Shp2 protein tyrosine phosphatase inhibitor activity of estramustine phosphate and its triterpenoid analogs

Bioorg Med Chem Lett. 2011 Jan 15;21(2):730-3. doi: 10.1016/j.bmcl.2010.11.117. Epub 2010 Dec 4.

Abstract

Shp2 protein tyrosine phosphate (PTP) is a novel target for anticancer drug discovery. We identified estramustine phosphate as a Shp2 PTP inhibitor from the National Cancer Institute Approved Oncology Drug set. A focused structure-activity relationship study indicated that the 17-phosphate group is required for the Shp2 PTP inhibitor activity of estramustine phosphate. A search for estramustine phosphate analogs led to identification of two triterpenoids, enoxolone, and celastrol, having Shp2 PTP inhibitor activity. With the previously reported PTP1B inhibitor trodusquemine, our study reveals steroids and triterpenoids with negatively charged phosphate, carboxylate, or sulfonate groups as novel pharmacophores of selective PTP inhibitors.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antineoplastic Agents, Hormonal / chemistry*
  • Antineoplastic Agents, Hormonal / pharmacology*
  • Estramustine / analogs & derivatives*
  • Estramustine / pharmacology*
  • Humans
  • Models, Molecular
  • Neoplasms / drug therapy
  • Neoplasms / enzymology
  • Protein Tyrosine Phosphatase, Non-Receptor Type 11 / antagonists & inhibitors*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 11 / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 11 / metabolism*
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / pharmacology

Substances

  • Antineoplastic Agents, Hormonal
  • Triterpenes
  • Estramustine
  • Protein Tyrosine Phosphatase, Non-Receptor Type 11