Protective Properties of Novel S-Acyl-Glutathione Thioesters Against Ultraviolet-induced Oxidative Stress (pages 442–452)
Daniel Wright, Mariagioia Zampagni, Elisa Evangelisti, Simona Conti, Giampiero D'Adamio, Andrea Goti, Matteo Becatti, Claudia Fiorillo, Niccolò Taddei, Cristina Cecchi and Gianfranco Liguri
Version of Record online: 1 OCT 2012 | DOI: 10.1111/j.1751-1097.2012.01231.x
Acyl-SG derivatives are capable of crossing plasma membrane thanks to their lipophilic acyl chain, which is attached via a thioester bond to the free sulfhydryl group of the GSH cysteine residue. Once internalized, acyl-SG derivatives are cleaved by cellular esterases, which release free reduced GSH, which acts as a scavenger and the parent fatty acid, which acts as a carrier and itself has inherent antioxidant properties. The protective effect of thioesters was dependent on the degree of acyl chain saturation, with more unsaturated linolenoyl-SG derivatives affording greater protection than palmitoyl-SG derivatives against UV-induced cell death, ROS production and lipid peroxidation.