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

Daniel Chavarria Carlos Fernandes Tiago Silva Jorge M P J Garrido Fernando Remiao Paulo J Oliveira Fernanda Borges

Published in: Organic & biomolecular chemistry (2019)

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.

Keyphrases

hydrogen peroxide
induced apoptosis
nitric oxide
oxidative stress
cell cycle arrest
risk assessment
human health
signaling pathway
anti inflammatory
endoplasmic reticulum stress
pi k akt