Repositioning of the antipsychotic trifluoperazine: Synthesis, biological evaluation and in silico study of trifluoperazine analogs as anti-glioblastoma agents

Eur J Med Chem. 2018 May 10:151:186-198. doi: 10.1016/j.ejmech.2018.03.055. Epub 2018 Mar 23.

Abstract

Repositioning of the antipsychotic drug trifluoperazine for treatment of glioblastoma, an aggressive brain tumor, has been previously suggested. However, trifluoperazine did not increase the survival time in mice models of glioblastoma. In attempt to identify an effective trifluoperazine analog, fourteen compounds have been synthesized and biologically in vitro and in vivo assessed. Using MTT assay, compounds 3dc and 3dd elicited 4-5 times more potent inhibitory activity than trifluoperazine with IC50 = 2.3 and 2.2 μM against U87MG glioblastoma cells, as well as, IC50 = 2.2 and 2.1 μM against GBL28 human glioblastoma patient derived primary cells, respectively. Furthermore, they have shown a reasonable selectivity for glioblastoma cells over NSC normal neural cell. In vivo evaluation of analog 3dc confirmed its advantageous effect on reduction of tumor size and increasing the survival time in brain xenograft mouse model of glioblastoma. Molecular modeling simulation provided a reasonable explanation for the observed variation in the capability of the synthesized analogs to increase the intracellular Ca2+ levels. In summary, this study presents compound 3dc as a proposed new tool for the adjuvant chemotherapy of glioblastoma.

Keywords: Brain cancer; Calcium; Glioblastoma; Orthotopic brain xenograft mouse model; Trifluoperazine; Trifluoperazine analogs.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Antineoplastic Agents / therapeutic use*
  • Antipsychotic Agents / chemistry
  • Antipsychotic Agents / pharmacology
  • Antipsychotic Agents / therapeutic use*
  • Brain / drug effects
  • Brain / metabolism
  • Brain / pathology
  • Brain Neoplasms / drug therapy*
  • Brain Neoplasms / metabolism
  • Brain Neoplasms / pathology
  • Calcium / metabolism
  • Cell Line, Tumor
  • Drug Repositioning
  • Glioblastoma / drug therapy*
  • Glioblastoma / metabolism
  • Glioblastoma / pathology
  • Humans
  • Mice
  • Molecular Docking Simulation
  • Trifluoperazine / analogs & derivatives
  • Trifluoperazine / pharmacology
  • Trifluoperazine / therapeutic use*
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Antipsychotic Agents
  • Trifluoperazine
  • Calcium