Theoretical calculations of stability constants and pKa values of metal complexes in solution: application to pyridoxamine-copper(II) complexes and their biological implications in AGE inhibition

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dc.contributor.author Casasnovas Perera, Rodrigo
dc.contributor.author Ortega Castro, Joaquín
dc.contributor.author Donoso Pardo, Josefa Laurentina
dc.contributor.author Frau Munar, Juan
dc.contributor.author Muñoz Izquierdo, Francisco
dc.date.accessioned 2018-10-30T12:48:21Z
dc.identifier.uri http://hdl.handle.net/11201/148330
dc.description.abstract [eng] Accurate prediction of thermodynamic constants of chemical reactions in solution is one of the current challenges in computational chemistry. We report a scheme for predicting stability constants (log β) and pKa values of metal complexes in solution by means of calculating free energies of ligand- and proton-exchange reactions using Density Functional Theory calculations in combination with a continuum solvent model. The accuracy of the predicted log β and pKa values (mean absolute deviations of 1.4 and 0.2 units respectively) is equivalent to the experimental uncertainties. This theoretical methodology provides direct knowledge of log β and pKa values of major and minor species, so it is of potential use in combination with experimental techniques to obtain a detailed description of the microscopic equilibria. In particular, the proposed methodology is shown to be especially useful for obtaining the real acidity constants of those chelates where the metal<br>ligand coordination changes as a result of ligand deprotonation. The stability and acidity constants of pyridoxamine<br>Cu2+ chelates calculated with the proposed methodology show that pyridoxamine is an efficient scavenging agent of Cu2+ under physiological pH conditions. This is of special interest as Cu2+ overload is involved in the formation of advanced glycation end-products (AGEs) and their associated degenerative medical conditions.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a: https://doi.org/10.1039/C3CP50840D
dc.relation.ispartof Physical Chemistry Chemical Physics, 2013, vol. 15, p. 16303-16313
dc.rights (c) Casasnovas Perera, Rodrigo et al., 2013
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title Theoretical calculations of stability constants and pKa values of metal complexes in solution: application to pyridoxamine-copper(II) complexes and their biological implications in AGE inhibition
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion
dc.date.updated 2018-10-30T12:48:21Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords DFT
dc.subject.keywords pKa calculations
dc.subject.keywords AGE inhibitors
dc.subject.keywords Pyridoxamine (PM)
dc.subject.keywords Theoretical study
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1039/C3CP50840D


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