One-electron oxidation reactions of purine and pyrimidine bases in cellular DNA

References

• Adhikary A, Kumar A, Becker D, Sevilla MD. 2006. The guanine cation radical: Investigation of deprotonation states by ESR and DFT. J Phys Chem B 110:24171–24180.
   PubMedGoogle Scholar
• Adhikary A, Khandur D, Sevilla MD. 2009. Direct observation of the hole protonation state and hole localization site in DNA-oligomers. J Am Chem Soc 131:8614–8619.
   PubMed Web of Science ®Google Scholar
• Adhikary A, Kumar A, Munafo SA, Khanduri D, Sevilla MD. 2010. Prototropic equilibria in DNA containing one-electron oxidized GC: Intra-duplex vs. duplex to solvent deprotonation. Phys Chem Chem Phys 12:5353–5368.
   PubMedGoogle Scholar
• Adhikary A, Kumar A, Heizer AN, Palmer BJ, Pottiboyina V, Liang Y, Wnuk SF, Sevilla MD 2013. Hydroxyl ion addition to one-electron oxidized thymine: Unimolecular interconversion of C5 to C6 OH-adducts. J Am Chem Soc 135:3121–3135.
   PubMedGoogle Scholar
• Angelov D, Charra M, Müller CW, Cadet J, Dimitrov S. 2003. Solution study of the NF-kappa B p50-DNA complex by UV laser protein-DNA cross-linking. Photochem Photobiol 77:592–596.
   PubMedGoogle Scholar
• Angelov D, Spassky A, Berger M, 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 119:11373–11380.
   Web of Science ®Google Scholar
• Aravindakumar CT, Schuchmann MN, Rao BSM, von Sonntag J, von Sonntag C. 2003. The reactions of cytidine and 2’-deoxycytidine with SO4•2 revisited. Pulse radiolysis and product studies. Org Biomolec Chem 1:401–408.
   PubMedGoogle Scholar
• Bachler V, Hildenbrand K. 1992. EPR-detection of the guanosyl radical cation in aqueous solution. Quantum chemically supported assignment of nitrogen and proton hyperfine couplings.Radiat Phys Chem 40:59–68.
   Google Scholar
• Barker S, Weinfeld M, Murray D. 2005a. DNA-protein crosslinks: Their induction, repair and biological consequences. Mutat Res 580:111–115.
   PubMedGoogle Scholar
• Barker S, Weinfeld M, Zheng J, Li L, Murray D. 2005b. Identification of mammalian proteins cross-linked to DNA by ionizing radiation. J Biol Chem 280:33826–33838.
   PubMed Web of Science ®Google Scholar
• Bellon S, Ravanat J-L, Gasparutto D, Cadet J. 2002. Cross-linked thymine-purine base tandem lesions: Synthesis, characterization, and measurement in gamma-irradiated isolated DNA. Chem Res Toxicol 15:598–606.
   PubMed Web of Science ®Google Scholar
• Bergeron F, Auvré F, Radicella J-P, Ravanat J-L. 2010. HO radicals induce an unexpected high proportion of tandem base lesions refractory to repair by DNA glycosylases. Proc Natl Acad Sci USA 107:5528–5533.
   PubMed Web of Science ®Google Scholar
• Box HC, Budzinski EE, Dawidzik JD, Wallace JC, Evans MS, Gobey JS. 1996. Radiation-induced formation of a crosslink between base moieties of deoxyguanosine and thymidine in deoxygenated solutions of d(CpGpTpA). Radiat Res 145:641–643.
   PubMed Web of Science ®Google Scholar
• Box HC, Dawidzik JB, Budzinski EE. 2001. Free radical-induced double lesions in DNA. Free Radic Biol Med 31:856–868.
   PubMed Web of Science ®Google Scholar
• Brem R, Karran P. 2012a. Multiple forms of DNA damage caused by UVA photoactivation of 6-thioguanine. Photochem Photobiol 88:5–15.
   PubMed Web of Science ®Google Scholar
• Brem R, Karran P. 2012b. Oxidation-mediated DNA cross-linking contributes to the toxicity of 6-thioguanine in human cells. Cancer Res 72:4787–4795.
   PubMed Web of Science ®Google Scholar
• Budzinski EE, Dawidzik JB, Rajecki MJ, Wallace JC, Schroder EA, Box HC. 1997. Isolation and characterization of the products of anoxic irradiation of d(CpGpTpA). Int J Radiat Biol 71:327–336.
   PubMedGoogle Scholar
• Cadet J, Douki T, 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.
   PubMed Web of Science ®Google Scholar
• Cadet J, Douki T, Gasparutto D, Ravanat J-L, Wagner JR. 2009. Chemical reactions of the radical cations of nucleobases in isolated and cellular DNA. Formation of single-base lesions. In: Greenberg MM, editor. Radical and radical ion reactivity in nucleic acid chemistry. New York: Wiley. pp 69–97.
   Google Scholar
• Cadet J, Douki T, Ravanat JL. 2010. Oxidatively generated base damage to cellular DNA. Free Radic Biol Med 49:9–21.
   PubMed Web of Science ®Google Scholar
• Cadet J, Ravanat J-L, TavernaPorro M, Menoni H, Angelov D. 2012. Oxidatively generated complex DNA damage: Tandem and clustered lesions. Cancer Lett 327:5–15.
   PubMed Web of Science ®Google Scholar
• Cadet J, Wagner JR. 2013. DNA base damage by reactive oxygen species, oxidizing agents, and UV radiation. Cold Spring Harbor Perspect Biol 5:a012559.
   PubMed Web of Science ®Google Scholar
• Candeias LP, Steenken S. 1989. Structure and acid-base properties of one-electron-oxidized deoxyguanosine, guanosine, and 1-methylguanosine. J Am Chem Soc 111:1094–1099.
   Web of Science ®Google Scholar
• Candeias LP, Steenken S. 1992. Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA. J Am Chem Soc 114:699–704.
   Web of Science ®Google Scholar
• Candeias LP, Steenken S. 1993. Electron transfer in di(deoxy)nucleoside phosphates in aqueous solution: Rapid migration of oxidative damage (via adenine) to guanine. J Am Chem Soc 115:2437–2440.
   Web of Science ®Google Scholar
• Candeias LP, Steenken S. 2000. Reaction of HO* with guanine derivatives in aqueous solution: Formation of two different redox-active OH-adduct radicals and their unimolecular transformation reactions. Properties of G(−H)*. Chem Eur J 6:475–484.
   PubMed Web of Science ®Google Scholar
• Cao H, Wang Y. 2007. Quantification 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.
   PubMed Web of Science ®Google Scholar
• Catteral H, Davies MJ, Gilbert BC. 1992. An EPR study of the transfer of radical-induced damage from the base to sugar in nucleic acid components: Relevance to the occurrence of strand-breakage. J Chem Soc Perkin Trans 2:1379–1385.
   Google Scholar
• Colis LC, Raychaudhury P, Basu AK. 2008. Mutational specificity of gamma-radiation-induced guanine-thymine and thymine-guanine intrastrand cross-links in mammalian cells and translesion synthesis past the guanine-thymine lesion by human DNA polymerase eta. Biochemistry 47:8070–8079.
   PubMedGoogle Scholar
• Crean C, Geacintov NE, Shafirovich V. 2008a. Intrastrand G-U cross-links generated by the oxidation of guanine in 5’-d(GCU) and 5’-r(GCU). Free Radic Biol Med 45:1125–1134.
   PubMedGoogle Scholar
• Crean C, Lee YA, Yun BH, Geacintov NE, Shafirovich V. 2008b. Oxidation of guanine by carbonate radicals derived from photolysis of carbonatotetramminecobalt(III) complexes and the pH dependence of intrastrand DNA cross-links mediated by guanine radical reactions. ChemBioChem 9:1985–1991.
   PubMed Web of Science ®Google Scholar
• Crean C, Uvaydov Y, Geacintov NE, Shafirovich V. 2008c. Oxidation of single-stranded oligonucleotides by carbonate radical anions: Generating intrastrand cross-links between guanine and thymine bases separated by cytosines. Nucleic Acids Res 36:742–755.
   PubMed Web of Science ®Google Scholar
• Cuquerella MC, Lhiaubet-Vallet V, Cadet J, Miranda MA. 2012. Benzophenone photosensitized DNA damage. Acc Chem Res 45: 1558–1570.
   PubMedGoogle Scholar
• Decarroz C, Wagner JR, van Lier JE, Murali Krishna M, Riesz P, 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.
   Web of Science ®Google Scholar
• Decarroz C, Wagner JR, Cadet J. 1987. Specific deprotonation reactions of the pyrimidine radical cation resulting from the menadione mediated photosensitization of 2’-deoxycytidine. Free Rad Res Commun 2:295–301.
   PubMedGoogle Scholar
• Deeble DJ, Schluchmann MN, Steenken S, von Sonntag C. 1990. Direct evidence for the formation of thymine radical cations from the reaction of SO4•− with thymine derivatives: A pulse radiolysis study with optical and conductance detection. J Phys Chem 94:8186–8192.
   Web of Science ®Google Scholar
• Dedon PC. 2008. The chemical toxicology of 2-deoxyribose oxidation in DNA. Chem Res Toxicol 21:206–219.
   PubMed Web of Science ®Google Scholar
• Douki T, Cadet J. 1999. Modification of DNA bases by photosensitized one-electron oxidation. Int J Radiat Biol 75:571–581.
   PubMed Web of Science ®Google Scholar
• Douki T, Angelov A, Cadet J. 2001. UV laser photolysis of DNA: Effects of duplex stability on charge transfer efficiency. J Am Chem Soc 123:11330–11336.
   Google Scholar
• Douki T, Ravanat J-L, Angelov D, Wagner JR, Cadet J. 2004. Effect of duplex stability on charge-transfer efficiency within DNA. Top Curr Chem 236:1–25.
   Web of Science ®Google Scholar
• Douki T, Rivière J, Cadet J. 2002. DNA tandem lesions containing 8-oxo-7,8-dihydroguanine and formamido residues arise from intramolecular addition of thymine peroxyl radicals to guanine. Chem Res Toxicol 15:445–454.
   PubMed Web of Science ®Google Scholar
• Douki T, Ravanat J-L, Pouget JP, Testard I, Cadet J. 2006. Minor contribution of direct ionization to DNA base damage induced by heavy ions. Int J Radiat Biol 82:119–127.
   PubMed Web of Science ®Google Scholar
• Frelon S, Douki T, Ravanat J-L, Tornabene C, Cadet J. 2000. High performance liquid chromatography – mass spectrometry measurement of radiation-induced base damage to isolated and cellular DNA. Chem Res Toxicol 13:1002–1010.
   PubMed Web of Science ®Google Scholar
• Georgakilas AG. 2011. Detection of clustered DNA lesions: Biological and clinical applications. World J Biol Chem 2:173–176.
   PubMedGoogle Scholar
• Georgakilas AG, O’Neill P, Stewart R. 2013. Induction and repair of clustered DNA lesions: What do we know so far?. Radiat Res 180: 100–109.
   PubMed Web of Science ®Google Scholar
• Goodhead DJ. 1994. Initial events in the cellular effects of ionizing radiations: Clustered damage in DNA. Int J Radiat Biol 65:7–17.
   PubMed Web of Science ®Google Scholar
• Gromova M, Balanzat E, Gervais B, Nardin R, Cadet J. 1998. Direct effect of heavy ions and electrons on thymidine in the solid state. Int J Radiat Biol 74:81–97.
   PubMed Web of Science ®Google Scholar
• Hildenbrand K. 1990. The SO4(−•)-induced oxidation of 2’- deoxyuridine-5’-phosphate, uridine-5’-phosphate and thymidine-5’-phosphate – an ESR study in aqueous-solution. Z Naturforsch C 45:47–58.
   PubMedGoogle Scholar
• Hildenbrandt K, Behrens G, Schulte-Frohlinde D, Herak JN. 1989. Comparison of the reaction of •OH and of SO the T* radicals with pyrimidine nucleosides. An electron spin resonance study in aqueous solution. J Chem Soc Perkin Trans 2:283–289.
   Google Scholar
• Hill MA, Stevens DL, Marsden SJ, Allot R, Turcu IC, Goodhead DT. 2002. Is the increased relative biological effectiveness of high LET particles due to spatial or temporal effects? Characterization and OER in V79-4 cells. Phys Med Biol 47:3543–3555.
   PubMed Web of Science ®Google Scholar
• Hong H, Cao, Wang Y, Wang Y. 2006. Identification and quantification of a guanine-thymine intrastrand cross-link lesion induced by Cu(II)/H2O2/ascorbate. Chem Res Toxicol 19:614–621.
   PubMed Web of Science ®Google Scholar
• Hong H, Cao H, Wang Y. 2007a. Formation and genotoxicity of a guanine-cytosine intrastrand cross-link lesion in vivo. Nucleic Acids Res 35:7118–7127.
   PubMed Web of Science ®Google Scholar
• Hong IS, Carter KN, Sato K, Greenberg MM. 2007b. Characterization and mechanism of formation of tandem lesions in DNA by a nucleobase peroxyl radical. J Am Chem Soc 129:4089–4098.
   PubMedGoogle Scholar
• Huie RE, Clifton CL, Neta P. 1991. Electron transfer reaction rates and equilibria of the carbonate and sulfate radical anions. Radiat Phys Chem 38:477–481.
   Web of Science ®Google Scholar
• Jiang Y, Hong H, Cao H, Wang Y. 2007. In vivo formation and in vitro replication of a guanine-thymine intrastrand cross-link lesion. Biochemistry 46:12757–12763.
   PubMed Web of Science ®Google Scholar
• Joy A, Ghosh AK, Schuster GB. 2006. One-electron oxidation of DNA oligomers that lack guanine: Reaction and strand cleavage at remote thymines by long-distance radical cation hopping. J Am Chem Soc 128:5346–5347.
   PubMed Web of Science ®Google Scholar
• Kasai H, Yamaizumi Z, Berger M, 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.
   Web of Science ®Google Scholar
• Kawanishi S, Murata M. 2006. Mechanism of DNA damage induced by bromate differs from general types of oxidative stress. Toxicology 221:172–178.
   PubMedGoogle Scholar
• Knobloch B, Linert W, Sigel H. 2005. Metal ion-binding properties of (N3)-deprotonated uridine, thymidine, and related pyrimidine nucleosides in aqueous solution. Proc Natl Acad Sci USA 102: 7459–7464.
   PubMedGoogle Scholar
• Kobayashi K, Tagawa S. 2003. Direct observation of guanine radical cation deprotonation in duplex DNA using pulse radiolysis. J Am Chem Soc 125:10213–10218.
   PubMed Web of Science ®Google Scholar
• Kobayashi K, Yamagami R., Tagawa S. 2008. Effect of base sequence and deprotonation of guanine cation radical in DNA. J Phys Chem B 112:10752–10757.
   PubMedGoogle Scholar
• Kurbanyan K, Nguyen KL, To P, Rivas EV, Lueras AMK, Kosinski C, Steryo M, Gonzalez A, Mah DA, Stemp EDA. 2003. DNA-protein cross-linking via guanine oxidation. Dependence upon protein and photosensitizer.Biochemistry 42:10269–10281.
   PubMedGoogle Scholar
• Kuttappan-Nair V, Samson-Thibault F, Wagner JR. 2010. Generation of 2′-deoxyadenosine N6-aminyl radicals from the photolysis of phenlhydrazone derivatives. Chem Res Toxicol 23:48–54.
   PubMedGoogle Scholar
• Madison AL, Perez ZA, To P, Maisonet T, Rios EV, Trejo Y, Ochoa-Paniagua C, Reno A, Stemp EDA. 2012. Dependence of DNA-protein cross-linking via guanine oxidation upon local sequence as studies restriction endonuclease inhibition. Biochemistry 5 1:362–369.
   Google Scholar
• Madugundu GS, Wagner JR, Cadet J, Kropachev K, Yun BH, Geacintov NE, Shafirovich V. 2013. Generation of guanine-thymine cross-links in human cells by one-electron oxidation mechanisms. Chem Res Toxicol 26:1031–1033.
   PubMed Web of Science ®Google Scholar
• Medinas DB, Cerchiaro G, Trindade DF, Augusto O. 2007. The carbonate radical and related oxidants derived from bicarbonate buffer. IUBMB Life 59:255–262.
   PubMed Web of Science ®Google Scholar
• Milligan JR, Aguilera JA, Paglinawan RA, Ward JF. 2000. Mechanism of DNA damage by thiocyanate radicals. Int J Radiat Biol 76: 1305–1314.
   PubMed Web of Science ®Google Scholar
• Mori T, Dizdaroglu M. 1994. Ionizing radiation causes greater DNA base damage in radiation-sensitive mutant M10 cells than in parent mouse lymphoma. Radiat Res 140:85–90.
   PubMedGoogle Scholar
• Nguyen KL, Steryo M, Kurbanyan K, Nowitzki KM, Butterfield SM, Ward SR, Stemp EAD. 2000. DNA protein cross-linking via from oxidation of guanine via the flash-quenching technique. J Am Chem Soc 122:3585–3594.
   Google Scholar
• Olinski R, Zastawny TH, Foksinski M, Windorbska W, Jaruga P, Dizdaroglu M. 1996. DNA base damage in lymphocytes of cancer patients undergoing radiation therapy. Cancer Lett 106:207–215.
   PubMedGoogle Scholar
• O’Neill P, Davies SE. 1987. Pulse radiolytic study of the interaction of SO4•− with deoxynucleosides. Possible implications for direct energy deposition. Int J Radiat Biol 52:577–587.
   Web of Science ®Google Scholar
• O’Neill P, Wardman P. 2009. Radiation chemistry comes before radiation biology. Int J Radiat Biol 85:9–25.
   PubMed Web of Science ®Google Scholar
• Pacher P, Beckman JS, Liaudet L. 2007. Nitric oxide and peroxynitrite in health and disease. Physiolog Rev 87:315–424.
   PubMed Web of Science ®Google Scholar
• Peoples AM, Lee J, Weinfeld M, Milligan JR, Bernhard WA. 2012. Yields of damage to C4’ deoxyribose and to pyrimidine in pUC18 by the direct effect of ionizing radiation. Nucleic Acids Res 40:6060–6069.
   PubMedGoogle Scholar
• Perrier S, Hau J, Gasparutto D, Cadet J, Favier A, Ravanat J-L. 2006. Characterization of lysine-guanine cross-links upon one-electron oxidation of a guanine-containing oligonucleotide in the presence of a trilysine peptide. J Am Chem Soc 128:5703–5710.
   PubMed Web of Science ®Google Scholar
• Pouget J-P, Frelon S, Ravanat J-L, Testard I, Odin F, Cadet J. 2002. Formation of modified DNA bases in cells exposed either to gamma radiation or to high-LET particles. Radiat Res 157:589–595.
   PubMed Web of Science ®Google Scholar
• Raychaudhury P, Basu AK. 2010. Replication past the gamma- radiation-induced guanine-thymine cross-link G[8,5-Me]T by human and yeast DNA polymerase eta. J Nucleic Acids 2010:101495.
   PubMedGoogle Scholar
• Raychaudhury P, Basu AK. 2011. Genetic requirement for mutagenesis of the G[8,5-Me]T cross-link in Escherichia coli: DNA polymerases IV and V compete for error-prone bypass. Biochemistry 50:2330–2338.
   PubMedGoogle Scholar
• Rashid R, Mark F, Schuchmannn HP, von Sonntag C. 1991. SO4(•−)-induced oxidation of 1,3,6-trimethyluracil and 1,3,5-trimethyluracil (1,3-dimethylthymine) by potassium peroxodisulphate in aqueous solution: An interesting contrast. Int J Radiat Biol 59:1081–1100.
   PubMed Web of Science ®Google Scholar
• Ravanat J- L, Saint-Pierre C, 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.
   PubMed Web of Science ®Google Scholar
• Reynisson J, Steenken S. 2002a. DFT calculations on the electrophilic reaction with water of the guanine and adenine radical cations. A model for the situation in DNA. Phys Chem Chem Phys 4:527–532.
   Web of Science ®Google Scholar
• Reynisson J, Steenken S. 2002b. DNA-base radicals. Their base pairing abilities as calculated by DFT. Phys Chem Chem Phys 4:5346–5352.
   Google Scholar
• Rokhlenko Y, Geacintov NE, Shafirovich V. 2012. Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc 134:4955–4962.
   PubMed Web of Science ®Google Scholar
• Romieu A, Bellon S, Gasparutto D, Cadet J. 2000. Synthesis and UV photolysis of oligodeoxynucleotides that contain 5-(phenylthiomethyl)-2’-deoxyuridine: A specific photolabile precursor of 5-(2’-deoxyuridilyl)methyl radical. Org Lett 2: 1085–1088.
   PubMed Web of Science ®Google Scholar
• Schuchmann HP, Deeble DJ, Olbrich G, von Sonntag C. 1987. The SO4(•−)-induced chain reaction of 1,3-dimethyluracil with peroxodisulphate. Int J Radiat Biol 51:441–453.
   Web of Science ®Google Scholar
• Seidel CAM, Schulz A, Sauer MHM. 1996. Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electron redox potentials and their correlation with static and dynamic quenching efficiencies.J Phys Chem 100:5541–5553.
   Web of Science ®Google Scholar
• Shafirovich V, Crean C, Geacintov NE. 2009. Reactions of reactive nitrogen species and carbonate radical anions with DNA. In: Greenberg MM, editor. Radical and radical ion reactivity in nucleic acid chemistry. Hoboken, NJ: John Willey & Sons, Inc. pp. 325–355.
   Google Scholar
• Shafirovich V, Dourandin A, Huang V, Geacintov NE. 2001. Carbonate radical is a site-selective oxidizing agent of guanines in double-stranded oligonucleotides. J Biol Chem 276:24621–24626.
   PubMed Web of Science ®Google Scholar
• Shaw AA, Cadet J. 1990. Radical combination processes under the direct effects of gamma radiation on thymidine. J Chem Soc Perkin Trans II:2063–2070.
   Google Scholar
• Spassky A, Angelov D. 1997. Influence of the local helical conformation on the guanine modifications generated from one-electron DNA oxidation. Biochemistry 36:6571–6576.
   PubMed Web of Science ®Google Scholar
• Stanbury DM. 1989. Reduction potentials involving inorganic free radicals in aqueous solution. Adv Inorg Chem 33:69–138.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• Steenken S. 1992. Electron-transfer-induced acidity/basicity and reactivity changes of purine and pyrimidine bases. Consequences of redox processes for DNA base pairs. Free Rad Res Commun 16:349–379.
   PubMed Web of Science ®Google Scholar
• Steenken S. 1997. Electron transfer in DNA? Competition by ultra-fast proton transfer?Biol Chem 378:1293–1297.
   PubMed Web of Science ®Google Scholar
• Steenken S, Jovanovic SV. 1997. How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution.J Am Chem Soc 119:617–618.
   Web of Science ®Google Scholar
• Steward RD, Yu VK, Georgakilas AG, Koumenis C, Park JH, Carlson DJ. 2011. Effects of radiation quality and oxygen on clustered DNA lesions and cell death. Radiat Res 176:587–602.
   PubMedGoogle Scholar
• Swarts SG, Becker D, Sevilla M, Wheeler KT. 1996. Radiation-induced DNA damage as a function of hydration. II. Base damage from electron-loss centers. Radiat Res 145:304–314.
   Google Scholar
• Swarts SG, Gilbert DC, Sharma KK, Razskazovskiy Y, Purkayastha S, Naumenko KA, Bernhard WA. 2007. Mechanisms of direct radiation damage in DNA, based on a study of the yields of base damage, deoxyribose damage, and trapped radicals in d(GCACGCGTGC)2. Radiat Res 168:367–381.
   PubMed Web of Science ®Google Scholar
• Tremblay S, Douki T, Cadet J, Wagner JR. 1999. 2’-Deoxycytidine glycols: A missing link in the free radical-mediated oxidation of DNA. J Biol Chem 274:20833–20838.
   PubMed Web of Science ®Google Scholar
• Tremblay S, Wagner JR. 2008. Dehydration, deamination and enzymatic repair of cytosine glycols from oxidized poly(dG-dC) and poly(dI-dC). Nucleic Acids Res 36:284–293.
   PubMedGoogle Scholar
• von Sonntag C, Schuchmann H-P. 1986. The radiolysis of pyrimidines in aqueous solutions: An updating review. Int J Radiat Biol 49:1–34.
   Web of Science ®Google Scholar
• von Sonntag C. 1987a. The chemical basis of radiation biology. Philadelphia: Taylor and Francis.
   Google Scholar
• von Sonntag C. 1987b. New aspects in the free-radical chemistry of pyrimidine nucleobases. Free Rad Res Commun 2:217–224.
   PubMedGoogle Scholar
• von Sonntag C. 1991. The chemistry of free-radical-mediated DNA damage. Basic Life Sci 58:287–317.
   PubMedGoogle Scholar
• von Sonntag C. 2006. Free radical induced DNA damage and its repair – a chemical perspective. New York: Springer.
   Google Scholar
• Wagner JR, van Lier JE, Berger M, Cadet J. 1994. Thymidine hydroperoxides: Structural assignment, conformational features, and thermal decomposition in water. J Am Chem Soc 116:2235–2242.
   Web of Science ®Google Scholar
• Wagner JR, Decarroz C, Berger M, Cadet J. 1999. Hydroxyl-radical- induced decomposition of 2’-deoxycytidine in aerated aqueous solutions. J Am Chem Soc 121:4101–4110.
   Web of Science ®Google Scholar
• Wagner JR, Cadet J. 2010. Oxidation reactions of cytosine DNA components by hydroxyl radical and one-electron oxidants in aerated aqueous solutions. Acc Chem Res 43:564–571.
   PubMed Web of Science ®Google Scholar
• Wang Y. 2008. Bulky DNA lesions induced by reactive oxygen species. Chem Res Toxicol 21:276–281.
   PubMed Web of Science ®Google Scholar
• Wardman P. 1989. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data 18:1637–16755.
   Web of Science ®Google Scholar
• Yang Z, Colis LC, Basu AK, Zou Y. 2005. Recognition and incision of γ-radiation-induced cross-linked guanine-thymine tandem lesion G[8,5-Me]T by UvrABC nuclease. Chem Res Toxicol 18:1339–1346.
   PubMed Web of Science ®Google Scholar
• Yun BH, Geacintov NE, Shafirovich V. 2011. Generation of guanine- thymidine cross-links in DNA by peroxynitrite/carbon dioxide. Chem Res Toxicol 24:1144–152.
   PubMed Web of Science ®Google Scholar
• Zhang Q, Wang Y. 2005. Generation of 5-(2′-deoxycytidyl)methyl radical and the formation of interstrand cross-link lesions in oligodeoxyribonucleotides. Nucleic Acids Res 33:1593–1603.
   PubMed Web of Science ®Google Scholar