TY - JOUR
T1 - Synthesis of enantiomerically pure glycerol derivatives containing an organochalcogen unit
T2 - In vitro and in vivo antioxidant activity
AU - Nobre, Patrick C.
AU - Vargas, Henrique A.
AU - Jacoby, Caroline G.
AU - Schneider, Paulo H.
AU - Casaril, Angela M.
AU - Savegnago, Lucielli
AU - Schumacher, Ricardo F.
AU - Lenardão, Eder J.
AU - Ávila, Daiana S.
AU - Rodrigues Junior, Luiz B.L.
AU - Perin, Gelson
N1 - Publisher Copyright:
© 2017
PY - 2020/1
Y1 - 2020/1
N2 - 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[rad]+ 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.
AB - 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[rad]+ 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.
KW - Antioxidant
KW - Caenorhabditis elegans
KW - Chalcogenoethers
KW - Chiral
KW - Organochalcogen
KW - PEG-400
UR - http://www.scopus.com/inward/record.url?scp=85028867221&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85028867221&partnerID=8YFLogxK
U2 - 10.1016/j.arabjc.2017.08.007
DO - 10.1016/j.arabjc.2017.08.007
M3 - Article
AN - SCOPUS:85028867221
SN - 1878-5352
VL - 13
SP - 883
EP - 899
JO - Arabian Journal of Chemistry
JF - Arabian Journal of Chemistry
IS - 1
ER -