Phenylalanine-containing hydroxamic acids as selective inhibitors of class IIb histone deacetylases (HDACs)

Bioorg Med Chem. 2008 Feb 15;16(4):2011-33. doi: 10.1016/j.bmc.2007.10.092. Epub 2007 Nov 4.

Abstract

We synthesized biarylalanine-containing hydroxamic acids and tested them on immunoprecipitated HDAC1 and HDAC6 and show a subtype selectivity for HDAC6 that was confirmed in cells by Western blot (tubulin vs histones). We obtained an X-ray structure with a HDAC6-selective inhibitor with the bacterial deacetylase HDAH. Docking studies were carried out using HDAC1 and HDAC6 protein models. Antiproliferative activity was shown on cancer cells for selected compounds.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Blotting, Western
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Computer Simulation
  • Crystallography, X-Ray
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Histone Deacetylase 1
  • Histone Deacetylase 6
  • Histone Deacetylase Inhibitors*
  • Histone Deacetylases
  • Histones
  • Humans
  • Hydroxamic Acids / chemical synthesis
  • Hydroxamic Acids / pharmacology*
  • Phenylalanine*
  • Protein Binding
  • Tubulin

Substances

  • Enzyme Inhibitors
  • Histone Deacetylase Inhibitors
  • Histones
  • Hydroxamic Acids
  • Tubulin
  • Phenylalanine
  • HDAC1 protein, human
  • HDAC6 protein, human
  • Histone Deacetylase 1
  • Histone Deacetylase 6
  • Histone Deacetylases