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dc.contributor.authorFuente Revenga, Mario de la-
dc.contributor.authorFernández-Sáez, Nerea-
dc.contributor.authorHerrera-Arozamena, Clara-
dc.contributor.authorMorales-García, José A.-
dc.contributor.authorAlonso-Gil, Sandra-
dc.contributor.authorPérez Castillo, Ana-
dc.contributor.authorCaignard, Daniel-Henri-
dc.contributor.authorRivara, Silvia-
dc.contributor.authorRodríguez-Franco, María Isabel-
dc.identifierdoi: 10.1021/acs.jmedchem.5b00245-
dc.identifierissn: 0022-2623-
dc.identifiere-issn: 1520-4804-
dc.identifier.citationJournal of Medicinal Chemistry 58(12): 4998-5014 (2015)-
dc.descriptionet al.-
dc.description.abstractHerein we present a new family of melatonin-based compounds, in which the acetamido group of melatonin has been bioisosterically replaced by a series of reversed amides and azoles, such as oxazole, 1,2,4-oxadiazole, and 1,3,4-oxadiazole, as well as other related five-membered heterocycles, namely, 1,3,4-oxadiazol(thio)ones, 1,3,4-triazol(thio)ones, and an 1,3,4-thiadiazole. New compounds were fully characterized at melatonin receptors (MT<inf>1</inf>R and MT<inf>2</inf>R), and results were rationalized by superimposition studies of their structures to the bioactive conformation of melatonin. We also found that several of these melatonin-based compounds promoted differentiation of rat neural stem cells to a neuronal phenotype in vitro, in some cases to a higher extent than melatonin. This unique profile constitutes the starting point for further pharmacological studies to assess the mechanistic pathways and the relevance of neurogenesis induced by melatonin-related structures.-
dc.description.sponsorshipWe gratefully acknowledge the financial support of the Spanish Ministry of Economy and Competitiveness (MINECO, Grants SAF2012-31035, SAF2010-16365, and SAF2014-52940-R), Fundación de Investigación Médica Mutua Madrileña Automovilística (Grant AP103952012), and Consejo Superior de Investigaciones Científicas (CSIC, Grant PIE-201280E074). The Centro de Investigación Biomédica en Red sobre Enfermedades Neurodegenerativas (CIBERNED) is funded by the Instituto de Salud Carlos III. M.d.l.F.R. thanks CSIC for a JAE-Predoctoral Contract, and J.A.M.-G. thanks CIBERNED for a postdoctoral fellowship . We also acknowledge Dr. Paula Morales for the binding assays on cannabinoid receptors and the National Institute on Mental Health-Psychoactive Drug Screening Program (NIMH-PDSP, Contract HHSN-271-2013-00017-C, Dr. Bryan Roth) for binding experiments on serotonin receptors and transporter.-
dc.publisherAmerican Chemical Society-
dc.titleNovel N-acetyl bioisosteres of melatonin: Melatonergic receptor pharmacology, physicochemical studies, and phenotypic assessment of their neurogenic potential-
dc.description.versionPeer Reviewed-
dc.contributor.funderInstituto de Salud Carlos III-
dc.contributor.funderCentro Investigación Biomédica en Red Enfermedades Neurodegenerativas (España)-
dc.contributor.funderConsejo Superior de Investigaciones Científicas (España)-
dc.contributor.funderNational Institute on Mental Health (US)-
dc.contributor.funderMinisterio de Economía y Competitividad (España)-
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