Tetrasulfanes as Selective Modulators of the Cellular Thiolstat

Abstract

Naturally occurring polysulfanes often exhibit a wide spectrum of biological activity, which results from their ability to react with, and hence modify cysteine residues in key proteins and enzymes of the cellular thiolstat. Such interactions frequently proceed via S-thiolation of cysteine residues and subsequent formation of Reactive Oxygen Species. Polysulfanes are highly effective, yet also surprisingly selective for cysteine residues and enable the control of numerous cellular processes ranging from an activation of antioxidant defenses to the induction of programed cell death. Unfortunately, the arsenal of natural tri- and tetrasulfanes is limited. Here, we showcase the synthesis of asymmetric tetrasulfanes, which exhibit an interesting nematocidal activity and represent a new generation of tailor-made polysulfanes with potential applications in the field of agriculture and medicine. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus Sulfur and Silicon and the Related Elements.