The hydrophobic substituent in aminophospholipids affects the formation kinetics of their Schiff bases

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dc.contributor.author Caldés, Catalina
dc.contributor.author Vilanova Canet, Bartolomé
dc.contributor.author Adrover Estelrich, Miguel
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-11-08T11:02:16Z
dc.identifier.uri http://hdl.handle.net/11201/148483
dc.description.abstract [eng] Schiff bases (SBs) are the initial products of non-enzymatic glycation reactions, which are associated to some diabetes-related diseases. In this work, we used physiological pH and temperature conditions to study the formation kinetics of the SBs of 1,2-dihexanoyl-sn-glycero-3-phosphoethanolamine (DPHE) and 1,2-dihexanoyl-sn-glycero-3-phospho-l-serine (DHPS) with various glycating compounds and with pyridoxal 5'-phosphate (an effective glycation inhibitor). Based on the obtained results, the hydrophobic environment simultaneously decreases the nucleophilic character of the amino group (k1) and increases its pKa, thereby increasing the formation rate of SB (kobs). Therefore, the presence of hydrophobic chains in aminophospholipids facilitates the formation and stabilization of SBs, and also, in a biological environment, their glycation. Additionally, the results confirm the inhibitory action of B6 vitamers on aminophospholipid glycation.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1016/j.bmcl.2013.01.100
dc.relation.ispartof Bioorganic & Medicinal Chemistry Letters, 2013, vol. 23, p. 2202-2206
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title The hydrophobic substituent in aminophospholipids affects the formation kinetics of their Schiff bases
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-11-08T11:02:16Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords <SUP>1</SUP>H-NMR
dc.subject.keywords Cinética química
dc.subject.keywords Chemical Kinetics
dc.subject.keywords HPLC
dc.subject.keywords Base de Schiff
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1016/j.bmcl.2013.01.100


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