Alpha,beta-unsaturated N-acylpyrrole peptidyl derivatives: new proteasome inhibitors

J Med Chem. 2010 Sep 9;53(17):6511-5. doi: 10.1021/jm100122e.

Abstract

Because of the encouraging results obtained using vinyl ester derivatives, we synthesized and tested a novel series of peptide-based proteasome inhibitors bearing a new pharmacophore unit at the C-terminal. N-Acylpyrrole moiety is a potential substrate for Michael addition by catalytic threonine. Several analogues have demonstrated a selective inhibition of the multicatalytic complex beta1 subunits, the capacity to permeate cellular membrane, and good pharmacokinetics properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacokinetics
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Catalytic Domain
  • Cell Line, Tumor
  • Cell Membrane Permeability
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Drug Stability
  • Humans
  • Models, Molecular
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacokinetics
  • Oligopeptides / pharmacology
  • Proteasome Endopeptidase Complex / blood
  • Proteasome Endopeptidase Complex / chemistry
  • Proteasome Inhibitors*
  • Protein Subunits / antagonists & inhibitors
  • Pyrroles / chemical synthesis*
  • Pyrroles / pharmacokinetics
  • Pyrroles / pharmacology
  • Structure-Activity Relationship
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / pharmacokinetics
  • Vinyl Compounds / pharmacology

Substances

  • Antineoplastic Agents
  • Oligopeptides
  • Proteasome Inhibitors
  • Protein Subunits
  • Pyrroles
  • Vinyl Compounds
  • Proteasome Endopeptidase Complex