Potent Grb2-SH2 domain antagonists not relying on phosphotyrosine mimics

Bioorg Med Chem Lett. 2003 Jul 7;13(13):2173-7. doi: 10.1016/s0960-894x(03)00385-8.

Abstract

Development of Grb2-SH2 domain antagonists is an effective approach to inhibit the growth of malignant cells by modulating Grb2-related Ras signaling. We report here potent Grb2-SH2 domain antagonists that do not rely on phosphotyrosine or its mimics. These non-phosphorylated antagonists were developed and further modified by constraining the backbone conformation and optimizing amino acid side chains of a phage library-derived peptide, G1TE. After extensive SAR studies and structural optimization, non-phosphorylated peptide 12 was discovered with an IC(50) of 75 nM. This potent peptidomimetic provides a novel template for the development of non-pTyr containing Grb2-SH2 domain antagonists and acts as a chemotherapeutic lead for the treatment of erbB2-related cancer.

MeSH terms

  • Adaptor Proteins, Signal Transducing*
  • Amino Acids / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology
  • Binding Sites
  • Circular Dichroism
  • Computer Simulation
  • GRB2 Adaptor Protein
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Molecular Mimicry
  • Peptide Library
  • Phosphorylation
  • Phosphotyrosine / pharmacology*
  • Proteins / antagonists & inhibitors*
  • Structure-Activity Relationship
  • src Homology Domains / drug effects*

Substances

  • Adaptor Proteins, Signal Transducing
  • Amino Acids
  • Antineoplastic Agents
  • GRB2 Adaptor Protein
  • Ligands
  • Peptide Library
  • Proteins
  • Phosphotyrosine