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Type I photosensitization of 2'-deoxyadenosine 5'-monophosphate (5'-dAMP) by biopterin and its photoproduct formylpterin.

Abstract
Biopterin (Bip) and its photoproducts 6-formylpterin (Fop) and 6-carboxypterin (Cap) accumulate in the skin of patients suffering from vitiligo, a chronic depigmentation disorder where the protection against UV radiation fails because of the lack of melanin. These compounds absorb in the UV-A inducing a potential photosensitizing action that can cause damage to DNA and other biomolecules. In this work, we have investigated the capability of these pterin derivatives (Pt) to act as photosensitizers under UV-A irradiation for the degradation of 2'-deoxyadenosine 5'-monophosphate (5'-dAMP) in aqueous solutions, as model DNA target. Steady-state and time-resolved experiments were performed and the effect of pH was evaluated. The results showed that photosensitized degradation of 5'-dAMP was only observed under acidic conditions, and a mechanistic analysis revealed the participation of the triplet excited state of the pterin derivatives ((3)Pt*) by electron transfer yielding the corresponding pair of radical ions (Pt(•-) and 5'-dAMP(•+)), with successive photosensitizer recovery by electron transfer from Pt(•-) to O2. Finally, 5'-dAMP(•+) participates in subsequent reactions to yield degradation products.
AuthorsMariana P Serrano, Claudio D Borsarelli, Andrés H Thomas
JournalPhotochemistry and photobiology (Photochem Photobiol) 2013 Nov-Dec Vol. 89 Issue 6 Pg. 1456-62 ISSN: 1751-1097 [Electronic] United States
PMID23837607 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright© 2013 The American Society of Photobiology.
Chemical References
  • Deoxyadenine Nucleotides
  • Pterins
  • 2'-deoxy-5'-adenosine monophosphate
Topics
  • Deoxyadenine Nucleotides (chemistry)
  • Pterins (chemistry)

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