Identification of novel piperazinylquinoxaline derivatives as potent phosphoinositide 3-kinase (PI3K) inhibitors

PLoS One. 2012;7(8):e43171. doi: 10.1371/journal.pone.0043171. Epub 2012 Aug 14.

Abstract

Background: Development of small-molecule inhibitors targeting phosphoinositide 3-kinase (PI3K) has been an appealing strategy for the treatment of various types of cancers.

Methodology/principal finding: Our approach was to perform structural modification and optimization based on previously identified morpholinoquinoxaline derivative WR1 and piperidinylquinoxaline derivative WR23 with a total of forty-five novel piperazinylquinoxaline derivatives synthesized. Most target compounds showed low micromolar to nanomolar antiproliferative potency against five human cancer cell lines using MTT method. Selected compounds showed potent PI3Kα inhibitory activity in a competitive fluorescent polarization assay, such as compound 22 (IC(50) 40 nM) and 41 (IC(50): 24 nM), which induced apoptosis in PC3 cells. Molecular docking analysis was performed to explore possible binding modes between target compounds and PI3K.

Conclusions/significance: The identified novel piperazinylquinoxaline derivatives that showed potent PI3Kα inhibitory activity and cellular antiproliferative potency may be promising agents for potential applications in cancer treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / pharmacology*
  • Apoptosis
  • Binding Sites
  • Cell Line, Tumor
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Enzyme Inhibitors / pharmacology*
  • Flow Cytometry / methods
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry / methods
  • Neoplasms / drug therapy*
  • Neoplasms / enzymology*
  • Phosphoinositide-3 Kinase Inhibitors*
  • Quinoxalines / pharmacology*
  • Tetrazolium Salts / pharmacology
  • Thiazoles / pharmacology

Substances

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Phosphoinositide-3 Kinase Inhibitors
  • Quinoxalines
  • Tetrazolium Salts
  • Thiazoles
  • thiazolyl blue

Grants and funding

PW was supported by the European Commission Eramus Mundus LiSUM project. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.