Oxidative modification of guanine bases initiated by Oxyl radicals derived from photolysis of Azo compounds

Journal of Physical Chemistry B

Volumn 114, Issue 19, 2010, Pages 6685-6692

  Shao, Jie ^a   Geacintov, Nicholas E ^a   Shafirovich, Vladimir ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; BIOMOLECULES; FREE RADICAL REACTIONS; FREE RADICALS; MASS SPECTROMETRY; OXIDATION; OXYGEN; PHOTOLYSIS;

355 NM LASER; AQUEOUS SOLUTIONS; AZO COMPOUND; CHARACTERISTIC ABSORPTION; CLASSICAL TESTS; DEOXYGUANOSINE (DG); END-PRODUCTS; GUANINE OXIDATION; GUANOSINES; LASER KINETIC SPECTROSCOPY; NEUTRAL RADICAL; ONE-ELECTRON OXIDATION; OXIDATIVE DAMAGE; OXIDATIVE MODIFICATION; RADICAL GENERATORS; SUPEROXIDES; TETRANITROMETHANE; UV-VISIBLE;

POSITIVE IONS;

EID: 77952356301     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp100686j     Document Type: Article

References (69)

1. Balkwill, F.; Mantovani, A. Lancet 2001, 357, 539-545
2. Coussens, L. M.; Werb, Z. Nature 2002, 420, 860-867
3. Aggarwal, B. B.; Vijayalekshmi, R. V.; Sung, B. Clin. Cancer Res. 2009, 15, 425-430
4. Grisham, M. B.; Jourdheuil, D.; Wink, D. A. Aliment. Pharmacol. Ther. 2000, 14 Suppl 1, 3-9
5. Dedon, P. C.; Tannenbaum, S. R. Arch. Biochem. Biophys. 2004, 423, 12-22
6. Cadet, J.; Douki, T.; Ravanat, J. L. Nat. Chem. Biol. 2006, 2, 348-349
7. Sodum, R. S.; Chung, F. L. Cancer Res. 1988, 48, 320-323
8. Chaudhary, A. K.; Nokubo, M.; Reddy, G. R.; Yeola, S. N.; Morrow, J. D.; Blair, I. A.; Marnett, L. J. Science 1994, 265, 1580-1582
9. El Ghissassi, F.; Barbin, A.; Nair, J.; Bartsch, H. Chem. Res. Toxicol. 1995, 8, 278-283
10. Mlakar, A.; Spiteller, G. Chem. Phys. Lipids 1996, 79, 47-53
11. Marnett, L. J. Carcinogenesis 2000, 21, 361-370
12. Lee, S. H.; Blair, I. A. Trends Cardiovasc. Med. 2001, 11, 148-155
13. Marnett, L. J. Toxicology 2002, 181-182, 219-222
14. Marnett, L. J.; Burcham, P. C. Chem. Res. Toxicol. 1993, 6, 771-785
15. Nath, R. G.; Chung, F. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 7491-7495
16. Moriya, M.; Zhang, W.; Johnson, F.; Grollman, A. P. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 11899-11903
17. Akasaka, S.; Guengerich, F. P. Chem. Res. Toxicol. 1999, 12, 501-507
18. Lee, S. H.; Oe, T.; Blair, I. A. Science 2001, 292, 2083-2086
19. Bartsch, H.; Nair, J.; Owen, R. W. Biol. Chem. 2002, 383, 915-921
20. Valentine, M. R.; Rodriguez, H.; Termini, J. Biochemistry 1998, 37, 7030-7038
21. Paul, T.; Young, M. J.; Hill, I. E.; Ingold, K. U. Biochemistry 2000, 39, 4129-4135
22. Sanchez, C.; Shane, R. A.; Paul, T.; Ingold, K. U. Chem. Res. Toxicol. 2003, 16, 1118-1123
23. Ingold, K. U. Curr. Med. Chem. 2003, 10, 2631-2642
24. Rodriguez, H.; Holmquist, G. P.; DAgostino, R., Jr.; Keller, J.; Akman, S. A. Cancer Res. 1997, 57, 2394-2403
25. Douki, T.; Riviere, J.; Cadet, J. Chem. Res. Toxicol. 2002, 15, 445-454
26. Labeque, R.; Marnett, L. J. J. Am. Chem. Soc. 1987, 109, 2828-2829
27. Neta, P.; Grodkowski, J.; Ross, A. B. J. Phys. Chem. Ref. Data. 1996, 25, 709-1050
28. Barclay, L. R. C.; Locke, S. J.; MacNeil, J. M.; VanKessel, J.; Burton, G. W.; Ingold, K. U. J. Am. Chem. Soc. 1984, 106, 2479-2481
29. Yamamoto, Y.; Haga, S.; Niki, E.; Kamiya, E. Bull. Chem. Soc. Jpn. 1984, 57, 1260-1264
30. Gieseg, S. P.; Pearson, J.; Firth, C. A. Free Radical Res. 2003, 37, 983-991
31. Schnitzer, E.; Pinchuk, I.; Lichtenberg, D. Eur. Biophys. J. 2007, 36, 499-515
32. Lucio, M.; Ferreira, H.; Lima, J. L.; Reis, S. Redox Rep. 2008, 13, 225-236
33. Yoshida, Y.; Itoh, N.; Saito, Y.; Hayakawa, M.; Niki, E. Free Radical Res. 2004, 38, 375-384
34. Cui, Y.; Kim, D. S.; Park, S. H.; Yoon, J. A.; Kim, S. K.; Kwon, S. B.; Park, K. C. Chem. Phys. Lipids 2004, 129, 43-52
35. Wada, S.; Tabuchi, Y.; Kondo, T.; Cui, Z. G.; Zhao, Q. L.; Takasaki, I.; Salunga, T. L.; Ogawa, R.; Arai, T.; Makino, K.; Furuta, I. Free Radical Res. 2007, 41, 73-81
36. Roche, M.; Tarnus, E.; Rondeau, P.; Bourdon, E. Cell Biol. Toxicol. 2009, 25, 635-644
37. Jung, K. J.; Lee, E. K.; Yu, B. P.; Chung, H. Y. Free Radical Biol. Med. 2009, 47, 983-991
38. Lim, P.; Sadre-Bazzaz, K.; Shurter, J.; Sarasin, A.; Termini, J. Biochemistry 2003, 42, 15036-15044
39. Lim, P.; Wuenschell, G. E.; Holland, V.; Lee, D. H.; Pfeifer, G. P.; Rodriguez, H.; Termini, J. Biochemistry 2004, 43, 15339-15348
40. Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618
41. Krainev, A. G.; Bigelow, D. J. J. Chem. Soc., Perkin Trans. 2 1996, 747-754
42. Wahl, R. U. R.; Zeng, L.; Madison, S. A.; DePinto, R. L.; Shay, B. J. J. Chem. Soc., Perkin Trans. 2 1998, 2009-2017
43. Kohri, S.; Fujii, H.; Oowada, S.; Endoh, N.; Sueishi, Y.; Kusakabe, M.; Shimmei, M.; Kotake, Y. Anal. Biochem. 2009, 386, 167-171
44. Candeias, L. P.; Steenken, S. J. Am. Chem. Soc. 1989, 111, 1094-1099
45. Neta, P.; Huie, R. E.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 1027-1284
46. Rabani, J.; Mulac, W. A.; Matheson, M. S. J. Phys. Chem. 1965, 69, 53-70
47. Misiaszek, R.; Crean, C.; Joffe, A.; Geacintov, N. E.; Shafirovich, V. J. Biol. Chem. 2004, 279, 32106-32115
48. Buettner, G. R.; Jurkiewicz, B. A. Radiat. Res. 1996, 145, 532-541
49. Bachurina, T. D.; Kedrinskii, I. A.; Kurochkina, N. A.; Yankovskii, A. A. Zhurn. Prikl. Khim. 1974, 47, 301-304
50. Shafirovich, V.; Dourandin, A.; Huang, W.; Luneva, N. P.; Geacintov, N. E. J. Phys. Chem. B 1999, 103, 10924-10933
51. Crean, C.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2008, 21, 358-373
52. Adam, W.; Fragale, D.; Klapstein, D.; Nau, W. M.; Wirtz, J. J. Am. Chem. Soc. 1995, 117, 12578-12992
53. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry; Marcel Dekker: New York, 1993.
54. Shafirovich, V.; Dourandin, A.; Huang, W.; Geacintov, N. E. J. Biol. Chem. 2001, 276, 24621-24626
55. von Sonntag, C.; Schuchmann, H.-P. Angew. Chem., Int. Ed. Engl. 1991, 30, 1229-1253
56. Steenken, S.; Jovanovic, S. V.; Bietti, M.; Bernhard, K. J. Am. Chem. Soc. 2000, 122, 2373-2374
57. Merenyi, G.; Lind, J.; Goldstein, S. J. Am. Chem. Soc. 2002, 124, 40-48
58. Stanbury, D. M. Adv. Inorg. Chem. 1989, 33, 69-138
59. Aveline, B. M.; Kochevar, I. E.; Redmond, R. W. J. Am. Chem. Soc. 1996, 118, 10113-10123
60. Buxton, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513-886
61. Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J.-L. J. Am. Chem. Soc. 1994, 116, 7403-7404
62. Bielski, B. H. J.; Cabelli, D. E.; Arudi, R. L.; Ross, A. B. J. Phys. Chem. Ref. Data 1985, 14, 1041-1100
63. Floyd, R. A.; Watson, J. J.; Wong, P. K.; Altmiller, D. H.; Rickard, R. C. Free Radical Res. Commun. 1986, 1, 163-172
64. Gasparutto, D.; Ravanat, J.-L.; Gerot, O.; Cadet, J. J. Am. Chem. Soc. 1998, 120, 10283-10286
65. Fridovich, I. Annu. Rev. Biochem. 1995, 64, 97-112
66. Jovanovic, S. V.; Jankovic, I.; Josimovic, L. J. Am. Chem. Soc. 1992, 114, 9018-9021
67. Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: Boca Raton, FL, 2003.
68. Steenken, S.; Jovanovic, S. V.; Candeias, L. P.; Reynisson, J. Chem.-Eur. J. 2001, 7, 2829-2833
69. Koppenol, W. H. FEBS Lett. 1990, 264, 165-167