Site-specific radical formation in DNA induced by Cu(II)–H2O2 oxidizing system, using ESR, immuno-spin trapping, LC-MS, and MS/MS

Bhattacharjee, Suchandra; Deterding, Leesa J.; Chatterjee, Saurabh; Jiang, Jiansheng; Ehrenshaft, Marilyn; Lardinois, Olivier M.; Ramirez, Dario C.; Tomer, Kenneth B.; Mason, Ronald P.

doi:10.1016/j.freeradbiomed.2011.02.034

Cited by 38 publications

(41 citation statements)

References 55 publications

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“…When incubations were carried out with other nucleosides, various DMPO adducts were detected, these coupling constants are in agreement with those previously published, 34,41 and are summarized in Table-1. It should be noted that these radical adducts were minor products (less than 10% of the total adducts formed) as DMPO-OH was the major adduct detected.…”

Section: Resultssupporting

confidence: 91%

DNA Cleavage and Detection of DNA Radicals Formed from Hydralazine and Copper (II) by ESR and Immuno-Spin Trapping

Sinha

Leinisch

Bhattacharjee

et al. 2014

Chem. Res. Toxicol.

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Metal ion-catalyzed oxidation of hydrazine and its derivatives leads to the formation of the hydrazyl radical and subsequently to oxy-radicals in the presence of molecular oxygen. Here we have examined the role of Cu2+-catalyzed oxidation of hydralazine in the induction of DNA damage. Neither 5, 5-dimethyl-1-pyrroline-N-oxide (DMPO) nor dimethyl sulfoxide (DMSO) were effective in inhibiting hydralazine-Cu2+-induced DNA damage. Singlet oxygen did not appear to participate in this DNA cleavage. The one-electron oxidation of hydralazine also leads to the formation of DNA radicals as confirmed by immuno-spin trapping with 5, 5-dimethyl-1-pyrroline-N-oxide. Electron spin resonance (ESR) and spin trapping studies further confirmed the formation of DNA radicals; predominantly 2′-deoxyadenosine radical adducts were detected, while some radicals were also detected with other nucleosides. Our results suggest that free hydroxyl radicals may not be the main damaging species causing DNA cleavage, and possibly, Cu-peroxide complexes, formed from Cu+-H2O2, areresponsible for this hydralazine-Cu2+-induced DNA cleavage.

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Section: Resultssupporting

confidence: 91%

DNA Cleavage and Detection of DNA Radicals Formed from Hydralazine and Copper (II) by ESR and Immuno-Spin Trapping

Sinha

Leinisch

Bhattacharjee

et al. 2014

Chem. Res. Toxicol.

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“…About 50% of the initial reactions of † OH occur at C4 of adenine (Vieira and Steenken 1990), leading to an adduct radical that rapidly undergoes dehydration to Ade-N6-yl radicals. This radical has recently been characterized in isolated DNA treated with Cu 2þ /H 2 O 2 by electron paramagnetic resonance DMPO radical adducts and MS analysis of stable nitrone products (Bhattacharjee et al 2011(Bhattacharjee et al , 2012. The chemistry of Ade-N6-yl radicals in DNA is not well † OH gives 8-hydroxy-7,8-dihydroguan-8-yl radicals (C8-OH adduct) and guanine-N2-yl radicals (Gua-N2-yl), which transform into guanine-C5-yl radicals (G(-H † ) guanyl radical, Gua-C5-yl).…”

Section: Adeninementioning

confidence: 99%

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

Cadet

Wagner

2013

Cold Spring Harbor Perspectives in Biology

676

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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“…21 The excessive ROS can damage vital cellular structures, such as lipids, DNA, RNA and proteins, 22,23 via the oxidation of relevant small molecular components, leading to a severe biological response such as mutation and cell death. 24,25 These damages induced by ROS can be attributed to the pathogenesis of inammatory disease, cardiovascular disease, cancer, diabetes, Alzheimer's disease, cataracts, autism and aging. 24,26 Human embryonic kidney (HEK) 293 cells are a specic cell line originating from HEK cells grown in tissue cultures; such cell lines have been widely used in cell biology as well as toxicology studies.…”

Section: Introductionmentioning

confidence: 99%

Resistance investigation of wheat bran polyphenols extracts on HEK293 cells against oxidative damage

et al. 2015

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Oxidative stress has been considered as a major cause of cellular injury in a variety of clinical abnormalities. One of popular methods to inhibit reactive-oxygen-species (ROS)-induced cellular injury is dietary or pharmaceutical augmentation of the endogenous antioxidant defense capacity. In this study, the resistance effects of wheat bran polyphenols extracts (WBPE) against H 2 O 2 -induced cytotoxicity in HEK293 cells were investigated. The phenolic components of WBPE were analysed using UPLC/TQD, and the presence of ferulic acid, p-coumaric acid, o-coumaric acid and gallic acid components were confirmed. The cytotoxicity of such contents and their effects on cell morphology were also evaluated.The results demonstrated that the incubation of WBPE-N9-4 with cells prior to H 2 O 2 exposure could significantly improve cell viability corresponding with increased catalase (CAT), superoxide dismutase (SOD), and glutathione peroxidase (GSH-Px) levels. Moreover, reduction in the levels of lactate dehydrogenase (LDH), malondialdehyde (MDA), and ROS generation were observed. The presence of WBPE-N9-4 inhibited H 2 O 2 -induced apoptosis in HEK293 cells, which was confirmed by the flow cytometry of sub-G1 DNA content and an Annexin V assay. It is reasonable to assume that WBPE-N9-4 has an excellent ability to prevent HEK293 cells from oxidative-damage. Our studies, for the first time, reveal that WBPE-N9-4 has resistance effects against H 2 O 2 -induced cytotoxicity in HEK293 cells.

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Site-specific radical formation in DNA induced by Cu(II)–H2O2 oxidizing system, using ESR, immuno-spin trapping, LC-MS, and MS/MS

Cited by 38 publications

References 55 publications

DNA Cleavage and Detection of DNA Radicals Formed from Hydralazine and Copper (II) by ESR and Immuno-Spin Trapping

DNA Cleavage and Detection of DNA Radicals Formed from Hydralazine and Copper (II) by ESR and Immuno-Spin Trapping

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

Resistance investigation of wheat bran polyphenols extracts on HEK293 cells against oxidative damage

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