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dc.contributor.authorRamis, Rafael
dc.contributor.authorOrtega-Castro, Joaquin 
dc.contributor.authorCaballero, Carmen
dc.contributor.authorCasasnovas, Rodrigo
dc.contributor.authorCerrillo, Antonia
dc.contributor.authorVilanova, Bartolome
dc.contributor.authorAdrover, Miguel
dc.contributor.authorFrau, Juan 
dc.date.accessioned2021-08-25T17:29:52Z
dc.date.available2021-08-25T17:29:52Z
dc.date.issued2019-09
dc.identifier.citationRamis Cortés R, Ortega-Castro J, Caballero C, Casanovas R, Cerrillo A, Vilanova Canet B, et al. How Does Pyridoxamine Inhibit the Formation of Advanced Glycation End Products? The Role of Its Primary Antioxidant Activity. Antioxidants. 2019 Sep;8(9):344.en
dc.identifier.urihttp://hdl.handle.net/20.500.13003/15153
dc.description.abstractPyridoxamine, one of the natural forms of vitamin B-6, is known to be an effective inhibitor of the formation of advanced glycation end products (AGEs), which are closely related to various human diseases. Pyridoxamine forms stable complexes with metal ions that catalyze the oxidative reactions taking place in the advanced stages of the protein glycation cascade. It also reacts with reactive carbonyl compounds generated as byproducts of protein glycation, thereby preventing further protein damage. We applied Density Functional Theory to study the primary antioxidant activity of pyridoxamine towards three oxygen-centered radicals (center dot OOH, center dot OOCH3 and center dot OCH3) to find out whether this activity may also play a crucial role in the context of protein glycation inhibition. Our results show that, at physiological pH, pyridoxamine can trap the center dot OCH3 radical, in both aqueous and lipidic media, with rate constants in the diffusion limit (>1.0 x 10(8) M-1 s-1). The quickest pathways involve the transfer of the hydrogen atoms from the protonated pyridine nitrogen, the protonated amino group or the phenolic group. Its reactivity towards center dot OOH and center dot OOCH3 is smaller, but pyridoxamine can still scavenge them with moderate rate constants in aqueous media. Since reactive oxygen species are also involved in the formation of AGEs, these results highlight that the antioxidant capacity of pyridoxamine is also relevant to explain its inhibitory role on the glycation process.en
dc.language.isoengen
dc.publisherMDPIen
dc.rightsAttribution 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.titleHow Does Pyridoxamine Inhibit the Formation of Advanced Glycation End Products? The Role of Its Primary Antioxidant Activityen
dc.typeresearch articleen
dc.description.fundingtextThis research was funded by the Ministerio de Economia y Competitividad (MINECO) and the European Fund for Regional Development (FEDER) (CTQ2014-55835-R), and by the Conselleria d'Educacio, Cultura i Universitats (Ajuts a accions especials d'R+D AAEE49/2015).en
dc.identifier.doi10.3390/antiox8090344
dc.identifier.essn2076-3921
dc.identifier.pmid31480509
dc.identifier.scopus2-s2.0-85073324606
dc.identifier.wos000487957300058
dc.issue.number9en
dc.journal.titleAntioxidantsen
dc.page.initial344en
dc.relation.publisherversionhttps://dx.doi.org/10.3390/antiox8090344en
dc.rights.accessRightsopen accessen
dc.subject.keywordpyridoxamineen
dc.subject.keywordDFTen
dc.subject.keywordAGEsen
dc.subject.keywordinhibitionen
dc.subject.keywordROSen
dc.volume.number8en


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