Structure guided design of a series of sphingosine kinase (SphK) inhibitors

Bioorg Med Chem Lett. 2013 Aug 15;23(16):4608-16. doi: 10.1016/j.bmcl.2013.06.030. Epub 2013 Jun 20.

Abstract

Sphingosine-1-phosphate (S1P) signaling plays a vital role in mitogenesis, cell migration and angiogenesis. Sphingosine kinases (SphKs) catalyze a key step in sphingomyelin metabolism that leads to the production of S1P. There are two isoforms of SphK and observations made with SphK deficient mice show the two isoforms can compensate for each other's loss. Thus, inhibition of both isoforms is likely required to block SphK dependent angiogenesis. A structure based approach was used to design and synthesize a series of SphK inhibitors resulting in the identification of the first potent inhibitors of both isoforms of human SphK. Additionally, to our knowledge, this series of inhibitors contains the only sufficiently potent inhibitors of murine SphK1 with suitable physico-chemical properties to pharmacologically interrogate the role of SphK1 in rodent models and to reproduce the phenotype of SphK1 (-/-) mice.

Keywords: Drug design; Murine SphK; Sphingosine kinase 1 inhibitor; Sphingosine kinase 2 inhibitor; Structure based.

MeSH terms

  • Animals
  • Cells, Cultured
  • Crystallography, X-Ray
  • Drug Design*
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Mice
  • Molecular Structure
  • Phosphotransferases (Alcohol Group Acceptor) / antagonists & inhibitors*
  • Phosphotransferases (Alcohol Group Acceptor) / chemistry*
  • Protein Isoforms / chemistry
  • Rats
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / pharmacology
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Protein Isoforms
  • Small Molecule Libraries
  • Phosphotransferases (Alcohol Group Acceptor)
  • sphingosine kinase