New flavonoid–N,N-dibenzyl(N-methyl)amine hybrids: Multi-target-directed agents for Alzheimer's disease endowed with neurogenic properties

The design of multi-target directed ligands (MTDLs) is a valid approach for obtaining effective drugs for complex pathologies. MTDLs that combine neuro-repair properties and block the first steps of neurotoxic cascades could be the so long wanted remedies to treat neurodegenerative diseases (NDs). B...

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Detalles Bibliográficos
Autores: Estrada, Martín, Herrera-Arozamena, Clara, Pérez, Concepción, Viña, Dolores, Morales-García, José A., Pérez Castillo, Ana, Ramos, Eva, Romero Jódar, Alejandro, Laurini, E., Pricl, Sabrina, Rodríguez-Franco, María Isabel
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/185467
Acceso en línea:http://hdl.handle.net/10261/185467
Access Level:acceso abierto
Palabra clave:Multi-target-directed ligands
Human cholinesterases
Human lipoxygenase-5
Human b-secretase
Alzheimer’s disease
Neurodegenerative diseases
Neurogenesis
Sigma receptors
Descripción
Sumario:The design of multi-target directed ligands (MTDLs) is a valid approach for obtaining effective drugs for complex pathologies. MTDLs that combine neuro-repair properties and block the first steps of neurotoxic cascades could be the so long wanted remedies to treat neurodegenerative diseases (NDs). By linking two privileged scaffolds with well-known activities in ND-targets, the flavonoid and the N,N-dibenzyl(N-methyl)amine (DBMA) fragments, new CNS-permeable flavonoid–DBMA hybrids (1–13) were obtained. They were subjected to biological evaluation in a battery of targets involved in Alzheimer’s disease (AD) and other NDs, namely human cholinesterases (hAChE/hBuChE), β-secretase (hBACE-1), monoamine oxidases (hMAO-A/B), lipoxygenase-5 (hLOX-5) and sigma receptors (σ R/σ R). After a funnel-type screening, 6,7-dimethoxychromone–DBMA (6) was highlighted due to its neurogenic properties and an interesting MTD-profile in hAChE, hLOX-5, hBACE-1 and σ R. Molecular dynamic simulations showed the most relevant drug-protein interactions of hybrid 6, which could synergistically contribute to neuronal regeneration and block neurodegeneration.