Anhydride modified cantharidin analogues: synthesis, inhibition of protein phosphatases 1 and 2A and anticancer activity

Bioorg Med Chem Lett. 2000 Aug 7;10(15):1687-90. doi: 10.1016/s0960-894x(00)00323-1.

Abstract

Two series of anhydride modified cantharidin analogues were synthesised and screened for their phosphatase inhibition (PP1 and PP2A) and cytotoxicity in various cancer cell lines (Ovarian A2780, ADDP; Osteosarcoma 143B; and Colon HCT116 and HT29). One series was synthesised by a novel, high yielding one-pot hydrogenation-ring-opening-esterification procedure, the other by acid catalysed acetal formation. Analogues 5-7 and 9 displayed moderate PP2A selectivity (ca. 5- to 20-fold) and inhibition typically in the low microM range (comparable, in some cases to cantharidin). The anticancer activity of these analogues varied with the cell line under study; however, many of them showed selective cytotoxicity for the colon tumour cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anhydrides / chemistry*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Cantharidin / analogs & derivatives*
  • Cantharidin / chemical synthesis
  • Cantharidin / pharmacology
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Isoenzymes / antagonists & inhibitors*
  • Phosphoprotein Phosphatases / antagonists & inhibitors*
  • Tumor Cells, Cultured

Substances

  • Anhydrides
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Isoenzymes
  • Phosphoprotein Phosphatases
  • Cantharidin