title: The hydrophobic substituent in aminophospholipids affects the formation kinetics of their Schiff bases.
abstract: 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.
authors: Institut Universitari d'Investigació en Ciències de la Salut (IUNICS), Departament de Química, Universitat de les Illes Balears, Cra. Valldemossa km 7.5, Ed. Mateu Orfila i Rotger, E-07122 Palma de Mallorca, Spain.
authors: Catalina
authors: C
authors: Caldés
authors: Bartolomé
authors: B
authors: Vilanova
authors: Miquel
authors: M
authors: Adrover
authors: Josefa
authors: J
authors: Donoso
authors: Francisco
authors: F
authors: Muñoz
mesh_terms: D006863:Hydrogen-Ion Concentration; D057927:Hydrophobic and Hydrophilic Interactions; D007700:Kinetics; D015394:Molecular Structure; D010714:Phosphatidylethanolamines / Q000138:chemical synthesis* / Q000737:chemistry; D010743:Phospholipids / Q000737:chemistry*; D012545:Schiff Bases / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
chemical_list: D010714:Phosphatidylethanolamines; D010743:Phospholipids; D012545:Schiff Bases; C048072:1,2-dihexanoylphosphatidylethanolamine