Synthesis, biological evaluation and molecular docking studies of flavone and isoflavone derivatives as a novel class of KSP (kinesin spindle protein) inhibitors

Eur J Med Chem. 2013:70:427-33. doi: 10.1016/j.ejmech.2013.09.042. Epub 2013 Oct 2.

Abstract

The kinesin spindle protein (KSP) is involved in the formation of bipolar mitotic spindle during cell division and it becomes a new target to overcome the neurotoxicity of MTs inhibitors. A series of flavone and isoflavone derivatives (1a-7c) have been designed, synthesized and evaluated as potential KSP inhibitors. Among them, 2c displayed the most potent inhibitory activity in vitro, which inhibited the growth of MCF-7 and Hela cell lines with IC50 values of 4.8 and 4.3 μM, respectively, and also exhibited significant KSP inhibitory activity (IC₅₀ = 0.023 μM). The new compounds can induce irregular monoastral spindles, the characteristic phenotype for KSP inhibiting agents. Docking simulation was further performed to determine the probable binding model.

Keywords: Antimitotic; Flavone; Isoflavone; KSP; Kinesin inhibitor; Monoastral spindles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Flavones / chemical synthesis
  • Flavones / chemistry
  • Flavones / pharmacology*
  • HeLa Cells
  • Humans
  • Isoflavones / chemical synthesis
  • Isoflavones / chemistry
  • Isoflavones / pharmacology*
  • Kinesins / antagonists & inhibitors*
  • Kinesins / metabolism
  • MCF-7 Cells
  • Models, Molecular
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Flavones
  • Isoflavones
  • KIF11 protein, human
  • Kinesins
  • flavone