On the relevance of hydroxyl radical to purine DNA damage

References

• Halliwell B, Gutteridge JMC. Free radicals in biology and medicine. 5th ed. Oxford: Oxford University Press; 2015.
   Google Scholar
• Chatgilialoglu C, Studer A, editors. Encyclopedia of radicals in chemistry, biology and materials. Vol 3: Chemical biology. Chichester: Wiley; 2012.
   Google Scholar
• Winterbourn CC. Reconciling the chemistry and biology of reactive oxygen species. Nat Chem Biol. 2008;4(5):278–286.
   PubMed Web of Science ®Google Scholar
• Buxton GV, Greenstock CL, Helman WP, et al. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (·OH)/O−) in aqueous solution. J Phys Chem Ref Data. 1988;17(2):513–886.
   Web of Science ®Google Scholar
• Wardman P. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J Phys Chem Ref Data. 1989;18(4):1637–1755.
   Web of Science ®Google Scholar
• Von Sonntag C. Free-radical-induced DNA damage and its repair. A chemical perspective. Berlin: Springer-Verlag; 2006.
   Google Scholar
• Dizdaroglu M, Jaruga P. Mechanisms of free radical-induced damage to DNA. Free Radic Res. 2012;46(4):382–419.
   PubMed Web of Science ®Google Scholar
• Cadet J, Davies KJA, Medeiros MHG, et al. Formation and repair of oxidatively generated damage in cellular DNA. Free Radic Biol Med. 2017;107:13–34.
   PubMed Web of Science ®Google Scholar
• Pogozelski WK, Tullius TD. Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar Moiety. Chem Rev. 1998;98(3):1089–1108.
   PubMed Web of Science ®Google Scholar
• Pitié M, Pratviel G. Activation of DNA carbon-hydrogen bonds by metal complexes. Chem Rev. 2010;110(2):1018–1059.
   PubMed Web of Science ®Google Scholar
• Greenberg MM. Reactivity of nucleic acid radicals. Adv Phys Org Chem. 2016;50:119–202.
   PubMed Web of Science ®Google Scholar
• Steenken S, Jovanovic SV. How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J Am Chem Soc. 1997;119(3):617–618.
   Web of Science ®Google Scholar
• Giese B. Long-distance electron transfer through DNA. Annu Rev Biochem. 2002;71:51–70.
   PubMed Web of Science ®Google Scholar
• Kawai K, Majima T. Hole transfer kinetics of DNA. Acc Chem Res. 2013;46(11):2616–2625.
   PubMed Web of Science ®Google Scholar
• Capobianco A, Caruso T, D'Ursi AM, et al. Delocalized hole domains in Guanine-rich DNA oligonucleotides. J Phys Chem B. 2015;119(17):5462–5466.
   PubMed Web of Science ®Google Scholar
• Cadet J, Douki T, Ravanat JL. Oxidatively generated damage to the guanine moiety of DNA: mechanistic aspects and formation in cells. Acc Chem Res. 2008;41(8):1075–1083.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, Ferreri C, Geacintov NE, et al. 5′,8-Cyclopurine lesions in DNA damage: chemical, analytical, biological and diagnostic significance. Cells. 2019;8(6):513.
   Web of Science ®Google Scholar
• Shafirovich V, Geacintov NE. Removal of oxidatively generated DNA damage by overlapping repair pathways. Free Radic Biol Med. 2017;107:53–61.
   PubMed Web of Science ®Google Scholar
• Kumar N, Raja S, Van Houten B. The involvement of nucleotide excision repair proteins in the removal of oxidative DNA damage. Nucleic Acids Res. 2020;48(20):11227–11243.
   PubMed Web of Science ®Google Scholar
• Whitaker AM, Schaich MA, Smith MR, et al. Base excision repair of oxidative DNA damage: from mechanism to disease. Front Biosci (Landmark Ed). 2017;22:1493–1522.
   PubMed Web of Science ®Google Scholar
• Aydogan B, Marshall DT, Swarts SG, et al. Site-specific OH attack to the sugar moiety of DNA: a comparison of experimental data and computational simulation. Radiat Res. 2002;157(1):38–44.
   PubMed Web of Science ®Google Scholar
• Balasubramanian B, Pogozelski WK, Tullius TD. DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone. Proc Natl Acad Sci U S A. 1998;95(17):9738–9743.
   PubMed Web of Science ®Google Scholar
• Chan W, Chen B, Wang L, et al. Quantification of the 2-deoxyribonolactone and nucleoside 5′-aldehyde products of 2-deoxyribose oxidation in DNA and cells by isotope-dilution gas chromatography mass spectrometry: differential effects of gamma-radiation and Fe2+-EDTA. J Am Chem Soc. 2010;132(17):6145–6153.
   PubMedGoogle Scholar
• Dedon PC. The chemical toxicology of 2-deoxyribose oxidation in DNA. Chem Res Toxicol. 2008;21(1):206–219.
   PubMed Web of Science ®Google Scholar
• Emanuel CJ, Newcomb M, Ferreri C, et al. Kinetics of 2′-deoxyuridin-1′-yl radical reactions. J Am Chem Soc. 1999;121(12):2927–2928.
   Web of Science ®Google Scholar
• Gimisis T, Chatgilialoglu C. Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system. Chem Commun. 1998;(12):1249–1250.
   Web of Science ®Google Scholar
• Chatgilialoglu C, Ferreri C, Terzidis MA. Purine 5′,8-cyclonucleoside lesions: chemistry and biology. Chem Soc Rev. 2011;40(3):1368–1382.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, Guerra M, Mulazzani QG. Model studies of DNA C5′ radicals. Selective generation and reactivity of 2′-deoxyadenosin-5′-yl radical. J Am Chem Soc. 2003;125(13):3839–3848.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, D'Angelantonio M, Kciuk G, et al. New insights into the reaction paths of hydroxyl radicals with 2'-deoxyguanosine. Chem Res Toxicol. 2011;24(12):2200–2206.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, Bazzanini R, Jimenez LB, et al. (5'S)- and (5'R)-5',8-cyclo-2'-deoxyguanosine: mechanistic insights on the 2'-deoxyguanosin-5'-yl radical cyclization. Chem Res Toxicol. 2007;20(12):1820–1824.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, Eriksson LA, Krokidis MG, et al. Oxygen dependent purine lesions in double-stranded oligodeoxynucleotides: kinetic and computational studies highlight the mechanism for 5',8-Cyclopurine Formation. J Am Chem Soc. 2020;142(12):5825–5833.
   PubMed Web of Science ®Google Scholar
• Navacchia ML, Chatgilialoglu C, Montevecchi PC. C5'-adenosinyl radical cyclization. A stereochemical investigation . J Org Chem. 2006;71(12):4445–4452.
   PubMed Web of Science ®Google Scholar
• Boussicault F, Kaloudis P, Caminal C, et al. The fate of C5' radicals of purine nucleosides under oxidative conditions. J Am Chem Soc. 2008;130(26):8377–8385.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, Krokidis MG, Masi A, et al. New insights into the reaction paths of hydroxyl radicals with purine moieties in DNA and double-stranded oligonucleotides. Molecules. 2019;24(21):3860.
   Web of Science ®Google Scholar
• Guerrero CR, Wang J, Wang Y. Induction of 8,5'-cyclo-2'-deoxyadenosine and 8,5'-cyclo-2'-deoxyguanosine in isolated DNA by Fenton-type reagents. Chem Res Toxicol. 2013;26(9):1361–1366.
   PubMed Web of Science ®Google Scholar
• Belmadoui N, Boussicault F, Guerra M, et al. Radiation-induced formation of purine 5',8-cyclonucleosides in isolated and cellular DNA: high stereospecificity and modulating effect of oxygen. Org Biomol Chem. 2010;8(14):3211–3219.
   PubMed Web of Science ®Google Scholar
• Ravanat JL, Breton J, Douki T, et al. Radiation-mediated formation of complex damage to DNA: a chemical aspect overview. Br J Radiol. 2014;87(1035):20130715.
   PubMed Web of Science ®Google Scholar
• Bergeron F, Auvré F, Radicella JP, et al. HO* radicals induce an unexpected high proportion of tandem base lesions refractory to repair by DNA glycosylases. Proc Natl Acad Sci U S A. 2010;107(12):5528–5533.
   PubMed Web of Science ®Google Scholar
• Ravanat JL, Saint-Pierre C, Cadet J. One-electron oxidation of the guanine moiety of 2'-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2'-deoxyguanosine . J Am Chem Soc. 2003;125(8):2030–2031.
   PubMed Web of Science ®Google Scholar
• Robert G, Wagner JR. Tandem lesions arising from 5-(uracilyl)methyl peroxyl radical addition to guanine: product analysis and mechanistic studies. Chem Res Toxicol. 2020;33(2):565–575.
   PubMed Web of Science ®Google Scholar
• Cui L, Ye W, Prestwich EG, et al. Comparative analysis of four oxidized guanine lesions from reactions of DNA with peroxynitrite, singlet oxygen, and γ-radiation. Chem Res Toxicol. 2013;26(2):195–202.
   PubMed Web of Science ®Google Scholar
• Rokhlenko Y, Geacintov NE, Shafirovich V. Lifetimes and reaction pathways of guanine radical cations and neutral guanine radicals in an oligonucleotide in aqueous solutions. J Am Chem Soc. 2012;134(10):4955–4962.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C, D'Angelantonio M, Guerra M, et al. A reevaluation of the ambident reactivity of the guanine moiety towards hydroxyl radicals. Angew Chem Int Ed Engl. 2009;48(12):2214–2217.
   PubMed Web of Science ®Google Scholar
• Terzidis MA, Prisecaru A, Molphy Z, et al. Radical-induced purine lesion formation is dependent on DNA helical topology. Free Radic Res. 2016;50(sup1):S91–S101.
   PubMed Web of Science ®Google Scholar
• Steenken S. Purine bases, nucleosides, and nucleotides: aqueous solution redox chemistry and transformation reactions of their radical cations and e- and OH adducts. Chem Rev. 1989;89(3):503–520.
   Web of Science ®Google Scholar
• Jaruga P, Kirkali G, Dizdaroglu M. Measurement of formamidopyrimidines in DNA. Free Radic Biol Med. 2008;45(12):1601–1609.
   PubMed Web of Science ®Google Scholar
• Dizdaroglu M, Kirkali G, Jaruga P. Formamidopyrimidines in DNA: mechanisms of formation, repair, and biological effects. Free Radic Biol Med. 2008;45(12):1610–1621.
   PubMed Web of Science ®Google Scholar
• Greenberg MM. The formamidopyrimidines: purine lesions formed in competition with 8-oxopurines from oxidative stress. Acc Chem Res. 2012;45(4):588–597.
   PubMed Web of Science ®Google Scholar
• Cadet J, Douki T, Ravanat JL. Oxidatively generated base damage to cellular DNA. Free Radic Biol Med. 2010;49(1):9–21.
   PubMed Web of Science ®Google Scholar
• Munk BH, Burrows CJ, Schlegel HB. Exploration of mechanisms for the transformation of 8-hydroxy guanine radical to FAPyG by density functional theory. Chem Res Toxicol. 2007;20(3):432–444.
   PubMed Web of Science ®Google Scholar
• Chaban GM, Wang D, Huo WM. Ab initio study of guanine damage by hydroxyl radical. J Phys Chem A. 2015;119(2):377–382.
   PubMed Web of Science ®Google Scholar
• Liu P, Wang Q, Niu M, et al. Multi-level quantum mechanics and molecular mechanics study of ring opening process of guanine damage by hydroxyl radical in aqueous solution. Sci Rep. 2017;7(1):7798.
   PubMedGoogle Scholar
• Francés-Monerris A, Merchán M, Roca-Sanjuán D. Mechanism of the OH radical addition to adenine from quantum-chemistry determinations of reaction paths and spectroscopic tracking of the intermediates. J Org Chem. 2017;82(1):276–288.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Burrows CJ. Formation and processing of DNA damage substrates for the hNEIL enzymes. Free Radic Biol Med. 2017;107:35–52.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Muller JG, Ji I, et al. Characterization of 2'-deoxyguanosine oxidation products observed in the Fenton-like system Cu(II)/H2O2/reductant in nucleoside and oligodeoxynucleotide contexts . Org Biomol Chem. 2011;9(9):3338–3348.
   PubMed Web of Science ®Google Scholar
• Thomas CS, Pollard HC, Razskazovskiy Y, et al. Sources of 2,5-diaminoimidazolone lesions in DNA damage initiated by hydroxyl radical attack. Free Radic Res. 2020;54(7):517–524.
   PubMed Web of Science ®Google Scholar
• Yu H, Venkatarangan L, Wishnok JS, et al. Quantitation of four guanine oxidation products from reaction of DNA with varying doses of peroxynitrite. Chem Res Toxicol. 2005;18(12):1849–1857.
   PubMed Web of Science ®Google Scholar
• Hebert SP, Schlegel HB. Computational study of the oxidation of guanine to form 5-Carboxyamido-5-formamido-2-iminohydantoin (2Ih). Chem Res Toxicol. 2019;32(11):2295–2304.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Muller JG, Dlouhy AC, et al. Structural context effects in the oxidation of 8-oxo-7,8-dihydro-2'-deoxyguanosine to hydantoin products: electrostatics, base stacking, and base pairing. J Am Chem Soc. 2012;134(36):15091–15102.
   PubMed Web of Science ®Google Scholar
• Steenken S, Jovanovic SV, Bietti M, et al. The trap depth (in DNA) of 8-oxo-7,8-dihydro-2′deoxyguanosine as derived from electron-transfer equilibria in aqueous solution. J Am Chem Soc. 2000;122(10):2373–2374.
   Web of Science ®Google Scholar
• Meggers E, Dussy A, Schäfer T, et al. Electron transfer in DNA from guanine and 8-oxoguanine to a radical cation of the carbohydrate backbone. Chem Eur J. 2000;6(3):485–492.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Burrow CJ. 8-Oxo-7,8-dihydro-2'-deoxyguanosine and abasic site tandem lesions are oxidation prone yielding hydantoin products that strongly destabilize duplex DNA. Org Biomol Chem. 2017;15(39):8341–8353.
   PubMed Web of Science ®Google Scholar
• White B, Tarun MC, Gathergood N, et al. Oxidised guanidinohydantoin (Ghox) and spiroiminodihydantoin (Sp) are major products of iron- and copper-mediated 8-oxo-7,8-dihydroguanine and 8-oxo-7,8-dihydro-2'-deoxyguanosine oxidation. Mol Biosyst. 2005;1(5-6):373–381.
   PubMedGoogle Scholar
• Crean C, Geacintov NE, Shafirovich V. Oxidation of guanine and 8-oxo-7,8-dihydroguanine by carbonate radical anions: insight from oxygen-18 labeling experiments. Angew Chem Int Ed Engl. 2005;44(32):5057–5060.
   PubMed Web of Science ®Google Scholar
• Niles JC, Wishnok JS, Tannenbaum SR. Spiroiminodihydantoin and guanidinohydantoin are the dominant products of 8-oxoguanosine oxidation at low fluxes of peroxynitrite: mechanistic studies with 18O. Chem Res Toxicol. 2004;17(11):1510–1519.
   PubMed Web of Science ®Google Scholar
• Gremaud JN, Martin BD, Sugden KD. Influence of substrate complexity on the diastereoselective formation of spiroiminodihydantoin and guanidinohydantoin from chromate oxidation. Chem Res Toxicol. 2010;23(2):379–385.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Burrows CJ. G-quadruplex folds of the human telomere sequence alter the site reactivity and reaction pathway of guanine oxidation compared to duplex DNA. Chem Res Toxicol. 2013;26(4):593–607.
   PubMed Web of Science ®Google Scholar
• Luo W, Muller JG, Burrows CJ. The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine. Org Lett. 2001;3(18):2801–2804.
   PubMed Web of Science ®Google Scholar
• Cooke MS, Evans MD, Dizdaroglu M, et al. Oxidative DNA damage: mechanisms, mutation, and disease. Faseb J. 2003;17(10):1195–1214.
   PubMed Web of Science ®Google Scholar
• Dizdaroglu M. Oxidatively induced DNA damage and its repair in cancer. Mutat Res Rev Mutat Res. 2015;763:212–245.
   PubMed Web of Science ®Google Scholar
• Figueroa-González G, Pérez-Plasencia C. Strategies for the evaluation of DNA damage and repair mechanisms in cancer. Oncol Lett. 2017;13(6):3982–3988.
   PubMed Web of Science ®Google Scholar
• Gonzalez-Hunt CP, Wadhwa M, Sanders LH. DNA damage by oxidative stress: measurement strategies for two genomes. Curr Opin Toxicol. 2018;7:87–94.
   Google Scholar
• Morton TH. Isotopic labelling in mass spectrometry. In Encyclopedia of spectroscopy and spectrometry. Vol. 2. 3rd ed. Oxford, UK: Elsevier/Academic Press; 2017. p. 501–511.
   Google Scholar
• Yu Y, Cui Y, Niedernhofe LJ, et al. Occurrence, biological consequences, and human health relevance of oxidative stress-induced DNA damage. Chem Res Toxicol. 2016;29(12):2008–2039.
   PubMed Web of Science ®Google Scholar
• Reddy MV, Randerath K. Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts. Carcinogenesis. 1986;7(9):1543–1551.
   PubMed Web of Science ®Google Scholar
• Gupta RC, Arif JM. An improved (32)P-postlabeling assay for the sensitive detection of 8-oxodeoxyguanosine in tissue DNA. Chem Res Toxicol. 2001;14(8):951–957.
   PubMed Web of Science ®Google Scholar
• Zhou GD, Moorthy B. Detection of bulky endogenous oxidative DNA lesions derived from 8,5’-cyclo-2’-deoxyadenosine by 32P-postlabeling assay. Curr Protoc Toxicol. 2015;64:17.17.1–17.17.14.
   Google Scholar
• Cooke MS, Olinski R, Loft S, European Standards Committee on Urinary (DNA) Lesion Analysis. Measurement and meaning of oxidatively modified DNA lesions in urine. Cancer Epidemiol Biomarkers Prev. 2008;17(1):3–14.
   PubMed Web of Science ®Google Scholar
• Okahashi Y, Iwamoto T, Suzuki N, et al. Quantitative detection of 4-hydroxyequilenin-DNA adducts in mammalian cells using an immunoassay with a novel monoclonal antibody. Nucleic Acids Res. 2010;38(12):e133.
   PubMed Web of Science ®Google Scholar
• Chung MK, Riby J, Li H, et al. A sandwich enzyme-linked immunosorbent assay for adducts of polycyclic aromatic hydrocarbons with human serum albumin. Anal Biochem. 2010;400(1):123–129.
   PubMed Web of Science ®Google Scholar
• Iwamoto T, Brooks PJ, Nishiwaki T, et al. Quantitative and in situ detection of oxidatively generated DNA damage 8,5'-cyclo-2'-deoxyadenosine using an immunoassay with a novel monoclonal antibody. Photochem Photobiol. 2014;90(4):829–836.
   PubMed Web of Science ®Google Scholar
• Mori T, Nakane H, Iwamoto T, et al. High levels of oxidatively generated DNA damage 8,5'-cyclo-2'-deoxyadenosine accumulate in the brain tissues of xeroderma pigmentosum group A gene-knockout mice. DNA Repair (Amst). 2019;80:52–58.
   PubMed Web of Science ®Google Scholar
• Liu S, Wang Y. Mass spectrometry for the assessment of the occurrence and biological consequences of DNA adducts. Chem Soc Rev. 2015;44(21):7829–7854.
   PubMed Web of Science ®Google Scholar
• Dizdaroglu M, Coskun E, Jaruga P. Measurement of oxidatively induced DNA damage and its repair, by mass spectrometric techniques. Free Radic Res. 2015;49(5):525–548.
   PubMed Web of Science ®Google Scholar
• Scanlan LD, Coskun SH, Jaruga P, et al. Measurement of oxidatively induced DNA damage in Caenorhabditis elegans with high-salt DNA extraction and isotope-dilution mass spectroscopy. Anal Chem. 2019;91(19):12149–12155.
   PubMed Web of Science ®Google Scholar
• Gassman NR, Coskun E, Stefanick DF, et al. Bisphenol A promotes cell survival following oxidative DNA damage in mouse fibroblasts. PLoS One. 2015;10(2):e0118819.
   PubMed Web of Science ®Google Scholar
• Jaruga P, Coskun E, Kimbrough K, et al. Biomarkers of oxidatively induced DNA damage in dreissenid mussels: a genotoxicity assessment tool for the Laurentian Great Lakes. Environ Toxicol. 2017;32(9):2144–2153.
   PubMed Web of Science ®Google Scholar
• Muftuoglu M, de Souza-Pinto NC, Dogan A, et al. Cockayne syndrome group B protein stimulates repair of formamidopyrimidines by NEIL1 DNA glycosylase. J Biol Chem. 2009;284(14):9270–9279.
   PubMed Web of Science ®Google Scholar
• Reipa V, Atha DH, Coskun SH, et al. Controlled potential electro-oxidation of genomic DNA. PLoS One. 2018;13(1):e0190907.
   PubMed Web of Science ®Google Scholar
• Calkins MJ, Vartanian V, Owen N, et al. Enhanced sensitivity of Neil1-/- mice to chronic UVB exposure. DNA Repair (Amst). 2016;48:43–50.
   PubMed Web of Science ®Google Scholar
• Frelon S, Douki T, Ravanat JL, et al. High-performance liquid chromatography-tandem mass spectrometry measurement of radiation-induced base damage to isolated and cellular DNA . Chem Res Toxicol. 2000;13(10):1002–1010.
   PubMed Web of Science ®Google Scholar
• Frelon S, Douki T, Favier A, et al. Hydroxyl radical is not the main reactive species involved in the degradation of DNA bases by copper in the presence of hydrogen peroxide. Chem Res Toxicol. 2003;16(2):191–197.
   PubMed Web of Science ®Google Scholar
• Malayappan B, Garrett TJ, Segal M, et al. Urinary analysis of 8-oxoguanine, 8-oxoguanosine, fapy-guanine and 8-oxo-2'-deoxyguanosine by high-performance liquid chromatography-electrospray tandem mass spectrometry as a measure of oxidative stress. J Chromatogr A. 2007;1167(1):54–62.
   PubMed Web of Science ®Google Scholar
• Kino K, Saito I, Sugiyama H. Product analysis of GG-specific photooxidation of DNA via electron transfer: 2-aminoimidazolone as a major guanine oxidation product. J Am Chem Soc. 1998;120(29):7373–7374.
   Web of Science ®Google Scholar
• Kupan A, Saulière A, Broussy S, et al. Guanine oxidation by electron transfer: one- versus two-electron oxidation mechanism. Chembiochem. 2006;7(1):125–133.
   PubMed Web of Science ®Google Scholar
• Terzidis MA, Chatgilialoglu C. An ameliorative protocol for the quantification of purine 5',8-cyclo-2'-deoxynucleosides in oxidized DNA. Front Chem. 2015;3:47.
   PubMed Web of Science ®Google Scholar
• Traube FR, Schiffers S, Iwan K, et al. Isotope-dilution mass spectrometry for exact quantification of noncanonical DNA nucleosides. Nat Protoc. 2019;14(1):283–312.
   PubMed Web of Science ®Google Scholar
• Wang J, Yuan B, Guerrero C, et al. Quantification of oxidative DNA lesions in tissues of Long-Evans Cinnamon rats by capillary high-performance liquid chromatography-tandem mass spectrometry coupled with stable isotope-dilution method. Anal Chem. 2011;83(6):2201–2209.
   PubMed Web of Science ®Google Scholar
• Terzidis MA, Ferreri C, Chatgilialoglu C. Radiation-induced formation of purine lesions in single and double stranded DNA: Revised quantification. Front Chem. 2015;3:18.
   PubMed Web of Science ®Google Scholar
• Chatgilialoglu C. Cyclopurine (cPu) lesions: what, how, and why? Free Radic Res. 2019;53(9-10):941–943.
   PubMed Web of Science ®Google Scholar
• Brooks PJ. The cyclopurine deoxynucleosides: DNA repair, biological effects, mechanistic insights, and unanswered questions. Free Radic Biol Med. 2017;107:90–100.
   PubMed Web of Science ®Google Scholar
• Wang J, Clauson CL, Robbins PD, et al. The oxidative DNA lesions 8,5'-cyclopurines accumulate with aging in a tissue-specific manner. Aging Cell. 2012;11(4):714–716.
   PubMed Web of Science ®Google Scholar
• Masi A, Sabbia A, Ferreri C, et al. Diastereomeric recognition of 5′,8-cyclo-2′-deoxyadenosine lesions by human Poly(ADP-ribose)polymerase 1 in a biomimetic model. Cells. 2019;8(2):116.
   Web of Science ®Google Scholar
• Xu M, Lai Y, Jiang Z, et al. A 5', 8-cyclo-2'-deoxypurine lesion induces trinucleotide repeat deletion via a unique lesion bypass by DNA polymerase β. Nucleic Acids Res. 2014;42(22):13749–13763.
   PubMed Web of Science ®Google Scholar
• Jiang Z, Xu M, Lai Y, et al. Bypass of a 5',8-cyclopurine-2'-deoxynucleoside by DNA polymerase β during DNA replication and base excision repair leads to nucleotide misinsertions and DNA strand breaks. DNA Repair (Amst)). 2015;33:24–34.
   PubMed Web of Science ®Google Scholar
• Krokidis MG, Terzidis MA, Efthimiadou E, et al. Purine 5',8-cyclo-2'-deoxynucleoside lesions: formation by radical stress and repair in human breast epithelial cancer cells. Free Radic Res. 2017;51(5):470–482.
   PubMed Web of Science ®Google Scholar
• Nyaga SG, Jaruga P, Lohani A, et al. Accumulation of oxidatively induced DNA damage in human breast cancer cell lines following treatment with hydrogen peroxide. Cell Cycle. 2007;6(12):1472–1478.
   PubMed Web of Science ®Google Scholar
• Mitra D, Luo X, Morgan A, et al. An ultraviolet-radiation-independent pathway to melanoma carcinogenesis in the red hair/fair skin background. Nature. 2012;491(7424):449–453.
   PubMed Web of Science ®Google Scholar
• Egler A, Fernandes E, Rothermund K, et al. Regulation of reactive oxygen species, DNA damage, and c-Myc function by peroxiredoxin 1. Oncogene. 2005;24(54):8038–8050.
   PubMed Web of Science ®Google Scholar
• Yu Y, Guerrero CR, Liu S, et al. Comprehensive assessment of oxidatively induced modifications of DNA in a rat model of human Wilson's Disease. Mol Cell Proteomics. 2016;15(3):810–817.
   PubMed Web of Science ®Google Scholar
• Krokidis M, Louka M, Efthimiadou E, et al. Membrane lipidome reorganization and accumulation of tissue DNA lesions in tumor-bearing mice: an exploratory study. Cancers. 2019;11(4):480.
   Web of Science ®Google Scholar
• Jaruga P, Rozalski R, Jawien A, et al. DNA damage products (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines as potential biomarkers in human urine for atherosclerosis. Biochemistry. 2012;51(9):1822–1824.
   PubMed Web of Science ®Google Scholar
• Kant M, Akış M, Çalan M, et al. Elevated urinary levels of 8-oxo-2'-deoxyguanosine, (5'R)- and (5'S)-8,5'-cyclo-2'-deoxyadenosines, and 8-iso-prostaglandin F2α as potential biomarkers of oxidative stress in patients with prediabetes. DNA Repair (Amst). 2016;48:1–7.
   PubMed Web of Science ®Google Scholar
• Marietta C, Brooks PJ. Transcriptional bypass of bulky DNA lesions causes new mutant RNA transcripts in human cells. EMBO Rep. 2007;8(4):388–393.
   PubMed Web of Science ®Google Scholar
• Brooks PJ. The 8,5'-cyclopurine-2'-deoxynucleosides: candidate neurodegenerative DNA lesions in xeroderma pigmentosum, and unique probes of transcription and nucleotide excision repair. DNA Repair (Amst). 2008;7(7):1168–1179.
   PubMed Web of Science ®Google Scholar
• Krokidis MG, Parlanti E, D’Errico M, et al. Purine DNA lesions at different oxygen concentration in DNA repair-impaired human cells (EUE-siXPA). Cells. 2019;8:1377.
   Web of Science ®Google Scholar
• D'Errico M, Parlanti E, Teson M, et al. New functions of XPC in the protection of human skin cells from oxidative damage. Embo J. 2006;25(18):4305–4315.
   PubMed Web of Science ®Google Scholar
• D'Errico M, Parlanti E, Teson M, et al. The role of CSA in the response to oxidative DNA damage in human cells. Oncogene. 2007;26(30):4336–4343.
   PubMed Web of Science ®Google Scholar
• Krokidis MG, D’Errico M, Pascucci B, et al. Oxygen-dependent accumulation of purine DNA lesions in cockayne syndrome cells. Cells. 2020;9(7):1671.
   Web of Science ®Google Scholar
• Masi A, Fortini P, Krokidis MG, et al. Increased levels of 5',8-cyclopurine DNA lesions in inflammatory bowel diseases. Redox Biol. 2020;34:101562.
   PubMed Web of Science ®Google Scholar
• Jackson SP, Bartek J. The DNA-damage response in human biology and disease. Nat. 2009;461(7267):1071–1078.
   Google Scholar
• Iyama T, Wilson DM. 3rd. DNA repair mechanisms in dividing and non-dividing cells. DNA Repair (Amst). 2013;12(8):620–636.
   PubMed Web of Science ®Google Scholar
• Lindahl T, Karran P, Wood RD. DNA excision repair pathways. Curr Opin Genet Dev. 1997;7(2):158–169.
   PubMed Web of Science ®Google Scholar
• Marteijn JA, Lans H, Vermeulen W, et al. Understanding nucleotide excision repair and its roles in cancer and ageing. Nat Rev Mol Cell Biol. 2014;15(7):465–481.
   PubMed Web of Science ®Google Scholar
• Barnes DE, Lindahl T. Repair and genetic consequences of endogenous DNA base damage in mammalian cells. Annu Rev Genet. 2004;38:445–476.
   PubMed Web of Science ®Google Scholar
• Hegde ML, Hazra TK, Mitra S. Early steps in the DNA base excision/single-strand interruption repair pathway in mammalian cells. Cell Res. 2008;18(1):27–47.
   PubMed Web of Science ®Google Scholar
• Fortini P, Dogliotti E. Base damage and single-strand break repair: mechanisms and functional significance of short- and long-patch repair subpathways. DNA Repair (Amst). 2007;6(4):398–409.
   PubMed Web of Science ®Google Scholar
• Robertson AB, Klungland A, Rognes T, et al. DNA repair in mammalian cells: base excision repair: the long and short of it. Cell Mol Life Sci. 2009;66(6):981–993.
   PubMed Web of Science ®Google Scholar
• Hanawalt PC. Subpathways of nucleotide excision repair and their regulation. Oncogene. 2002;21(58):8949–8956.
   PubMed Web of Science ®Google Scholar
• Sugasawa K, Okamoto T, Shimizu Y, et al. A multistep damage recognition mechanism for global genomic nucleotide excision repair. Genes Dev. 2001;15(5):507–521.
   PubMed Web of Science ®Google Scholar
• Nouspikel T. DNA repair in mammalian cells: nucleotide excision repair: variations on versatility. Cell Mol Life Sci. 2009;66(6):994–1009.
   PubMedGoogle Scholar
• van Steeg H, Kraemer KH. Xeroderma pigmentosum and the role of UV-induced DNA damage in skin cancer. Mol Med Today. 1999;5(2):86–94.
   PubMedGoogle Scholar
• Hanawalt PC, Spivak G. Transcription-coupled DNA repair: two decades of progress and surprises. Nat Rev Mol Cell Biol. 2008;9(12):958–970.
   PubMed Web of Science ®Google Scholar
• Markkanen E. Not breathing is not an option: how to deal with oxidative DNA damage. DNA Repair (Amst). 2017;59:82–105.
   PubMed Web of Science ®Google Scholar
• Tubbs A, Nussenzweig A. Endogenous DNA damage as a source of genomic instability in cancer. Cell. 2017;168(4):644–656.
   PubMed Web of Science ®Google Scholar
• Fridovich I. Superoxide radical and superoxide dismutases. Annu Rev Biochem. 1995;64:97–112.
   PubMed Web of Science ®Google Scholar
• Geancitov NE, Shafirovich V. Reactions of small reactive species with DNA. In: Chatgilialoglu C, Studer A, editors. Encyclopedia of radicals in chemistry, biology and materials. Vol. 3. Chichester, UK: Wiley; 2012. p. 1283–1317.
   Google Scholar
• Winterbourn CC. Biological chemistry of reactive oxygen species. In: Chatgilialoglu C, Studer A, editors. Encyclopedia of radicals in chemistry, biology and materials. Vol. 3. Chichester, UK: Wiley; 2012. p. 1259–1281.
   Google Scholar
• Illes E, Mizrahi A, Marks V, et al. Carbonate-radical-anions, and not hydroxyl radicals, are the products of the Fenton reaction in neutral solutions containing bicarbonate. Free Radic Biol Med. 2019;131:1–6.
   PubMed Web of Science ®Google Scholar
• Illes E, Patra SG, Marks V, et al. The FeII(citrate) Fenton reaction under physiological conditions. J Inorg Biochem. 2020; 206:111018.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Burrows CJ. Iron Fenton oxidation of 2'-deoxyguanosine in physiological bicarbonate buffer yields products consistent with the reactive oxygen species carbonate radical anion not the hydroxyl radical. Chem Commun (Camb)). 2020;56(68):9779–9782.
   PubMed Web of Science ®Google Scholar
• Fleming AM, Burrows CJ. On the irrelevancy of hydroxyl radical to DNA damage from oxidative stress and implications for epigenetics. Chem Soc Rev. 2020;49(18):6524–6528.
   PubMed Web of Science ®Google Scholar
• Sedelnikova OA, Redon CE, Dickey JS, et al. Role of oxidatively induced DNA lesions in human pathogenesis. Mutat Res. 2010;704(1-3):152–159.
   PubMed Web of Science ®Google Scholar