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The Fate of C5 Radicals of Purine Nucleosides Under Oxidative Conditions (Articolo in rivista)
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- The Fate of C5 Radicals of Purine Nucleosides Under Oxidative Conditions (Articolo in rivista) (literal)
- Anno
- 2008-01-01T00:00:00+01:00 (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
- 10.1021/ja800763j (literal)
- Alternative label
Boussicault, F.; Kaloudis, P.; Caminal, C.; Mulazzani, Q. G.; Chatgilialoglu, C. (2008)
The Fate of C5 Radicals of Purine Nucleosides Under Oxidative Conditions
in Journal of the American Chemical Society (Print)
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- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
- Boussicault, F.; Kaloudis, P.; Caminal, C.; Mulazzani, Q. G.; Chatgilialoglu, C. (literal)
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- Titolo
- The Fate of C5 Radicals of Purine Nucleosides Under Oxidative Conditions (literal)
- Abstract
- The factors that influence the reactivity of C5' radicals in purine moieties under aerobic conditions are unknown not only in DNA, but also in simple nucleosides. 5',8-Cyclopurine lesions are the result of a rapid C5' radical attack to the purine moieties before the reaction with oxygen. These well-known lesions among the DNA modifications were suppressed by the presence of molecular oxygen in solution. Here we elucidate the chemistry of three purine-substituted C5' radicals (i.e., 2'-deoxyadenosin-5'-yl, 2'-deoxyinosin-5'-yl, and 2'-deoxyguanosin-5'-yl) under oxidative conditions using gamma-radiolysis coupled with product studies. 2'-Deoxyadenosin-5'-yl and 2'-deoxyinosin-5'-yl radicals were selectively generated by the reaction of hydrated electrons (e(aq)(-)) with 8-bromo-2'-deoxyadenosine and 8-bromo-2'-deoxyinosine followed by a rapid radical translocation from the C8 to the C5' position. Trapping these two C5' radicals with Fe(CN)(6)(3-) gave corresponding hydrated 5'-aldehydes in good yields that were isolated and fully characterized. When an oxygen concentration in the range of 13-266 mu M (typical oxygenated tissues) is used, the hydrated 5'-aldehyde is accompanied by the 5',8-cyclopurine nucleoside. The formation of 5',8-cyclopurines is relevant in all experiments, and the yields increased with decreasing 02 concentration. The reaction of HO(center dot) radicals with 2'-deoxyadenosine and 2'-deoxyguanosine under normoxic conditions was also investigated. The minor path of C5' radicals formation was found to be ca. 10% by quantifying the hydrated 5'-aldehyde in both experiments. Rate constants for the reactions of the 2'-deoxyadenosin-5'-yl with cysteine and glutathione in water were determined by pulse radiolysis to be (2.1 +/- 0.5) x 10(7) and (4.9 +/- 0.6) x 10(7) M(-1) s(-1) at 22 degrees C, respectively. (literal)
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