NDLI: Photooxygenation mechanisms in naproxen-amino acid linked systems.

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Photooxygenation mechanisms in naproxen-amino acid linked systems.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Vayá, Ignacio Andreu, Inmaculada Jiménez, M. Consuelo Miranda, Miguel A.
Description	Author Affiliation: Vayá I ( Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universitat Politècnica de València, Camino de Vera s/n, E-46022 Valencia, Spain. mcjimene@qim.upv.es mmiranda@qim.upv.es.)
Abstract	The photooxygenation of model compounds containing the two enantiomers of naproxen (NPX) covalently linked to histidine (His), tryptophan (Trp) and tyrosine (Tyr) has been investigated by steady state irradiation, fluorescence spectroscopy and laser flash photolysis. The NPX-His systems presented the highest oxygen-mediated photoreactivity. Their fluorescence spectra matched that of isolated NPX and showed a clear quenching by oxygen, leading to a diminished production of the NPX triplet excited state ((3)NPX-His). Analysis of the NPX-His and NPX-Trp photolysates by UPLC-MS-MS revealed in both cases the formation of two photoproducts, arising from the reaction of singlet oxygen ((1)O2) with the amino acid moiety. The most remarkable feature of NPX-Trp systems was a fast and stereoselective intramolecular fluorescence quenching, which prevented the efficient formation of (3)NPX-Trp, thus explaining their lower reactivity towards photooxygenation. Finally, the NPX-Tyr systems were nearly unreactive and exhibited photophysical properties essentially coincident with those of the parent NPX. Overall, these results point to a type II photooxygenation mechanism, triggered by generation of (1)O2 from the (3)NPX* chromophore.
File Format	HTM / HTML
ISSN	1474905X
Issue Number	2
Volume Number	13
e-ISSN	14749092
Journal	Photochemical & Photobiological Sciences
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2014-02-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Chemistry Discipline Biology Amino Acids Chemistry Naproxen Oxygen Photolysis Absorption Models, Molecular Molecular Conformation Journal Article Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry

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