Abstract
The oxygen radical absorbance capacity (ORAC) method was used to detect the antiperoxyradical ability of organoselenium compounds: selenophene and its derivative, 2-amino-4,5,6,7-tetrahydro-1-selenophene-3-carbonitrile (ATSe); while as a comparison, the sulfur-containing analogue of selenophene—thiophene and its derivative—2-amino-4,5,6,7-tetrahydro-1-thiophene-3-carbonitrile (ATS)—was selected. Cyclic voltammetry (CV), differential pulse voltammetry (DPV) and squarewave voltammetry (SWV) methods were used to determine the redox characteristics of organoselenium and organosulfur compounds. The antiradical activity and capacity of the studied compounds were also measured by using stable radical 2,2ʹ-diphenyl-1-picrylhydrazyl (DPPH). Detected anodic peaks of the oxidation of selenophene, thiophene and their derivatives in CV, DPV and SWV in the interval of −1200 ÷ (+1600) mV potentials in regard to the Ag/Ag+ medium of acetonitrile prove the presence of antiperoxyradical activity in regard to oxidizers, i.e., peroxyradicals. The chemical mechanism of the antiperoxyradical ability of selenophene, thiophene and their organic derivatives is proposed.
Highlights
Studies of the chemical mechanism of organoselenium antioxidant action are urgent
“scavenge” free radicals and other reactive oxygen-containing species (ROS), the excess generation of which causes many pathological conditions known as oxidative stress [8,9,10,11,12]
60 -dihydroxyspiro[isobenzofuran-1(3H), 9ʹ-[9H]xanthen]-3-one-fluorescein disodium salt (Fl), DPPH, DPPH, selenophene, and thiophene were purchased the Sigma-Aldrich (USA) chemical selenophene, and thiophene were purchased from thefrom
Summary
Studies of the chemical mechanism of organoselenium antioxidant action are urgent. In recent years, special interest has been given to selenium-containing compounds as antioxidants, regulating free radical reactions in the organism, and significantly affecting its state [1,2,3,4,5,6,7]. The selection of seleno- and sulfo-organic compounds, such as thiophene, selenophene and their derivatives: aminocarbonitriles (Scheme 1), was conditioned by the following reasons: 2. 3. It was supposed that the presence of sulfo- and seleno-groups in the conjugated system will reduce the unpleasant odor of such compounds, which is an urgent problem. It was supposed that the presence of sulfo- and seleno-groups in the conjugated system will reduce the unpleasant odor of such compounds, which is an urgent problem It can molecular system will reduce the unpleasant odor of such compounds, which is an urgent be assumed, for example, by comparing Ebselen (entered into medical practice) with diethyl problem. The presence of aminogroups molecular system by analogy with aromatic amines, along with sulfo- and seleno-groups, connected to the conjugated molecular system by analogy with aromatic amines, along with may serve as additional antiradical centers [15]. Using the DPV voltammetry method to characterize quantitively thethe redox properties ofofthe studied sulfurand selenium-containing compounds, as as well as toa find a correlation with studied sulfurand selenium-containing compounds, as well to find correlation with their their antiradical antiradical properties.properties
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