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{Photolabile N-hydroxypyrid-2(1H)-one derivatives of guanine nucleosides: a new method for independent guanine radical generation}

Citation:

Kaloudis P, Paris C, Vrantza D, Encinas S, Pérez-Ruiz R, Miranda MA, Gimisis T, Perez-Ruiz R, Miranda MA, Gimisis T. {Photolabile N-hydroxypyrid-2(1H)-one derivatives of guanine nucleosides: a new method for independent guanine radical generation}. Org. Biomol. Chem. [Internet]. 2009;7:–.

Abstract:

One-electron oxidized guanine is an important reactive intermediate in the formation of oxidatively generated damage in DNA and a variety of methods have been utilized for the abstraction of a single electron from the guanine moiety. In this study, an alternative approach for the site specific, independent generation of the guanine radical, utilizing N-hydroxypyrid-2(1H)-one as a photolabile modifier of guanine, is proposed. Novel photolabile 6-[(1-oxido-2-pyridinyl)oxo]-6-deoxy- and 2′,6-dideoxy-guanosine derivatives capable of generating the neutral guanine radical (G(-H) •) upon photolysis were synthesized and characterized. The generation of G(-H) proceeds through homolysis of the N-O bond and was confirmed through continuous photolysis product analysis and trapping studies, as well as laser flash photolysis experiments. © The Royal Society of Chemistry 2009.

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