Drug-photosensitized protein modification: identification of the reactive sites and elucidation of the reaction mechanisms with tiaprofenic acid/albumin as model system

Chemical Research in Toxicology
M A MirandaZ Sarabia

Abstract

Certain drugs can photosensitive the formation of protein modifications, which are thought to be responsible for the occurrence of photoallergy. In the present work, the UV irradiation of serum albumin in the presence of tiaprofenic acid has been studied as a model system for drug-photosensitized protein modifications. The photolysates evidenced that His, Tyr, and Trp are the reactive sites of the protein. The experimental results strongly suggest that formal hydrogen abstraction from the OH or NH groups of Tyr or Trp by the excited drug is the key photochemical process. Competition between cage escape and in cage recombination of the resulting radical pairs governs the final outcome: protein photo-cross-linking versus drug-protein adduct formation. These findings are highly relevant to understand the process of photohapten formation, the first event in the onset of photoallergy.

References

Nov 1, 1991·Photochemistry and Photobiology·C S Foote
Jul 1, 1991·Journal of the American Academy of Dermatology·E HölzleG Plewig
Jan 1, 1997·Photochemistry and Photobiology·J M WesselsM A Rodgers
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Citations

Jul 15, 2004·Toxicology in Vitro : an International Journal Published in Association with BIBRA·G ViolaV Cecchetti
Sep 22, 2001·Toxicology in Vitro : an International Journal Published in Association with BIBRA·J MoserM A Miranda
Nov 6, 2003·Toxicology in Vitro : an International Journal Published in Association with BIBRA·V Lhiaubet-ValletM A Miranda
Feb 24, 2001·Journal of Photochemistry and Photobiology. B, Biology·Z SarabiaG M van Henegouwen
Feb 24, 2001·Journal of Photochemistry and Photobiology. B, Biology·J MoserA Hye
Jun 26, 1998·Journal of Photochemistry and Photobiology. B, Biology·F Boscá, M A Miranda
Jul 23, 2003·Photochemistry and Photobiology·Yu-Ying HeColin F Chignell
Apr 30, 2004·Photochemistry and Photobiology·Gian Gaetano AloisiGiampietro Viola
May 5, 2005·Photochemistry and Photobiology·Julia Pérez-PrietoMiguel A Miranda
Apr 27, 2010·Photodermatology, Photoimmunology & Photomedicine·Alastair Kerr, James Ferguson
Oct 2, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Ignacio VayáMiguel A Miranda
Mar 27, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Giuseppina BracchittaGuido De Guidi
Aug 30, 2012·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Giuseppina BracchittaGuido De Guidi
Dec 24, 2003·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Julia Pérez-PrietoMiguel A Miranda
Sep 22, 2006·Bioorganic & Medicinal Chemistry·Paola BarrajaFrancesco Dall'Acqua
Oct 28, 2008·Bioorganic & Medicinal Chemistry·Paola BarrajaFrancesco Dall'acqua
Jun 21, 2003·The Journal of Organic Chemistry·Julia Pérez-PrietoMiguel A Miranda

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