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Insights into the Discovery of Novel Neuroprotective Agents: A Comparative Study between Sulfanylcinnamic Acid Derivatives and Related Phenolic Analogues

1
CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
2
CNC–Center for Neuroscience and Cell Biology, University of Coimbra, UC Biotech, Biocant Park, 3060-197 Cantanhede, Portugal
3
Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, Portugal
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UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, 4050-313 Porto, Portugal
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Departamento de Química Orgánica, Facultad de Farmacia, 15782 Santiago de Compostela, Spain
6
Instituto de Ciencias Químicas Aplicadas, Universidad Autónoma de Chile, Santiago 8900000, Chile
*
Author to whom correspondence should be addressed.
Both authors contributed equally to this work.
Academic Editor: Dimitra Hadjipavlou-Litina
Molecules 2019, 24(23), 4405; https://doi.org/10.3390/molecules24234405
Received: 23 October 2019 / Revised: 26 November 2019 / Accepted: 28 November 2019 / Published: 2 December 2019
(This article belongs to the Special Issue Cinnamic Acids and Analogs: Food and Health Applications)
Exogenous antioxidants may be beneficial therapeutic tools to tackle the oxidative damage in neurodegenerative diseases by regulation of the redox state that is critical for cell viability and organ function. Inspired by natural plant polyphenols, a series of cinnamic acid-based thiophenolic and phenolic compounds were synthesized and their antioxidant and neuroprotective properties were studied. In general, our results showed that the replacement of the hydroxyl group (OH) by a sulfhydryl group (SH) increased the radical scavenging activity and enhanced the reaction rate with 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and galvinoxyl radical (GO). These results correlated well with the lower oxidation potential (Ep) values of thiophenols. However, a lower peroxyl radical (ROO) scavenging activity was observed for thiophenols in oxygen radical absorbance capacity (ORAC-FL) assay. Furthermore, the introduction of 5-methoxy and 5-phenyl groups in the aromatic ring of 4-thioferulic acid (TFA) 2 and ferulic acid (FA) 1 did not significantly improve their antioxidant activity, despite the slight decrease of Ep observed for compounds 5, 6, and 9. Concerning cinnamic acid amides, the antioxidant profile was similar to the parent compounds. None of the compounds under study presented significant cytotoxic effects in human differentiated neuroblastoma cells. Thiophenolic amide 3 stands out as the most promising thiophenol-based antioxidant, showing cellular neuroprotective effects against oxidative stress inducers (hydrogen peroxide and iron). View Full-Text
Keywords: cinnamic acid; 4-thioferulic acid derivatives; ferulic acid derivatives; antioxidant activity; cytotoxicity; neuroprotection cinnamic acid; 4-thioferulic acid derivatives; ferulic acid derivatives; antioxidant activity; cytotoxicity; neuroprotection
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Chavarria, D.; Fernandes, C.; Aguiar, B.; Silva, T.; Garrido, J.; Remião, F.; Oliveira, P.J.; Uriarte, E.; Borges, F. Insights into the Discovery of Novel Neuroprotective Agents: A Comparative Study between Sulfanylcinnamic Acid Derivatives and Related Phenolic Analogues. Molecules 2019, 24, 4405.

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