Tautomeric equilibria in 8-oxopurines: Implications for mutagenicity

Journal of Computer-Aided Molecular Design

Volumn 12, Issue 4, 1998, Pages 373-

  Venkateswarlu, Divi ^a   Leszczynski, Jerzy ^a  

^a JACKSON STATE UNIVERSITY   (United States)

Author keywords

8 oxopurines; Molecular orbital calculations; Mutagenicity; Tautomerism

Indexed keywords

CALCULATIONS; CONTINUUM MECHANICS; GASES; IONIZING RADIATION; MOLECULAR ORBITALS; ORBITAL CALCULATIONS; QUANTUM THEORY; SOLUTIONS;

8-OXOGUANINE; 8-OXOPURINE; CELLULAR DAMAGE; DNA DAMAGES; GAS-PHASES; MOLECULAR ORBITAL CALCULATIONS; MUTAGENICITY; TAUTOMERIC EQUILIBRIA; TAUTOMERICS; TAUTOMERISM;

FREE RADICALS;

DNA; MUTAGENIC AGENT; PURINE DERIVATIVE; SOLVENT; WATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; COMPUTER SIMULATION; DNA DAMAGE; GENETICS; ISOMERISM; QUANTUM THEORY; RADIATION EXPOSURE; THERMODYNAMICS;

COMPUTER SIMULATION; DNA; DNA DAMAGE; ISOMERISM; MODELS, CHEMICAL; MUTAGENS; PURINONES; QUANTUM THEORY; SOLVENTS; THERMODYNAMICS; WATER;

EID: 0032110140     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/a:1008067110965     Document Type: Article

References (72)

1. Breen, A.P. and Murphy, J.A., Free Radic. Biol. Med., 18 (1995) 1033.
2. Frenkel, K., Pharmacol. Ther., 53 (1992) 127.
3. Cheng, K.C., Cahill, D.S., Kasai, H., Nishimura, S. and Loeb, L.A., J. Biol. Chem., 267 (1992) 166.
4. Colson, A.O. and Sevilla, M.D., Int. J. Radiat. Biol., 67 (1995) 627.
5. Park, E.M., Shigenaga, M.K., Degan, P., Korn, T.S., Kitzler, J.W., Wehr, C.M., Kolachana, P. and Ames, B.N., Proc. Natl. Acad. Sci. USA, 89 (1992) 3375.
6. Ames, B.N., Free Radic. Res. Commun., 7 (1989) 121.
7. Cross, C.E., Halliwell, B., Borish, E.T., Pryor, W.A., Ames, B.N., Saul, R.I., McCord, J.M. and Harman, D., Ann. Intern. Med., 107 (1987) 526.
8. Floyd, R.A., Carcinogenesis, 11 (1990) 1447.
9. Alliwell, B. and Gutteridge, J.M.C., Free Radicals in Biology and Medicine, 2nd ed., Clarendon, Oxford, 1989.
10. Kasai, H., Nishimura, S., Kurokawa, Y. and Hayashi, Y., Carcinogenesis, 8 (1987) 1959.
11. Wang, Y.J., Ho, Y.S., Lo, M.J. and Lin, J.K., Chem. Biol. Interact., 94 (1995) 135.
12. Breimer, L.H., Br. J. Cancer, 57 (1988) 6.
13. Kasai, H. and Nishimura, S., Nucleic Acids Res., 12 (1984) 2137.
14. Lipscomb, L.A., Peek, M.E., Morningstar, M.L., Verghis, S.M., Miller, E.M., Rich, A., Essigmann, J.M. and Williams, L.D., Proc. Natl. Acad. Sci. USA, 92 (1995) 719.
15. Kouchakdjian, M., Bodepudi, V., Shibutani, S., Eisenberg, M., Johnson, F., Grollman, A.P. and Patel, D.J., Biochemistry, 30 (1991) 1403.
16. Leonard, G.A., Guy, A., Brown, T., Teoule, R. and Hunter, W.N., Biochemistry, 31 (1992) 8415.
17. Culp, S.J., Cho, B.P., Kadlubar, F.F. and Evans, F.E., Chem. Res. Toxicol., 2 (1989) 416.
18. Cho, B.P. and Evans, F.E., Nucleic Acids Res., 19 (1991) 1041.
19. Aida, M. and Nishimura, S., Mutat. Res., 192 (1987) 83.
20. Wood, M.L., Dizdaroglu, M., Gajewski, E. and Essigmann, J.M., Biochemistry, 29 (1990) 7024.
21. Moriya, M., Ou, C., Bodepudi, V., Johnson, F., Takeshita, M. and Grollman, A.P., Mutat. Res., 254 (1991) 281.
22. Kuchino, Y., Mori, F., Kasai, H., Inoue, H., Iwai, S., Miura, K., Ohtsuka, E. and Nishimura, S., Nature, 327 (1987) 77.
23. Shibutani, S., Takeshita, M. and Grollman, A.P., Nature, 349 (1991) 431.
24. Kamiya, H., Murata-Kamiya, N., Koizume, S., Inoue, H., Nishimura, S. and Ohtusuka, E., Carcinogenesis, 16 (1995) 883.
25. Wood, M.L., Esteve, A., Morningstar, M.L., Kuziemko, G.M. and Essigmann, J.M., Nucleic Acids Res., 20 (1992) 6023.
26. a. Leszczynski, J., J. Phys. Chem., 96 (1992) 1649.
27. b. Leszczynski, J., J. Phys. Chem., 97 (1993) 3520.
28. a. Leszczynski, J., Int. J. Quantum Chem., Quantum Biol. Symp., 18 (1991) 9.
29. b. Rostkowska, H., Szczepaniak, K., Nowak, J.M., Leszczynski, J., Kubulat, K. and Person, W.B., J. Am. Chem. Soc., 112 (1990) 2147.
30. c. Leszczynski, J. and Lammertsma, K., J. Phys. Chem., 95 (1991) 3128.
31. a. Kwiatkowski, J.S. and Leszczynski, J., J. Mol. Struct. (THEOCHEM), 208 (1990) 35.
32. b. Leszczynski, J., Chem. Phys. Lett., 174 (1990) 347.
33. c. Leszczynski, J., J. Mol. Struct. (THEOCHEM), 311 (1994) 37.
34. d. Leszczynski, J., J. Phys. Chem., 102 (1998) 2357.
35. See, for example, Hehre, W.J., Radom, L., Schleyer, P.v.R. and Pople, J.A., Ab Initio Molecular Orbital Theory, Wiley, New York, NY, 1986.
36. a. Hehre, W.J., Ditchfield, R. and Pople, J.A., J. Chem. Phys., 56 (1972) 2257.
37. b. Hariharan, RC. and Pople, J.A., Theor. Chim. Acta, 28 (1973) 213.
38. Evan, R.E., Giesen, D.J., Welch, A., Cramer, C.J. and Truhlar, D.G., Theor. Chim. Acta, 983 (1996) 281.
39. a. McLean, A.D. and Chandler, G.S., J. Chem. Phys., 72 (1980) 5639.
40. b. Krishnan, R., Binkley, J.S., Seeger, R. and Pople, J.A., J. Chem. Phys., 72 (1980) 650.
41. GAUSSIAN 94, Revision E.1, Frisch, M.G., Trucks, G.W., Schlegel, H.B., Gill, P.M.W., Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, T., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, M.A., Zakrzewski, V.G., Ortiz, J.V., Foresman, J.B., Cioslowski, J., Stefanov, B.B., Nanayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, M.W, Wong, Andres, J.L., Replogle, E.S., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., Defrees, D.J., Baker, J., Stewart, J.P., Head-Gordon, M., Gonzalez, C. and Pople, J.A., Gaussian Inc., Pittsburgh, PA, 1995.
42. Cramer, C.J., Hawkins, G.D., Lynch, G.G., Giesen, D.J., Truhlar, D.G. and Liotard, D.A., AMSOL 4.5.1, QCPE Program 606, v. 4.5.
43. Cramer, C.J. and Truhlar, D.G., Science, 256 (1992) 213.
44. a. Cramer, C.J. and Truhlar, D.G., J. Comput. Chem., 13 (1992) 1089.
45. b. Cramer, C.J. and Truhlar, D.G., J. Comput.-Aided Mol. Design, 6 (1992) 629.
46. a. Hernandez, B., Orozco, M. and Luque, F.J., J. Comput.-Aided Mol. Design, 10 (1996) 535.
47. b. Hernandez, B., Orozco, M. and Luque, F.J., J. Comput-Aided Mol. Design, 11 (1997) 153.
48. c. Hernandez, B., Luque, F.J. and Orozco, M., J. Org. Chem., 61 (1996) 5964.
49. Miertus, S., Scrocco, E. and Tomasi, J., J. Chem. Phys., 55 (1981) 117.
50. Ha, T.-K., Keller, M.J., Gunde, R. and Gunthard, H.H., J. Mol. Struct. (THEOCHEM), 364 (1996) 161.
51. Katritzky, A.R., Handbook of Heterocyclic Chemistry, Pergamon, Oxford, 1985, pp. 121-123.
52. Reichardt, C., Solvents and Solvent Effects in Organic Chemistry, VCH, New York, NY, 1990, pp. 98-104.
53. Beak, P., Acc. Chem. Res., 10 (1977) 186.
54. Cramer, C.J. and Truhlar, D.G., J. Am. Chem. Soc., 115 (1993) 8810.
55. Woodcock, S., Green, D.V.S., Vincent, M.A., Hillier, I.H., Guest, M.F. and Sherwood, P., J. Chem. Soc. Perkin Trans. 2, (1992) 2151.
56. a. Lowdin, P.O., Rev. Mod. Phys., 35 (1963) 724.
57. b. Lowdin, P.O., In Pullman, B. (Ed.) Electronic Aspects of Biochemistry, Academic Press, New York, NY, 1964, p. 167.
58. c. Lowdin, P.O., Mutat. Res., 2 (1965) 218.
59. a. Szczesniak, M., Szczepaniak, K., Kwiatkowski, J.S., KuBulat, K. and Person, W.B., J. Am. Chem. Soc., 110 (1988) 8319.
60. b. Szczesniak, M., Szczepaniak, K. and Person, W.B., J. Am. Chem. Soc., 114 (1992) 2731.
61. c. Szczesniak, K. and Szczepaniak, M., J. Mol. Struct. (THEOCHEM), 156 (1987) 29.
62. d. Szczesniak, K., Szczepaniak, M., Szajda, W., Person, W.B. and Leszczynski, J., Can. J. Chem., 69 (1991) 1705.
63. a. Broughton, J.W. and Pulay, P., Int. J. Quantum Chem., 47 (1993) 49.
64. b. Estrin, D.A., Paglieri, L. and Corongiu, G., J. Phys. Chem., 98 (1994) 5653.
65. a. Gould, I.R. and Hillier, I.H., Chem. Phys. Lett., 161 (1989) 185.
66. b. Les, A., Adamowicz, L. and Bartlett, R.J., J. Phys. Chem., 93 (1989) 4001.
67. c. Hall, R.J., Burton, N.A., Hillier, I.H. and Young, P.E., Chem. Phys. Lett., 220 (1994) 129.
68. a. Florian, J. and Leszczynski, J., J. Mol. Phys., 84 (1995) 469.
69. b. Florian, J. and Leszczynski, J., J. Am. Chem. Soc., 118 (1996) 3010.
70. a. Hrouda, V., Florian, J. and Hobza, P., J. Phys. Chem., 97 (1993) 1542.
71. b. Florian, J., Hrouda, V. and Hobza, P., J. Am. Chem. Soc., 116 (1994) 1457.
72. Fersht, A.R. and Knill-Jones, J.W., J. Mol. Biol., 165 (1983) 633.