DNA-protein cross-linking via guanine oxidation: Dependence upon protein and photosensitizer

Biochemistry

Volumn 42, Issue 34, 2003, Pages 10269-10281

  Kurbanyan, Kristina ^a   Nguyen, Kim L ^a   To, Phuong ^a   Rivas, Eunice V ^a   Lueras, Alexis M K ^a   Kosinski, Cynthia ^a   Steryo, Mary ^a   González, Arcelia ^a   Mah, Daisy Ann ^a   Stemp, Eric D A ^a  

^a Mount St Mary's College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALBUMIN;

ABSORPTION; CROSSLINKING; DNA; FREE RADICALS; OXIDATION; PHOTOSENSITIZERS;

PROTEINS;

1,10 PHENANTHROLINE; 2,2' BIPYRIDINE; ACRIDINE ORANGE; ALBUMIN; CYTIDINE; CYTOCHROME; CYTOCHROME C; DIPYRIDOPHENAZINE; ETHIDIUM; GUANINE; GUANINE DERIVATIVE; MANNITOL; PHENAZINE DERIVATIVE; PHOTOSENSITIZING AGENT; PLASMID DNA; RUTHENIUM; SCAVENGER; UNCLASSIFIED DRUG;

ABSORPTION; AMINO ACID SUBSTITUTION; ARTICLE; COVALENT BOND; DNA PROTEIN COMPLEX; ELECTRON TRANSPORT; OXIDATION; PHOTOSENSITIZATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING;

ANIMALS; BASE SEQUENCE; CATTLE; CROSS-LINKING REAGENTS; CYTOCHROME C GROUP; DNA; DNA DAMAGE; ELECTROCHEMISTRY; ELECTROPHORESIS, POLYACRYLAMIDE GEL; GUANINE; HEME; HISTONES; HORSES; HYDROXYL RADICAL; MOLECULAR SEQUENCE DATA; OXIDATION-REDUCTION; PHOTOCHEMISTRY; PHOTOSENSITIZING AGENTS; PIPERIDINES; SERUM ALBUMIN, BOVINE;

BOVINAE;

EID: 0041823513     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi020713p     Document Type: Article

References (110)

1. Kelly, S. O., and Barton, J. K. (1999) Metal Ions Biol. 36, 211.
2. Wiseman, H., and Halliwell, B. (1996) Biochem. J. 313, 17.
3. Ames, B. N., Shigenaga, M. K., and Hagen, T. M. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 7915.
4. Burrows, C. J., and Muller, J. G. (1998) Chem. Rev. 98, 1109.
5. Costa, M. (1990) J. Cell. Biochem. 44, 127.
6. Faraggi, M., Broitman, F., Trent, J. B., and Klapper, M. H. (1996)- J. Phys. Chem. 100, 14751.
7. Steenken, S. (1992) Free Radical Res. Commun. 16, 349.
8. Steenken, S., and Jovanovic, S. (1997) J. Am. Chem. Soc. 119, 617.
9. Sugiyama, H., and Saito, I. (1996) J. Am. Chem. Soc. 118, 7063.
10. Prat, F., Houk, K. N., and Foote, C. S. (1998) J. Am. Chem. Soc. 120, 845.
11. Hall, D. B., Holmlin, R. E., and Barton, J. K. (1996) Nature 382, 731.
12. Núñez, M. E., and Barton, J. K. (2000) Curr. Opin. Chem. Biol. 4, 199.
13. Schuster, G. B. (2000) Acc. Chem. Res. 33, 253.
14. Giese, B. (2000) Acc. Chem. Res. 33, 631.
15. Nakatani, K., Dohno, C., and Saito, I. (1999) J. Am. Chem. Soc. 121, 10854.
16. Arkin, M. R., Stemp, E. D. A., Pulver, S. C., and Barton, J. K. (1997) Chem. Biol. 4, 389.
17. Núñez, M. E., Hall, D. B., and Barton J. K. (1999) Chem. Biol. 6, 85.
18. Gasper, S. M., and Schuster, G. B. (1997) J. Am. Chem. Soc. 119, 12762.
19. Meggers, E., Michel-Beyerle, M. E., and Giese, B. (1998) J. Am. Chem. Soc. 120, 12950.
20. Giese, B., Wessely, S., Spormann, M., Lindemann, U., Meggers, E., and Michel-Beyerle, M. E. (1999) Angew. Chem., Int. Ed. 38, 996.
21. Saito, I., Nakamura, T., Nakatani, K., Yoshioka, Y., Yamaguchi, K., and Sugiyama, H. (1998) J. Am. Chem. Soc. 120, 12686.
22. Yoshioka, Y., Kitagawa, Y., Takano, Y., Yamaguchi, K., Nakamura, T., and Saito, I. (1999) J. Am. Chem. Soc. 121, 8712.
23. Davis, W. B., Naydenova, I., Haselsberger, R., Ogrodnik, A., Giese, B., and Michel-Beyerle, M. E. (2000) Angew. Chem., Int. Ed. 39, 3649.
24. Ly, D., Sanii, L., and Schuster, G. B. (1999) J. Am. Chem. Soc. 121, 9400.
25. Steenken, S., Jovanovic, S. V., Bietti, M., and Bernhard, K. (2000) J. Am. Chem. Soc. 122, 2373.
26. Ikeda, H., and Saito, I. (1998) J. Am. Chem. Soc. 121, 10836.
27. Nakatani, K., Dohno, C., and Saito, I. (2000) J. Am. Chem. Soc. 122, 5893.
28. Foote, C. S. (1991) Photochem. Photobiol. 54, 659.
29. Saito, I., Takayama, M., Sugiyama, H., and Nakamura, T. (1997) J. Photochem. Photobiol., A 106, 141.
30. Saito, I., Takayama, M., Sugiyama, H., and Nakatani, K. (1995) J. Am. Chem. Soc. 117, 6406.
31. Kasai, H., Yamaizumi, Z., Berger, M., and Cadet, J. (1992) J. Am. Chem. Soc. 114, 9692.
32. Cullis, P. M., Malone, M. E., and Merson-Davies, L. A. (1996) J. Am. Chem. Soc. 118, 2775.
33. Angelov, D., Spassky, A., Berger, M., and Cadet, J. (1997) J. Am. Chem. Soc. 119, 11373.
34. O'Neill, P., Parker, A. W., Plumb, M. A., and Siebbeles, L. D. A. (2001) J. Phys. Chem. B 105, 5283.
35. Napier, M. E., Loomis, C. R., Sistare, M. F., Kim, J., Eckhardt, A. E., and Thorp, H. H. (1997) Bioconjugate Chem. 8, 906.
36. Johnston, D. H., Glasgow, K. C., and Thorp, H. H. (1995) J. Am. Chem. Soc. 117, 8933.
37. Stemp, E. D. A., Arkin, M. R., and Barton, J. K. (1997) J. Am. Chem. Soc. 119, 2921.
38. Chang, I. J., Gray, H. B., and Winkler, J. R. (1991) J. Am. Chem. Soc. 113, 7056.
39. Dunn, D. A., Lin, V. H., and Kochevar, I. E. (1992) Biochemistry 31, 11620.
40. Candeias, L. P., and Steenken, S. (1989) J. Am. Chem. Soc. 111, 1094.
41. Stemp, E. D. A., and Barton, J. K. (2000) Inorg. Chem. 39, 3868.
42. Wagenknecht, H.-A., Stemp, E. D. A., and Barton, J. K. (2000) J. Am. Chem. Soc. 122, 1.
43. Wagenknecht, H.-A., Stemp, E. D. A., and Barton, J. K. (2000) Biochemistry 39, 5483.
44. Wagenknecht, H.-A., Rajski, S. R., Pascaly, M., Stemp, E. D. A., and Barton, J. K. (2001) J. Am. Chem. Soc. 123, 4400.
45. Cadet, J., Douki, T., Gasparutto, D., Gromova, M., Pouget, J.-P., Ravanat, J.-L., Romieu, A., and Sauviago, S. (1999) Nucl. Instrum. Methods Phys. Res. B 151, 1.
46. Douki, T., and Cadet, J. (1999) Int. J. Radiat. Biol. 75, 571.
47. Luo, W., Muller, J. G., Rachlin, E. M., and Burrows, C. J. (2000) Org. Lett. 2, 613.
48. Leipold, M. D., Muller, J. G., Burrows, C. J., and David, S. S. (2000) Biochemistry 39, 14984.
49. Hazra, T. K., Muller, J. G., Manuel, R. C., Burrows, C. J., Lloyd, R. S., and Mitra, S. (2001) Nucleic Acids Res. 29, 1967.
50. Morin, B., and Cadet, J. (1994) Photochem. Photobiol. 60, 102.
51. Morin, B., and Cadet, J. (1995) Chem. Res. Toxicol. 8, 192.
52. Morin, B., and Cadet, J. (1995) J. Am. Chem. Soc. 117, 12408.
53. Hickerson, R. P., Chepanoske, C. L., Williams, S. D., David, S. S., and Burrows, C. J. (1999) J. Am. Chem. Soc. 121, 9901.
54. Chakrabarti, S. K., Bai, C. J., and Subramanian, K. S. (1999) Toxicol. Appl. Pharmacol. 154, 245.
55. Quievryn, G., Goulart, M., Messer, J., and Zhitkovich, A. (2001) Mol. Cell. Biochem. 222, 107.
56. Gavin, I. M., Melnick, S. M., Yurina, N. P., Khabarova, M. I., and Bavykin, S. G. (1998) Anal. Biochem. 263, 26.
57. Altman, S. A., Zastawny, T. H., Randers-Eichhorn, L., Cacciuttolo, M. A., Akman, S. A., Dizdaroglu, M., and Rao, G. (1995) Free Radical Biol. Med. 19, 897.
58. Shaham, J., Bomstein, Y., Meltzer, A., Kaufman, Z., Palma, E., and Ribak, J. (1996) Carcinogenesis 17, 121.
59. Kuykendall, J. R., and Bogdanffy, M. S. (1992) Mutat. Res. 238, 131.
60. Amin, D. P., and Witz, G. (2001) Int. J. Toxicol. 20, 69.
61. Fornace, A. J., and Little, J. B. (1979) Cancer Res. 39, 704.
62. Kulcharyk, P. A., and Heinecke, J. W. (2001) Biochemistry 40, 3648.
63. Gebicki, S., and Gebicki, J. M. (1999) Biochem. J. 338, 629.
64. Singh, N., and Lai, H. (1998) Mutat. Res. 400, 313.
65. Mandel, R., Kolomijtseva, G., and Brahms, J. G. (1979) Eur. J. Biochem. 96, 257.
66. Strniste, G. F., and Rall, S. C. (1976) Biochemistry 15, 1712.
67. Blazek, E. R., and Hariharan, P. V. (1984) Photochem. Photobiol. 40, 5.
68. Ramakrishnan, N., Clay, M. E., Xue, L., Evans, H. H., Rodriguez-Antunez, A., and Oleinick, N. L. (1988) Photochem. Photobiol. 48, 297.
69. Villanueva, A., Canete, M., Trigueros, C., Rodriguez-Borlado, L., and Juarranz, A. (1993) Biopolymers 33, 239.
70. Nguyen, K. L., Steryo, M., Kurbanyan, K., Nowitzki, K. M., Butterfield, S. M., Ward, S. R., and Stemp, E. D. A. (2000) J. Am. Chem. Soc. 122, 3585.
71. Amouyal, E., Homsi, A., Chambron, J.-C., and Sauvage, J.-P. (1990) J. Chem. Soc., Dalton Trans. 841.
72. Meyer, T. J., and Taube, H. (1968) Inorg. Chem. 7, 2369.
73. Hartshorn, R. M., and Barton, J. K. (1992) J. Am. Chem. Soc. 114, 5919.
74. Juris, A., Balzani, V., Barigelletti, F., Campagna, S., Belser, P., and von Zelewsky, A. (1988) Coord. Chem. Rev. 84, 85.
75. Kapuscinski, J., and Darzynkiewicz, Z. (1987) J. Biomol. Struct. Dyn. 5, 127.
76. Saucier, J. M., Festy, B., and LePecq, J.-B. (1971) Biochimie 53, 973.
77. Watanabe, T., and Honda, K. (1982) J. Phys. Chem. 86, 2617.
78. Margoliash, E., and Frohwirt, N. (1959) Biochem. J. 71, 570.
79. Revzin, A. (1989) Biotechniques 7, 346.
80. Maniatis, T., and Fritsch, E. F. (1982) Molecular Cloning, Cold Spring Harbor Laboratory, Plainview, NY.
81. Nackerdien, Z., Kasprzak, K. S., Rao, G., Halliwell, B., and Dizdaroglu, M. (1991) Cancer Res., 51, 5837.
82. Ramikrishnan, V. (1997) Annu. Rev. Biophys. Biomol. Struct. 26, 83.
83. Koppenol, W. H., and Margoliash, E. (1982) J. Biol. Chem. 257, 4426.
84. Stemp, E. D. A., Holmlin, R. E., and Barton, J. K. (2000) Inorg. Chim. Acta 297, 88.
85. Fleischer, M. B., Waterman, K. C., Turro, N. J., and Barton, J. K. (1986) Inorg. Chem. 25, 3549.
86. Demas, J. N., Harris, E. W., and McBride, R. P. (1977) J. Am. Chem. Soc. 99, 3547.
87. Petit, J.-M., Denis-Gay, M., and Ratinaud, M.-H. (1993) Biol. Cell 78, 1.
88. Amagasa, J. (1986) J. Radiat. Res. 27, 339.
89. Epe, B., Pflaum, M., and Boiteux, S. (1993) Mutat. Res. 299, 135.
90. Decuyper, J., Houbaherin, N., Calbergbacq, C. M., and Vandevorst, A. (1984) Photochem. Photobiol. 40, 149.
91. Burns, V. W. F. (1969) Arch. Biochem. Biophys. 133, 420.
92. Olmstead, J., III, and Kearns, D. R. (1977) Biochemistry 16, 3647.
93. Atherton, S. J., and Beaumont, P. C. (1984) Photobiochem. Photobiophys. 8, 103.
94. Weatherly, S. C., Yang, I. V., and Thorp, H. H. (2001) J. Am. Chem. Soc. 123, 1236.
95. Atherton, S. J., and Beaumont, P. C. (1987) J. Phys. Chem. 91, 3993.
96. Atherton, S. J., and Beaumont, P. C. (1990) Radiat. Phys. Chem. 36, 819.
97. Hall, D. B., Kelley, S. O., and Barton, J. K. (1998) Biochemistry 37, 15933.
98. Hall, D. B. (1998) Ph.D. Thesis, California Institute of Technology.
99. Williams, T. T., and Barton, J. K. (2002) J. Am. Chem. Soc. 124, 1840.
100. Barnett, R. N., Cleveland, C. L., Joy, A., Landman, U., and Schuster, G. B. (2001) Science 294, 567.
101. Wessels, J. M., Foote, C. S., Ford, W. E., and Rodgers, M. A. J. (1997) Photochem. Photobiol. 65, 96.
102. Eberhardt, M. K. (2001) Reactive Oxygen Metabolites: Chemistry and Medical Consequences, CRC Press, New York.
103. Breen, A. P., and Murphy, J. P. (1995) Free Radical Biol. Med. 18, 1033.
104. Weir Lipton, M. S., Fuciarelli, A. F., Springer, D. L., and Edmonds, C. G. (1996) Radiat. Res. 145, 681-686.
105. Dizdaroglu, M. (1994) Methods Enzymol. 234, 3.
106. Dizdaroglu, M., Gajewski, E., Reddy, P., and Margolis, S. A. (1989) Biochemistry 28, 3625.
107. Nackerdien, Z., Rao, G., Cacciuttolo, M. A., Gajewski, E., and Dizdaroglu, M. (1991) Biochemistry 30, 4873.
108. Olinski, R., Nackerdien, Z., and Dizdaroglu, M. (1992) Arch. Biochem. Biophys. 297, 139.
109. Pruetz, W. A. (1989) Int. J. Radiat. Biol. 56, 21.
110. Zheng, S., Newton, G. L., Gonick, G., Fahey, R. C. and Ward, J. F. (1988) Radiat. Res. 114, 11.