Inhibition of protein kinase C-driven nuclear factor-kappaB activation: synthesis, structure-activity relationship, and pharmacological profiling of pathway specific benzimidazole probe molecules

J Med Chem. 2010 Jun 24;53(12):4793-7. doi: 10.1021/jm1000248.

Abstract

A unique series of biologically active chemical probes that selectively inhibit NF-kappaB activation induced by protein kinase C (PKC) pathway activators have been identified through a cell-based phenotypic reporter gene assay. These 2-aminobenzimidazoles represent initial chemical tools to be used in gaining further understanding on the cellular mechanisms driven by B and T cell antigen receptors. Starting from the founding member of this chemical series 1a (notated in PubChem as CID-2858522), we report the chemical synthesis, SAR studies, and pharmacological profiling of this pathway-selective inhibitor of NF-kappaB activation.

Publication types

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

MeSH terms

  • Animals
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacokinetics
  • Benzimidazoles / pharmacology
  • Cell Line
  • Cell Membrane Permeability
  • Genes, Reporter
  • Hepatocytes / cytology
  • Hepatocytes / drug effects
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Interleukin-2 / biosynthesis
  • Interleukin-8 / biosynthesis
  • Male
  • Mice
  • Microsomes, Liver / metabolism
  • NF-kappa B / antagonists & inhibitors*
  • NF-kappa B / genetics
  • NF-kappa B / physiology
  • Protein Kinase C / physiology*
  • Receptors, Antigen, B-Cell / physiology
  • Receptors, Antigen, T-Cell / physiology
  • Signal Transduction
  • Small Molecule Libraries
  • Structure-Activity Relationship

Substances

  • 1-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(2-((3-hydroxypropyl)amino)-5,6-dimethyl-1H-benzo(d)imidazol-1-yl)ethanone
  • Benzimidazoles
  • Interleukin-2
  • Interleukin-8
  • NF-kappa B
  • Receptors, Antigen, B-Cell
  • Receptors, Antigen, T-Cell
  • Small Molecule Libraries
  • Protein Kinase C