TY - JOUR
TI - Photolabile N-hydroxypyrid-2(1H)-one derivatives of guanine nucleosides: a new method for independent guanine radical generation
AU - Panagiotis Kaloudis
AU - Cecilia Paris
AU - Despoina Vrantza
AU - Susana Encinas
AU - Raul Pérez-Ruiz
AU - Miguel A. Miranda
AU - Thanasis Gimisis
JO - Organic and Biomolecular Chemistry
PY - 2009
VL - 7
TODO - 23
SP - 4965
PB - Royal Society of Chemistry (RSC)
SN - 1477-0520, 1477-0539
TODO - 10.1039/b909138f
TODO - null
TODO - 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. {\textcopyright} The Royal Society of Chemistry 2009.
ER -