Discovery of a Chemical Probe Bisamide (CCT251236): An Orally Bioavailable Efficacious Pirin Ligand from a Heat Shock Transcription Factor 1 (HSF1) Phenotypic Screen

J Med Chem. 2017 Jan 12;60(1):180-201. doi: 10.1021/acs.jmedchem.6b01055. Epub 2016 Dec 22.

Abstract

Phenotypic screens, which focus on measuring and quantifying discrete cellular changes rather than affinity for individual recombinant proteins, have recently attracted renewed interest as an efficient strategy for drug discovery. In this article, we describe the discovery of a new chemical probe, bisamide (CCT251236), identified using an unbiased phenotypic screen to detect inhibitors of the HSF1 stress pathway. The chemical probe is orally bioavailable and displays efficacy in a human ovarian carcinoma xenograft model. By developing cell-based SAR and using chemical proteomics, we identified pirin as a high affinity molecular target, which was confirmed by SPR and crystallography.

MeSH terms

  • Administration, Oral
  • Amides / administration & dosage
  • Amides / chemistry*
  • Amides / pharmacology
  • Biological Availability
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Carrier Proteins / chemistry*
  • DNA-Binding Proteins / chemistry*
  • Dioxygenases
  • Drug Discovery
  • Heat Shock Transcription Factors
  • Ligands
  • Nuclear Proteins / chemistry*
  • Proton Magnetic Resonance Spectroscopy
  • Quinolines / administration & dosage
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Spectrometry, Mass, Electrospray Ionization
  • Transcription Factors / chemistry*

Substances

  • Amides
  • CCT251236
  • Carrier Proteins
  • DNA-Binding Proteins
  • HSF1 protein, human
  • Heat Shock Transcription Factors
  • Ligands
  • Nuclear Proteins
  • Quinolines
  • Transcription Factors
  • Dioxygenases
  • PIR protein, human