(5′R)-and (5′S)-purine 5′,8-cyclo-2′-deoxyribonucleosides: reality or artifactual measurements? A reply to Chatgilialoglu’s comments (this issue)

References

• Cadet J, Di Mascio P, Wagner JR. Radiation-induced (5′R)- and (5′S)-purine 5′,8-cyclo-2′-deoxyribonucleosides in human cells: a revisited analysis of HPLC-MS/MS measurements. Free Radic Res. 2019;53(5):574–577.
   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
• Chatgilialoglu C. Cyclopurine (cPu) lesions. What, how and why. Free Radic Res. 2019;50. DOI:10.1080/10715762.2019.1643017
   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
• Barbier E, Lagorce A, Hachemi A, et al. Oxidative DNA damage and repair in the radioresistant archaeon Thermococcus gammatolerans. Chem Res Toxicol. 2016;29(11):1796–1809.
   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
• 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
• Wagner JR, Cadet J. Oxidation reactions of cytosine DNA components by hydroxyl radical and one-electron oxidants in aerated aqueous solutions. Acc Chem Res. 2010;43(4):564–571.
   PubMed Web of Science ®Google Scholar
• Cadet J, Wagner JR. DNA base damage by reactive oxygen species, oxidizing agents, and UV radiation. Cold Spring Harb Perspect Biol. 2013;5(2):a012559.
   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
• Di Mascio P, Martinez GR, Miyamoto S, et al. Singlet molecular oxygen reactions with nucleic acids, lipids, and proteins. Chem Rev. 2019;119(3):2043–2086.
   PubMed Web of Science ®Google Scholar
• Garcia CC, Freitas FP, Di Mascio P, et al. Ultrasensitive simultaneous quantification of 1,N2-etheno-2′-deoxyguanosine and 1,N2-propano-2′-deoxyguanosine in DNA by an online liquid chromatography-electrospray tandem mass spectrometry assay. Chem Res Toxicol. 2010;23(7):1245–1255.
   PubMed Web of Science ®Google Scholar
• Garcia CC, Angeli JP, Freitas FP, et al. [13C2]-Acetaldehyde promotes unequivocal formation of 1,N2-propano-2. J Am Chem Soc. 2011;133(24):9140–9143.
   PubMed Web of Science ®Google Scholar
• Romieu A, Gasparutto D, Molko D, et al. Site-specific introduction of (5′S)-5′,8-Cyclo-2′-deoxyadenosine into oligodeoxyribonucleotides. J Org Chem. 1998;63(15):5245–5249.
   Web of Science ®Google Scholar
• Romieu A, Gasparutto D, Cadet J. Synthesis and characterization of oligonucleotides containing 5. Chem Res Toxicol. 1999;12(5):412–421.
   PubMed Web of Science ®Google Scholar
• Terzidis MA, Chatgilialoglu C. An ameliorative protocol for the quantification of purine 5. Front Chem. 2015;3:47.
   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
• 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
• Pouget JP, Ravanat JL, Douki T, et al. Measurement of DNA base damage in cells exposed to low doses of gamma-radiation: comparison between the HPLC-EC and comet assays. Int J Radiat Biol. 1999;75(1):51–58.
   PubMed Web of Science ®Google Scholar
• Pouget JP, Frelon S, Ravanat JL, et al. Formation of modified DNA bases in cells exposed either to gamma radiation or to high-LET particles. Radiat Res. 2002;157(5):589–595.
   PubMed Web of Science ®Google Scholar
• Douki T, Ravanat JL, Pouget JP, et al. Minor contribution of direct ionization to DNA base damage induced by heavy ions. Int J Radiat Biol. 2006;82(2):119–127.
   PubMed Web of Science ®Google Scholar
• Madugundu GS, Cadet J, Wagner JR. Hydroxyl-radical-induced oxidation of 5-methylcytosine in isolated and cellular DNA. Nucleic Acids Res. 2014;42(11):7450–7460.
   PubMed Web of Science ®Google Scholar
• Sauvaigo S, Petec-Calin C, Caillat S, et al. Comet assay coupled to repair enzymes for the detection of oxidative damage to DNA induced by low doses of gamma-radiation: use of YOYO-1, low-background slides, and optimized electrophoresis conditions. Anal Biochem. 2002;303(1):107–109.
   PubMed Web of Science ®Google Scholar
• Cadet J, Douki T, Ravanat JL. Measurement of oxidatively generated base damage in cellular DNA. Mutat Res. 2011;711(1-2):3–12.
   PubMed Web of Science ®Google Scholar
• Cadet J, Douki T, Ravanat JL, et al. Measurement of oxidatively generated base damage to nucleic acids in cells: facts and artifacts. Bioanal Rev. 2012;4(2-4):55–74.
   Google Scholar
• ESCODD (European Standards Committee on Oxidative DNA Damage), Gedik CM, Collins A. Establishing the background level of base oxidation in human lymphocyte DNA: results of an interlaboratory validation study. FASEB J. 2005;19(1):82–84.
   PubMed Web of Science ®Google Scholar
• Collins AR, Cadet J, Mőller L, et al. Are we sure we know how to measure 8-oxo-7,8-dihydroguanine in DNA from human cells? Arch Biochem Biophys. 2004;423(1):57–65.
   PubMed Web of Science ®Google Scholar
• Ravanat JL, Douki T, Duez P, et al. Cellular background level 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. 2002;23(11):1911–1918.
   PubMed Web of Science ®Google Scholar
• Badouard C, Ménézo Y, Panteix G, et al. Determination of new types of DNA lesions in human sperm. Zygote. 2008;16(1):9–13.
   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. 2019;80:52–58.
   PubMed Web of Science ®Google Scholar
• Osterod M, Hollenbach S, Hengstler JG, et al. Age-related and tissue-specific accumulation of oxidative DNA base damage in 7,8-dihydro-8-oxoguanine-DNA glycosylase (Ogg1) deficient mice. Carcinogenesis. 2001;22(9):1459–1463.
   PubMed Web of Science ®Google Scholar