Oxidatively Generated Damage to Isolated and Cellular DNA

The Chemical Biology of DNA Damage

Volumn , Issue , 2010, Pages 53-80

  Cadet, Jean ^a   Douki, Thierry ^a   Ravanat, Jean Luc ^a  

^a CEA GRENOBLE   (France)

Author keywords

DNA damage; Hydroxyl radical; Oxidatively generated damage; Secondary oxidation; Single base damage; Tandem base lesion

Indexed keywords

EID: 79956225143     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630110.ch3     Document Type: Chapter

References (147)

1. Cadet, J., Berger, M., Douki, T., and Ravanat, J.-L. (1997) Oxidative damage to DNA: formation, measurement and biological significance. Rev. Physiol. Biochem. Pharmacol., 131, 1-87.
2. Cadet, J., Douki, T., Gasparutto, D., and Ravanat, J.-L. (2003) Oxidative damage to DNA: formation, measurement and biochemical features. Mutat. Res., 531, 5-23.
3. Douki, T., Ravanat, J.-L., Angelov, D., Wagner, J.R., and Cadet, J. (2004) Effects of duplex stability on charge transfer efficiency within DNA. Top. Curr. Chem., 236, 1-25.
4. Gimisis, T. and Cismas, C. (2006) Isolation, characterization, and independent synthesis of guanine oxidation products. Eur. J. Org. Chem., 1351-1378.
5. Pratviel, G. and Meunier, B. (2006) Guanine oxidation: one-and two-electron reactions. Chem. Eur. J., 12, 6018-6030.
6. Neeley, W.L. and Essigmann, J.M. (2006) Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products. Chem. Res. Toxicol., 19, 491-505.
7. Cadet, J., Ravanat, J.-L., Martinez, G.R., Medeiros, M.H.G., and Di Mascio, P. (2006) Singlet oxygen oxidation of isolated and cellular DNA: product formation and mechanistic insights. Photochem. Photobiol., 82, 1219-1225.
8. Cadet, J. and Di Mascio, P. (2006) Peroxides in biological systems, in Functional Groups in Organic Chemistry-The Chemistry of Peroxides, vol. 2 (ed. Z. Rappoport), John Wiley & Sons, Inc., Hoboken, NJ, pp. 915-1000.
9. Cadet, J., Douki, T., and Ravanat, J.-L. (2008) Oxidatively generated damage to the guanine moiety of DNA: mechanistic aspects and formation in cells. Acc. Chem. Res., 41, 1075-1083.
10. Pogozelski, W.K. and Tullius, T.D. (1998) Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar moiety. Chem. Rev., 98, 1089-1107.
11. Aydogan, B., Marshall, D.T., Swarts, S.G., Turner, J.E., Boone, A.J., Richards, N.G., and Bolch, W.E. (2002) Site-specific OH attack to the sugar moiety of DNA: a comparison of experimental data with computational simulation. Radiat. Res., 157, 38-44.
12. Dedon, P.C. (2008) The chemical toxicology of 2-deoxyribose oxidation in DNA. Chem. Res. Toxicol., 21, 206-219.
13. Steenken, S. (1989) Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e-and OH adducts. Chem. Rev., 89, 503-520.
14. Von Sonntag C. (ed.) (2006) Free-Radical Induced DNA Damage and its Repair: A Chemical Perspective, Springer, Heidelberg.
15. Grand, A., Morell, C., Labet, V., Cadet, J., and Eriksson, L.A. (2007) • H atom and • OH reactions with 5-metylcytosine. J. Phys. Chem. A, 111, 8968-8972.
16. Munk, B.H., Burrows, C.J., and Schlegel, H.B. (2007) Exploration of mechanisms for the transformation of 8-hydroxyguanine radical to FAPyG by density functional theory. Chem. Res. Toxicol., 20, 432-444.
17. Munk, B.H., Burrows, C.J., and Schlegel, H.B. (2008) An exploration of mechanisms for the transformation of 8-oxoguanine to guanidinohydantoin and spiroiminodihydantoin by density functional theory. J. Am. Chem. Soc., 130, 5245-5256.
18. Labet, V., Grand, A., Cadet, J., and Eriksson, L.A. (2008) Deamination of the radical cation of base moiety of 2 ′-deoxycytidine: a theoretical study. ChemPhysChem, 9, 1195-1203.
19. Labet, V., Morell, C., Grand, A., Cadet, J., Cimino, P., and Barone, V. (2008) Formation of cross-linked adducts between guanine and thymine mediated by hydroxyl radical and one-electron oxidation: a theoretical study. Org. Biomol. Chem., 6, 3300-3305.
20. Cadet, J. and Berger, M. (1985) Radiation-induced decomposition of the purine bases within DNA and related model compounds. Int. J. Radiat. Biol., 47, 127-143.
21. Hariharan, P.V. and Cerutti, P.A. (1972) Formation and repair of γ-ray induced thymine damage in Micrococcus radiodurans. J. Mol. Biol., 66, 65-81.
22. Cadet, J., Douki, T., and Ravanat, J.-L. (1997) Artifacts associated with the measurement of oxidized DNA bases. Environ. Health Perspect., 105, 1034-1039.
23. Halliwell, B. and Dizdaroglu, M. (1992) The measurement of oxidative damage to DNA by HPLC and GC-MS techniques. Free Radic. Res. Commun., 16, 75-87.
24. Ravanat, J.-L., Douki, T., Duez, P., Gremaud, E., Herbert, K., Hofer, T., Lassere, L., Saint-Pierre, C., Favier, A., and Cadet, J. (2002) Cellular background of 8-oxo-7,8-dihydro-2 ′-deoxyguanosine: an isotope based method to evaluate artefactual oxidation of DNA during its extraction and subsequent work-up. Carcinogenesis, 23, 1911-1918.
25. Chao, M.R., Yen, C.C., and Hu, C.W. (2008) Prevention of artifactual oxidation in determination of cellular 8-oxo-7,8-dihydro-2 ′-deoxyguanosine by isotope-dilution LC-MS/MS with automated solid-phase extraction. Free Radic. Biol. Med., 44, 464-473.
26. Collins, A.R., Cadet, J., Möller, L., Poulsen, H., and Vina, J. (2004) Are we sure we know how to measure 8-oxo-7,8-dihydroguanine in DNA from human cells? Arch. Biochem. Biophys., 423, 57-65.
27. ESCODD (2005) Establishing the background level of base oxidation in human lymphocyte DNA: results of an inter-laboratory validation study. FASEB J., 19, 82-84.
28. Floyd, R.A., Watson, J.J., Wong, P.K., Altmiller, D.H., and Rickard, R.C. (1986) Hydroxyl free radical adduct of deoxyguanosine: sensitive detection and mechanism of formation. Free Radic. Res. Commun., 1, 163-172.
29. Kasai, H. (1997) Analysis of a form of oxidative DNA damage, 8-hydroxy-2 ′-deoxyguanosine, as a marker of cellular oxidative stress during carcinogenesis. Mutat. Res., 387, 147-163.
30. Ravanat, J.L., Duretz, B., Guiller, A., Douki, T., and Cadet, J. (1998) Isotope dilution high-performance liquid chromatography-electrospray tandem mass spectrometry assay for the measurement of 8-oxo-7,8-dihydro-2 ′-deoxyguanosine in biological samples. J. Chromatogr. B, 715, 349-356.
31. Badouard, C., Ménézo, Y., Panteix, G., Ravanat, J.-L., Douki, T., and Favier, A. (2008) Determination of new types of DNA lesions in human sperm. Zygote, 16, 9-13.
32. Cadet, J. and Vigny, P. (1990) The photochemistry of nucleic acids, in Bioorganic Photochemistry vol. 1 (ed. H. Morrison), John Wiley & Sons, Inc., New York, pp. 1-272.
33. Martinez, G.R., Ravanat, J.-L., Medeiros, M.H.G., Cadet, J., and Di Mascio, P. (2000) Synthesis of a naphthalene endoperoxide as a source of 18 O-labeled singlet oxygen for mechanistic studies. J. Am. Chem. Soc., 122, 10212-10213.
34. Ravanat, J.L., Di Mascio, P., Martinez, G.R., Medeiros, M.H., and Cadet, J. (2000) Singlet oxygen induces oxidation of cellular DNA. J. Biol. Chem., 275, 40601-40604.
35. Sheu, C. and Foote, C.S. (1993) Endoperoxide formation in a guanosine derivative. J. Am. Chem. Soc., 115, 10446-10447.
36. Sheu, C., Kang, P., Khan, S., and Foote, C.S. (2002) Low-temperature photosensitized oxidation of a guanosine derivative and formation of an imidazole ring-opened product. J. Am. Chem. Soc., 124, 3905-3913.
37. Kang, P. and Foote, C.S. (2002) Formation of transient intermediates in low-temperature photosensitized oxidation of an 8-13 C-guanosine. J. Am. Chem. Soc., 124, 4865-4873.
38. Ravanat, J.-L., Saint-Pierre, C., Di Mascio, P., Martinez, G.R., Medeiros, M.H.G., and Cadet, J. (2001) Damage to isolated DNA mediated by singlet oxygen. Helv. Chim. Acta, 84, 3702-3709.
39. Niles, J.C., Wishnok, J.S., and Tannenbaum, S.R. (2001) Spiroiminodi hydantoin is the major product of 8-oxo-7,8-dihydroguanosine with peroxynitrite in the presence of thiols and guanosine oxidation by methylene blue. Org. Lett., 3, 963-936.
40. Ye, Y., Muller, J.G., Luo, W., Mayne, C.L., Shallop, A.J., Jones, R.A., and Burrows, C.J. (2003) Formation of 13 C-, 15 N-, and 18 O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen. Implications for structure and mechanism. J. Am. Chem. Soc., 125, 13926-13927.
41. Boiteux, S., Gajewski, E., Laval, J., and Dizdaroglu, M. (1992) Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry, 31, 106-110.
42. Ravanat, J.-L., Sauvaigo, S., Caillat, S., Martinez, G.R., Medeiros, M.H.G., Di Mascio, P., Favier, A., and Cadet, J. (2004) Singlet-oxygen-mediated damage to cellular DNA determined by the comet assay associated with DNA repair enzymes. B iol. Chem., 385, 7-20.
43. Cadet, J., Douki, T., and Sage, E. (2005) Ultraviolet radiation-mediated damage to cellular DNA. Mutat. Res., 571, 3-17.
44. Mouret, S., Baudouin, C., Charveron, M., Favier, A., Cadet, J., and Douki, T. (2006) Cyclobutane pyrimidine dimers are predominant DNA lesions in whole human skin exposed to UVA radiation. Proc. Natl. Acad. Sci. USA, 103, 13765-13770.
45. Pouget, J.-P., Douki, T., Richard, M.-J., and Cadet, J. (2000) DNA damage induced in cells by γ and UVA radiation as measured by HPLC/GC-MS and HPLC-EC and comet assay. Chem. Res. Toxicol., 13, 541-549.
46. Pouget, J.-P., Ravanat, J.-L., Douki, T., Richard, M.-J., and Cadet, J. (1999) Measurement of DNA base damage in cells exposed to low doses of γ radiation: comparison between the HPLC/ECD and the comet assays. Int. J. Radiat. Biol., 75, 51-58.
47. Pouget, J.P., Frelon, S., Ravanat, J.-L., Testard, I., Odin, F., and Cadet, J. (2002) Formation of modified DNA to DNA in cells exposed to either γ radiation or high-LET particles. Radiat. Res., 157, 589-595.
48. Douki, T., Ravanat, J.L., Pouget, J.-P., Testard, I., and Cadet, J. (2006) Minor contribution of direct ionization to DNA base damage induced by heavy ions. Int. J. Radiat. Biol., 82, 119-127.
49. Frelon, S., Douki, T., Ravanat, J.-L., Pouget, J.-P., Tornabene, C., and Cadet, J. (2000) High-performance liquid chromatography-tandem mass spectrometry measurement of radiation-induced base damage to isolated and cellular DNA. Chem. Res. Toxicol., 13, 1002-1010.
50. Von Sonntag, C. (ed.) (1987) The Chemical Basis of Radiation Biology, Taylor & Francis, London.
51. Fujita, S. and Steenken, S. (1981) Pattern of OH radical addition to uracil and methyl-and carboxyl-substituted uracils. Electron transfer of OH adducts with N, N, N ′, N ′-tetramethyl-p-phenylenediamine and tetranitromethane. J. Am. Chem. Soc., 103, 2540-2545.
52. Jovanovic, S.V. and Simic, M.G. (1986) Mechanism of OH radical reactions with thymine and uracil derivatives. J. Am. Chem. Soc., 108, 5968-5972.
53. Isildar, M., Schuchmann, M.N., Schulte-Frohlinde, D., and von Sonntag, C. (1982) Oxygen uptake in the radiolysis of aqueous solutions of nucleic acids and their constituents. Int. J. Radiat. Biol., 41, 525-533.
54. Wagner, J.R., Van Lier, J.E., and Johnston, L.J. (1990) Quinone sensitized electron transfer photooxidation of nucleic acids: chemistry of thymine and thymidine radical cations in aqueous solution. Photochem. Photobiol., 52, 333-343.
55. Cadet, J. and Téoule, R. (1975) Radiolyse γ de la thymidine en solution aqueuse aérée. 1.-Identification des hydroperoxydes. B ull. Soc. Chim. Fr., 879-884.
56. Wagner, J.R., Van Lier, J.E., Berger, M., and Cadet, J. (1994) Thymidine hydroperoxides. Structural assignment, conformational features, and thermal decomposition in water. J. Am. Chem. Soc., 116, 2235-2242.
57. Davies, A.G. (1961) O-O heterolysis: intermolecular nucleophilic substitution at oxygen, in Organic Peroxides, Butterworth, London, pp. 128-142.
58. Lutsig, M.J., Cadet, J., Boorstein, R.J., and Teebor, G.W. (1992) Synthesis of the diastereomers of thymidine glycol, determination of concentrations and rates of interconversion of their cis-trans epimers at equilibrium and demonstration of differential alkali lability within DNA. Nucleic Acids Res., 20, 4839-4845.
59. Douki, T., Delatour, T., Paganon, F., and Cadet, J. (1996) Measurement of oxidative damage at pyrimidine bases in γ-irradiated DNA. Chem. Res. Toxicol., 9, 1145-1151.
60. Douki, T., Rivière, J., and Cadet, J. (2002) DNA tandem lesions containing 8-oxo-7,8-dihydroguanine and formamide residues arise from intramolecular addition of thymine peroxyl radical to guanine. Chem. Res. Toxicol., 15, 445-454.
61. Douki, T., Martini, R., Ravanat, J.L., Turesky, R.J., and Cadet, J. (1997) Measurement of 2,6-diamino-4-hydroxy-5-formamidopyrimidine and 8-oxo-7,8-dihydroguanine in isolated DNA exposed to γ radiation in aqueous solution. Carcinogenesis, 18, 2385-2891.
62. Candeias, L.P. and Steenken, S. (2000) Reaction of HO • with guanine derivatives in aqueous solution: formation of two different redox-active OH-adduct radical and their unimolecular transformation reactions. Properties of G(-H) •. Chem. Eur. J., 6,475-484.
63. Misiaszek, R., Crean, C., Joffe, A., Geacintov, N.E., and Shafirovich, V. (2004) Oxidative DNA damage associated with combination of guanine and superoxide radicals and repair mechanisms via radical trapping. J. Biol. Chem., 279, 32106-32115.
64. Cadet, J., Berger, M., Buchko, G.W., Joshi, P., Raoul, S., and Ravanat, J.-L. (1994) 2,2-Diamino-4-[(3,5-di-O-acetyl-2 ′-deoxy-β-d-erythro-pentofuranosyl) amino]-5-(2 H)-oxazolone. J. Am. Chem. Soc., 116, 7403-7404.
65. Raoul, S., Berger, M., Buchko, G.W., Joshi, P.C., Morin, B., Weinfeld, M., and Cadet, J. (1996) 1 H, 13 C and 15 N NMR analysis and chemical features of the two main radical oxidation products of 2 ′-deoxyguanosine: oxazolone and imidazolone nucleosides. J. Chem. Soc. Perkin Trans. 2, 371-381.
66. Vialas, C., Pratviel, G., Claporols, C., and Meunier, B. (1998) Efficient oxidation of 2 ′-deoxyguanosine by Mn-TMPyP/KHSO 5 to imidazolone dIz without formation of 8-Oxo-dG. J. Am. Chem. Soc., 120, 11548-11553.
67. Matter, B., Malejka-Giganti, D., Csallany, A.S., and Tretyakova, N. (2006) Quantitative analysis of the oxidative DNA lesion, 2,2-diamino-4-[(-2-deoxy-β-d-erythro-pentofuranosyl) amino]-5(2 H)-oxazolone (oxazolone) in vitro and in vivo by isotope dilution-capillary HPLC-ESI-MS/MS. Nucleic Acids Res., 34, 5449-5460.
68. Berger, M., De Hazen, M., Nejjari, A., Fournier, J., Guignard, J., Pezerat, H., and Cadet, J. (1993) Radical oxidation reactions of the purine moiety of 2 ′-deoxyribonucleosides and DNA by iron-containing minerals. Carcinogenesis, 14, 41-46.
69. Raoul, S., Bardet, M., and Cadet, J. (1995) Gamma irradiation of 2 ′-deoxyadenosine in oxygen-free aqueous solutions: identification and conformational features of formamidopyrimidine nucleoside derivatives. Chem. Res. Toxicol., 8, 924-933.
70. Frelon, S., Douki, T., and Cadet, J. (2002) Radical oxidation of the adenine moiety of nucleoside and DNA: 2-hydroxy-2 ′-deoxyadenosine is a minor decomposition product. Free Radic. Res., 36, 499-508.
71. Mori, T. and Dizdaroglu, M. (1994) Ionizing radiation causes greater DNA base damage in radiation-sensitive mutant M10 cells than in parent mouse lymphoma L5178Y cells. Radiat. Res., 140, 65-90.
72. Mori, T., Hori, Y. and Dizdaroglu, M. (1993) DNA base damage generated in vivo in hepatic chromatin of mice upon whole body γ-irradiation. Int. J. Radiat. Biol., 64, 645-650.
73. Becker, D. and Sevilla, M. (1993) The chemical consequences of radiation damage to DNA. Adv. Radiat. Biol., 17, 121-180.
74. Symons, M.C.R. (1995) Electron-spin-resonance studies of radiation-damage to DNA and proteins. Radiat. Phys. Chem., 45, 837-845.
75. Angelov, D., Spassky, A., Berger, M., and Cadet, J. (1997) High-intensity UV laser photolysis of DNA and purine 2 ′-deoxyribonucleosides: formation of 8-oxopurine damage and oligonucleotide strand cleavage as revealed by HPLC and gel electrophoresis studies. J. Am. Chem. Soc., 119, 11373-11360.
76. Douki, T., Angelov, D., and Cadet, J. (2001) UV laser photolysis of DNA: effect of duplex stability on charge transfer efficiency. J. Am. Chem. Soc., 123, 11360-11366.
77. Ballmaier, D. and Epe, B. (2006) DNA damage by bromate: mechanism and consequences. Toxicology, 221, 166-171.
78. Joffe, A., Geacintov, N.E., and Shafirovich, V. (2003) DNA lesions derived from the site selective oxidation of guanine by carbonate radical anions. Chem. Res. Toxicol., 16, 1528-1538.
79. Medinas, D.B., Cerchiaro, G., Trindale, D.F., and Augusto, O. (2007) The carbonate radical and related oxidants derived from bicarbonate buffer. IUBMB Life, 59, 255-262.
80. Kasai, H., Yamaizumi, Z., Berger, M., and Cadet, J. (1992) Photosensitized formation of 7,8-dihydro-8-oxo-2 ′-deoxyguanosine (8-hydroxy-2 ′-deoxyguanosine) in DNA by riboflavin: a non singlet oxygen mediated reaction. J. Am. Chem. Soc., 114, 9692-9694.
81. Decarroz, C., Wagner, J.R., Van Lier, J.E., Krishna, C.M., Riesz, P., and Cadet, J. (1986) Sensitized photo-oxidation of thymidine by 2-methyl-1,4-naphthoquinone. Characterization of the stable photoproducts. Int. J. Radiat. Biol., 50, 491-505.
82. Giese, B. and Spichty, M. (2000) Long-distance charge transport through DNA: quantification and extension of the hopping model. ChemPhysChem, 1, 195-198.
83. Schuster, G.B. (2000) Long-range charge transfer in DNA: transient structural distortions control the distance dependence. Acc. Chem. Res., 33, 2253-2260.
84. Boon, E.M. and Barton, J.K. (2002) Charge transfer in DNA. Curr. Opin. Struct. Biol., 12, 320-329.
85. Osakada, Y., Kawai, K., Fujitsuka, M., and Majima, T. (2006) Charge transfer through DNA nanoscaled assembly programmable with DNA building blocks. Proc. Natl. Acad. Sci. USA, 103, 18072-18076.
86. Henderson, J.P., Byun, J., and Heinecke, J.W. (1999) Molecular chlorine generated by the myeloperoxidase hydrogen-chloride system of phagocytes produces 5-chlorocytosine in bacterial DNA. J. Biol. Chem., 274, 33440-33448.
87. Suzuki, T., Friesen, M.D., and Ohshima, H. (2003) Identification of products formed by reaction of 3 ′,5 ′-di-O-actyl-2 ′-deoxyguanosine with hypochlorous acid or a myeloperoxidase-H 2 O 2-Cl-system. Chem. Res. Toxicol., 16, 382-389.
88. Badouard, C., Masuda, M., Nishino, H., Cadet, J., Favier, A., and Ravanat, J.-L. (2005) Detection of chlorinated DNA and RNA nucleosides by HPLC coupled to mass spectrometry as potential biomarkers of inflammation. J. Chromatogr. B, 827, 26-31.
89. Masuda, M., Suzuki, T., Friesen, M.D., Ravanat, J.-L., Cadet, J., Pignatelli, B., Nishino, H., and Ohshima, H. (2001) Chlorination of guanosine and other nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils. J. Biol. Chem., 276, 40486-40496.
90. Buyn, J., Henderson, J.P., and Heinecke, J.W. (2003) Identification and quantification of mutagenic halogenated cytosines by gas chromatography, fast atom bombardment, and electrospray ionization tandem mass spectrometry. Anal. Biochem., 317, 201-209.
91. Badouard, C., Douki, T., Faure, P., Halimi, S., Cadet, J., Favier, A., and Ravanat, J.-L. (2005) DNA lesions as biomarkers of inflammation and oxidative stress: a preliminary evaluation, in Free Radicals and Diseases, Gene Expression, Cellular Metabolism and Pathophysiology (ed. T. Grune), IOS Press, Amsterdam, pp. 1-9.
92. Olive, P.L. (2009) Impact of the comet assay in radiobiology. Mutat. Res., 681, 13-23.
93. Gradzka, I. (2005) A non-radioactive, PGFE-based assay for low levels of DNA double-strand breaks in mammalian cells. DNA Repair, 4, 1129-1139.
94. Muslimovic, A., Ismail, I.H., Gao, Y., and Hammarsten, O. (2008) An optimized method for measurement of γ-H2AX in blood mononuclear and cultured cells. Nat. Protoc., 3, 1187-1193.
95. Box, H.C., Budzinski, E.E., Freund, H.G., Evans, M.S., Patrzyc, H.B., Wallace, J.C., and MacCubbin, A.E. (1993) Vicinal lesions in X-irradiated DNA? Int. J. Radiat. Biol., 64, 261-263.
96. Box, H.C., Freund, H.G., Budzinski, E.E., Wallace, J.C., and MacCubbin, A.E. (1995) Free radical-induced double base lesions. Radiat. Res., 141, 91-94.
97. Bourdat, A.G., Douki, T., Frelon, S., Gasparutto, D., and Cadet, J. (2000) Tandem base lesions are generated by hydroxyl radical within isolated DNA in aerated aqueous solution. J. Am. Chem. Soc., 122, 4549-4556.
98. Hong, I.S., Carter, K.N., Sato, K., and Greenberg, M.M. (2007) Characterization and mechanism of formation of tandem lesions in DNA by a nucleobase peroxyl radical. J. Am. Chem. Soc., 129, 4089-4098.
99. Ghosh, A., Joy, A., Schuster, G.B., Douki, T., and Cadet, J. (2008) Selective one-electron oxidation of duplex DNA oligomers: reactions at thymines. Org. Biomol. Chem., 6, 916-928.
100. Romieu, A., Bellon, S., Gasparutto, D., and Cadet, J. (2000) Synthesis and UV photolysis of oligodeoxynucleotides that contain 5-(phenyl-thiomethyl)-2 ′-deoxyuridine: a specific photolabile precursor of 5-(2 ′-deoxyuridilyl)methyl radical. Org. Lett., 2, 1085-1088.
101. Bellon, S., Ravanat, J.-L., Gasparutto, D., and Cadet, J. (2002) Cross-linked thymine-purine base tandem lesions: synthesis, characterization, and measurement in γ-irradiated DNA. Chem. Res. Toxicol., 15, 598-606.
102. Bellon, S., Gasparutto, D., Saint-Pierre, C., and Cadet, J. (2006) Guanine-thymine intrastrand cross-linked lesion containing oligonucleotides: from chemical synthesis to in vitro enzymatic replication. Org. Biomol. Chem., 4, 3831-3837.
103. Hong, H., Cao, H., and Wang, Y. (2006) Identification and quantification of a guanine-thymine instrastrand cross-link lesion induced by Cu(II) H 2 O 2 /ascorbate. Chem. Res. Toxicol., 19, 614-621.
104. Wang, Y. (2008) Bulky DNA lesions induced by reactive oxygen species. Chem. Res. Toxicol., 21, 276-281.
105. Zhang, Q. and Wang, Y. (2003) Independent generation of 5-(2 ′-deoxycytidinyl) methyl radical and the formation of a novel crosslink lesion between 5-methylcytosine and guanine. J. Am. Chem. Soc., 125, 12795-12802.
106. Zhang, Q. and Wang, Y. (2005) Generation of 5-(2 ′-deoxycytidyl)methyl radical and the formation of intrastrand cross-link lesions in oligodeoxyribonucleotides. N ucleic Acids Res., 33, 1593-1603.
107. Cao, H. and Wang, Y. (2007) Quantifi-cation of oxidative single-base and intrastrand cross-link lesions in unmethylated and CpG-methylated DNA induced by Fenton-type reagents. Nucleic Acids Res., 35, 4833-4844.
108. Xerri, B., Morell, C., Grand, A., Cadet, J., Cimino, P., and Barone, V. (2006) Radiation-induced formation of DNA intrastrand crosslinks between thymine and adenine bases. A theoretical approach. Org. Biomol. Chem., 4, 3986-3992.
109. Gu, C. and Wang, Y. (2004) LC-MS/MS identification and yeast polymerase η bypass of a novel γ-irradiation-induced intrastrand cross-link lesion G[8-5]C. Biochemistry, 43, 6745-6750.
110. Jiang, Y., Hong, H., Cao, H., and Wang, Y. (2007) In vivo formation and in vitro replication of a guanine-thymine intrastrand cross-link lesion. Biochemistry, 46, 12757-12763.
111. Hong, H., Cao, H., and Wang, Y. (2007) Formation and genotoxicity of a guanine-cytosine intrastrand cross-link lesion in vivo. Nucleic Acids Res., 35, 7118-7127.
112. Chen, B., Zhou, X., Taghizadeh, K., Chen, J., Stubbe, J., and Dedon, P.C. (2007) GC/MS methods to quantify the 2-deoxypentos-4-ulose and 3 ′-phosphoglycolate pathways of 4 ′ oxidation of 2-deoxyribose in DNA: application to DNA damage produced by γ radiation and bleomycin. Chem. Res. Toxicol., 20, 1701-1708.
113. Chatgilialoglu, C. and Gimisis, T. (1998) Fate of the C-14 peroxyl radical in the 2 ′-deoxyurdine system. Chem. Commun., 1249-1259.
114. Dedon, P.C. and Goldberg, I.H. (1992) Free-radical mechanism involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem. Res. Toxicol., 5, 311-322.
115. Regulus, P., Spessotto, S., Gateau, M., Cadet, J., Favier, A., and Ravanat, J.-L. (2004) Detection of new radiation-induced DNA degradation lesions by liquid chromatography coupled to tandem mass spectrometry. Rapid Commun. Mass Spectrom., 18, 2223-2228.
116. Regulus, P., Duroux, B., Bayle, P.-A., Favier, A., Cadet, J., and Ravanat, J.-L. (2007) Oxidation of the sugar moiety of DNA by ionizing radiation or bleomycin could induce the formation of a cluster DNA lesion. Proc. Natl. Acad. Sci. USA, 104, 14032-14037.
117. Sczepanski, J.T., Jacobs, A.C., and Greenberg, M.M. (2008) Self promoted interstrand cross-link formation by an abasic site. J. Am. Chem. Soc., 130, 9646-9647.
118. Mariaggi, N., Cadet, J., and Téoule, R. (1976) Cyclisation radicalaire de la désoxy-2 ′-adénosine en solution aqueuse, sous l'effet du rayonnement γ. Tetrahedron, 32, 2385-2387.
119. Keck, K. (1968) Bildung von cyclonucleotiden bei bestrahlung wassiriger losungen von purinnucleotide. Z. Naturforsch., 23b, 1034-1043.
120. Raleigh, J.A., Kremers, W., and Whitehouse, R. (1976) Radiation chemistry of nucleotides: 8,5 ′-cyclonucleotide formation and phosphate release initiated by hydroxyl radical attack on adenosine monophosphates. Radiat. Res., 65, 414-422.
121. Dizdaroglu, M. (1986) Free-radical-induced formation of an 8,5 ′-cyclo-2 ′-deoxyguanosine moiety in deoxyribonucleic acid. Biochem. J., 238, 247-254.
122. Chatgilialoglu, C., Guerra, M., and Mulazzani, Q.G. (2003) Model studies of DNA C5 ′ radicals. Selective generation and reactivity of 2 ′-deoxyadenos-5 ′-yl radical. J. Am. Chem. Soc., 125, 3839-1848.
123. Navacchia, M.L., Chatgilialoglu, C., and Montevecchi, P.C. (2006) C5 ′-Adenosyl radical cyclization. A stereochemical investigation. J. Org. Chem., 71, 4445-4452.
124. Chatgilialoglu, C., Bazzanini, R., Jimenez, L.B., and Miranda, M. (2007) (5 ′ S)-and (5 ′ R)-5 ′,8-cyclo-2 ′-deoxyguanosine: mechanistic insights on the 2 ′-deoxyguanosin-5 ′-yl radical cyclization. C hem. Res. Toxicol., 20, 1820-1824.
125. Dizdaroglu, M., Jaruga, P., and Rodriguez, H. (2001) Identification and quantification of 8,5 ′-cyclo-2 ′-deoxyadenosine in DNA by liquid chromatography mass spectrometry. Free Radic. Biol. Med., 30, 774-784.
126. Jaruga, P., Birincioglu, M., Rodriguez, H., and Dizdaroglu, M. (2002) Mass spectrometric assays for the tandem lesion 8,5 ′-cyclo-2 ′ deoxyguanosine in mammalian DNA. Biochemistry, 41, 3703-3711.
127. Jaruga, P., Theruvathu, J., Dizdaroglu, M., and Brooks, P.J. (2004) Complete release of (5 ′ S)-8,5 ′-cyclo-2 ′-deoxyadenosine from dinucleotides, oligonucleotides and DNA, and direct comparison of its levels in cellular DNA with other oxidatively induced DNA lesions. Nucleic Acids Res., 32, e87.
128. Brooks, P.J. (2007) The case for 8,5 ′-cyclopurine-2 ′-deoxynucleosides as endogenous lesions that cause neurodegeneration in xeroderma pigmentosum. N euroscience, 145, 1407-1417.
129. Boussicault, F., Kaladis, P., Caminal, C., Mulazzani, Q.G., and Chatgilialoglu, C. (2008) The fate of the C5 ′ radicals of purine nucleosides under oxidative conditions. J. Am. Chem. Soc., 130, 8377-8385.
130. D'Errico, M., Parlanti, E., Teson, M., Bernades De Jesus, B.M., Degan, P., Calcagnile, A., Jaruga, P., Bjørås, M., Crescenzi, M., Pedrini, A.M., Egly, J.-M., Zambruno, G., Stefanini, M., Dizdaroglu, M., and Dogliotti, E. (2006) New functions of XPC in the protection of human skin cells from oxidative damage. EMBO J., 25, 4305-4315.
131. D'Errico, M., Parlanti, E., Teson, M., Degan, P., Lemma, T., Calcagnile, A., Iavarone, I., Jaruga, P., Ropolo, M., Pedrini, A.M., Orioli, D., Frosina, G., Zambruno, G., and Stefanini, M.E. (2007) The role of CSA in the response to oxidative DNA damage in human cells. Oncogene, 26, 4336-4343.
132. Steenken, S. and Jovanovic, S.V. (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solutions. J. Am. Chem. Soc., 119, 617-618.
133. Bernstein, R., Prat, F., and Foote, C.S. (1999) On the mechanism of DNA cleavage by fullerenes investigated in model systems. Electron transfer from guanosine and 8-oxoguanosine to C 60. J. Am. Chem. Soc., 121, 464-465.
134. Luo, W., Muller, J.G., Rachlin, E.M., and Burrows, C.J. (2000) Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett., 2, 613-616.
135. Luo, W., Muller, J.G., Rachlin, E.M., and Burrows, C.J. (2001) Characterization of hydantoin products from one-electron oxidation of 8-oxo-7,8-dihydroguanosine in a nucleoside model. Chem. Res. Toxicol., 14, 927-938.
136. Luo, W., Muller, J.G., and Burrows, C.J. (2001) The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org. Lett., 3, 2801-2804.
137. Ravanat, J.-L., Saint-Pierre, C., and Cadet, J. (2003) One-electron oxidation of the guanine moiety of 2 ′-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2 ′-deoxyguanosine. J. Am. Chem. Soc., 125, 2030-2031.
138. Crean, C., Geacintov, N.E., and Shafirovich, V. (2005) Oxidation of 8-oxo-7,8-dihydroguanine by carbonate radical anions; insight from oxygen-18 labeling experiments. Angew. Chem. Int. Ed., 44, 5057-5060.
139. McCallum, J.E.B., Kuniyoshi, C.Y., and Foote, C.S. (2004) Characterization of 5-hydroxy-8-oxo-7,8-dihydroguanosine in the photosensitized oxidation of 8-oxo-7,8-dihydroguanosine and its rearrangement to spiroiminodihydantoin. J. Am. Chem. Soc., 126, 16777-16782.
140. Slade, P.G., Hailer, M.K., Martin, B.D., and Sugden, K.D. (2005) Guanine-specific oxidation of double-stranded DNA by Cr(VI) and ascorbic acid forms spiroiminodihydantoin and 8-oxo-2 ′-deoxyguanosine. Chem. Res. Toxicol., 18, 1140-1149.
141. Hailer, M.K., Slade, P.G., Martin, B.D., and Sugden, K.D. (2005) Nei deficient Escherichia coli are sensitive to chromate and accumulate the oxidized guanine lesion spiroiminodihydantoin. Chem. Res. Toxicol., 18, 1378-1383.
142. Tuo, J., Muftuoglu, M., Chen, C., Jaruga, P., Selzer, R.R., Brosh, R.M., Jr., Rodriguez, H., Dizdaroglu, M., and Bohr, V.A. (2001) The Cockayne syndrome group B gene product is involved in general genome base excision repair of 8-hydroxyguanine in DNA. J. Biol. Chem., 276, 45772-45779.
143. Tuo, J., Jaruga, P., Rodriguez, H., Dizdaroglu, M., and Bohr, V.A. (2002) The Cockayne syndrome group B gene product is involved in cellular repair of 8-hydroxyadenine in DNA. J. Biol. Chem., 277, 30832-30837.
144. Tuo, J., Jaruga, P., Rodriguez, H., Bohr, V.A., and Dizdaroglu, M. (2003) Primary fibroblasts of Cockayne syndrome patients are defective in cellular repair of 8-hydroxyguanine and 8-hydroxyadenine from oxidative stress. FASEB J., 17, 668-674.
145. Friedman, K.A. and Keller, A. (2001) On the non-uniform distribution of guanine in introns of human genes: possible protection of exons against oxidation by proximal introns poly-G sequences. J. Phys. Chem. B, 105, 11859-11865.
146. Friedman, K.A. and Keller, A. (2004) Guanosine distribution and oxidation resistance in eight eukaryotic genomes. J. Am. Chem. Soc., 126, 2368-2371.
147. Kanvah, S. and Schuster, G.B. (2005) The sacrificial role of easily oxidizable sites in the protection of DNA from damage. N ucleic Acids Res., 33, 5133-5138.