Use of the nitrile oxide cycloaddition (NOC) reaction for molecular probe generation: a new class of enzyme selective histone deacetylase inhibitors (HDACIs) showing picomolar activity at HDAC6

J Med Chem. 2008 Aug 14;51(15):4370-3. doi: 10.1021/jm8002894. Epub 2008 Jul 22.

Abstract

A series of hydroxamate based HDAC inhibitors containing a phenylisoxazole as the CAP group has been synthesized using nitrile oxide cycloaddition chemistry. An HDAC6 selective inhibitor having a potency of approximately 2 picomolar was identified. Some of the compounds were examined for their ability to block pancreatic cancer cell growth and found to be about 10-fold more potent than SAHA. This research provides valuable, new molecular probes for use in exploring HDAC biology.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Histone Deacetylase Inhibitors*
  • Histone Deacetylases / chemistry
  • Histone Deacetylases / metabolism
  • Humans
  • Models, Molecular
  • Molecular Probes / chemical synthesis*
  • Molecular Probes / chemistry
  • Molecular Probes / classification
  • Molecular Probes / pharmacology*
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxides / chemistry*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Histone Deacetylase Inhibitors
  • Molecular Probes
  • Nitriles
  • Oxides
  • Histone Deacetylases