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Daniel Wright, Mariagioia Zampagni, Elisa Evangelisti, Simona Conti, Giampiero D'Adamio, Andrea Goti, Matteo Becatti, Claudia Fiorillo, Niccolò Taddei, Cristina Cecchi and Gianfranco Liguri Protective Properties of Novel S-Acyl-Glutathione Thioesters Against Ultraviolet-induced Oxidative Stress Photochemistry and Photobiology 89

Article first published online: 1 OCT 2012 | DOI: 10.1111/j.1751-1097.2012.01231.x

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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.

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