiempirical molecular orbital calculations. J. Mol. Struct. (THEOCHEM) 236, 269-282.