Oxidatively generated base damage to cellular DNA by hydroxyl radical and one-electron oxidants: Similarities and differences

Archives of Biochemistry and Biophysics

Volumn 557, Issue , 2014, Pages 47-54

  Cadet, Jean ^a,b   Wagner, J Richard ^b  

^a CEA GRENOBLE   (France)

^b UNIVERSITY OF SHERBROOKE   (Canada)

Author keywords

Clustered DNA damage; DNA protein cross links; Interstrand cross links; Intrastrand cross links; Oxidized nucleobases; Radical cations; Tandem base lesions

Indexed keywords

CARBON; CATION; CELL DNA; DEOXYRIBONUCLEOSIDE; GUANINE; HYDROXYL RADICAL; OXIDIZING AGENT; PEROXY RADICAL; PROTEIN; PYRIMIDINE DERIVATIVE; THYMINE;

AEROBIC METABOLISM; ARTICLE; DEGRADATION; DNA CROSS LINKING; DNA DAMAGE; DNA MODIFICATION; DNA STRAND BREAKAGE; ELECTRON; ELECTROSPRAY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; OXIDATION; PRIORITY JOURNAL; PROTEIN CROSS LINKING; TANDEM MASS SPECTROMETRY;

CLUSTERED DNA DAMAGE; DNA-PROTEIN CROSS-LINKS; INTERSTRAND CROSS-LINKS; INTRASTRAND CROSS-LINKS; OXIDIZED NUCLEOBASES; RADICAL CATIONS; TANDEM BASE LESIONS;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA DAMAGE; ELECTRONS; HYDROXYL RADICAL; OXIDANTS; OXIDATION-REDUCTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 84904717958     PISSN: 00039861     EISSN: 10960384     Source Type: Journal    
DOI: 10.1016/j.abb.2014.05.001     Document Type: Article

References (126)

1. C. Canugovi, M. Misiak, L.K. Ferrarelli, D.L. Croteau, and V.A. Bohr DNA Repair (Amst) 12 2013 578 587
2. R.S. Sohal, and W.C. Orr Free Radic. Biol. Med. 52 2012 539 555
3. D. Ziech, R. Franco, A. Pappa, and M.I. Panayiotidis Mutat. Res. 711 2011 167 173
4. S. Toyokuni IUBMB Life 60 2008 441 447
5. S. Maynard, S.H. Schurman, C. Harboe, N.C. de Souza-Pinto, and V.A. Bohr Carcinogenesis 30 2009 2 10
6. A. Borghini, T. Cervelli, A. Galli, and M.G. Andreassi Atherosclerosis 230 2013 202 209
7. J. Wang, S. Xiong, C. Xie, W.R. Markesbery, and M.A. Lovell J. Neurochem. 93 2005 953 962
8. Z. Sheng, S. Oka, D. Tsuchimoto, N. Abolhassani, H. Nomaru, K. Sakumi, H. Yamada, and Y. Nakabeppu J. Clin. Invest. 122 2012 4344 4361
9. G. Pratviel, and B. Meunier Chemistry 12 2006 6018 6030
10. J. Cadet, T. Douki, and J.-L. Ravanat Acc. Chem. Res. 41 2008 1075 1083
11. J. Cadet, T. Douki, and J.-L. Ravanat Free Radic. Biol. Med. 40 2010 9 21
12. J.R. Wagner, and J. Cadet Acc. Chem. Res. 43 2010 564 571
13. J. Cadet, J.-L. Ravanat, M. TavernaPorro, H. Menoni, and D. Angelov Cancer Lett. 327 2012 5 15
14. L. Cui, W. Ye, E.G. Prestwich, J.S. Wishnok, K. Taghizadeh, P.C. Dedon, and S.R. Tannenbaum Chem. Res. Toxicol. 26 2013 195 202
15. A.M. Fleming, and C.J. Burrows Chem. Res. Toxicol. 26 2013 593 607
16. J. Cadet, and J.R. Wagner Cold Spring Harb. Perspect. Biol. 5 2013 a012559
17. C. von Sonntag Free-Radical-Induced DNA Damage and its Repair. A Chemical Perspective 2006 Springer-Verlag Berlin, Heidelberg, New-York
18. P.C. Dedon Chem. Res. Toxicol. 21 2008 206 219
19. M. Pitié, and G. Pratviel Chem. Rev. 110 2010 1018 1059
20. A. Azqueta, and A.R. Collins Arch. Toxicol. 87 2013 949 968
21. A.R. Collins Biochim. Biophys. Acta 1840 2013 794 800
22. J. Cadet, T. Douki, and J.-L. Ravanat Mutat. Res. 711 2011 3 12
23. J. Wang, B. Yuan, C. Guerrero, R. Bahde, S. Gupta, and Y. Wang Anal. Chem. 83 2011 2201 2209
24. J. Cadet, T. Douki, J.-L. Ravanat, and J.R. Wagner Bioanal. Rev. 4 2012 55 74
25. T. Bessho, K. Tano, S. Nishimura, and H. Kasai Carcinogenesis 14 1993 1069 1071
26. A.R. Collins Adv. Food Nutr. Res. 68 2013 283 290
27. J.-L. Ravanat, P. Di Mascio, G.R. Martinez, M.H. Medeiros, and J. Cadet J. Biol. Chem. 275 2000 40601 40604
28. J.-P. Pouget, S. Frelon, J.-L. Ravanat, I. Testard, F. Odin, and J. Cadet Radiat. Res. 157 2002 589 595
29. T. Douki, J.-L. Ravanat, J.-P. Pouget, I. Testard, and J. Cadet Int. J. Radiat. Biol. 82 2006 119 127
30. Y. Jiang, H. Hong, H. Cao, and Y. Wang Biochemistry 46 2007 12757 12763
31. H. Hong, H. Cao, and Y. Wang Nucleic Acids Res. 35 2007 7118 7127
32. N. Belmadoui, F. Boussicault, M. Guerra, J.-L. Ravanat, C. Chatgilialoglu, and J. Cadet Org. Biomol. Chem. 8 2010 3211 3219
33. J. Wang, C.L. Clauson, P.D. Robbins, L.J. Niedernhofer, and Y. Wang Aging Cell 11 2012 714 716
34. F. Samson-Thibault, G.S. Madugundu, S. Gao, J. Cadet, and J.R. Wagner Chem. Res. Toxicol. 25 2012 1902 1911
35. G.S. Madugundu, J.R. Wagner, J. Cadet, K. Kropachev, B.H. Yun, N.E. Geacintov, and V. Shafirovich Chem. Res. Toxicol. 26 2013 1031 1033
36. Y. Wang Chem. Res. Toxicol. 21 2008 276 281
37. C. Crean, Y. Uvaydov, N.E. Geacintov, and V. Shafirovich Nucleic Acids Res. 36 2008 742 755
38. C. Chatgilialoglu, C. Ferreri, and M.A. Terzidis Chem. Soc. Rev. 40 2011 1368 1382
39. J. Cadet, T. Douki, and E. Sage Mutat. Res. 571 2005 3 17
40. B. Epe Photochem. Photobiol. Sci. 11 2011 98 106
41. G. Bauer Anticancer Res. 33 2013 3589 3602
42. J. Cadet, T. Douki, J.-L. Ravanat, and P. Di Mascio Photochem. Photobiol. Sci. 8 2009 903 911
43. L.F. Agnez-Lima, A.H.S. Oliveira, A.R.S. Timoteo, K.M. Lima-Bessa, G.R. Martinez, M.H.G. Medeiros, P. Di Mascio, R.S. Galhardo, and C.F.M. Menck Mutat. Res. 751 2012 15 28
44. H. Parker, and C.C. Winterbourn Front. Immunol. 3 2013 1 6
45. T. Nakano, M. Masuda, T. Suzuki, and H. Ohshima Biosci. Biotechnol. Biochem. 76 2012 2208 2213
46. C. Badouard, M. Masuda, H. Nishino, J. Cadet, A. Favier, and J.-L. Ravanat J. Chromatogr. B 827 2005 26 31
47. H. Nikjoo, and P. Girard Int. J. Radiat. Biol. 88 2012 87 97
48. A.G. Georgakilas, P. O'Neill, and R.D. Stewart Radiat. Res. 180 2013 100 109
49. B. Kalyanaraman Redox Biol. 1 2013 244 257
50. J. Cadet, S. Loft, R. Olinski, M.D. Evans, K. Bialkowski, J.R. Wagner, P.C. Dedon, P. Moeller, M.M. Greenberg, and M.S. Cooke Free Radic. Res. 48 2012 367 381
51. R. Misiaszek, C. Crean, A. Joffe, N.E. Geacintov, and V. Shafirovich J. Biol. Chem. 279 2004 32106 32115
52. J. Cadet, M. Berger, T. Douki, and J.-L. Ravanat Rev. Physiol. Biochem. Pharmacol. 131 1997 1 87
53. S. Frelon, T. Douki, A. Favier, and J. Cadet Chem. Res. Toxicol. 16 2003 191 197
54. V. Shafirovich, A. Dourandin, W. Huang, and N.E. Geacintov J. Biol. Chem. 276 2001 24621 24626
55. C.C. Winterbourn Nat. Chem. Biol. 4 2008 278 286
56. D.B. Medinas, G. Cerchiaro, D.F. Trindade, and O. Augusto IUBMB Life 59 2007 255 262
57. P. O'Neill, and P. Wardman Int. J. Radiat. Biol. 85 2009 9 25
58. T. Douki, D. Angelov, and J. Cadet J. Am. Chem. Soc. 123 2001 11360 11366
59. T. Douki, J.-L. Ravanat, D. Angelov, J.R. Wagner, and J. Cadet Top. Curr. Chem. 236 2004 1 25
60. M. Murata, Y. Bansho, S. Inoue, K. Ito, S. Ohnishi, and S. Kawanishi Chem. Res. Toxicol. 14 2001 678 685
61. R. Brem, and P. Karran Photochem. Photobiol. 88 2012 5 13
62. C. Chatgilialoglu, M. D'Angelantonio, M. Guerra, P. Kaloudis, and Q.G. Mulazzani Angew. Chem. Int. Ed. 48 2009 2214 2217
63. H.C. Box, E.E. Budzinski, J.B. Dawidzik, J.C. Wallace, M.S. Evans, and J.S. Gobey Radiat. Res. 145 1996 641 643
64. S. Bellon, J.-L. Ravanat, D. Gasparutto, and J. Cadet Chem. Res. Toxicol. 15 2002 598 606
65. V. Labet, C. Morell, A. Grand, J. Cadet, P. Cimino, and V. Barone Org. Biomol. Chem. 6 2008 3300 3305
66. H. Hong, and Y. Wang Anal. Chem. 79 2007 322 326
67. J. Wang, H. Cao, C. You, B. Yuan, R. Bahde, S. Gupta, C. Nishigori, L.J. Niedernhofer, P.J. Brooks, and Y. Wang Nucleic Acids Res. 40 2012 7368 7374
68. Q. Zhang, and Y. Wang J. Am. Chem. Soc. 125 2003 12595 12802
69. Q. Zhang, and Y. Wang Nucleic Acids Res. 33 2005 1593 1603
70. H. Cao, and Y. Wang Nucleic Acids Res. 35 2007 4833 4844
71. Q. Zhang, and Y. Wang J. Am. Chem. Soc. 126 2004 13287 13297
72. Q. Zhang, and Y. Wang Chem. Res. Toxicol. 18 2005 1897 1906
73. H.C. Box, H.G. Freund, E.E. Budzinski, J.C. Wallace, and A.E. Maccubbin Radiat. Res. 141 1995 91 94
74. E.E. Budzinski, J.D. Dawidzik, J.C. Wallace, H.G. Freund, and H.C. Box Radiat. Res. 142 1995 107 109
75. A.G. Bourdat, T. Douki, S. Frelon, D. Gasparutto, and J. Cadet J. Am. Chem. Soc. 122 2000 4549 4556
76. T. Douki, J. Rivière, and J. Cadet Chem. Res. Toxicol. 15 2002 445 454
77. C. Dupont, C. Patel, J.-L. Ravanat, and E. Dumont Org. Biomol. Chem. 11 2013 3038 3045
78. F. Bergeron, F. Auvré, J.P. Radicella, and J.-L. Ravanat Proc. Natl. Acad. Sci. U.S.A. 107 2010 5528 5533
79. S. Hong, K.N. Carter, K. Sato, and M.M. Greenberg J. Am. Chem. Soc. 129 2007 4089 4098
80. A. Ghosh, A. Joy, G.B. Schuster, T. Douki, and J. Cadet Org. Biomol. Chem. 6 2008 916 928
81. I.S. Hong, K.N. Carter, K. Sato, and M.M. Greenberg J. Am. Chem. Soc. 129 2007 4089 4098
82. H. Huang, S. Imoto, and M.M. Greenberg Biochemistry 48 2009 7833 7841
83. M.L. TavernaPorro, and M.M. Greenberg J. Am. Chem. Soc. 135 2013 16268 16371
84. J.M.N. San Pedro, and M.M. Greenberg J. Am. Chem. Soc. 136 2014 3928 3936
85. B. Balasubramanian, W.K. Pogozelski, and T.D. Tullius Proc. Natl. Acad. Sci. U.S.A. 95 1998 9738 9743
86. W.K. Pogozelski, and T.D. Tullius Chem. Rev. 98 1998 1089 1108
87. C.S. Price, Y. Razskzovskiy, and W.A. Bernhard Radiat. Res. 174 2010 645 649
88. T. Watanabe, T. Bando, Y. Xu, R. Tashiro, and H. Sugiyama J. Am. Chem. Soc. 127 2005 44 45
89. Y. Xu, R. Tashiro, and H. Sugiyama Nat. Protoc. 2 2007 78 87
90. S.M. Hecht J. Nat. Prod. 63 2000 156 168
91. J. Chen, and J. Stubbe Nat. Rev. Cancer 5 2005 102 112
92. S. Purkayastha, J.R. Milligan, and W.A. Bernhard Radiat. Res. 168 2007 357 366
93. W. Chan, B. Chen, L. Wang, K. Taghizadeh, M.S. Demott, and P.C. Dedon J. Am. Chem. Soc. 132 2010 6145 6153
94. M. Roginskaya, R. Mosheni, T.J. Moore, W.A. Bernhard, and Y. Razskazovskiy Radiat. Res. 181 2014 131 137
95. S. Dutta, G. Chowdhury, and K.S. Gates J. Am. Chem. Soc. 129 2007 1852 1853
96. N.E. Price, K.M. Johnson, J. Wang, M.I. Fekry, Y. Wang, and H.S. Gates J. Am. Chem. Soc. 136 2014 3485 3490
97. M.M. Greenberg Acc. Chem. Res. 47 2014 646 655
98. P. Regulus, B. Duroux, P.A. Bayle, A. Favier, J. Cadet, and J.-L. Ravanat Proc. Natl. Acad. Sci. U.S.A. 104 2006 14032 14037
99. P. Regulus, S. Spessotto, M. Gateau, J. Cadet, A. Favier, and J.-L. Ravanat Rapid Commun. Mass Spectrom. 18 2004 2223 2228
100. J.T. Sczepanski, A.C. Jacobs, A. Majumdar, and M.M. Greenberg J. Am. Chem. Soc. 131 2009 11132 11139
101. J.T. Sczepanski, C.N. Hiemstra, and M.M. Greenberg Biorg. Med. Chem. 19 2011 5788 5793
102. I. Kuraoka, C. Bender, A. Romieu, J. Cadet, R.D. Wood, and T. Lindhal Proc. Natl. Acad. Sci. U.S.A. 97 2000 3832 3837
103. P.J. Brooks, D.S. Wise, D.A. Berry, J.V. Kosmoski, M.J. Smerdon, R.L. Somers, H. Mackie, A.Y. Spoonde, E.J. Ackerman, K. Coleman, R.E. Tarone, and J.H. Robbins J. Biol. Chem. 275 2000 22355 22362
104. K. Kropachev, S. Ding, M.A. Terzidis, A. Masi, Z. Liu, Y. Cai, M. Kolbanovskiy, C. Chatgilialoglu, S. Broyde, N.E. Geacintov, and V. Shafirovich Nucleic Acids Res. 42 2014 5020 5032
105. M. D'Errico, E. Parlanti, M. Teson, B.M. Bernades de Jesus, P. Degan, A. Calcagnile, P. Jaruga, M. Bjøras, M. Crescenzi, A.M. Pedrini, J.M. Egly, G. Zambruno, M. Stefanini, M. Dizdaroglu, and E. Dogliotti EMBO J. 25 2006 4305 4315
106. M. D'Errico, E. Parlanti, M. Teson, P. Degan, T. Lemma, A. Calcagnile, I. Iavarone, P. Jaruga, M. Ropolo, A.M. Pedrini, D. Orioli, G. Frosina, G. Zambruno, M. Dizdaroglu, M. Stefanini, and E. Dogliotti Oncogene 26 2007 4336 4343
107. F. Boussicault, P. Kaloudis, C. Caminal, Q.G. Mulazzani, and C. Chatgilialoglu J. Am. Chem. Soc. 130 2008 8377 8385
108. C. Chatgilialoglu, M. D'Angelantonio, G. Kciuk, and K. Bobrowski Chem. Res. Toxicol. 24 2011 2200 2206
109. C.R. Guerrero, J. Wang, and Y. Wang Chem. Res. Toxicol. 26 2013 1361 1368
110. J. Cadet, J.R. Wagner, V. Shafirovich, and N.E. Geacintov Int. J. Radiat. Biol. 2014 (Epub ahead of print)
111. B.H. Yun, N.E. Geacintov, and V. Shafirovich Chem. Res. Toxicol. 24 2011 1144 1152
112. S. Cuesta-López, H. Menoni, D. Angelov, and M. Peyrard Nucleic Acids Res. 39 2011 5276 5283
113. N.R. Attard, and P. Karran Photochem. Photobiol. Sci. 11 2011 62 68
114. R. Brem, I. Daehn, and P. Karran DNA Repair (Amst) 10 2011 869 876
115. S. Barker, M. Weinfeld, and D. Murray Mutat. Res. 580 2005 111 135
116. R. Olinski, Z.Z. Nackerdien, and M. Dizdaroglu Arch. Biochem. Biophys. 297 1992 139 143
117. M. Dizdaroglu, and P. Jaruga Free Radic. Res. 46 2012 387 419
118. S. Barker, M. Weinfeld, J. Zheng, L. Li, and D. Murray J. Biol. Chem. 280 2005 33826 33838
119. M.I. Shoulkamy, T. Nakano, M. Ohshima, R. Hirayama, A. Uzawa, Y. Furusawa, and H. Ide Nucleic Acids Res. 40 2012 e143
120. S. Perrier, J. Hau, D. Gasparutto, J. Cadet, A. Favier, and J.-L. Ravanat J. Am. Chem. Soc. 128 2006 5703 5710
121. K.L. Nguyen, M. Steryo, K. Kurbanyan, K.M. Nowitzki, S.M. Butterfield, S.R. Ward, and E.D.A. Stemp J. Am. Chem. Soc. 122 2000 3585 3594
122. A.L. Madison, Z.A. Perez, P. To, T. Maisonet, E.V. Rios, Y. Trejo, C. Ochoa-Paniagua, A. Reno, and E.D.A. Stemp Biochemistry 51 2012 362 369
123. K. Kurbanyan, K.L. Nguyen, P. To, E.V. Rivas, A.M.K. Lueras, C. Kosinski, M. Steryo, A. Gonzalez, D.A. Mah, and E.D.A. Stemp Biochemistry 42 2003 10269 10281
124. D. Angelov, M. Charra, C.W. Müller, J. Cadet, and S. Dimitrov Photochem. Photobiol. 77 2003 592 596
125. H. Kasai, Z. Yamaizumi, M. Berger, and J. Cadet J. Am. Chem. Soc. 114 1992 9692 9694
126. Y. Rokhlenko, J. Cadet, N.E. Geacintov, and V. Shafirovich J. Am. Chem. Soc. 136 2014 4955 4962