Issue 44, 2019
From the journal:

Organic & Biomolecular Chemistry

Bioisosteric OH- to SH-replacement changes the antioxidant profile of ferulic acid†

Daniel Chavarria, ORCID logo ‡ab   Carlos Fernandes, ORCID logo ‡a   Tiago Silva, ORCID logo ab   Jorge Garrido, ORCID logo c   Fernando Remião, ORCID logo d   Paulo J. Oliveira ORCID logo b  and  Fernanda Borges ORCID logo *a  

* Corresponding authors

a CIQUP/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, 4169-007 Porto, Portugal
E-mail: fborges@fc.up.pt

b CNC - Center for Neuroscience and Cell Biology, University of Coimbra, UC Biotech, Biocant Park, Cantanhede, Portugal

c Department of Chemical Engineering, School of Engineering (ISEP), Polytechnic of Porto, 4200-072 Porto, Portugal

d UCIBIO-REQUIMTE, Laboratory of Toxicology, Department of Biological Sciences, Faculty of Pharmacy, University of Porto, Porto, Portugal

Abstract

We report the synthesis of 4-thioferulic acid (TFA), a new ferulic acid (FA) derivative, and highlight the differences between the two compounds concerning rate and mechanism of radical scavenging activity, redox potential, acidity of the phenol/thiophenol moieties, cytotoxicity in differentiated SH-SY5Y cells, and neuroprotection against hydrogen peroxide (H2O2) and tert-butyl hydroperoxide (t-BHP) in the same cellular model.

Graphical abstract: Bioisosteric OH- to SH-replacement changes the antioxidant profile of ferulic acid

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Article information

DOI
https://doi.org/10.1039/C9OB01875A
Article type
Paper
Submitted
26 Aug 2019
Accepted
23 Oct 2019
First published
23 Oct 2019

Org. Biomol. Chem., 2019,17, 9646-9654

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Bioisosteric OH- to SH-replacement changes the antioxidant profile of ferulic acid

D. Chavarria, C. Fernandes, T. Silva, J. Garrido, F. Remião, P. J. Oliveira and F. Borges, Org. Biomol. Chem., 2019, 17, 9646 DOI: 10.1039/C9OB01875A

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