Peptide structure stabilization by membrane anchoring and its general applicability to the development of potent cell-permeable inhibitors

Chembiochem. 2011 Apr 11;12(6):914-21. doi: 10.1002/cbic.201000563. Epub 2011 Mar 1.

Abstract

Isolated protein motifs that are involved in interactions with their binding partners can be used to inhibit these interactions. However, peptides corresponding to protein fragments tend to have no defined secondary or tertiary structure in the absence of scaffolding by the rest of protein molecule. This results in low inhibitor potency. NMR and CD spectroscopy studies of lipopeptide inhibitors of the Hedgehog pathway revealed that membrane anchoring allows the cell membrane to function as a scaffold and facilitate the folding of short peptides. In addition, lipidation enhances cell permeability and increases the concentration of the compounds near the membrane, thus facilitating potent inhibition. The general applicability of this rational approach was further confirmed by the generation of selective antagonists of the insulin-like growth factor 1 receptor with GI(50) values in the nanomolar range. Lipopeptides corresponding to protein fragments were found to serve as potent and selective inhibitors of a number of nondruggable molecular targets.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Cell Line, Tumor
  • Cell Membrane Permeability / drug effects
  • Circular Dichroism
  • Hedgehog Proteins / antagonists & inhibitors*
  • Hedgehog Proteins / metabolism
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Peptides / chemistry*
  • Peptides / pharmacology
  • Protein Structure, Tertiary
  • Receptor, IGF Type 1 / antagonists & inhibitors
  • Receptor, IGF Type 1 / metabolism

Substances

  • Hedgehog Proteins
  • Peptides
  • Receptor, IGF Type 1