Organothiophosphate

Organothiophosphates or organophosphorothioates are a subclass of organophosphorus compounds and of thiophosphate compounds. They are the organic compounds that contain a phosphate group in which one or more oxygen atoms is substituted by sulfur. Many are used as pesticides, some have medical applications, and some are used as oil additives.[1] They generally have the chemical formula (RO)3PS, [(RO)2P(S)O]−, R(RO)2PS, etc.

Selected organothiophosphates

Oligonucleotide phosphorothioates (OPS) are modified oligonucleotides where one of the oxygen atoms in the phosphate moiety is replaced by sulfur. These compounds are the basis of antisense therapy, e.g., the drugs fomivirsen (Vitravene), oblimersen, alicaforsen, and mipomersen (Kynamro).[2]

Further examples of these include:

Variants with P=S double bonds were developed as insecticides because of their reduced mammalian toxicity. The phosphorothioate P=S bond is converted to the toxic P=O bond in the target insect. Similar oxidative conversion in mammals is slower, conferring lower toxicity in mammals.

  1. ^ Svara, Jürgen; Weferling, Norbert; Hofmann, Thomas (2006). "Phosphorus Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_545.pub2. ISBN 3527306730.
  2. ^ Kurreck, Jens (2003). "Antisense technologies. Improvement through novel chemical modifications". European Journal of Biochemistry. 270 (8): 1628–1644. doi:10.1046/j.1432-1033.2003.03555.x. PMID 12694176.