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This study was designed to examine the antioxidant activity in vitro of novel mono- and diselenide compounds. We compared whether the formation of p-methyl-selenol from compounds 1-phenyl-3-(p-tolylselanyl)propan-2-amine (C1) and 1,2-dip-tolyldiselenide (C4) and o-methoxy-selenol from compounds 1-(2-methoxyphenylselanyl)-3-phenylpropan-2-amine (C2) and 1,2-bis(2-methoxyphenyl)diselenide (C3) may be involved in their antioxidant effects. The compounds were tested against Fe(II) and sodium nitroprusside (SNP)-induced lipid peroxidation in rat brain and liver homogenates. Likewise, the antioxidant capacity of the compounds was assessed by their ability to decolorize the DPPH radical as well as the Fe(II) chelating assay through the reduction of molybdenum(VI) (Mo6+) to molybdenum(V) (Mo5+). This colorimetric assay was also used to quantify thiol peroxidase (GPx) and oxidase activity and thioredoxin reductase (TrxR) activity. The results showed that the novel selenide compounds inhibit the thiobarbituric acid reactive species (TBARS) induced by different pro-oxidants, but the monoselenides effects were significant only at concentrations higher than the concentrations of the diselenides. Similarly, the total antioxidant activity was higher in the diselenides. Moreover, GPx and TrxR activity was only observed for the diselenides, which indicates that these compounds are more stable selenol molecules than monoselenides., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

β-Seleno amines were screened for in vitro antioxidant activity. The compounds (C1-C4) were tested against lipid peroxidation induced by iron and sodium nitroprusside in rat brain and liver homogenates. The compounds showed inhibition against thiobarbituric acid reactive species (TBARS) induced by different pro-oxidants (10μM FeSO(4) and 5μM sodium nitroprusside (SNP) in rat brain and liver homogenates. The compounds exhibited strong antioxidant activity in 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and phosphomolybdenum assays. The IC(50) values revealed that the β-seleno amines in which the amino group was protected with protecting groups tert-butyloxycarbonyl (Boc) and Tosyl (Ts) groups showed better antioxidant profiles compared to the free monoselenides. The total antioxidant activity of C1, C2, C3 and C4 were found to be 85.2±11.5, 114±7.9, 138±8.5, 125.81±5.2μM/ml of ascorbic acid respectively. Therefore, these compounds may be used as synthetic antioxidants., (Copyright © 2012 Elsevier B.V. All rights reserved.)

The antioxidant properties of organoselenium compounds have been extensively investigated because oxidative stress is a hallmark of a variety of chronic human diseases. Here, we reported the influence of substituent groups in the antioxidant activity of β-selenoamines. We have investigated whether they exhibited glutathione peroxidase-like (GPx-like) activity and whether they could be substrate of thioredoxin reductase (TrxR). In the DPPH assay, the β-selenium amines did not exhibit antioxidant activity. However, the β-selenium amines with p-methoxy and tosyl groups prevented the lipid peroxidation. The β-selenium amine compound with p-methoxy substituent group exhibited thiol-peroxidase-like activity (GPx-like activity) and was reduced by the hepatic TrxR. These results contribute to understand the influence of structural alteration of non-conventional selenium compounds as synthetic mimetic of antioxidant enzymes of mammalian organisms.