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Neurogenic potential assessment and pharmacological characterization of 6-Methoxy-1,2,3,4-tetrahydro-β-carboline (Pinoline) and Melatonin-Pinoline Hybrids

AuthorsFuente Revenga, Mario de la; Pérez, Concepción; Morales-García, José A. ; Alonso-Gil, Sandra ; Pérez Castillo, Ana ; Yáñez, Matilde; Rodríguez-Franco, María Isabel
KeywordsMonoamine oxidases
Melatonergic receptors
Serotonergic receptors
Issue Date2015
PublisherAmerican Chemical Society
CitationACS Chemical Neuroscience 6(5): 800-810 (2015)
Abstract6-Methoxy-1,2,3,4-tetrahydro-β-carboline (pinoline) and N-acetyl-5-methoxytryptamine (melatonin) are both structurally related to 5-hydroxytryptamine (serotonin). Here we describe the design, synthesis, and characterization of a series of melatonin rigid analogues resulting from the hybridization of both pinoline and melatonin structures. The pharmacological evaluation of melatonin-pinoline hybrids comprises serotonergic and melatonergic receptors, metabolic enzymes (monoamine oxidases), antioxidant potential, the in vitro blood-brain barrier permeability, and neurogenic studies. Pinoline at trace concentrations and 2-acetyl-6-methoxy-1,2,3,4-tetrahydro-β-carboline (2) were able to stimulate early neurogenesis and neuronal maturation in an in vitro model of neural stem cells isolated from the adult rat subventricular zone. Such effects are presumably mediated via serotonergic and melatonergic stimulation, respectively.
DescriptionThis work received the honour of being the Cover of the ACS Chemical Neuroscience in its issue of May 2015
Publisher version (URL)http://dx.doi.org/10.1021/acschemneuro.5b00041
Identifiersdoi: 10.1021/acschemneuro.5b00041
issn: 1948-7193
e-issn: 1948-7193
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