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

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Nieto, Carla and Cornago, María and Cabildo, María and Sanz, Dionisia and Claramunt, Rosa and Torralba Martínez, María del Carmen and Torres, María del Rosario and Martínez Casanova, Diana and Sánchez-Alegre, Yaiza and Escudero, Esther and Lavandera, José (2018) Evaluation of the Antioxidant and Neuroprotectant Activities of New Asymmetrical 1,3-Diketones. Molecules, 23 (8). p. 1837. ISSN 1420-3049

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Official URL: https://doi.org/10.3390/molecules23081837




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.


Item Type:Article
Uncontrolled Keywords:neurodegeneration; oxidative stress; neuroprotectant; antioxidant; β-diketones; drug-like properties
Subjects:Sciences > Chemistry > Chemistry, Inorganic
ID Code:66548
Deposited On:30 Jun 2021 14:28
Last Modified:06 Jul 2021 09:15

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