1H,13C and15N nuclear magnetic resonance analysis and chemical features of the two main radical oxidation products of 2′-deoxyguanosine: oxazolone and imidazolone nucleosides

Raoul, S.; Berger, M.; Buchko, Garry W.; Joshi, P. C.; Morin, Bénédicte; Weinfeld, Michael; Cadet, Jean

doi:10.1039/p29960000371

Cited by 116 publications

(91 citation statements)

References 45 publications

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“…spectrum of IIa was found to be identical to that reported for 2-amino-5-[(2-deoxy-␤-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (39). Furthermore, the mass spectrum of IIa using GC/MS in electron ionization mode revealed ions at m/z ϭ 328, 313, 285, and 198, a spectrum identical to that reported for 2,5-diaminoimidazol-4-one (29).…”

Section: Characterization Of IIsupporting

confidence: 77%

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Niles

Burney

Singh

et al. 1999

Proc. Natl. Acad. Sci. U.S.A.

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Of the DNA bases, peroxynitrite (ONOO ؊ ) is most reactive toward 2-deoxyguanosine (dGuo), but even more reactive with 8-oxo-7,8-dihydro-2-deoxyguanosine (8-oxodGuo), requiring a 1,000-fold excess of dGuo to provide 50% protection against the reaction with 8-oxodGuo. Therefore, it seems reasonable that 8-oxodGuo is a potentially important target in DNA and that the structures of the reaction products with ONOO ؊ should be characterized.

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Section: Characterization Of IIsupporting

confidence: 77%

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Niles

Burney

Singh

et al. 1999

Proc. Natl. Acad. Sci. U.S.A.

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“…The digestion mixture was passed through a Millipore centrifugal filter to remove enzymes and subjected to HPLC-MS/MS analysis. The authentic 2-amino-5-[(2-deoxy-␤-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one was synthesized by photosensitization of 2Ј-deoxyguanosine (dG) with benzophenone, isolated by reversed-phase HPLC, and converted to 2,2-diamino-4-[(2-deoxy-␤-D-erythro-pentofuranosyl)amino]-2,5-dihydrooxazol-5-one (dZ) as described earlier (19).…”

Section: Methodsmentioning

confidence: 99%

Oxidative DNA Damage Associated with Combination of Guanine and Superoxide Radicals and Repair Mechanisms via Radical Trapping

Misiaszek

Crean

Joffe

et al. 2004

Journal of Biological Chemistry

209

250

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“…We did find a DNA strand with a mass compatible with one guanine base transformed into imidazolone (3, Scheme 5; t R = 42.5 min, m/z = 1183.4 amu). [39,40] However, most of the other products were not analyzed due to their low abundance. From this data, we concluded that the manganese porphyrin was not reactive toward this sequence of DNA and that the oxidation of an isolated intrastrand guanine was 1000 times less reactive than the (A·T) 3 site with Mn-TMPyP/KHSO 5 .…”

Section: Double-stranded Oligonucleotides Containing No (A·t) 3 Sitementioning

confidence: 99%

“…The initial GG strand eluted at a retention time of t R = 40 min with a m/z = 909.75 amu and z = 2 ( Table 3). The products of guanine oxidation were the imidazolone (3, Scheme 5; t R = 38 min, m/z = 890.35 amu), [39,40] the dehydroguanidinohydantoin (4; t R = 38 min, m/z = 911.75 amu), [36,42,43] and a proposed N-formylamido-iminohydantoin (5; t R = 32.8 min, m/z = 926.55 amu) [32,33] derivative. On this sequence, which was selected to present an oxidation-sensitive GG site, the guanine [a] DM: Mass of the modified oligonucleotide minus the mass of the initial oligonucleotide.…”

Section: Double-stranded Oligonucleotides Containing No (A·t) 3 Sitementioning

confidence: 99%

Use of Short Duplexes for the Analysis of the Sequence‐Dependent Cleavage of DNA by a Chemical Nuclease, a Manganese Porphyrin

et al. 2005

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A manganese porphyrin, manganese(III)-bis(aqua)-meso-tetrakis(4-N-methylpyridiniumyl)porphyrin, in the presence of KHSO5 is able to perform deoxyribose or guanine oxidation depending on its mode of interaction with DNA. These two reactions involve an oxygen-atom transfer or an electron transfer, respectively. The oxidative reactivity of the manganese-oxo porphyrin was compared on short oligonucleotide duplexes of different sequences. The major mechanism of DNA damage is due to deoxyribose hydroxylation at a site of strong interaction, an (A.T)3 sequence. Guanine oxidation by electron transfer was found not to be competitive with this major mechanism. It was found that a single intrastrand guanine was three orders of magnitude less reactive than an (A.T)3 sequence. The reactivity of a 5'-GG sequence was found to be intermediate and was estimated to be two orders of magnitude less than that of an (A.T)3 site. Short oligonucleotide duplexes, as double-stranded-DNA models, proved to be convenient tools for the study of the comparative reactivity of this reagent toward different sequences of DNA. However, they showed a particular reactivity at their terminal base pairs (the "end effect") that biased their modeling capacity for double-helix-DNA models.

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¹H,¹³C and¹⁵N nuclear magnetic resonance analysis and chemical features of the two main radical oxidation products of 2′-deoxyguanosine: oxazolone and imidazolone nucleosides

Cited by 116 publications

References 45 publications

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Peroxynitrite reaction products of 3′,5′-di -O- acetyl-8-oxo-7,8-dihydro-2′-deoxyguanosine

Oxidative DNA Damage Associated with Combination of Guanine and Superoxide Radicals and Repair Mechanisms via Radical Trapping

Use of Short Duplexes for the Analysis of the Sequence‐Dependent Cleavage of DNA by a Chemical Nuclease, a Manganese Porphyrin

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