Antioxidant Properties of Camphene-Based Thiosemicarbazones: Experimental and Theoretical Evaluation

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Lijuan YangShifa Wang

Abstract

The thiosemicarbazone derivatives have a wide range of biological activities, such as antioxidant activity. In this study, the antiradical activities of six camphene-based thiosemicarbazones (TSC-1~6) were investigated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and peroxyl radical scavenging capacity (PSC) assays, respectively, and the results reveal that TSC1~6 exhibited good abilities for scavenging free radicals in a dose-dependent way. Compound TSC-2 exhibited the best effect of scavenging DPPH radical, with the lowest EC50 (0.208 ± 0.004 mol/mol DPPH) as well as the highest bimolecular rate constant Kb (4218 M-1 s-1), which is 1.18-fold higher than that of Trolox. Meanwhile, TSC-2 also obtained the lowest EC50 (1.27 µmol of Trolox equiv/µmol) of scavenging peroxyl radical. Furthermore, the density functional theory (DFT) calculation was carried out to further explain the experimental results by calculating several molecular descriptors associated with radical scavenging activity. These theoretical data suggested that the electron-donating effect of the diethylamino group in TSC-2 leads to the enhancement of the scavenging activities and the studied compounds may prefer to undergo the hydrogen atom transfer process.

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Citations

Feb 14, 2021·Materials Science & Engineering. C, Materials for Biological Applications·R L FariasA V G Netto
Mar 29, 2021·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Lijuan YangShifa Wang
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Maciej SpiegelZbigniew Sroka

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