Paradoxical Behavior of Organodiselenides: Pro-Oxidant to Antioxidant

Abstract

Over the years, organodiselenides have emerged as the biologically relevant class of molecules. On one hand, such compounds are known for pro-oxidant effects leading to toxicity in biological systems. On the other hand, there are growing evidences about their bio-mimetic activities as catalysts such as glutathione peroxidase (GPx)-like activity. Our recent work has explored this paradoxical behavior of diselenides in developing antioxidants and/or anticancer agents. For this, a number of alkyl and aryldiselenides have been evaluated in different biological models. The results have shown that aryl diselenides specifically pyridinediselenides alter the ratio of the intracellular thiol redox pairs (GSH and GSSG) towards reduction (antioxidant) rather than oxidation(pro-oxidant) to protect normal cells against radiation damage as well asto induce cytotoxicity in tumor cells. Further, these studies have also postulated that intracellular redox state, level of thioredoxin reductase (TrxR) and reductive intermediates (like selenol and/or selone) might play a very important role in the manifestation of the toxicities of aryl diselenides in cells

Organic selenocompounds: are they the panacea for human illnesses?

“…315 The -SeH group attached to a pyridine ring undergoes tautomerization to form a selone, i.e., the R-CQSe has greater chemical stability than that of R-SeH, which is responsible for the reactive oxygen species (ROS) scavenging process and participates in the GPX-like cycle of some OSeCs. 25,316 As commented above, in mice, diphenyl diselenide is metabolized, and there was a clear rupture of the Se-C bond 122 and the release of Se to the inorganic Se pool that can feed the synthesis of selenoproteins. Although HSe À derived from the metabolism of diphenyl diselenide can also react with electrophilic forms of Hg, the increase in the excretion of Hg from the body of methylmercury-treated mice cannot be explained by the formation of HgSe salts.…”

“…, the R–CSe has greater chemical stability than that of R-SeH, which is responsible for the reactive oxygen species (ROS) scavenging process and participates in the GPX-like cycle of some OSeCs. 25,316…”

Glutathione Peroxidase-like Antioxidant Activity of 1,3-Benzoselenazoles: Synthesis and In Silico Molecular Docking Studies as Pancreatic Lipase Inhibitors

“…Organoselenium compounds have nowadays received a great attention as potential medicinal agents, crucial applications in synthetic organic chemicals, building block of complex molecules, and in material sciences . Additionally, it has been found that organoselenium compounds have dual characteristics, acting as an antioxidant for healthy cells and a pro-oxidant for cancer cells . Due to their utility in organic synthesis, many classes of organoselenium compounds have been studied to date. , …”