Structure guided design of potential inhibitors of human calcium-calmodulin dependent protein kinase IV containing pyrimidine scaffold

Bioorg Med Chem Lett. 2016 Feb 1;26(3):782-788. doi: 10.1016/j.bmcl.2015.12.098. Epub 2015 Dec 30.

Abstract

Calmodulin dependent protein kinase IV (CAMKIV) belongs to the serine/threonine protein kinase family and considered as an encouraging target for the development of novel anticancer agents. The interaction and binding behavior of three designed inhibitors of human CAMKIV, containing pyrimidine scaffold, was monitored by in vitro fluorescence titration and molecular docking calculations under physiological condition. In silico docking studies were performed to screen several compounds containing pyrimidine scaffold against CAMKIV. Molecular docking calculation predicted the binding of these ligands in active-site cavity of the CAMKIV structure correlating such interactions with a probable inhibition mechanism. Finally, three active pyrimidine substituted compounds (molecules 1-3) have been successfully synthesized and characterized by (1)H and (13)C NMR. Molecule 3 is showing very high binding-affinity for the CAMKIV, with a binding constant of 2.2×10(8), M(-1) (±0.20). All three compounds are nontoxic to HEK293 cells up to 50 μM. The cell proliferation inhibition study showed that the molecule 3 has lowest IC50 value (46±1.08 μM). The theoretical and experimental observations are significantly correlated. This study reveals some important observations to generate an improved pyrimidine based compound that holds promise as a therapeutic agent for the treatment of cancer and neurodegenerative diseases.

Keywords: Calcium–calmodulin dependent protein kinase IV; Cancer and neurodegenerative diseases; Drug target; Fluorescence binding study; High affinity ligands; Molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Calcium-Calmodulin-Dependent Protein Kinase Type 4 / antagonists & inhibitors*
  • Calcium-Calmodulin-Dependent Protein Kinase Type 4 / metabolism
  • Cell Line
  • Cell Proliferation / drug effects
  • Drug Design*
  • HEK293 Cells
  • Humans
  • Molecular Docking Simulation
  • Protein Kinase Inhibitors / chemistry*
  • Protein Kinase Inhibitors / metabolism
  • Protein Kinase Inhibitors / pharmacology
  • Protein Structure, Tertiary
  • Pyrimidines / chemistry*
  • Pyrimidines / metabolism
  • Pyrimidines / pharmacology
  • Spectrometry, Fluorescence
  • Thermodynamics

Substances

  • Protein Kinase Inhibitors
  • Pyrimidines
  • Calcium-Calmodulin-Dependent Protein Kinase Type 4