Privileged scaffolds for blocking protein-protein interactions: 1,4-disubstituted naphthalene antagonists of transcription factor complex HOX-PBX/DNA

Bioorg Med Chem Lett. 2004 Aug 2;14(15):3875-9. doi: 10.1016/j.bmcl.2004.05.068.

Abstract

Structure-based-design studies, with the crystal structure of the HOXB1-PBX1/DNA transcription factor complex, were used to identify 1,4-disubstituted naphthalenes as potential antagonists. An initial library of 32 analogs was synthesized, two of which were found to be more potent than the reported activity for a 12 amino acid peptide antagonist. Antagonists were also identified of the related BRN1/DNA and BRN2/DNA transcription factor complexes indicating that a 1,4-disubstituted naphthalene may be a privileged scaffold for preparing screening libraries targeting this family of transcription factor complexes.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Crystallography, X-Ray
  • DNA / antagonists & inhibitors
  • DNA-Binding Proteins / antagonists & inhibitors*
  • DNA-Binding Proteins / chemistry
  • Homeodomain Proteins / antagonists & inhibitors*
  • Homeodomain Proteins / chemistry
  • Humans
  • Kinetics
  • Models, Molecular
  • Naphthalenes / chemical synthesis
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacology*
  • Pre-B-Cell Leukemia Transcription Factor 1
  • Proto-Oncogene Proteins / antagonists & inhibitors*
  • Proto-Oncogene Proteins / chemistry
  • Transcription Factors / antagonists & inhibitors*

Substances

  • DNA-Binding Proteins
  • HOXB1 homeodomain protein
  • Homeodomain Proteins
  • Naphthalenes
  • Pre-B-Cell Leukemia Transcription Factor 1
  • Proto-Oncogene Proteins
  • Transcription Factors
  • PBX1 protein, human
  • DNA