Discovery of Inhibitor of Wnt Production 2 (IWP-2) and Related Compounds As Selective ATP-Competitive Inhibitors of Casein Kinase 1 (CK1) δ/ε

J Med Chem. 2018 May 10;61(9):4087-4102. doi: 10.1021/acs.jmedchem.8b00095. Epub 2018 May 1.

Abstract

Inhibitors of Wnt production (IWPs) are known antagonists of the Wnt pathway, targeting the membrane-bound O-acyltransferase porcupine (Porcn) and thus preventing a crucial Wnt ligand palmitoylation. Since IWPs show structural similarities to benzimidazole-based CK1 inhibitors, we hypothesized that IWPs could also inhibit CK1 isoforms. Molecular modeling revealed a plausible binding mode of IWP-2 in the ATP binding pocket of CK1δ which was confirmed by X-ray analysis. In vitro kinase assays demonstrated IWPs to be ATP-competitive inhibitors of wtCK1δ. IWPs also strongly inhibited the gatekeeper mutant M82FCK1δ. When profiled in a panel of 320 kinases, IWP-2 specifically inhibited CK1δ. IWP-2 and IWP-4 also inhibited the viability of various cancer cell lines. By a medicinal chemistry approach, we developed improved IWP-derived CK1 inhibitors. Our results suggest that the effects of IWPs are not limited to Porcn, but also might influence CK1δ/ε-related pathways.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / metabolism*
  • Benzimidazoles / chemistry
  • Benzimidazoles / metabolism
  • Benzimidazoles / pharmacology
  • Binding, Competitive
  • Casein Kinase 1 epsilon / antagonists & inhibitors*
  • Casein Kinase 1 epsilon / chemistry
  • Casein Kinase 1 epsilon / metabolism
  • Casein Kinase Idelta / antagonists & inhibitors*
  • Casein Kinase Idelta / chemistry
  • Casein Kinase Idelta / metabolism
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design*
  • Humans
  • Models, Molecular
  • Protein Conformation
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacology*
  • Wnt Proteins / biosynthesis*

Substances

  • Benzimidazoles
  • Protein Kinase Inhibitors
  • Wnt Proteins
  • Adenosine Triphosphate
  • Casein Kinase 1 epsilon
  • Casein Kinase Idelta