Journal
NEW JOURNAL OF CHEMISTRY
Volume 41, Issue 15, Pages 7273-7282Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7nj00739f
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Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET) [PIP 2013-0304]
- Universidad Nacional de La Plata (UNLP) [X712]
- Centre National de la Recherche Scientifique (CNRS)
- CONICET through Programme de Cooperation Scientifique (CONICET-CNRS/PICS) [05920]
- CONICET
- Agencia de Promocion Cientifica y Tecnologica (ANPCyT) [PICT-2012-0508]
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UV-A radiation (320-400 nm) induces modifications to different biomolecules through photosensitized reactions. Oxidized pterins are efficient photosensitizers that accumulate in the skin affected by vitiligo, and photoinduce the oxidation of guanine in a process initiated by an electron transfer from the nucleo-base to the triplet excited state of the photosensitizer. In this work, we have investigated the degradation of 2 '-deoxyguanosine 5 '-monophosphate (dGMP) photosensitized by pterin (Ptr), the parent compound of oxidized pterins, in aqueous solutions under UV-A irradiation. We have identified five products containing the oxidized guanine moiety: the deoxyribonucleoside 5 '-monophosphate derivatives of imidazolone, dehydroguanidinohydantoin, guanidinohydantoin, oxazolone and spiroiminodihydantoin. An additional product with a much higher molecular weight, denoted P680, was also detected. The MS/MS analyses show that this compound contains an intact guanine moiety and a modified one. The dependence of the rate of product formation in different experimental conditions was analyzed and a general mechanistic scheme is proposed.
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