The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect

Show simple item record Adrover Estelrich, Miguel Vilanova Canet, Bartolomé Muñoz Izquierdo, Francisco Donoso Pardo, Josefa Laurentina Frau Munar, Juan 2019-01-08T11:44:46Z
dc.description.abstract [eng] Amadori compounds act as precursors in the formation of advanced glycation end products (AGEs) by non-enzymatic protein glycation, which are involved in ensuing protein damage. Pyridoxamine is a potent drug against protein glycation, and can act on several pathways in the glycation process. Nevertheless, the pyridoxamine inhibition action on Amadori compounds oxidation is still unclear. In this work, we have studied the Schiff base formation between pyridoxamine and various Amadori models at pH 7.4 at 37 °C in the presence of NaCNBH3. We detected an adduct formation, which suggests that pyridoxamine reacts with the carbonyl group in Amadori compounds. The significance of this mechanism is tested by comparison of the obtained kinetics rate constants with that obtained for 4-(aminomethyl)-pyridine, a structural analogue of pyridoxamine without post-Amadori action. We also study the chelating effect of pyridoxamine on metal ions. We have determined the complexation equilibrium constants between pyridoxamine, N-(1-deoxy-d-fructos-1-yl)-l-tryptophan, aminoguanidine, and ascorbic acid in the presence of Zn2+. The results show that the strong stability of pyridoxamine complexes is the key in its post-Amadori inhibition action. On the other hand results explain the lack of inhibition of aminoguanidine (a glycation inhibitor) in the post-Amadori reactions.
dc.format application/pdf
dc.relation.isformatof Versió postprint del document publicat a:
dc.relation.ispartof Bioorganic & Medicinal Chemistry, 2008, vol. 16, num. 10, p. 5557-5569
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title The pyridoxamine action on Amadori compounds: A reexamination of its scavenging capacity and chelating effect
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/acceptedVersion 2019-01-08T11:44:46Z info:eu-repo/date/embargoEnd/2075-01-01
dc.embargo 2075-01-01
dc.subject.keywords Amadori
dc.subject.keywords Chemical Kinetics
dc.subject.keywords Pyridoxamine (PM)
dc.subject.keywords RMN
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess

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