DNA sequence context as a determinant of the quantity and chemistry of guanine oxidation produced by hydroxyl radicals and one-electron oxidants

Journal of Biological Chemistry

Volumn 283, Issue 51, 2008, Pages 35569-35578

  Margolin, Yelena ^a,c   Shafirovich, Vladimir ^b   Geacintov, Nicholas E ^b   DeMott, Michael S ^a   Dedon, Peter C ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

^b NEW YORK UNIVERSITY   (United States)

^c HARVARD SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLLOIDS; DNA; ELECTRONS; ESCHERICHIA COLI; FOOD ADDITIVES; FREE RADICAL REACTIONS; FUNCTIONAL GROUPS; GELATION; GENES; IONIZATION POTENTIAL; IONIZING RADIATION; NUCLEIC ACIDS; ORGANIC ACIDS; OXIDANTS; OXIDATION; POSITIVE IONS; RADIATION EFFECTS;

ABASIC SITES; CHARGE MIGRATIONS; CRITICAL DETERMINANTS; DIFFERENT DAMAGES; DIFFERENT EFFECTS; DNA GLYCOSYLASE; E. COLI; ELECTRON OXIDATIONS; ELECTRON TRANSFERS; EXONUCLEASE; FENTON CHEMISTRIES; FORMAMIDOPYRIMIDINE; GUANINE OXIDATIONS; GUANINE RADICALS; HYDROXYL RADICALS; NUCLEOBASE; NUCLEOTIDE SEQUENCES; OLIGODEOXYNUCLEOTIDES; OXIDATION PATHWAYS; OXIDATIVE DAMAGES; OXIDIZING AGENTS; STRAND BREAKS; STRONG OXIDANTS;

PHOTOOXIDATION;

DNA FORMAMIDOPYRIMIDINE GLYCOSYLASE; EDETATE IRON; EXODEOXYRIBONUCLEASE III; GUANINE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; NUCLEIC ACID BASE; OLIGONUCLEOTIDE; PIPERIDINE; RIBOFLAVIN;

ARTICLE; DNA DAMAGE; DNA SEQUENCE; DNA STRAND BREAKAGE; ELECTRON; ESCHERICHIA COLI; GAMMA RADIATION; PHOTOOXIDATION; PRIORITY JOURNAL;

BASE SEQUENCE; DNA; DNA DAMAGE; GAMMA RAYS; GUANIDINE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IRON; OLIGODEOXYRIBONUCLEOTIDES; OXIDANTS; OXIDATION-REDUCTION;

ESCHERICHIA COLI;

EID: 58149085464     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M806809200     Document Type: Article

References (79)

1. Breen, A. P., and Murphy, J. A. (1995) Free Radic. Biol. Med. 18, 1033-1077
2. von Sonntag, C. (1987) The Chemical Basis of Radiation Biology, Taylor & Francis, New York
3. Roots, R., and Okada, S. (1975) Radiat. Res. 64, 306-320
4. Jones, G. D., Boswell, T. V., Lee, J., Milligan, J. R., Ward, J. F., and Weinfeld, M. (1994) Int. J. Radiat. Biol. 66, 441-445
5. Becker, D., and Sevilla, M. D. (1993) Adv. Radiat. Biol. 17, 121-180
6. Cadet, J., Delatour, T., Douki, T., Gasparutto, D., Pouget, J. P., Ravanat, J. L., and Sauvaigo, S. (1999) Mutat. Res. 424, 9-21
7. Frelon, S., Douki, T., Favier, A., and Cadet, J. (2002) J. Chem. Soc. Perkin Trans. I, 2866-2870
8. Yang, X., Wang, X. B., Vorpagel, E. R., and Wang, L. S. (2004) Proc. Natl. Acad. Sci. U. S. A. 101, 17588-17592
9. Ito, K., and Kawanishi, S. (1997) Biochemistry 36, 1774-1781
10. Henderson, P. T., Jones, D., Hampikian, G., Kan, Y., and Schuster, G. B. (1999) Proc. Natl. Acad. Sci. U. S. A. 96, 8353-8358
11. Hall, D. B., Holmlin, R. E., and Barton, J. K. (1996) Nature 382, 731-735
12. Saito, I., Nakamura, T., Nakatani, K., Yoshioka, Y., Yamaguchi, K., and Sugiyama, H. (1998) J. Am. Chem. Soc. 120, 12686-12687
13. Steenken, S., and Jovanovic, S. V. (1997) J. Am. Chem. Soc. 119, 617-618
14. Sugiyama, H., and Saito, I. (1996) J. Am. Chem. Soc. 118, 7063-7068
15. Senthilkumar, K., Grozema, F. C., Guerra, C. F., Bickelhaupt, F. M., and Siebbeles, L. D. A. (2003) J. Am. Chem. Soc. 125, 13658-13659
16. Cullis, P. M., Davis, A. S., Malone, M. E., Podmore, I. D., and Symons, M. C. R. (1992) J. Chem. Soc. Perkins Trans. II, 1409-1412
17. Sevilla, M. D., Becker, D., Yan, M., and Summerfield, S. R. (1991) J. Phys. Chem. 95, 3409-3415
18. Bernhard, W. A. (1989) J. Phys. Chem. 93, 2187-2189
19. Cullis, P. M., Evans, P., and Malone, M. E. (1996) Chem. Commun. 985-986
20. Gregoli, S., Olast, M., and Bertinchamps, A. (1982) Radiat. Res. 89, 238-254
21. Milligan, J. R., Aguilera, J. A., and Ward, J. F. (1993) Radiat. Res. 133, 151-157
22. Ito, T., Baker, S. C., Stickley, C. D., Peak, J. G., and Peak, M. J. (1993) Int. J. Radiat. Biol. 63, 289-296
23. Purkayastha, S., Milligan, J. R., and Bernhard, W. A. (2007) Radiat. Res. 168, 357-366
24. Purkayastha, S., and Bernhard, W. A. (2004) J. Phys. Chem. B 108, 18377-18382
25. Steenken, S., Jovanovic, S. V., Bietti, M., and Bernhard, K. (2000) J. Am. Chem. Soc. 122, 2373-2374
26. Doddridge, Z. A., Cullis, P. M., Jones, G. D. D., and Malone, M. E. (1998) J. Am. Chem. Soc. 120, 10998-10999
27. Ding H., and Greenberg, M. M. (2007) J. Am. Chem. Soc. 129, 772-773
28. Margolin, Y., Cloutier, J. F., Shafirovich, V., Geacintov, N. E., and Dedon, P. C. (2006) Nat. Chem. Biol. 2, 365-366
29. Dedon, P. C. (2008) Chem. Res. Toxicol. 21, 206-219
30. Putney, S. D., Benkovic, S. J., and Schimmel, P. R. (1981) Proc. Natl. Acad. Sci. U. S. A. 78, 7350-7354
31. Greenberg, M. M., Weledji, Y. N., Kim, J., and Bales, B. C. (2004) Biochemistry 43, 8178-8183
32. Kow, Y. W. (1989) Biochemistry 28, 3280-3287
33. Price, M. A., and Tullius, T. D. (1992) Methods Enzymol. 212, 194-219
34. Murata-Kamiya, N., Kamiya, H., Muraoka, M., Kaji, H., and Kasai, H. (1997) J. Radiat. Res. 38, 121-131
35. Dedon, P. C., and Goldberg, I. H. (1992) Chem. Res. Toxicol. 5, 311-332
36. Balasubramanian, B., Pogozelski, W. K., and Tullius, T. D. (1998) Proc. Natl. Acad. Sci. U. S. A. 95, 9738-9743
37. Qian, S. Y., and Buettner, G. R. (1999) Free Radic. Biol. Med. 26, 1447-1456
38. Yoshioka, Y., Kitagawa, Y., Takano, Y., Yamaguchi, K., Nakamura, T., and Saito, I. (1999) J. Am. Chem. Soc. 121, 8712-8719
39. Spassky, A., and Angelov, D. (1997) Biochemistry 36, 6571-6576
40. Haraguchi, K., Delaney, M. O., Wiederholt, C. J., Sambandam, A., Hantosi, Z., and Greenberg, M. M. (2002) J. Am. Chem. Soc. 124, 3263-3269
41. Gasparutto, D., Ravanat, J.-L., Gerot, O., and Cadet, J. (1998) J. Am. Chem. Soc. 120, 10283-10286
42. Tchou, J., Kasai, H., Shibutani, S., Chung, M. H., Laval, J., Grollman, A. P., and Nishimura, S. (1991) Proc. Natl. Acad. Sci. U. S. A. 88, 4690-4694
43. Tretyakova, N. Y., Wishnok, J. S., and Tannenbaum, S. R. (2000) Chem. Res. Toxicol. 13, 658-664
44. Tretyakova, N. Y., Burney, S., Pamir, B., Wishnok, J. S., Dedon, P. C., Wogan, G. N., and Tannenbaum, S. R. (2000) Mutat. Res. 447, 287-303
45. Joffe, A., Geacintov, N. E., and Shafirovich, V. (2003) Chem. Res. Toxicol. 16, 1528-1538
46. Ravanat, J. L., Saint-Pierre, C., and Cadet, J. (2003) J. Am. Chem. Soc. 125, 2030-2031
47. Crean, C., Lee, Y. A., Yun, B. H., Geacintov, N. E., and Shafirovich, V. (2008) ChemBioChem 9, 1985-1991
48. Pouget, J. P., Frelon, S., Ravanat, J. L., Testard, I., Odin, F., and Cadet, J. (2002) Radiat. Res. 157, 589-595
49. Douki, T., Riviere, J., and Cadet, J. (2002) Chem. Res. Toxicol. 15, 445-454
50. Paul, T., Young, M. J., Hill, I. E., and Ingold, K. U. (2000) Biochemistry 39, 4129-4135
51. Rodriguez, H., Holmquist, G. P., D'Agostino, R., Jr., Keller, J., and Akman, S. A. (1997) Cancer Res. 57, 2394-2403
52. Luo, G. M., Qi, D. H., Zheng, Y. G., Mu, Y., Yan, G. L., Yang, T. S., and Shen, J. C. (2001) FEBS Lett. 492, 29-32
53. Rush, J. D., and Koppenol, W. H. (1986) J. Biol. Chem. 261, 6730-6733
54. Wink, D. A., Nims, R. W., Saavedra, J. E., Utermahlen, W. E., Jr., and Ford, P. C. (1994) Proc. Natl. Acad. Sci. U. S. A. 91, 6604-6608
55. Sawyer, D. T., Kang, C., Llobet, A., and Redman, C. (1993) J. Am. Chem. Soc. 115, 5817-5818
56. Koppenol, W. H., and Liebman, J. F. (1984) J. Phys. Chem. 88, 99-101
57. Reinke, L. A., Rau, J. M., and McCay, P. B. (1994) Free Radic. Biol. Med. 16, 485-492
58. Welch, K. D., Davis, T. Z., and Aust, S. D. (2002) Arch. Biochem. Biophys. 397, 360-369
59. Candeias, L. P., and Steenken, S. (2000) Chemistry 6, 475-484
60. Cadet, J., Douki, T., and Ravanat, J. L. (2008) Acc. Chem. Res. 41, 1075-1083
61. Misiaszek, R., Crean, C., Joffe, A., Geacintov, N. E., and Shafirovich, V. (2004) J. Biol. Chem. 279, 32106-32115
62. Giese, B., Amaudrut, J., Kohler, A.-K., Spormann, M., and Wessely, S. (2001) Nature 412, 318-320
63. Kobayashi, K., and Tagawa, S. (2003) J. Am. Chem. Soc. 125, 10213-10218
64. Shafirovich, V., and Geacintov, N. E. (2004) in Long-Range Charge Transfer in DNA II (Schuster, G. B., and Beratan, D., eds) pp. 129-157, Springer-Verlag, Berlin
65. Cadet, J., and Berger, M. (1985) Int. J. Radiat. Biol. Relat. Stud. Phys. Chem. Med. 47, 127-143
66. Dizdaroglu, M., Dirksen, M. L., Simic, M. G., and Robbins, J. H. (1986) Fed. Proc. 45, 1626
67. von Sonntag, C. (2006) Free Radical-induced DNA Damage and Its Repair: A Chemical Perspective, Springer-Verlag, Berlin
68. Douki, T., and Cadet, J. (1999) Int. J. Rad. Biol. 75, 571-581
69. Kino, K., and Sugiyama, H. (2001) Chem. Biol. 8, 369-378
70. Matter, B., Malejka-Giganti, D., Csallany, A. S., and Tretyakova, N. (2006) Nucleic Acids Res. 34, 5449-5460
71. Leipold, M. D., Muller, J. G., Burrows, C. J., and David, S. S. (2000) Biochemistry 39, 14984-14992
72. Cadet, J., Douki, T., Gasparutto, D., and Ravanat, J. L. (2003) Mutat. Res. 531, 5-23
73. Cadet, J., Berger, M., Buchko, G. W., Joshi, P. C., Raoul, S., and Ravanat, J.-L. (1994) J. Am. Chem. Soc. 116, 7403-7404
74. Dedon, P. C., and Tannenbaum, S. R. (2004) Arch. Biochem. Biophys. 423, 12-22
75. Box, H. C. (2001) Radiat. Res. 155, 634-636
76. Box, H. C., Dawidzik, J. B., Wallace, J. C., Hauer, C. R., Stack, R. F., Rajecki, M. J., and Budzinski, E. E. (1999) Radiat. Res. 152, 575-582
77. Packer, M. J., Dauncey, M. P., and Hunter, C. A. (2000) J. Mol. Biol. 295, 85-103
78. Delaney, J. C., and Essigmann, J. M. (2008) Chem. Res. Toxicol. 21, 232-252
79. McCulloch, S. D., and Kunkel, T. A. (2008) Cell Res. 18, 148-161