New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine

Chatgilialoglu, Chryssostomos; D’Angelantonio, Mila; Kciuk, Gabriel; Bobrowski, Krzysztof

doi:10.1021/tx2003245

Cited by 70 publications

(90 citation statements)

References 34 publications

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“…The formation of 2,2,4-triamino-5(2H )-oxazolone (oxazolone), a welldocumented † OH and one-electron oxidation product of Gua nucleoside , has been detected in the hepatic DNA of diabetic rats, albeit the yield was tenfold lower than that of 8-oxoGua (Matter et al 2006). The formation of oxazolone is rationalized in terms of initial † OH-mediated H-atom abstraction from the 2-amino group of guanine (Chatgilialoglu et al 2011a) as a more relevant alternative to † OH addition at C4 followed by dehydration, which was initially proposed several years ago (Candeias and Steenken 2000). The resulting N-centered radical rearranges to the G (-H) † guanyl radical, which is also generated by deprotonation of the guanine radical cation produced by one-electron oxidation.…”

Section: Guaninementioning

confidence: 99%

DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation

Cadet

Wagner

2013

Cold Spring Harbor Perspectives in Biology

720

510

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Emphasis has been placed in this article dedicated to DNA damage on recent aspects of the formation and measurement of oxidatively generated damage in cellular DNA in order to provide a comprehensive and updated survey. This includes single pyrimidine and purine base lesions, intrastrand cross-links, purine 5 0 ,8-cyclonucleosides, DNA-protein adducts and interstrand cross-links formed by the reactions of either the nucleobases or the 2-deoxyribose moiety with the hydroxyl radical, one-electron oxidants, singlet oxygen, and hypochlorous acid. In addition, recent information concerning the mechanisms of formation, individual measurement, and repair-rate assessment of bipyrimidine photoproducts in isolated cells and human skin upon exposure to UVB radiation, UVA photons, or solar simulated light is critically reviewed.I n this article, we emphasize recent developments in the formation of damage to cellular DNA mediated by reactive oxygen species (ROS) and oxidizing agents, including singlet oxygen, the hydroxyl radical ( † OH), one-electron oxidants, hypochlorous acid (HOCl), and ten-eleven translocation (TET) oxygenases involved in epigenetic regulation. These advances have been possible because of the development of sensitive and powerful high-performance liquid chromatography-mass spectrometry (HPLC-MS)/ mass spectrometry (MS) methods allowing one to revise previously reported data obtained using methods such as gas chromatographymass spectrometry (GC-MS), immunoassays, and HPLC with single MS detection (Cadet et al. , 2012a. Considerable progress has also been made in the elucidation of oxidative degradation pathways of isolated DNA and related model compounds (for recent comprehensive reviews, see Gimisis and Cismaş 2006;Neeley and Essigmann 2006;Pratviel and Meunier 2006;von Sonntag 2006;Cadet et al. 2008Cadet et al. , 2010Cadet et al. , 2012bDedon 2008;Burrows 2009;Wagner and Cadet 2010). In addition, there is much complementary information on solar-radiation-induced formation of bipyrimidine photoproducts in the DNA of fibroblasts, keratinocytes, and human skin. In particular, the distribution of UVA and UVB photoproducts has been determined, allowing accurate determination of their rates of repair (Cadet et al.

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Section: Guaninementioning

confidence: 99%

DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation

Cadet

Wagner

2013

Cold Spring Harbor Perspectives in Biology

720

510

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“…Instead, DNA damage is mediated by · OH and other species capable of modifying DNA including inter alia : peroxynitrite, carbonate radical, and nitrogen trioxide (Cadet et al, 2012). In particular, · OH rapidly reacts with DNA bases and the ribose sugar at diffusion-controlled rates (e.g., guanine: k ~ 5–8 × 10 9 M −1 s −1 , Chatgilialoglu et al, 2011). The chemistry of · OH mediated DNA damage is complex but the salient points are: (1) · OH reacts with DNA indiscriminately via addition ( k ~ 4–9 × 10 9 M −1 s −1 ) or hydrogen abstraction reactions ( k ~ 2 × 10 9 M −1 s −1 ; Von Sonntag, 2006) and (2) the resultant radical products can then react with other radicals (e.g., O 2 .− and NO) or O 2 to generate a modified DNA adduct (Dizdaroglu, 2012; Dizdaroglu and Jaruga, 2012).…”

Section: Exercise-induced Dna Damage: the Key Role Of Hydroxyl Radicalmentioning

confidence: 99%

The basic chemistry of exercise-induced DNA oxidation: oxidative damage, redox signaling, and their interplay

et al. 2015

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Acute exercise increases reactive oxygen and nitrogen species generation. This phenomenon is associated with two major outcomes: (1) redox signaling and (2) macromolecule damage. Mechanistic knowledge of how exercise-induced redox signaling and macromolecule damage are interlinked is limited. This review focuses on the interplay between exercise-induced redox signaling and DNA damage, using hydroxyl radical (·OH) and hydrogen peroxide (H2O2) as exemplars. It is postulated that the biological fate of H2O2 links the two processes and thus represents a bifurcation point between redox signaling and damage. Indeed, H2O2 can participate in two electron signaling reactions but its diffusion and chemical properties permit DNA oxidation following reaction with transition metals and ·OH generation. It is also considered that the sensing of DNA oxidation by repair proteins constitutes a non-canonical redox signaling mechanism. Further layers of interaction are provided by the redox regulation of DNA repair proteins and their capacity to modulate intracellular H2O2 levels. Overall, exercise-induced redox signaling and DNA damage may be interlinked to a greater extent than was previously thought but this requires further investigation.

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“…It is well documented that • OH radicals can produce both G(-H) •35 and side-chain amino acid 26 radicals. In vivo generation of hydroxyl radicals occurs via two major pathways: (1) Fenton reaction involving the reduction of H 2 O 2 by ferrous or copper ions 43 , and (2) radiolysis of water molecules through the indirect effects of ionizing radiation.…”

Section: Resultsmentioning

confidence: 99%

Generation of guanine–amino acid cross-links by a free radical combination mechanism

Uvaydov

Geacintov

Shafirovich

2014

Phys. Chem. Chem. Phys.

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A direct method has been developed for the in vitro synthesis of stable DNA – protein cross-links (DPC’s) between guanine and amino acids (lysine, arginine). This method employs the combination of guanine neutral radicals, G(-H)•, and side-chain C-centered amino acid radicals. The latter were generated indirectly after first causing the selective photoionization of 2-aminopurine (2AP) embedded in the oligonucleotide, 5’-d(CC[2AP]TCGCTACC) by intense nanosecond 308 nm excimer laser pulses. The 2AP radical cation deprotonates rapidly to form the 2AP(-H)• neutral radical which, in turn, oxidizes the nearby guanine to form the neutral guanine G(-H)• radical, as described previously (Shafirovich et al. J. Phys. Chem. B, 2001, 105, 8431). In parallel, the hydrated electrons generated by the photoionization of 2AP, are scavenged by nitrous oxide to generate hydroxyl radicals. In the presence of a large excess of the amino acids, the hydroxyl radicals oxidize the latter to produce C-centered amino acid radicals that combine with the G(-H)• radicals to form the guanine-amino acid cross-linked oligonucleotide product. Analogous products were generated by photoionizing the free nucleoside, 2’,3’,5’-tri-O-acetylguanoise, (tri-O-Ac-Guo) using intense nanosecond 266 nm Nd: Yag laser pulse irradiation. The guanine – amino acid cross-links thus produced either site-specifically positioned in oligonucleotides, or in the free nucleoside tri-O-Ac-Guo were isolated by HPLC methods and identified by high resolution LC-TOF/MS and LC-MS/MS methods. The possibility is discussed that analogous guanine-amino acid cross-linked products could be formed in vivo under single hit radical generation mechanisms during oxidative stress.

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New Insights into the Reaction Paths of Hydroxyl Radicals with 2′-Deoxyguanosine

Cited by 70 publications

References 34 publications

DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation

DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation

The basic chemistry of exercise-induced DNA oxidation: oxidative damage, redox signaling, and their interplay

Generation of guanine–amino acid cross-links by a free radical combination mechanism

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