An exploration of mechanisms for the transformation of 8-oxoguanine to guanidinohydantoin and spiroiminodihydantoin by density functional theory

Journal of the American Chemical Society

Volumn 130, Issue 15, 2008, Pages 5245-5256

  Munk, Barbara H ^a   Burrows, Cynthia J ^b   Schlegel, H Bernhard ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL MIGRATION; RING OPENING;

DENSITY FUNCTIONAL THEORY; ELECTRONS; POTENTIAL ENERGY; PROTONS; SOLVATION;

DRUG PRODUCTS;

2 AMINO 5 HYDROXY 7,9 DIHYDROPURINE 6,8 DIONE; 8 HYDROXYGUANINE; CARBAMIC ACID; GUANIDINOHYDANTOIN; HYDANTOIN; HYDROXIDE; SPIROIMINODIHYDANTOIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL MODIFICATION; CHEMICAL REACTION; DECARBOXYLATION; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; HYDRATION; HYDROLYSIS; PROTON TRANSPORT; REACTION ANALYSIS; SOLVATION;

GUANIDINES; GUANINE; GUANOSINE; HYDANTOINS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHASE TRANSITION; SOLUTIONS; SPIRO COMPOUNDS; WATER;

EID: 42149116842     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja7104448     Document Type: Article

References (71)

1. Gimisis, T.; Cismas, C. Eur. J. Org. Chem. 2006, 1351-1378.
2. Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1151.
3. Breen, A. P.; Murphy, J. A. Free Radical Biol. Med. 1995, 18, 1033-1077.
4. Pratviel, G.; Meunier, B. Chem.-Eur. J. 2006, 12, 6018-6030.
5. Beckman, K. B.; Ames, B. N. J. Biol. Chem. 1997, 272, 19633-19636.
6. Foksinski, M.; Rozalski, R.; Guz, J.; Ruszkowska, B.; Sztukowska, P.; Piwowarski, M.; Klungland, A.; Olinski, R. Free Radical Biol. Med. 2004, 37, 1449-1454.
7. Steenken, S.; Jovanovic, S. V.; Bietti, M.; Bernhard, K. J. Am. Chem. Soc. 2000, 122, 2373-2374.
8. Luo, W. C.; Muller, J. G.; Rachlin, E. M.; Burrows, C. J. Chem. Res. Toxicol. 2001, 14, 927-938.
9. Luo, W. C.; Muller, J. G.; Rachlin, E. M.; Burrows, C. J. Org. Lett. 2000, 2, 613-616.
10. Hickerson, R. P.; Prat, F.; Muller, J. G.; Foote, C. S.; Burrows, C. J. J. Am. Chem. Soc. 1999, 121, 9423-9428.
11. Cadet, J.; Douki, T.; Gasparutto, D.; Ravanat, J. L. Mutat. Res. 2003, 531, 5-23.
12. Hah, S. S.; Kim, H. M.; Sumbad, R. A.; Henderson, P. T. BioMed. Chem. Lett. 2005, 15, 3627-3631.
13. Hosford, M. E.; Muller, J. G.; Burrows, C. J. J. Am. Chem. Soc. 2004, 126, 9540-9541.
14. Luo, W. C.; Muller, J. G.; Burrows, C. J. Org. Lett. 2001, 3, 2801-2804.
15. McCallum, J. E. B.; Kuniyoshi, C. Y.; Foote, C. S. J. Am. Chem. Soc. 2004, 126, 16777-16782.
16. Joffe, A.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2003, 16, 1528-1538.
17. Misiaszek, R.; Crean, C.; Joffe, A.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2004, 17, 1765-1765.
18. Misiaszek, R.; Crean, C.; Geacintov, N. E.; Shafirovich, V. J. Am. Chem. Soc. 2005, 127, 2191-2200.
19. Misiaszek, R.; Crean, C.; Joffe, A.; Geacintov, N. E.; Shafirovich, V. J. Biol. Chem. 2004, 279, 32106-32115.
20. Neeley, W. L.; Essigmann, J. M. Chem. Res. Toxicol. 2006, 19, 491-505.
21. Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. Org. Lett. 2001, 3, 963-966.
22. Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 2004, 17, 1510-1519.
23. Ye, Y.; Muller, J. G.; Luo, W. C.; Mayne, C. L.; Shallop, A. J.; Jones, R. A.; Burrows, C. J. J. Am. Chem. Soc. 2003, 125, 13926-13927.
24. Yu, H. B.; Venkatarangan, L.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 2005, 18, 1849-1857.
25. Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. Nitric Oxide 2006, 14, 109-121.
26. Niles, J. C.; Venkatarangan, L. M.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 2002, 15, 1675-1676.
27. Slade, P. G.; Priestley, N. D.; Sugden, K. D. Org. Lett. 2007, 9, 4411-4414.
28. Kornyushyna, O.; Berges, A. M.; Muller, J. G.; Burrows, C. J. Biochemistry 2002, 41, 15304-15314.
29. Misiaszek, R.; Uvaydov, Y.; Crean, C.; Geacintov, N. E.; Shafirovich, V. J. Biol. Chem. 2005, 280, 6293-6300.
30. Poje, M.; Sokolicmaravic, L. Tetrahedron 1988, 44, 6723-6728.
31. Kahn, K.; Serfozo, P.; Tipton, P. A. J. Am. Chem. Soc. 1997, 119, 5435-5442.
32. Duarte, V.; Gasparutto, D.; Yamaguchi, L. F.; Ravanat, J. L.; Martinez, G. R.; Medeiros, M. H. G.; Di Mascio, P.; Cadet, J. J. Am. Chem. Soc. 2000, 122, 12622-12628.
33. Handbook of Bond Dissociation Energies in Organic Compounds; Luo, Y.-R., Ed.; CRC Press LLC: Boca Raton, FL, 2003.
34. Jia, L.; Shafirovich, V.; Shapiro, R.; Geacintov, N. E.; Broyde, S. Biochemistry 2005, 44, 13342-13353.
35. Jia, L.; Shafirovich, V.; Shapiro, R.; Geacintov, N. E.; Broyde, S. Biochemistry 2005, 44, 6043-6051.
36. Durandin, A.; Jia, L.; Crean, C.; Kolbanovskiy, A.; Ding, S.; Shafirovich, V.; Broyde, S.; Geacintov, N. E. Chem. Res. Toxicol. 2006, 19, 908-913.
37. Frisch, M. J.; et al.; Gaussian Development Version, Revision E.05, F01, F02, and G01 ed.; Gaussian, Inc.: Wallingford, CT, 2006. See Supporting Information for full ref.
38. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
39. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
40. Lee, C.; Yang, W.; Parr, R. D. Phys. Rev. B 1988, 37, 785-789.
41. Ditchfield, R.; Hehre, W. J.; Pople, J. A. J. Chem. Phys. 1971, 54, 724-728.
42. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257-2261.
43. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222.
44. Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209-214.
45. Gordon, M. S. Chem. Phys. Lett. 1980, 76, 163-168.
46. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; Defrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665.
47. Munk, B. H.; Burrows, C. J.; Schlegel, H. B. Chem. Res. Toxicol. 2007, 20, 432-444.
48. Kendall, R. A.; Dunning, T. H.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796-6806.
49. Cances, E.; Mennucci, B. J. Chem. Phys. 2001, 114, 4744-4745.
50. Cances, E.; Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041.
51. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158.
52. Mennucci, B.; Cances, E.; Tomasi, J. J. Phys. Chem. B 1997, 101, 10506-10517.
53. Tomasi, J.; Cammi, R.; Mennucci, B. Int. J. Quantum Chem. 1999, 75, 783-803.
54. Chipman, D. M. J. Chem. Phys. 2000, 112, 5558-5565.
55. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502-16513.
56. McQuarrie, D. A. Statistical Thermodynamics; University Science Books: Mill Valley, CA, 1973.
57. Reynisson, H.; Steenken, S. Phys. Chem. Chem. Phys. 2002, 4, 527-532.
58. Wetmore, S. D.; Boyd, R. J.; Eriksson, L. A. J. Phys. Chem. B 1998, 102, 9332-9343.
59. Colson, A. O.; Sevilla, M. D. Int. J. Radiat. Biol. 1995, 67, 627-645.
60. Hush, N. S.; Chueng, A. S. Chem. Phys. Lett. 1975, 34, 11-13.
61. Orlov, V. M.; Smirnov, A. N.; Varshavsky, Ya, M. Tetrahedron Lett. 1976, 48, 4377-4378.
62. Steenken, S. Biol. Chem. 1997, 378, 1293-1297.
63. Gervasio, F. L.; Laio, A.; Iannuzzi, M.; Parrinello, M. Chem.-Eur. J. 2004, 10, 4846-4852.
64. Matsui, T.; Shigeta, Y.; Hirao, K. J. Phys. Chem. B 2007, 111, 1176-1181.
65. Williams, I. H.; Spangler, D.; Femec, D. A.; Maggiora, G. M.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 31-40.
66. Jena, N. R.; Mishra, P. C. J. Phys. Chem. B 2005, 109, 14205-14218.
67. Suzuki, T.; Friesen, M. D.; Ohshima, H. Chem. Res. Toxicol. 2003, 16, 382-389.
68. Cucinotta, C. S.; Ruini, A.; Catellani, A.; Stirling, A. ChemPhysChem 2006, 7, 1229-1234.
69. Lee, D.; Kim, C. K.; Lee, B. S.; Lee, I.; Lee, B. C. J. Comput. Chem. 1997, 18, 56-69.
70. Capon, B.; Zucco, C. J. Am. Chem. Soc. 1982, 104, 7567-7572.
71. Johansen, M. E.; Muller, J. G.; Xu, X. Y.; Burrows, C. J. Biochemistry 2005, 44, 5660-5671.