Why p-OMe- and p-Cl-β-Methylphenethylamines Display Distinct Activities upon MAO-B Binding

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dc.contributor.authorFierro, Angélica
dc.contributor.authorEdmondson, Dale E.
dc.contributor.authorCelis-Barros, Cristian
dc.contributor.authorRebolledo-Fuentes, Marco
dc.contributor.authorZapata-Torres, Gerald
dc.date.accessioned2016-06-21T18:55:50Z
dc.date.available2016-06-21T18:55:50Z
dc.date.issued2016
dc.descriptionIndexación: Web of Sciencees
dc.description.abstractDespite their structural and chemical commonalities, p-chloro-beta-methylphenethylamine and p-methoxy-beta-methylphenethylamine display distinct inhibitory and substrate activities upon MAO-B binding. Density Functional Theory (DFT) quantum chemical calculations reveal that beta-methylation and para-substitution underpin the observed activities sustained by calculated transition state energy barriers, attained conformations and key differences in their interactions in the enzyme's substrate binding site. Although both compounds meet substrate requirements, it is clear that beta-methylation along with the physicochemical features of the para-substituents on the aromatic ring determine the activity of these compounds upon binding to the MAO B-isoform. While data for a larger set of compounds might lend generality to our conclusions, our experimental and theoretical results strongly suggest that the contrasting activities displayed depend on the conformations adopted by these compounds when they bind to the enzyme.es
dc.description.urihttp://journals.plos.org/plosone/article?id=10.1371/journal.pone.0154989
dc.identifier.citationPLoS ONE 11 (5)es
dc.identifier.issn1932-6203
dc.identifier.otherhttp://dx.doi.org/10.1371/journal.pone.0154989
dc.identifier.urihttp://repositorio.unab.cl/xmlui/handle/ria/829
dc.language.isoenes
dc.publisherPUBLIC LIBRARY SCIENCEes
dc.subjectMONOAMINE-OXIDASE-Bes
dc.subjectNONCOVALENT INTERACTION REGIONSes
dc.subjectCHEMICAL CLUSTER APPROACHes
dc.subjectBENZYLAMINE ANALOGSes
dc.subjectSELECTIVE-INHIBITIONes
dc.subjectMAO-Bes
dc.subjectSUBSTRATEes
dc.subjectMODELes
dc.subjectMECHANISMSes
dc.subjectRESOLUTIONes
dc.titleWhy p-OMe- and p-Cl-β-Methylphenethylamines Display Distinct Activities upon MAO-B Bindinges
dc.typeArtículoes
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