Synthesis and conformation-activity relationships of the peptide isosteres of FK228 and largazole

J Am Chem Soc. 2009 Mar 4;131(8):2900-5. doi: 10.1021/ja807772w.

Abstract

The peptide isosteres (10 and 11) of the naturally occurring and potent histone deacetylase (HDAC) inhibitors FK228 and largazole have been synthesized and evaluated side-by-side with FK228, largazole, and SAHA for inhibition of the class I HDACs 1, 2, 3, and 6.

Publication types

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

MeSH terms

  • Catalytic Domain
  • Depsipeptides / chemical synthesis
  • Depsipeptides / chemistry*
  • Histone Deacetylase 1 / antagonists & inhibitors
  • Histone Deacetylase 1 / chemistry
  • Histone Deacetylase Inhibitors / chemical synthesis
  • Histone Deacetylase Inhibitors / chemistry*
  • Histone Deacetylase Inhibitors / pharmacology
  • Humans
  • Isomerism
  • Lactams, Macrocyclic / chemical synthesis
  • Lactams, Macrocyclic / chemistry
  • Models, Molecular
  • Structure-Activity Relationship
  • Thermodynamics
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*

Substances

  • Depsipeptides
  • Histone Deacetylase Inhibitors
  • Lactams, Macrocyclic
  • Thiazoles
  • largazole
  • romidepsin
  • HDAC1 protein, human
  • Histone Deacetylase 1