Cell-permeable bicyclic peptide inhibitors against intracellular proteins

J Am Chem Soc. 2014 Jul 16;136(28):9830-3. doi: 10.1021/ja503710n. Epub 2014 Jul 2.

Abstract

Cyclic peptides have great potential as therapeutic agents and research tools but are generally impermeable to the cell membrane. Fusion of cyclic peptides with a cyclic cell-penetrating peptide produces bicyclic peptides that are cell-permeable and retain the ability to recognize specific intracellular targets. Application of this strategy to protein tyrosine phosphatase 1B and a peptidyl-prolyl cis-trans isomerase (Pin1) isomerase resulted in potent, selective, proteolytically stable, and biologically active inhibitors against the enzymes.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / pharmacology*
  • Cell Line, Tumor
  • Cell Membrane Permeability
  • Cell-Penetrating Peptides / chemical synthesis*
  • Cell-Penetrating Peptides / pharmacology*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / pharmacology*
  • Peptidylprolyl Isomerase / antagonists & inhibitors
  • Peptidylprolyl Isomerase / chemistry
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors
  • Structure-Activity Relationship

Substances

  • Bridged Bicyclo Compounds
  • Cell-Penetrating Peptides
  • Enzyme Inhibitors
  • Peptides, Cyclic
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1
  • Peptidylprolyl Isomerase