Nitrosative guanine deamination: Ab initio study of deglycation of N-protonated 5-cyanoimino-4-oxomethylene-4,5-dihydroimidazoles

Chemical Research in Toxicology

Volumn 17, Issue 9, 2004, Pages 1157-1169

  Rayat, Sundeep ^a   Wu, Zhengyu ^a   Glaser, Rainer ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 CYANOIMINO 4 OXOMETHYLENE 4,5 DIHYDROIMIDAZOLE; 5 CYANOIMINOIMIDAZOLE 4 CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; GUANINE; IMIDAZOLE DERIVATIVE; N [4 (OXOMETHYLENE)IMIDAZOL 5 YL]CARBODIIMIDE; N [4 (OXOMETHYLENE)IMIDAZOL 5 YL]CYANAMIDE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CROSS LINKING; DEALKYLATION; DEAMINATION; NITROSATION; PROTON TRANSPORT; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

DEALKYLATION; DEAMINATION; GUANINE; HYDROLYSIS; IMIDAZOLES; IMINES; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROSATION; THERMODYNAMICS;

EID: 4644224960     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0499416     Document Type: Article

References (62)

1. Strecker, A. (1861) Untersuchungen über die chemischen Beziehungen zwischen Guanin, Xanthin, Theobromin, Caffein und Kreatinin. Annals 118, 151-177.
2. Kossel, A. (1985) Ueber das Adenin. Berichte 18, 1929-1930.
3. Kossel, A., and Neumann, A. (1894) Darstellung und Spaltungsproducte der Nucleinsaeure. Z. Physiol. Chem. 27, 2215-2222.
4. Geiduschek, E. P. (1961) Reversible denaturation of deoxyribonucleic acid (DNA). Proc. Natl. Acad. Sci. U.S.A. 47, 950-955.
5. Geiduschek, E. P. (1962) On the factors controlling the reversibility of DNA denaturation. J. Mol. Biol. 4, 467-487.
6. Caulfield, J. L., Wishnok, J. S., and Tannenbaum, S. R. (2003) Nitric oxide-induced interstrand cross-links in DNA. Chem. Res. Toxicol. 16, 571-574.
7. O'Sullivan, D. A. (1970) Air pollution. Chem. Eng. News 48, 37-41, 45, 46, 50, 54, 55, 57, 58.
8. Feldman, P. L., Griffith, O. W., and Stuehr, D. J. (1993) The surprising life of nitric oxide. Chem. Eng. News 71, 26-38.
9. Wolff, E. A., and Wasserman, A. E. (1972) Nitrates, nitrites, and nitrosamines. Science 177, 15-19.
10. Marnett, L. J. (1996) Nitric ocide: chemical events in toxicity. Chem. Res. Toxicol. 9, 807-808.
11. Wink, D. A., Kasprzak, K. S., Maragos, C. M., Elespuru, R. K., Misra, M., Dunams, T. M., Cebula, T. A., Koch, W. H., Andrews, A. W., Allen, J. S., and Keefer, L. K. (1991) DNA deaminating ability and genotoxicity on nitric oxide and its progenitors. Science 254, 1001-1003.
12. Kosaka, H., Wisnok, J. S., Miwa, M., Leaf, C. D., and Tannenbaum, S. R. (1989) Nitrosation by stimulated macrophages. Inhibitors, enhancers and substrates. Carcinogensis 10, 563-566.
13. Davis, K. L., Martin, E., Turko, I. V., and Murad, F. (2001) Novel effects of nitric oxide. Annu. Rev. Pharmacol. Toxicol. 41, 203-236.
14. Jackson, A. L., and Loeb, L. A. (2001) The contribution of endogenous sources of DNA damage to the multiple mutations in cancer. Mutat. Res. 477, 7-21.
15. Kane, J. M., 3rd, Sjears, L. L., 2nd, Hierholer, C., Ambs, S., Billiar, T. R., and Posner, M. C. (1997) Chronic hepatitis C virus infection in humans: Induction of hepatic nitric oxide synthase and proposed mechanisms for carcinogenesis. J. Surg. Res. 69, 321-324.
16. Grisham, M. B., Jourd'heuil, D., and Wink, D. A. (1999) Physiological chemistry of superoxide and nitric oxide interactions: Implications in DNA damage and repair. NATO ASI Ser., Ser. A: Life Sci. 302, 125-134.
17. Ohshima, H., Yermilov, V., Yoshie, Y., and Rubio, J. (1999) DNA damage induced by reactive nitrogen species. NATO ASI Ser., Ser. A: Life Sci. 302, 329-339.
18. Nair, J., Ohshima, H., Nair, U. J., and Bartsch, H. (1996) Endogenous formation of nitrosamines and oxidative DNA-damaging agents in tobacco users. Crit. Rev. Toxicol. 26, 149-161.
19. Ohshima, H., and Bartsch, H. (1994) Chronic infections and inflammatory processes as cancer risk factors: possible role of nitric oxide in carcinogenesis. Mutat. Res. 305, 253-264.
20. Suzuki, T., Yamaoka, R., Nishi, M., Ide, H., and Makino, K. (1996) Isolation and characterization of a novel product, 2′-deoxyoxanosine, from 2′-deoxyguanosine, oligodeoxyribonucleotide, and calf thymus DNA treated by nitrous acid and nitric oxide. J. Am. Chem. Soc. 118, 2515-2516.
21. Dong, M., Wang, C., Deen, W. M., and Dedon, P. C. (2003) Absence of 2′-deoxyoxanosine and presence of a basic sites in DNA exposed to nitric oxide at controlled physiological concentrations. Chem. Res. Toxicol. 16, 1044-1055.
22. Glaser, R., and Son, M.-S. (1996) Pyrimidine ring opening in the unimolecular dediazoniation of guanine diazonium ion. An ab initio theoretical study of the mechanism of nitrosative guanosine deamination. J. Am. Chem. Soc. 118, 10942-10943.
23. Glaser, R., Rayat, S., Lewis, M., Son, M.-S., and Meyer, S. (1999) Theoretical studies of DNA base deamination. 2. Ab initio study of DNA base diazonium ions and of their linear, unimolecular dediazoniation paths. J. Am. Chem. Soc. 121, 6108-6119.
24. Glaser, R., and Lewis, M. (1999) Single- and double-proton-transfer in the aggregate between cytosine and guaninediazonium ion. Org. Lett. 1, 273-276.
25. Rayat, S. (2003) Ph.D. Dissertation, University of Missouri-Columbia.
26. Qian, M., and Glaser, R. (2004) 5-Cyanoamino-4-imidazolecarboxamide and nitrosative guanine deamination: Experimental evidence for pyrimidine ring-opening during deamination. J. Am. Chem. Soc. 126, 2274-2275.
27. Rayat, S., Majumdar, P., Tipton, P., and Glaser, R. (2004) 5-Cyanoimino-4-oxomethylene-4,5-dihydroimidazole and 5-cyanoamino-4- imidazolecarboxylic acid intermediates in nitrosative guanosine deamination. Evidence from (18)O-labeling experiments. J. Am. Chem. Soc. Accepted for publication.
28. Bothe, E., Dessouki, A. M., and Schulte-Frohlinde, D. (1980) Rate and mechanism of the ketene hydrolysis in aqueous solution. J. Phys. Chem. 84, 3270-3272.
29. Duan, X., and Page, M. (1995) Theoretical investigation of competing mechanisms in the thermal unimolecular decomposition of acetic acid and the hydration reaction of ketene. J. Am. Chem. Soc. 117, 5114-5119.
30. Kabir, S. H., Saikaly, H. R., and Tidwell, T. (1979) Acid-catalyzed hydration of di-tert-butylketene. J. Am. Chem. Soc. 101, 1059-1060.
31. Song, B. D., and Jencks, W. P. (1989) Mechanism of solvolysis of substituted benzoyl halides. J. Am. Chem. Soc. 111, 8470-8479.
32. Marcus, R. A., and Eyring, H. (1964) Chemical and electrochemical electron-transfer theory. Annu. Rev. Phys. Chem. 15, 155-196.
33. Marcus, R. A. (1964) Generalization of the activated complex theory of reaction rates. II. Classical mechanical treatment. J. Chem. Phys. 41, 2624-2633.
34. N2 reactions and the periodic table. J. Am. Chem. Soc. 121, 7724-7725.
35. N2 Mechanism, John Wiley & Sons, New York.
36. (b) See section 2.4.3.
37. N2 alkyl cation transfer reactions between neutral and protonated alcohols. J. Phys. Chem. A 107, 668-675.
38. Horenstein, B. A., Parkin, D. W., Estupinan, B., and Schramm, V. L. (1991) Transition-state analysis of nucleoside hydrolase from crithidia fasciculate. Biochemistry 30, 10788-10795.
39. Lewandowicz, A., and Schramm, V. L. (2004) Transition state analysis for human and Plasmodium falciparum purine nucleoside phosphorylases. Biochemistry 43, 1458-1468.
40. Farcasiu, D., and Horsley, J. A. (1980) Ab initio calculations and carbon-13 NMR study on the methoxymethyl cation. J. Am. Chem. Soc. 102, 4906-4911.
41. Caserio, M. C., and Kim, J. K. (1982) Ab initio calculations and carbon-13 NMR study on the methoxymethyl cation. J. Org. Chem. 47, 2940-2944.
42. Okada, S., Abe, Y., Taniguchi, S., and Yamabe, S. (1987) Kinetic and theoretical study on the ion/molecule reactions of methoxymethyl cation with ammonia. J. Am. Chem. Soc. 109, 295-300.
43. Rayat, S., and Glaser, R. (2003) 5-Cyanoimino-4-oxomethylene- dihydroimidazole and nitrosative guanine deamination. A theoretical study of geometries, electronic structures and N-protonation. J. Org. Chem. 68, 9882-9892.
44. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Zakrzewski, V. G., Montgomery, J. A., Jr., Stratmann, R. E., Burant, J. C., Dapprich, S., Millam, J. M., Daniels, A. D., Kudin, K. N., Strain, M. C., Farkas, O., Tomasi, J., Barone, V., Cossi, M., Cammi, R., Mennucci, B., Pomelli, C., Adamo, C., Clifford, S., Ochterski, J., Petersson, G. A., Ayala, P. Y., Cui, Q., Morokuma, K., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Cioslowski, J., Ortiz, J. V., Baboul, A. G., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Gomperts, R., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Andres, J. L., Gonzalez, C., Head-Gordon, M., Replogle, E. S., and Pople, J. A. (1998) Gaussian 98, Revision A.9, Gaussian, Inc., Pittsburgh, PA.
45. Cramer, C. (2002) Essentials of Computational Chemistry, Wiley, New York.
46. Hehre, W. J., Random, L., Schleyer, P. v. R., and Pople, J. A. (1986) Ab Initio Molecular Orbital Theory, John Wiley & Sons, New York.
47. Cramer, C. J., and Truhlar, D. (1999) Implicit solvation models: equilibria, structure, spectra, and dynamics. Chem. Rev. 99, 2161-2200.
48. Foresman, J. B., Keith, T. A., Wiberg, K. B., Snoonian, J., and Frisch, M. J. (1996) Solvent effects. 5. Influence of cavity shape, truncation of electrostatics, and electron correlation on ab initio reaction field calculations. J. Phys. Chem. 100, 16098-16104.
49. Glendening, E. D., Reed, A. E., Carpenter, J. E., and Weinhold, F. NBO Version 3.1.
50. Glendening, E. D., Badenhoop, J. K., and Weinhold, F. (1998) Natural resonance theory. III. Chemical applications. J. Comput. Chem. 19, 628-646.
51. Glendening, E. D., and Weinhold, F. (1998) Natural resonance theory. I. General formalism. J. Comput. Chem. 19, 593-609.
52. Hiraoka, K., and Kebarle, P. (1977) Condensation reactions involving carbonium ions in the gas phase. Synthesis of protonated acids in gaseous methane containing carbon monoxide and water vapor. J. Am. Chem. Soc. 99, 366-370.
53. Meot-Ner, M. (1979) Competitive condensation and proton-transfer reactions. Temperature and pressure effects and the detailed mechanism. J. Am. Chem. Soc. 101, 2389-2395.
54. Meot-Ner, M. (1978) Solvation of the proton by hydrogen cyanide and acetonitrile. Condensation of hydrogen cyanide with ions in the gas phase. J. Am. Chem. Soc. 100, 4694-4699.
55. Mautner, M., Ross, M. M., and Campana, J. E. (1985) Stable hydrogen-bonded isomers of covalent ions. Association of carbonium ions with n-donors. J. Am. Chem. Soc. 107, 4839-4845.
56. Glaser, R., and Farmer, D. (1997) The cation-dinitrogen interaction in "benzyldiazonium ion." Preferential electrostatic complex formation and dinitrogen catalysis of benzyl cation rotational automerization. Chem. Eur. J. 3, 1244-1253.
57. Replogle, E. S., Trucks, G. W., and Staley, S. W. (1991) Electron correlation effects on the calculated dipole moments of fulvene and cyclopentadiene. J. Phys. Chem. 95, 6908-6912.
58. A postcoordination complex 21 containing 11b might well exist in which the protonated methanol engaged in H-bonding with the cyano-N atom.
59. Desiraju, G. R. (2002) Hydrogen bridges in crystal engineering: Interactions without borders. Acc. Chem. Res. 35, 565-573.
60. Hydrogen bonds of neutral donors to electron deficient cations in this way are not well-explored to date. For related studies of ion neutral complexes (INC), see, for example, Aschi, M., Attina, M., and Cacace, F. (1998) Lifetimes of geaseous ion-molecule complexes. Chem. Eur. J. 4, 1535-1541.
61. N2Ar reactions of benzenediazonium ion with water. On the conception of "unimolecular dediazoniation" in solvolysis reactions. J. Am. Chem. Soc. Accepted for publication.
62. N2 reaction that avoids its deep potential energy minimum. Science 296, 875-878.