Synthesis of enantiomerically pure glycerol derivatives containing an organochalcogen unit: In vitro and in vivo antioxidant activity
| Autor: | Caroline Gross Jacoby, Henrique A. Vargas, Patrick C. Nobre, Luiz Brasil Lopes Rodrigues Junior, Gelson Perin, Lucielli Savegnago, Paulo H. Schneider, Daiana Silva Ávila, Angela Maria Casaril, Ricardo F. Schumacher, Eder J. Lenardão |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Antioxidant
ABTS biology Chemistry DPPH General Chemical Engineering medicine.medical_treatment 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Lipid peroxidation lcsh:Chemistry chemistry.chemical_compound lcsh:QD1-999 Catalase In vivo Solketal biology.protein medicine Organic chemistry 0210 nano-technology Hydrogen peroxide |
| Zdroj: | Arabian Journal of Chemistry, Vol 13, Iss 1, Pp 883-899 (2020) |
| ISSN: | 1878-5352 |
| Popis: | We describe here the synthesis of enantiomerically pure chalcogenoethers obtained through the reaction of nucleophilic species of chalcogen (S, Se and Te), generated in situ from the respective diorganyl dichalcogenides, with (R)- and (S)-tosyl solketal. Furthermore, some of the chalcogenoethers were treated with acidic cation exchange resin Dowex-(H+) leading to the respective deprotected enantiomerically pure 3-phenylchalcogenyl-1,2-diols. In order to explore the biological potential of these molecules, the antioxidant activity of some organochalcogens was evaluated by several in vitro assays. Overall, the chalcogenoethers containing Te were better scavengers of DPPH and ABTS·+ radicals, had higher ferric reducing capacity and prevented lipid peroxidation. To analyze the effects of these compounds in vivo, we used the alternative model Caenorhabditis elegans. Chalcogenoethers treatment, especially (S)- and (R)-2,2-dimethyl-4-(phenylselanylmethyl)-1,3-dioxolane, conferred protection against the mortality-induced by hydrogen peroxide. Accordingly, these chalcogenoethers were able to modulate the antioxidant enzyme catalase. Notably, the compounds did not present toxicity in worm’s reproduction. To sum up, our study demonstrated that Te- containing chalcogenoethers were promising in vitro scavengers, while Se molecules were more prone to protect against a stressor in vivo. In this sense, the antioxidant activity of chalcogenoethers, especially with Se and Te, indicates that these molecules may have biological application in an attempt to reduce the oxidative stress. Keywords: Organochalcogen, Chiral, Chalcogenoethers, PEG-400, Antioxidant, Caenorhabditis elegans |
| Databáze: | OpenAIRE |
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