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dc.contributor.author Corvalán, Natalia Andrea
dc.contributor.author Zygadlo, Julio Alberto
dc.contributor.author Garcia, Daniel Asmed
dc.date.available 2017-10-12T21:24:56Z
dc.date.issued 2009-05
dc.identifier.citation Corvalán, Natalia Andrea; Zygadlo, Julio Alberto; Garcia, Daniel Asmed; Stereo-selective activity of menthol on GABA(A) receptor; Wiley; Chirality; 21; 5; 5-2009; 525-530
dc.identifier.issn 0899-0042
dc.identifier.uri http://hdl.handle.net/11336/26539
dc.description.abstract Menthol is a naturally occurring compound, which has three chiral centers that define eight possible optically actives stereoisomers. Neuroactivity of menthol and related agents by affecting neuronal intracellular signaling or by modulation of neurotransmitter-gated currents has been reported. Furthermore, stereo-selectivity of menthol in its analgesic activity as well as in its sensory properties and other biological activities was also described. The present study is the first contribution to the description of stereo-selectivity of GABAA receptor against the most possible isomers of menthol, discussed in terms of their chirality. The results showed that only (+)-menthol, among the five stereoisomers analyzed, was active, stimulating in a dose-response manner the binding of an allosteric GABAA receptor ligand. Taking into account these results, and comparing them with those of some active phenolic compounds, it is strongly suggested that the existence of a relative spatial location of its substituents with respect to the ring (equatorial position of all substituents and (1S,2R,5S)-configuration) as well as the presence in the cyclic molecule of an aliphatic non polar group (isopropyl) with free rotation near to a polar group (hydroxyl) are crucial points to demonstrate activity on the receptor.
dc.format application/pdf
dc.language.iso eng
dc.publisher Wiley
dc.rights info:eu-repo/semantics/restrictedAccess
dc.rights.uri https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject MENTHOL
dc.subject STEREO-ISOMERS
dc.subject STEREO-SELECTIVITY
dc.subject GABAA-RECEPTOR
dc.subject.classification Bioquímica y Biología Molecular
dc.subject.classification Ciencias Biológicas
dc.subject.classification CIENCIAS NATURALES Y EXACTAS
dc.title Stereo-selective activity of menthol on GABA(A) receptor
dc.type info:eu-repo/semantics/article
dc.type info:ar-repo/semantics/artículo
dc.type info:eu-repo/semantics/publishedVersion
dc.date.updated 2017-10-10T18:33:12Z
dc.identifier.eissn 1520-636X
dc.journal.volume 21
dc.journal.number 5
dc.journal.pagination 525-530
dc.journal.pais Estados Unidos
dc.journal.ciudad Hoboken
dc.description.fil Fil: Corvalán, Natalia Andrea. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil Fil: Zygadlo, Julio Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
dc.description.fil Fil: Garcia, Daniel Asmed. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas, Físicas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.journal.title Chirality
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/chir.20631
dc.relation.alternativeid info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/chir.20631/abstract


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info:eu-repo/semantics/restrictedAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)