Design, synthesis and biological evaluation of quinoline derivatives as HDAC class I inhibitors

Eur J Med Chem. 2017 Jun 16:133:11-23. doi: 10.1016/j.ejmech.2017.03.064. Epub 2017 Mar 28.

Abstract

Inhibition of histone deacetylase (HDAC) has been regarded as a potential therapeutic approach for treatment of multiple diseases including cancer. Based on pharmacophore model of HDAC inhibitors, a series of quinoline-based N-hydroxycinnamamides and N-hydroxybenzamides were designed and synthesized as potent HDAC inhibitors. All target compounds were evaluated for their in vitro HDAC inhibitory activities and anti-proliferative activities and the best compound 4a surpass Vorinostat in both enzymatic inhibitory activity and cellular anti-proliferative activity. In terms of HDAC isoforms selectivity, compounds 4a exhibited preferable inhibition for class I HDACs, especially for HDAC8, the IC50 value (442 nM) was much lower than that of Vorinostat (7468 nM). Subsequently, we performed class I & IIa HDACs whole cell enzyme assay to evaluate inhibitory activity in whole cell context. Compounds 4a and 4e displayed much better cellular activity for class I HDACs than that for class IIa HDACs, which indicated that 4a and 4e might be potent class I HDAC inhibitors. Meanwhile, flow cytometry analysis showed that compound 4a and 4e can promote cell apoptosis in vitro.

Keywords: Anti-proliferative; Class I HDACs; Class I celluar activity; Hydroxamic acid; Pro-apoptosis activity; Quinoline.

MeSH terms

  • Apoptosis / drug effects
  • Benzamides / chemical synthesis
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Coumaric Acids / chemical synthesis
  • Coumaric Acids / chemistry*
  • Coumaric Acids / pharmacology*
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Histone Deacetylase Inhibitors / chemical synthesis
  • Histone Deacetylase Inhibitors / chemistry*
  • Histone Deacetylase Inhibitors / pharmacology*
  • Histone Deacetylases / metabolism
  • Humans
  • K562 Cells
  • Models, Molecular
  • Neoplasms / drug therapy*
  • Neoplasms / metabolism
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Benzamides
  • Coumaric Acids
  • Histone Deacetylase Inhibitors
  • Quinolines
  • Histone Deacetylases