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Molecules 2018, 23(8), 1837; https://doi.org/10.3390/molecules23081837

Evaluation of the Antioxidant and Neuroprotectant Activities of New Asymmetrical 1,3-Diketones

1
Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, Universidad Nacional de Educación a distancia (UNED), Paseo Senda del Rey 9, E-28040 Madrid, Spain
2
Departamento de Química Inorgánica I and CAI de Difracción de Rayos-X, Facultad de Ciencias Químicas, Universidad Complutense de Madrid (UCM), E-28040 Madrid, Spain
3
Instituto de Medicina Molecular Aplicada (IMMA), Facultad de Medicina, Universidad CEU San Pablo, Campus de Montepríncipe, Boadilla, E-28668 Madrid, Spain
*
Authors to whom correspondence should be addressed.
Academic Editor: Jia Zhou
Received: 10 June 2018 / Revised: 16 July 2018 / Accepted: 17 July 2018 / Published: 24 July 2018
(This article belongs to the Special Issue Neuroprotective Agents)
Full-Text   |   PDF [4229 KB, uploaded 24 July 2018]   |  

Abstract

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. View Full-Text
Keywords: neurodegeneration; oxidative stress; neuroprotectant; antioxidant; β-diketones; drug-like properties neurodegeneration; oxidative stress; neuroprotectant; antioxidant; β-diketones; drug-like properties
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Nieto, C.I.; Cornago, M.P.; Cabildo, M.P.; Sanz, D.; Claramunt, R.M.; Torralba, M.C.; Torres, M.R.; Martínez Casanova, D.; Sánchez-Alegre, Y.R.; Escudero, E.; Lavandera, J.L. Evaluation of the Antioxidant and Neuroprotectant Activities of New Asymmetrical 1,3-Diketones. Molecules 2018, 23, 1837.

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