title: High- and low-spin Fe(III) complexes of various AGE inhibitors.
abstract: Density functional theory calculations [CPCM/UM06/6-31+G(d,p)] were used to elucidate the structures and relative stability of Fe(III) complexes with various ligands that inhibit the formation of advanced glycation end products (AGEs) or iron overloaded disease (viz. aminoguanidine, pyridoxamine, LR-74, Amadori compounds, and ascorbic acid). EDTA was used as the free energy reference ligand. The distorted neutral octahedral complex containing one iron atom and three molecules of pyridoxamine [Fe(PM)(3)] was found to be the most stable. The stability of the complexes decreases in the following chelate sequence: pyridoxamine, Amadori complex, aminoguanidine, LR inhibitor, and ascorbic acid.
authors.affiliation: Institut d'Investigació en Ciències de la Salut (IUNICS), Departament de Química, Universitat de les Illes Balears, E-07122 Palma de Mallorca, Spain.
authors.forename: J
authors.initials: J
authors.lastname: Ortega-Castro
authors.forename: J
authors.initials: J
authors.lastname: Frau
authors.forename: R
authors.initials: R
authors.lastname: Casasnovas
authors.forename: D
authors.initials: D
authors.lastname: Fernández
authors.forename: J
authors.initials: J
authors.lastname: Donoso
authors.forename: F
authors.initials: F
authors.lastname: Muñoz
mesh_terms: D001205:Ascorbic Acid / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry*; D004492:Edetic Acid / Q000737:chemistry; D005290:Ferric Compounds / Q000737:chemistry*; D017127:Glycation End Products, Advanced / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry; D007700:Kinetics; D008024:Ligands; D015394:Molecular Structure; D011422:Propionates / Q000737:chemistry; D011733:Pyridoxamine / Q000737:chemistry; D011789:Quantum Theory; D011804:Quinolines / Q000737:chemistry; D013816:Thermodynamics
chemical_list: C507130:2-(8-quinolinoxy)propionic acid; D056831:Coordination Complexes; D005290:Ferric Compounds; D017127:Glycation End Products, Advanced; D006146:Guanidines; D008024:Ligands; D011422:Propionates; D011804:Quinolines; D011733:Pyridoxamine; D004492:Edetic Acid; D001205:Ascorbic Acid; C004479:pimagedine