Discovery of a Napabucasin PROTAC as an Effective Degrader of the E3 Ligase ZFP91

J Med Chem. 2021 Feb 11;64(3):1626-1648. doi: 10.1021/acs.jmedchem.0c01897. Epub 2021 Jan 28.

Abstract

Napabucasin, undergoing multiple clinical trials, was reported to inhibit the signal transducer and transcription factor 3 (STAT3). To better elucidate its mechanism of action, we designed a napabucasin-based proteolysis targeting chimera (PROTAC), XD2-149 that resulted in inhibition of STAT3 signaling in pancreatic cancer cell lines without inducing proteasome-dependent degradation of STAT3. Proteomics analysis of XD2-149 revealed the downregulation of the E3 ubiquitin-protein ligase ZFP91. XD2-149 degrades ZFP91 with DC50 values in the nanomolar range. The cytotoxicity of XD2-149 was significantly, but not fully, reduced with ZFP91 knockdown providing evidence for its multi-targeted mechanism of action. The NQO1 inhibitor, dicoumarol, rescued the cytotoxicity of XD2-149 but not ZFP91 degradation, suggesting that the NQO1-induced cell death is independent of ZFP91. ZFP91 plays a role in tumorigenesis and is involved in multiple oncogenic pathways including NF-κB and HIF-1α.

Publication types

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

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology*
  • Cell Line, Tumor
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Gene Knockdown Techniques
  • Humans
  • Hypoxia-Inducible Factor 1, alpha Subunit / drug effects
  • Mutant Chimeric Proteins / chemistry*
  • NAD(P)H Dehydrogenase (Quinone) / antagonists & inhibitors
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / pharmacology*
  • Pancreatic Neoplasms / drug therapy
  • Pancreatic Neoplasms / physiopathology
  • Proteolysis
  • STAT3 Transcription Factor / antagonists & inhibitors
  • Signal Transduction / drug effects
  • Structure-Activity Relationship
  • Ubiquitin-Protein Ligases / chemistry
  • Ubiquitin-Protein Ligases / genetics*

Substances

  • Benzofurans
  • Hypoxia-Inducible Factor 1, alpha Subunit
  • Mutant Chimeric Proteins
  • Naphthoquinones
  • STAT3 Transcription Factor
  • STAT3 protein, human
  • napabucasin
  • NAD(P)H Dehydrogenase (Quinone)
  • NQO1 protein, human
  • Ubiquitin-Protein Ligases
  • ZFP91 protein, human