http://www.cnr.it/ontology/cnr/individuo/prodotto/ID51201

Comparison of isoelectronic 8-HO-G and 8-NH2-G derivatives in redox processes (Articolo in rivista)

Type

Articolo in rivista (Classe)
Prodotto della ricerca (Classe)

Label

Comparison of isoelectronic 8-HO-G and 8-NH2-G derivatives in redox processes (Articolo in rivista) (literal)

Anno

2009-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

10.1021/ja9065464 (literal)

Alternative label

Kaloudis, P.; D'Angelantonio, M.; Guerra, M.; Spadafora, M.; Cismas, C.; Gimisis, T.; Mulazzani, Q. G.; Chatgilialoglu, C. (2009)
Comparison of isoelectronic 8-HO-G and 8-NH2-G derivatives in redox processes
in Journal of the American Chemical Society (Print); American Chemical Society, Washington (Stati Uniti d'America)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

Kaloudis, P.; D'Angelantonio, M.; Guerra, M.; Spadafora, M.; Cismas, C.; Gimisis, T.; Mulazzani, Q. G.; Chatgilialoglu, C. (literal)

Pagina inizio

15895 (literal)

Pagina fine

15902 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

http://pubs.acs.org/doi/abs/10.1021/ja9065464 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume

131 (literal)

Rivista

Journal of the American Chemical Society (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

8 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo

43 (literal)

Note

ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

Kaloudis, P. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna D'Angelantonio, M. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna Guerra, M - - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna Spadafora. M, - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna Cismas, C. - Univ Athens, Dept Chem, Athens 15771, Greece Gimisis, T. - Univ Athens, Dept Chem, Athens 15771, Greece MUlazzani, QG. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna Chatgilialoglu, C. - Istituto per la Sintesi Organica e la Fotoreattività - CNR - Bologna (literal)

Titolo

Comparison of isoelectronic 8-HO-G and 8-NH2-G derivatives in redox processes (literal)

Abstract

8-Oxo-7,8-dihydroguanine (8-oxo-G) is the major lesion of oxidatively generated DNA damage. Despite two decades of intense study, several fundamental properties remain to be defined. Its isoelectronic 8-aminoguanine (8-NH(2)-G) has also received considerable attention from a biological point of view, although its chemistry involving redox processes remains to be discovered. We investigated the one-electron oxidation and one-electron reduction reactions of 8-oxo-G and 8-NH2-G derivatives. The reactions of hydrated electrons (e(aq)(-)) and azide radicals (N(3)(center dot)) with both derivatives were studied by pulse radiolysis techniques, and the transient absorption spectra were assigned to specific tautomers computationally by means of time-dependent DFT (TD-B3LYP/6-311G**//B1B95/6-31+G**) calculations. The protonated electron adducts of 8-NH(2)-G and 8-oxo-G showed a substantial difference in their absorption spectra, the unpaired electron being mainly delocalized in the imidazolyl ring and in the six-membered ring, respectively. On the other hand, the deprotonated forms of one-electron oxidation of 8-NH(2)-G and 8-oxo-G showed quite similar spectral characteristics. In a parallel study, the one-electron reduction of 8-azidoguanine (8-N(3)-G) afforded the same transient of one-electron oxidation of 8-NH(2)-G, which represents another example of generation of one-electron oxidized guanine derivatives under reducing conditions. Moreover, the fate of transient species was investigated by radiolytic methods coupled with product studies and allowed self- and cross-termination rate constants associated with these reactions to be estimated. (literal)

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