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Open AccessArticle

New Insights into the Reaction Paths of Hydroxyl Radicals with Purine Moieties in DNA and Double-Stranded Oligodeoxynucleotides

1
Istituto per la Sintesi Organica e la Fotoreattività, Consiglio Nazionale delle Ricerche, 40129 Bologna, Italy
2
Center for Advanced Technologies, Adam Mickiewicz University, 61-614 Poznań, Poland
3
Institute of Nanoscience and Nanotechnology, N.C.S.R. “Demokritos”, 15310 Agia Paraskevi Attikis, Greece
4
Departamento de Quimíca Organíca, Facultad de Farmacia y Bioquimíca, Universidad de Buenos Aires, Junin 954, Buenos Aires CP 1113, Argentina
5
Centre of Radiation Research and Technology, Institute of Nuclear Chemistry and Technology, Dorodna 16, 03-195 Warsaw, Poland
*
Authors to whom correspondence should be addressed.
Academic Editor: Michael Smietana
Molecules 2019, 24(21), 3860; https://doi.org/10.3390/molecules24213860
Received: 24 September 2019 / Revised: 22 October 2019 / Accepted: 23 October 2019 / Published: 26 October 2019
(This article belongs to the Special Issue Biomimetic Radical Chemistry and Applications)
The reaction of hydroxyl radical (HO) with DNA produces many primary reactive species and many lesions as final products. In this study, we have examined the optical spectra of intermediate species derived from the reaction of HO with a variety of single- and double-stranded oligodeoxynucleotides and ct-DNA in the range of 1 μs to 1 ms by pulse radiolysis using an Intensified Charged Coupled Device (ICCD) camera. Moreover, we applied our published analytical protocol based on an LC-MS/MS system with isotopomeric internal standards to enable accurate and precise measurements of purine lesion formation. In particular, the simultaneous measurement of the four purine 5′,8-cyclo-2′-deoxynucleosides (cPu) and two 8-oxo-7,8-dihydro-2′-deoxypurine (8-oxo-Pu) was obtained upon reaction of genetic material with HO radicals generated either by γ-radiolysis or Fenton-type reactions. Our results contributed to the debate in the literature regarding absolute level of lesions, method of HO radical generation, 5′R/5′S diastereomeric ratio in cPu, and relative abundance between cPu and 8-oxo-Pu. View Full-Text
Keywords: DNA damage; 5′,8-cyclopurines; 8-oxo-dG; free radicals; pulse radiolysis; gamma radiolysis; Fenton reaction; oligonucleotides DNA damage; 5′,8-cyclopurines; 8-oxo-dG; free radicals; pulse radiolysis; gamma radiolysis; Fenton reaction; oligonucleotides
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MDPI and ACS Style

Chatgilialoglu, C.; Krokidis, M.G.; Masi, A.; Barata-Vallejo, S.; Ferreri, C.; Terzidis, M.A.; Szreder, T.; Bobrowski, K. New Insights into the Reaction Paths of Hydroxyl Radicals with Purine Moieties in DNA and Double-Stranded Oligodeoxynucleotides. Molecules 2019, 24, 3860.

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