Arecoline tripeptide inhibitors of proteasome

J Med Chem. 2004 Mar 11;47(6):1587-90. doi: 10.1021/jm0309102.

Abstract

The 26S proteasome is a multicatalytic protease complex that plays an essential role in intracellular protein degradation. We have synthesized and tested a series of arecoline peptide derivatives where the peptide portion derives from a screening of tripeptide sequences, and the arecoline moiety has been considered as a potential substrate for catalytic threonine. Derivatives 17-19 are the best compounds of the series, showing chymotryptic-like (beta5) inhibition (IC(50) congruent with 1 microM) and favorable pharmacokinetic properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Arecoline / analogs & derivatives*
  • Arecoline / chemical synthesis*
  • Arecoline / pharmacology
  • Cysteine Endopeptidases / blood
  • Cysteine Endopeptidases / chemistry
  • Cysteine Endopeptidases / metabolism*
  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / pharmacology
  • Drug Stability
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Multienzyme Complexes / blood
  • Multienzyme Complexes / chemistry
  • Multienzyme Complexes / metabolism*
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology
  • Proteasome Endopeptidase Complex

Substances

  • Cysteine Proteinase Inhibitors
  • Enzyme Inhibitors
  • Multienzyme Complexes
  • Oligopeptides
  • Arecoline
  • Cysteine Endopeptidases
  • Proteasome Endopeptidase Complex