Identification of Potent, Selective, and Orally Bioavailable Small-Molecule GSPT1/2 Degraders from a Focused Library of Cereblon Modulators

J Med Chem. 2021 Jun 10;64(11):7296-7311. doi: 10.1021/acs.jmedchem.0c01313. Epub 2021 May 27.

Abstract

Whereas the PROTAC approach to target protein degradation greatly benefits from rational design, the discovery of small-molecule degraders relies mostly on phenotypic screening and retrospective target identification efforts. Here, we describe the design, synthesis, and screening of a large diverse library of thalidomide analogues against a panel of patient-derived leukemia and medulloblastoma cell lines. These efforts led to the discovery of potent and novel GSPT1/2 degraders displaying selectivity over classical IMiD neosubstrates, such as IKZF1/3, and high oral bioavailability in mice. Taken together, this study offers compound 6 (SJ6986) as a valuable chemical probe for studying the role of GSPT1/2 in vitro and in vivo, and it supports the utility of a diverse library of CRBN binders in the pursuit of targeting undruggable oncoproteins.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adaptor Proteins, Signal Transducing / chemistry*
  • Adaptor Proteins, Signal Transducing / genetics
  • Adaptor Proteins, Signal Transducing / metabolism
  • Administration, Oral
  • Animals
  • Binding Sites
  • Cell Line, Tumor
  • Half-Life
  • Humans
  • Ikaros Transcription Factor / metabolism
  • Mice
  • Molecular Dynamics Simulation
  • Peptide Termination Factors / metabolism*
  • Proteolysis / drug effects*
  • Retrospective Studies
  • Small Molecule Libraries / administration & dosage
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / metabolism
  • Small Molecule Libraries / pharmacology*
  • Structure-Activity Relationship
  • Thalidomide / administration & dosage
  • Thalidomide / analogs & derivatives
  • Thalidomide / metabolism
  • Thalidomide / pharmacology
  • Ubiquitin-Protein Ligases / chemistry*
  • Ubiquitin-Protein Ligases / genetics
  • Ubiquitin-Protein Ligases / metabolism

Substances

  • Adaptor Proteins, Signal Transducing
  • CRBN protein, human
  • IKZF1 protein, human
  • Peptide Termination Factors
  • Small Molecule Libraries
  • peptide-chain-release factor 3
  • Ikaros Transcription Factor
  • Thalidomide
  • Ubiquitin-Protein Ligases