Thiotaurine: From Chemical and Biological Properties to Role in H2S Signaling

Adv Exp Med Biol. 2019:1155:755-771. doi: 10.1007/978-981-13-8023-5_66.

Abstract

In the last decade thiotaurine, 2-aminoethane thiosulfonate, has been investigated as an inflammatory modulating agent as a result of its ability to release hydrogen sulfide (H2S) known to play regulatory roles in inflammation. Thiotaurine can be included in the "taurine family" due to structural similarity to taurine and hypotaurine, and is characterized by the presence of a sulfane sulfur moiety. Thiotaurine can be produced by different pathways, such as the spontaneous transsulfuration between thiocysteine - a persulfide analogue of cysteine - and hypotaurine as well as in vivo from cystine. Moreover, the enzymatic oxidation of cysteamine to hypotaurine and thiotaurine in the presence of inorganic sulfur can occur in animal tissues and last but not least thiotaurine can be generated by the transfer of sulfur from mercaptopyruvate to hypotaurine catalyzed by a sulfurtransferase. Thiotaurine is an effective antioxidant agent as demonstrated by its ability to counteract the damage caused by pro-oxidants in the rat. Recently, we observed the influence of thiotaurine on human neutrophils functional responses. In particular, thiotaurine has been found to prevent human neutrophil spontaneous apoptosis suggesting an alternative or additional role to its antioxidant activity. It is likely that the sulfane sulfur of thiotaurine may modulate neutrophil activation via persulfidation of target proteins. In conclusion, thiotaurine can represent a biologically relevant sulfur donor acting as a biological intermediate in the transport, storage and release of sulfide.

Keywords: Antioxidant; H2S donor; H2S signaling; Hydrogen sulfide; Hypotaurine; Inflammation; Neutrophils; Reactive sulfur species; Sulfane sulfur; Thiotaurine.

Publication types

  • Review

MeSH terms

  • Animals
  • Antioxidants / pharmacology
  • Apoptosis
  • Humans
  • Hydrogen Sulfide*
  • Neutrophils / cytology
  • Neutrophils / drug effects
  • Rats
  • Signal Transduction
  • Sulfides
  • Taurine / analogs & derivatives*
  • Taurine / physiology

Substances

  • Antioxidants
  • Sulfides
  • Taurine
  • thiotaurine
  • Hydrogen Sulfide