Small-molecule inhibitors of cytokine-mediated STAT1 signal transduction in β-cells with improved aqueous solubility

J Med Chem. 2013 May 23;56(10):4125-9. doi: 10.1021/jm400397x. Epub 2013 May 13.

Abstract

We previously reported the discovery of BRD0476 (1), a small molecule generated by diversity-oriented synthesis that suppresses cytokine-induced β-cell apoptosis. Herein, we report the synthesis and biological evaluation of 1 and analogues with improved aqueous solubility. By replacing naphthyl with quinoline moieties, we prepared active analogues with up to a 1400-fold increase in solubility from 1. In addition, we demonstrated that 1 and analogues inhibit STAT1 signal transduction induced by IFN-γ.

Publication types

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

MeSH terms

  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology
  • Apoptosis / drug effects
  • Blotting, Western
  • Caspase 3 / metabolism
  • Caspase 7 / metabolism
  • Cell Line
  • Chemistry, Pharmaceutical
  • Cytokines / antagonists & inhibitors*
  • Cytokines / physiology
  • Humans
  • Indicators and Reagents
  • Insulin-Secreting Cells / drug effects*
  • Interferon-gamma / pharmacology
  • Phosphorylation
  • STAT1 Transcription Factor / antagonists & inhibitors*
  • Signal Transduction / drug effects*
  • Solubility
  • Structure-Activity Relationship
  • Thermodynamics
  • Urea / analogs & derivatives
  • Urea / chemistry
  • Urea / pharmacology

Substances

  • Aniline Compounds
  • Cytokines
  • Indicators and Reagents
  • STAT1 Transcription Factor
  • Interferon-gamma
  • Urea
  • Caspase 3
  • Caspase 7