Vicinal Lesions in X-irradiated DNA?

Box, Harold C.; Budzinski, Edwin E.; Freund, Harold G.; Evans, Marianne S.; Patrzyc, Helen B.; Wallace, John C.; Maccubbin, Alexander E.

doi:10.1080/09553009314551411

Cited by 44 publications

(20 citation statements)

References 6 publications

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“…Two of these guanine containing tandem base lesions including G[8 - 5m]T and G[8 - 5]C (Figure 6) whose formation involves 5-(uracilyl) methyl and 6-hydroxy-5,6-dihydrocytosyl radicals, respectively, as the reactive intermediates have been measured in cellular DNA using an accurate and sensitive HPLC-MS 3 assay [90,91]. Following the pioneering work of Box and his collaborators [92], evidence has been provided that pyrimidine peroxyl radicals generated by either • OH or one-electron oxidants are able to efficiently react with adjacent purine [36] and pyrimidine bases [37] leading to the formation of tandem base lesions in isolated DNA [38]. However, none of these intra-strand cross-links has been detected so far in cellular DNA.…”

Section: Classes Of Oxidatively Generated Damagementioning

confidence: 99%

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

Cadet

Loft

Oliński

et al. 2012

Free Radical Research

123

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A broad scientific community is involved in investigations aimed at delineating the mechanisms of formation and cellular processing of oxidatively generated damage to nucleic acids. Perhaps as a consequence of this breadth of research expertise, there are nomenclature problems for several of the oxidized bases including 8-oxo-7,8-dihydroguanine (8-oxoGua), a ubiquitous marker of almost every type of oxidative stress in cells. Efforts to standardize the nomenclature and abbreviations of the main DNA degradation products that arise from oxidative pathways are reported. Information is also provided on the main oxidative radicals, non-radical oxygen species, one-electron agents and enzymes involved in DNA degradation pathways as well in their targets and reactivity. A brief classification of oxidatively generated damage to DNA that may involve single modifications, tandem base modifications, intrastrand and interstrand cross-links together with DNA-protein cross-links and base adducts arising from the addition of lipid peroxides breakdown products is also included.

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Section: Classes Of Oxidatively Generated Damagementioning

confidence: 99%

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

Cadet

Loft

Oliński

et al. 2012

Free Radical Research

123

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“…The first evidence for implication of † OH in the formation of tandem base modifications in aerated aqueous solutions came from the pioneering work of Box and his collaborators (Box et al 1993). More recently, it was shown that pyrimidine peroxyl radicals formed by oxidative reactions involving either † OH or one-electron oxidants are able to efficiently add to adjacent purine (Douki et al 2002a) and pyrimidine bases , giving rise to tandem base lesions in isolated DNA (Bourdat et al 2000).…”

Section: Lesions Formed In the Presence Of Omentioning

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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“…A first example of tandem lesions, with a 8-oxodG and a formamido (dβF) residue being neighboring to each other, was reported by Box et al (12,21). Recently Bourdat et al (15) showed that the amount of these tandem lesions, dβF-8-oxodG and its isomeric 8-oxodG-dβF, formed from γ radiation cannot account for the total amount of tandem lesions involving 8-oxodG.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, several types of tandem DNA lesions (12)(13)(14)(15)(16)(17)(18)(19)(20), where damage involves two adjacent nucleosides, have been isolated and characterized. A first example of tandem lesions, with a 8-oxodG and a formamido (dβF) residue being neighboring to each other, was reported by Box et al (12,21).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Thermodynamic Studies of Oligodeoxyribonucleotides Containing Tandem Lesions of Thymidine Glycol and 8-Oxo-2‘-deoxyguanosine

Wang

2006

Chem. Res. Toxicol.

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Thymidine glycol (Tg), which is also known as 5,6-dihydroxy-5,6-dihydrothymidine, and 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) are two major types of DNA damage products induced by reactive oxygen species (ROS). Here we report the synthesis of oligodeoxyribonucleotides (ODNs) containing both Tg and 8-oxodG. The dual incorporation of the two single-base lesions was achieved by using a phosphoramidite building block of 8-oxodG with ultramild base protecting group and a building block of Tg whose nucleobase hydroxyl groups were protected with acetyl functionality. The availability of ODNs carrying neighboring 8-oxodG and Tg provided authentic substrates for assessing the formation and examining the replication and repair of this kind of tandem lesions. In addition, thermodynamic parameters derived from melting temperature data revealed that tandem lesions destabilized the double helix to a greater extent than either of the two single-base lesions alone. The thermodynamic results could offer a basis for understanding the repair of the tandem base lesions.

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Vicinal Lesions in X-irradiated DNA?

Abstract: Irradiation of the dinucleoside monophosphate d(GpT) in an oxygenated solution gives products characterized by damage on one or both guanine and thymine bases, the yields of which were proportional to radiation dose .

Cited by 44 publications

References 6 publications

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

Biologically relevant oxidants and terminology, classification and nomenclature of oxidatively generated damage to nucleobases and 2-deoxyribose in nucleic acids

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

Synthesis and Thermodynamic Studies of Oligodeoxyribonucleotides Containing Tandem Lesions of Thymidine Glycol and 8-Oxo-2‘-deoxyguanosine

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