Design, synthesis and glutathione peroxidase-like properties of ovothiol-derived diselenides.
Eleven imidazole diselenides derived from the naturally occurring family of antioxidants, the ovothiols, were synthetised by cyclisation of selenoamides with trimethylsilyltrifluoromethanesulfonate or refluxing of cyanoamines in a selenium/sodium borohydride mixture. These compounds were assayed for their glutathione peroxidase-like (GSH Px-like) activity and their capacity to be reduced by glutathione. The most active molecules of the series were 4 times more potent in the GSH Px-like test than the widely known reference compound, ebselen. This catalytic activity was mediated by the formation of the antioxidant selenol intermediate upon partial but significant exchange reaction with glutathione.
Bailly
Fabrice
F
Laboratoire de Chimie Organique Macromoléculaire, CNRS UMR 8009, USTL, Bâtiment C3, UST Lille I, 59655 Villeneuve d'Ascq, France. fabrice.bailly@univ-lille1.fr
Azaroual
Nathalie
N
Bernier
Jean-Luc
JL
D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D019803:Glutathione Disulfide / Q000032:analysis; D005979:Glutathione Peroxidase / Q000737:chemistry / Q000378:metabolism*; D008762:Methylhistidines / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D018036:Selenium Compounds / Q000032:analysis
D000975:Antioxidants; D008762:Methylhistidines; D016566:Organoselenium Compounds; D018036:Selenium Compounds; C442270:selenol; C050085:ovothiol C; D005979:Glutathione Peroxidase; D019803:Glutathione Disulfide