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Chiral synthetic pseudopeptidic derivatives as triplet excited state quenchers |
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| Authors: | Xavier J. Salom-Roig,M. Isabel Burguete,Santiago V. Luis,Miguel A. Miranda,Julia Pé rez-Prieto |
| Affiliation: | a Institut de Biomolécules Max Mousseron (IBMM), UMR 5247, Synthèses Stéréosélectives, Place Eugène Bataillon, Université Montpellier II, France b Departamento de Química Inorgánica y Orgánica;Universitat Jaume I, Av. Sos Baynat, s/n, 12071 Castellón, Spain c Departamento de Química/Instituto de Tecnología Química (UPV-CSIC), Universidad Politécnica de Valencia, Camino de Vera, s/n, 46071 Valencia, Spain d Departamento de Química Orgánica / ICMOL, Universidad de Valencia, Av. Vicent Andrés Estellés, s/n, 46100 Burjassot, Valencia, Spain |
| Abstract: | The behavior of 6 pseudopeptidic models, synthesized by connecting different protected amino acids (Trp, Tyr, Phe, and Lys) with various diamino spacers, as quenchers of the triplet excited state of tiaprofenic acid (and its methyl ester), has been investigated. A series of quenching constants have been determined, which depend on the nature of the quencher and on the stereochemistry of the excited drug. A significant degree of stereodifferentiation has been found for the peptidomimetic synthesized with Phe and Tyr linked by a piperazine bridge. The obtained results support the utility of laser flash photolysis (LFP) as a tool to investigate the interactions between photoexcited drugs and simple models of binding sites in proteins. |
| Keywords: | Laser flash photolysis Photochemistry Triplet excited state Quenching |
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