Kinetics of deamination and Cu(II)/H 2 O 2 /Ascorbate-induced formation of 5-methylcytosine glycol at CpG sites in duplex DNA

Cao, Huachuan; Jiang, Yong; Wang, Yinsheng

doi:10.1093/nar/gkp615

Cited by 23 publications

(24 citation statements)

References 40 publications

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“…The initial addition of † OH and O 2 to the 5,6-double bond of 5-methylcytosine leads to the formation of intermediate hydroperoxyl radicals and 5(6)-hydroperoxides, which decompose to 5-methylcytosine 5,6-glycol, 5-hydroxy-5-methylhydantoin, and 1-carbamoyl-4,5-dihydroxy-5-methyl-2-oxoimidazolidine derivatives. In contrast to the 5,6-glycols of 2 0 -deoxycytidine, the corresponding 5,6-glycols of 5-methyl-2 0 -deoxycytidine are about 30-fold more stable toward deamination in aqueous neutral solution (Cao et al 2009). Lastly, H-atom abstraction from the methyl group of 5-methylcytosine produces 5-hydroxymethylcytosine and 5-formylcytosine, similar to the case of thymine oxidation.…”

Section: Cytosine and 5-methylcytosinementioning

confidence: 99%

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

Cadet

Wagner

2013

Cold Spring Harbor Perspectives in Biology

704

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: Cytosine and 5-methylcytosinementioning

confidence: 99%

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

Cadet

Wagner

2013

Cold Spring Harbor Perspectives in Biology

704

510

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“…42 Similar mechanisms may account for the formation of 5-methyl-2′-deoxycytidine (5-mdC) glycol, which can undergo deamination to yield thymidine glycol. 43–47 The formation of 5-mdC glycol may be involved in the C → T transition mutations occurring at CpG dinucleotide sites, a type of mutation ubiquitously found in human cancers. 48,49 Exposure to ionizing radiation 50,51 and reaction with oxidizing agents, including KMnO 4 , OsO 4 , 52 and Fenton reagents, 47 can result in the formation of thymidine glycol in DNA.…”

Section: Chemistry Of Oxidative Stress-induced Dna Damagementioning

confidence: 99%

“…The lesion-containing dinucleotide was thus utilized for the quantification of thymidine glycol in DNA using LC-MS/MS coupled with the stable isotope-dilution method. 47,299,300 This method has been applied for probing oxidative stress in white blood cell DNA of ovarian cancer patients 301 and BRCA mutation carriers 302 as well as for examining the effect of smoking cessation 303 and antioxidant usage 304 on levels of oxidatively induced DNA damage. Rather than being highly mutagenic, thymidine glycol strongly inhibits DNA replication.…”

Section: Implications Of Oxidative Stress-induced Dna Lesions In Hmentioning

confidence: 99%

Occurrence, Biological Consequences, and Human Health Relevance of Oxidative Stress-Induced DNA Damage

Cui

Niedernhofer

et al. 2016

Chem. Res. Toxicol.

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146

135

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A variety of endogenous and exogenous agents can induce DNA damage and lead to genomic instability. Reactive oxygen species (ROS), an important class of DNA damaging agents, are constantly generated in cells as a consequence of endogenous metabolism, infection/inflammation, and/or exposure to environmental toxicants. A wide array of DNA lesions can be induced by ROS directly, including single-nucleobase lesions, tandem lesions, and hypochlorous acid (HOCl)/hypobromous acid (HOBr)-derived DNA adducts. ROS can also lead to lipid peroxidation, whose byproducts can also react with DNA to produce exocyclic DNA lesions. A combination of bioanalytical chemistry, synthetic organic chemistry, and molecular biology approaches have provided significant insights into the occurrence, repair, and biological consequences of oxidatively induced DNA lesions. The involvement of these lesions in the etiology of human diseases and aging was also investigated in the past several decades, suggesting that the oxidatively induced DNA adducts, especially bulky DNA lesions, may serve as biomarkers for exploring the role of oxidative stress in human diseases. The continuing development and improvement of LC-MS/MS coupled with the stable isotope-dilution method for DNA adduct quantification will further promote research about the clinical implications and diagnostic applications of oxidatively induced DNA adducts.

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“…Thymidine glycol could also arise from the deamination of 5-methylcytosine glycol, a common oxidatively induced lesion of 5-methylcytosine (Figure 1) (18, 45). Thus, the 5′-Tg-(8-oxodG)-3′ tandem lesion may form from ROS attack at methylated CpG site and contribute to CpG mutagenesis (18, 46). …”

Section: Introductionmentioning

confidence: 99%

Efficient Formation of the Tandem Thymine Glycol/8-Oxo-7,8-dihydroguanine Lesion in Isolated DNA and the Mutagenic and Cytotoxic Properties of the Tandem Lesions in Escherichia coli Cells

Yuan

Jiang

Wang

et al. 2009

Chem. Res. Toxicol.

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Reactive oxygen species can induce the formation of not only single-nucleobase lesions, which have been extensively studied, but also tandem lesions. Herein we report a high frequency of formation of a type of tandem lesion, where two commonly observed oxidatively induced single-nucleobase lesions, i.e., thymidine glycol (Tg) and 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) are vicinal to each other, in calf thymus DNA upon exposure to Cu(II)/ascorbate along with H2O2 or γ rays. We further explored how the tandem lesions perturb the efficiency and fidelity of DNA replication by assessing the replication products formed from the propagation, in Escherichia coli cells, of the single-stranded pYMV1 shuttle vectors containing two tandem lesions [5′-(8-oxodG)-Tg-3′ and 5′-Tg-(8-oxodG)-3′] or an isolated Tg or 8-oxodG. The bypass efficiencies for the two tandem lesions were approximately one half of those for the two isolated single-nucleobase lesions. The presence of an adjacent Tg could lead to significant increases in G→T transversion at the 8-oxodG site compared to that of a single 8-oxodG lesion; the frequencies of G→T mutation were approximately 18%, 32% and 28% for 8-oxodG that are isolated, in 5′-(8-oxodG)-Tg-3′ and in 5′-Tg-(8-oxodG)-3′, respectively. Moreover, both pol IV and pol V are involved, in part, in bypassing the Tg, either present alone or as part of the tandem lesions, in Escherichia coli cells. Together, our results support that complex lesions could exert greater cytotoxic and mutagenic effects than when the composing individual lesions are present alone.

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Kinetics of deamination and Cu(II)/H 2 O 2 /Ascorbate-induced formation of 5-methylcytosine glycol at CpG sites in duplex DNA

Cited by 23 publications

References 40 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

Occurrence, Biological Consequences, and Human Health Relevance of Oxidative Stress-Induced DNA Damage

Efficient Formation of the Tandem Thymine Glycol/8-Oxo-7,8-dihydroguanine Lesion in Isolated DNA and the Mutagenic and Cytotoxic Properties of the Tandem Lesions in Escherichia coli Cells

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