Fluorescence linked enzyme chemoproteomic strategy for discovery of a potent and selective DAPK1 and ZIPK inhibitor

ACS Chem Biol. 2013 Dec 20;8(12):2715-23. doi: 10.1021/cb400407c. Epub 2013 Oct 17.

Abstract

DAPK1 and ZIPK (also called DAPK3) are closely related serine/threonine protein kinases that regulate programmed cell death and phosphorylation of non-muscle and smooth muscle myosin. We have developed a fluorescence linked enzyme chemoproteomic strategy (FLECS) for the rapid identification of inhibitors for any element of the purinome and identified a selective pyrazolo[3,4-d]pyrimidinone (HS38) that inhibits DAPK1 and ZIPK in an ATP-competitive manner at nanomolar concentrations. In cellular studies, HS38 decreased RLC20 phosphorylation. In ex vivo studies, HS38 decreased contractile force generated in mouse aorta, rabbit ileum, and calyculin A stimulated arterial muscle by decreasing RLC20 and MYPT1 phosphorylation. The inhibitor also promoted relaxation in Ca(2+)-sensitized vessels. A close structural analogue (HS43) with 5-fold lower affinity for ZIPK produced no effect on cells or tissues. These findings are consistent with a mechanism of action wherein HS38 specifically targets ZIPK in smooth muscle. The discovery of HS38 provides a lead scaffold for the development of therapeutic agents for smooth muscle related disorders and a chemical means to probe the function of DAPK1 and ZIPK across species.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Animals
  • Aorta / cytology
  • Aorta / drug effects
  • Aorta / enzymology
  • Binding, Competitive
  • Calcium / metabolism
  • Death-Associated Protein Kinases / antagonists & inhibitors*
  • Death-Associated Protein Kinases / genetics
  • Death-Associated Protein Kinases / metabolism
  • Green Fluorescent Proteins / genetics
  • Green Fluorescent Proteins / metabolism*
  • HEK293 Cells
  • High-Throughput Screening Assays
  • Humans
  • Ileum / cytology
  • Ileum / drug effects
  • Ileum / enzymology
  • Mice
  • Muscle Contraction / drug effects
  • Muscle, Smooth / cytology
  • Muscle, Smooth / drug effects*
  • Muscle, Smooth / enzymology
  • Myocytes, Smooth Muscle / cytology
  • Myocytes, Smooth Muscle / drug effects*
  • Myocytes, Smooth Muscle / enzymology
  • Myosin-Light-Chain Kinase / antagonists & inhibitors
  • Myosin-Light-Chain Kinase / metabolism
  • Myosin-Light-Chain Phosphatase
  • Phosphorylation
  • Primary Cell Culture
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Proteomics
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Pyrimidinones / chemistry
  • Pyrimidinones / pharmacology*
  • Rabbits
  • Recombinant Fusion Proteins / genetics
  • Recombinant Fusion Proteins / metabolism*

Substances

  • (2-((1-(3-chlorophenyl)-4-oxo-4,5-dihydro-1H-pyrazolo(3,4-d)pyrimidin-6-yl)thio)propanamide
  • Protein Kinase Inhibitors
  • Pyrazoles
  • Pyrimidinones
  • Recombinant Fusion Proteins
  • Green Fluorescent Proteins
  • Adenosine Triphosphate
  • DAPK1 protein, human
  • Dapk3 protein, mouse
  • Death-Associated Protein Kinases
  • Myosin-Light-Chain Kinase
  • Myosin-Light-Chain Phosphatase
  • Ppp1r12a protein, mouse
  • Calcium