A density functional theory study of the free-​radical scavenging activity of aminoguanidine. Comparison with its reactive carbonyl compound and metal scavenging activities

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dc.contributor.author Ramis, R.
dc.contributor.author Casasnovas, R.
dc.contributor.author Marino, L.
dc.contributor.author Frau, J.
dc.contributor.author Adrover, M.
dc.contributor.author Vilanova, B.
dc.contributor.author Mora-Diez, N.
dc.contributor.author Ortega-Castro, J.
dc.date.accessioned 2023-12-20T09:01:22Z
dc.identifier.uri http://hdl.handle.net/11201/163253
dc.description.abstract [eng] Since protein glycation is related to several human diseases, it is very important to develop molecules that can inhibit its effects. This work adds the reaction of Aminoguanidine (AG) with the methoxy (˙OCH3) and hydroperoxyl (˙OOH) radicals at the UM05-2X-SMD/6-311+G(d,p) level of theory in water and pentyl ethanoate to simulate the physiological aqueous and lipidic environments. At physiological pH, AG is an effective ˙OCH3 and a moderate ˙OOH scavenger in nonpolar solvents (where AG is predominantly neutral), acting exclusively by hydrogen-atom transfer. However, reactions in a polar solvent (where AG is predominantly cationic) have smaller rate constants. Therefore, the ability of AG to scavenge free radicals seems to depend on the polarity of the environment. Taken together, the results reported herein and in previous works suggest that the scavenging of reactive carbonyl species is the main mechanism of action of aminoguanidine in the context of protein glycation inhibition.
dc.format application/pdf
dc.relation.isformatof Versió preprint del document publicat a: https://doi.org/10.1002/qua.25911
dc.relation.ispartof International Journal of Quantum Chemistry, 2019, vol. 119, num. 13, p. e25911-1-e25911-8
dc.subject.classification 54 - Química
dc.subject.other 54 - Chemistry. Crystallography. Mineralogy
dc.title A density functional theory study of the free-​radical scavenging activity of aminoguanidine. Comparison with its reactive carbonyl compound and metal scavenging activities
dc.type info:eu-repo/semantics/article
dc.type info:eu-repo/semantics/submittedVersion
dc.date.updated 2023-12-20T09:01:23Z
dc.date.embargoEndDate info:eu-repo/date/embargoEnd/2100-01-01
dc.embargo 2100-01-01
dc.subject.keywords DFT
dc.subject.keywords free radical scavenging
dc.subject.keywords aminoguanidine
dc.rights.accessRights info:eu-repo/semantics/embargoedAccess
dc.identifier.doi https://doi.org/10.1002/qua.25911


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