Structure-based design of covalent Siah inhibitors

Chem Biol. 2013 Aug 22;20(8):973-82. doi: 10.1016/j.chembiol.2013.06.008. Epub 2013 Jul 25.

Abstract

The E3 ubiquitin ligase Siah regulates key cellular events that are central to cancer development and progression. A promising route to Siah inhibition is disrupting its interactions with adaptor proteins. However, typical of protein-protein interactions, traditional unbiased approaches to ligand discovery did not produce viable hits against this target, despite considerable effort and a multitude of approaches. Ultimately, a rational structure-based design strategy was successful for the identification of Siah inhibitors in which peptide binding drives specific covalent bond formation with the target. X-ray crystallography, mass spectrometry, and functional data demonstrate that these peptide mimetics are efficient covalent inhibitors of Siah and antagonize Siah-dependent regulation of Erk and Hif signaling in the cell. The proposed strategy may result useful as a general approach to the design of peptide-based inhibitors of other protein-protein interactions.

Publication types

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

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Binding Sites
  • Crystallography, X-Ray
  • Drug Design*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Models, Molecular
  • Molecular Sequence Data
  • Nuclear Proteins / antagonists & inhibitors*
  • Nuclear Proteins / chemistry
  • Nuclear Proteins / metabolism
  • Peptides / chemistry*
  • Peptides / pharmacology
  • Peptidomimetics / chemistry*
  • Peptidomimetics / pharmacology
  • Protein Interaction Maps / drug effects
  • Signal Transduction / drug effects
  • Ubiquitin-Protein Ligases / antagonists & inhibitors*
  • Ubiquitin-Protein Ligases / chemistry
  • Ubiquitin-Protein Ligases / metabolism

Substances

  • Enzyme Inhibitors
  • Nuclear Proteins
  • Peptides
  • Peptidomimetics
  • Ubiquitin-Protein Ligases
  • seven in absentia proteins

Associated data

  • PDB/4I7B
  • PDB/4I7C
  • PDB/4I7D