Please use this identifier to cite or link to this item:
Title: Insights into the Discovery of Novel Neuroprotective Agents: A Comparative Study between Sulfanylcinnamic Acid Derivatives and Related Phenolic Analogues
Authors: Chavarria, Daniel 
Fernandes, Carlos
Aguiar, Brandon
Silva, Tiago 
Garrido, Jorge 
Remião, Fernando 
Oliveira, Paulo J. 
Uriarte, Eugenio 
Borges, Fernanda
Keywords: cinnamic acid; 4-thioferulic acid derivatives; ferulic acid derivatives; antioxidant activity; cytotoxicity; neuroprotection
Issue Date: 2-Dec-2019
Publisher: MDPI
Project: UID/QUI/00081 
FCT, POPH and FEDER/COMPETE and NORTE-01-0145-FEDER-000028 
COST Action CA15135 
Serial title, monograph or event: Molecules
Volume: 24
Issue: 23
Abstract: 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).
ISSN: 1420-3049
DOI: 10.3390/molecules24234405
Rights: openAccess
Appears in Collections:I&D CNC - Artigos em Revistas Internacionais

Show full item record


checked on Nov 20, 2023


checked on Nov 2, 2023

Page view(s)

checked on Nov 28, 2023

Google ScholarTM




This item is licensed under a Creative Commons License Creative Commons