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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

6-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...

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Published in:	ACS chemical neuroscience 2015-05, Vol.6 (5), p.800-810
Main Authors:	de la Fuente Revenga, Mario, Pérez, Concepción, Morales-García, José A, Alonso-Gil, Sandra, Pérez-Castillo, Ana, Caignard, Daniel-Henri, Yáñez, Matilde, Gamo, Ana M, Rodríguez-Franco, María Isabel
Format:	Article
Language:	English
Subjects:	Animals Antioxidants - chemical synthesis Antioxidants - chemistry Antioxidants - pharmacology Carbolines - chemical synthesis Carbolines - chemistry Carbolines - pharmacology Humans Male Melatonin - chemical synthesis Melatonin - chemistry Melatonin - pharmacology Neural Stem Cells - drug effects Neurogenesis - drug effects Rats Rats, Wistar
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creator	de la Fuente Revenga, Mario Pérez, Concepción Morales-García, José A Alonso-Gil, Sandra Pérez-Castillo, Ana Caignard, Daniel-Henri Yáñez, Matilde Gamo, Ana M Rodríguez-Franco, María Isabel
description	6-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.
doi_str_mv	10.1021/acschemneuro.5b00041
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subjects	Animals Antioxidants - chemical synthesis Antioxidants - chemistry Antioxidants - pharmacology Carbolines - chemical synthesis Carbolines - chemistry Carbolines - pharmacology Humans Male Melatonin - chemical synthesis Melatonin - chemistry Melatonin - pharmacology Neural Stem Cells - drug effects Neurogenesis - drug effects Rats Rats, Wistar
title	Neurogenic Potential Assessment and Pharmacological Characterization of 6‑Methoxy-1,2,3,4-tetrahydro-β-carboline (Pinoline) and Melatonin–Pinoline Hybrids
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