Evaluation of the antioxidant and neuroprotectant activities of new asymmetrical 1,3-diketones

A series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH...

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Detalles Bibliográficos
Autores: Nieto Gómez, Carla Isabel, Comago, María del Pilar, Sanz del Castillo, Dionisia, Claramunt, Rosa M., Torralba, María del Carmen, Torres, M. Rosario, Martínez Casanova, Diana, Sánchez Alegre, Yaiza Rebeca, Escudero, Esther, Lavandera, José Luis, Cabildo, Pilar
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universidad Nacional de Educación a Distancia
Repositorio:e-spacio. Repositorio Institucional de la UNED
Idioma:español
OAI Identifier:oai:e-spacio.uned.es:20.500.14468/23584
Acceso en línea:https://hdl.handle.net/20.500.14468/23584
Access Level:acceso abierto
Palabra clave:23 Química
neurodegeneration
oxidative stress
neuroprotectant
antioxidant
β-diketones
drug-like properties
Descripción
Sumario:A series of fourteen new asymmetrical 1,3-diketone derivatives have been synthesized and evaluated in the ABTS, FRAP and DPPH assays as a new chemotype with antioxidant and drug-like properties. All the compounds displayed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y cell line. Among them, (3Z,5E)-6-(2,5-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (6b) and (3Z,5E)-6-(2,3-difluoro-4-hydroxy-phenyl)-1,1,1-trifluoro-4-hydroxyhexa-3,5-dien-2-one (7b) with excellent solubility and chemical stability in biorelevant media, have also shown a similar Fe+2 chelation behavior to that of curcumin. Additionally, both derivatives 6b and 7b have afforded good neuroprotection activity against H2O2 induced oxidative stress in the same neuronal cell line, with a significant reduction of intracellular ROS levels, in parallel with a good recovery of the Mitochondrial Membrane Potential (ΔΨm). Compounds 6b and 7b with a promising antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitute a new interesting chemical class with high potential as new therapeutic agents against neurodegenerative diseases.

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