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Insights into the discovery of novel neuroprotective agents: A comparative study between sulfanylcinnamic acid derivatives and related phenolic analogues

dc.contributor.authorChavarria D.
dc.contributor.authorFernandes C.
dc.contributor.authorAguiar B.
dc.contributor.authorSilva T.
dc.contributor.authorGarrido J.
dc.contributor.authorRemião F.
dc.contributor.authorOliveira P.J.
dc.contributor.authorUriarte E.
dc.contributor.authorBorges F.
dc.date.accessioned2020-09-02T22:14:51Z
dc.date.available2020-09-02T22:14:51Z
dc.date.issued2019
dc.identifier10.3390/molecules24234405
dc.identifier.citation24, 23, -
dc.identifier.issn14203049
dc.identifier.urihttps://hdl.handle.net/20.500.12728/4014
dc.descriptionExogenous 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). © 2019 by the authors.
dc.language.isoen
dc.publisherMDPI AG
dc.subject4-thioferulic acid derivatives
dc.subjectAntioxidant activity
dc.subjectCinnamic acid
dc.subjectCytotoxicity
dc.subjectFerulic acid derivatives
dc.subjectNeuroprotection
dc.subjectantioxidant
dc.subjectcinnamic acid
dc.subjectcinnamic acid derivative
dc.subjectneuroprotective agent
dc.subjectphenol derivative
dc.subjectscavenger
dc.subjectthiol derivative
dc.subjectthiophenol
dc.subjectchemical phenomena
dc.subjectchemical structure
dc.subjectchemistry
dc.subjectdrug development
dc.subjecthuman
dc.subjectoxidation reduction reaction
dc.subjectstructure activity relation
dc.subjecttumor cell line
dc.subjectAntioxidants
dc.subjectCell Line, Tumor
dc.subjectChemical Phenomena
dc.subjectCinnamates
dc.subjectDrug Discovery
dc.subjectFree Radical Scavengers
dc.subjectHumans
dc.subjectMolecular Structure
dc.subjectNeuroprotective Agents
dc.subjectOxidation-Reduction
dc.subjectPhenols
dc.subjectStructure-Activity Relationship
dc.subjectSulfhydryl Compounds
dc.titleInsights into the discovery of novel neuroprotective agents: A comparative study between sulfanylcinnamic acid derivatives and related phenolic analogues
dc.typeArticle


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