In this article we present the synthesis, characterization, and in vitro biological and biochemical activities of new chalcogenozidovudine derivatives as antioxidant (inhibition of TBARS in brain membranes and thiol peroxidase-like activity) as well as antitumoral agents in bladder carcinoma 5637. A prominent response was obtained for the selected chalcogenonucleosides, showing effective antioxidant and antitumoral activities.

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.

This article presents the preparation and biological activities of new 5'-arylchalcogeno-3-aminothymidine derivatives as antioxidants (inhibition of lipid peroxidation, scavenging of the free radical 2,2-diphenylpicrylhydrazyl and demonstration of a thiol peroxidase-like activity) as well as antitumoral agents against bladder carcinoma 5637. The chalcogeno-aminothymidines presented prominent activity in the tests for both biological properties, showing a direct relation with the chalcogenium atom.

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HighlightsNovel organic selenium compounds presented low toxicity over C. elegans survival.Defecation cycles were decreased by Novel organic selenium compounds, except C1.Novel organic selenium compounds, except C1 decreased AChE enzyme activity.All compounds tested prevented from juglone stress.C2 selenium compound decreased GST-4::GFP fluorescence under juglone stress.

The synthesis of chiral azido organochalcogenium compounds prepared from inexpensive and commerciallyavailable a-amino alcohols through diazo transfer reaction are disclosed. The products were obtained in good yields in a modulate synthetic route, affording an efficient methodology for preparing new chiral b-aryl-chalcogenium azide compounds. These com-pounds were evaluated for in vitro antitumoral lung carcinoma A549 as well as electrochemical and antioxidant assays. They presented prominent activities of apoptosis and cell cycle arrest induction as well as antioxidant properties. Additionally, the toxicities in vivo for the most effective compounds were evaluated and no overt sign of toxicity was observed.

Over the past years, organoselenium compounds have been aimed as targets of interest in organic synthesis. Diphenyl diselenide [(PhSe)2] is an important example of this class showing several pharmacological properties. However, the poor water-solubility and its low oral bioavailability may be considered an obstruction for the clinical utility of this compound. For this reason, the use of nanocapsules is a prominent approach to increase the bioavailability of lipophylic molecules. This study aims to prepare diphenyl diselenide-loaded nanocapsules with two different concentrations, by interfacial deposition of the preformed polymer in order to develop a system to improve its oral bioavailability. The drug-loaded nanocapsules with 1.56 and 5 mg ml−1 and unloaded nanocapsule suspensions presented macroscopic homogeneous aspect, as well as submicronic sizes, low polydispersity, negative zeta potentials and slightly acid or neutral pH values. The biological tests of selenium distribution in different tissues of mice show a higher bioavailability of the (PhSe)2 nanocapsules when compared with the free (PhSe)2, both administered by per oral route at the dose of 50 mg/kg, showing a prominent influence of the nanocarries systems for biological properties of this organochalcogenium compound.