Adenosine-binding motif mimicry and cellular effects of a thieno[2,3-d]pyrimidine-based chemical inhibitor of atypical protein kinase C isoenzymes

Biochem J. 2013 Apr 15;451(2):329-42. doi: 10.1042/BJ20121871.

Abstract

The aPKC [atypical PKC (protein kinase C)] isoforms ι and ζ play crucial roles in the formation and maintenance of cell polarity and represent attractive anti-oncogenic drug targets in Ras-dependent tumours. To date, few isoform-specific chemical biology tools are available to inhibit aPKC catalytic activity. In the present paper, we describe the identification and functional characterization of potent and selective thieno[2,3-d]pyrimidine-based chemical inhibitors of aPKCs. A crystal structure of human PKCι kinase domain bound to a representative compound, CRT0066854, reveals the basis for potent and selective chemical inhibition. Furthermore, CRT0066854 displaces a crucial Asn-Phe-Asp motif that is part of the adenosine-binding pocket and engages an acidic patch used by arginine-rich PKC substrates. We show that CRT0066854 inhibits the LLGL2 (lethal giant larvae 2) phosphorylation in cell lines and exhibits phenotypic effects in a range of cell-based assays. We conclude that this compound can be used as a chemical tool to modulate aPKC activity in vitro and in vivo and may guide the search for further aPKC-selective inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / metabolism
  • Adenosine Triphosphate / chemistry
  • Adenosine Triphosphate / metabolism
  • Amino Acid Sequence
  • Animals
  • Binding Sites
  • Cell Line
  • Cell Movement / drug effects
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Cytoskeletal Proteins / metabolism
  • Dogs
  • Drug Evaluation, Preclinical / methods
  • High-Throughput Screening Assays
  • Humans
  • Inhibitory Concentration 50
  • Isoenzymes / antagonists & inhibitors
  • Molecular Mimicry
  • Molecular Sequence Data
  • Phosphorylation
  • Protein Kinase C / antagonists & inhibitors*
  • Protein Kinase C / chemistry
  • Protein Kinase C / metabolism
  • Protein Kinase Inhibitors / chemical synthesis
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrimidines / chemistry*
  • Pyrimidines / pharmacology
  • Thiophenes / chemistry
  • Thiophenes / pharmacology*

Substances

  • CRT0066854
  • Cytoskeletal Proteins
  • Isoenzymes
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Thiophenes
  • llgl2 protein, human
  • Adenosine Triphosphate
  • PKC-3 protein
  • Protein Kinase C
  • Adenosine