Roscovitine-derived, dual-specificity inhibitors of cyclin-dependent kinases and casein kinases 1

J Med Chem. 2008 Sep 11;51(17):5229-42. doi: 10.1021/jm800109e. Epub 2008 Aug 13.

Abstract

Cyclin-dependent kinases (CDKs) and casein kinases 1 (CK1) are involved in the two key molecular features of Alzheimer's disease, production of amyloid-beta peptides (extracellular plaques) and hyper-phosphorylation of Tau (intracellular neurofibrillary tangles). A series of 2,6,9-trisubstituted purines, structurally related to the CDK inhibitor roscovitine, have been synthesized. They mainly differ by the substituent on the C-6 position. These compounds were screened for kinase inhibitory activities and antiproliferative effects. Several biaryl derivatives displayed potent inhibition of both CDKs and CK1. In particular, derivative 13a was a potent inhibitor of CDK1/cyclin B (IC 50: 220 nM), CDK5/p25 (IC 50: 80 nM), and CK1 (IC 50: 14 nM). Modeling of these molecules into the ATP-binding pocket of CK1delta provided a rationale for the increased selectivity toward this kinase. 13a was able to prevent the CK1-dependent production of amyloid-beta in a cell model. CDK/CK1 dual-specificity inhibitors may have important applications in Alzheimer's disease and cancers.

Publication types

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

MeSH terms

  • Amyloid beta-Peptides / antagonists & inhibitors
  • Amyloid beta-Peptides / biosynthesis
  • Animals
  • Binding Sites
  • Casein Kinase I / antagonists & inhibitors*
  • Cell Line
  • Cyclin-Dependent Kinases / antagonists & inhibitors*
  • Humans
  • Inhibitory Concentration 50
  • Models, Molecular
  • Protein Kinase Inhibitors / analogs & derivatives
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology
  • Purines / chemistry*
  • Purines / pharmacology
  • Roscovitine
  • Structure-Activity Relationship

Substances

  • Amyloid beta-Peptides
  • Protein Kinase Inhibitors
  • Purines
  • Roscovitine
  • Casein Kinase I
  • Cyclin-Dependent Kinases