Novel indolylindazolylmaleimides as inhibitors of protein kinase C-beta: synthesis, biological activity, and cardiovascular safety

J Med Chem. 2005 Mar 24;48(6):1725-8. doi: 10.1021/jm049478u.

Abstract

Novel indolylindazolylmaleimides were synthesized and examined for kinase inhibition. We identified low-nanomolar inhibitors of PKC-beta with good to excellent selectivity vs other PKC isozymes and GSK-3beta. In a cell-based functional assay, 8f and 8i effectively blocked IL-8 release induced by PKC-betaII (IC(50) = 20-25 nM). In cardiovascular safety assessment, representative lead compounds bound to the hERG channel with high affinity, potently inhibited ion current in a patch-clamp experiment, and caused a dose-dependent increase of QT(c) in guinea pigs.

MeSH terms

  • Animals
  • Cell Line
  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • Glycogen Synthase Kinase 3 / antagonists & inhibitors
  • Glycogen Synthase Kinase 3 / chemistry
  • Glycogen Synthase Kinase 3 beta
  • Guinea Pigs
  • Humans
  • Indazoles / chemical synthesis*
  • Indazoles / pharmacology
  • Indazoles / toxicity
  • Indoles / chemical synthesis*
  • Indoles / pharmacology
  • Indoles / toxicity
  • Interleukin-8 / metabolism
  • Isoenzymes / antagonists & inhibitors
  • Isoenzymes / chemistry
  • Long QT Syndrome / chemically induced
  • Maleimides / chemical synthesis*
  • Maleimides / pharmacology
  • Maleimides / toxicity
  • Models, Molecular
  • Patch-Clamp Techniques
  • Potassium Channel Blockers / chemical synthesis
  • Potassium Channel Blockers / chemistry
  • Potassium Channel Blockers / pharmacology
  • Potassium Channels, Voltage-Gated / drug effects
  • Potassium Channels, Voltage-Gated / metabolism
  • Protein Kinase C / antagonists & inhibitors*
  • Protein Kinase C / chemistry
  • Protein Kinase C beta
  • Structure-Activity Relationship

Substances

  • ERG1 Potassium Channel
  • Ether-A-Go-Go Potassium Channels
  • Indazoles
  • Indoles
  • Interleukin-8
  • Isoenzymes
  • KCNH2 protein, human
  • Maleimides
  • Potassium Channel Blockers
  • Potassium Channels, Voltage-Gated
  • GSK3B protein, human
  • Glycogen Synthase Kinase 3 beta
  • Protein Kinase C
  • Protein Kinase C beta
  • Glycogen Synthase Kinase 3