Discovery of substituted sulfonamides and thiazolidin-4-one derivatives as agonists of human constitutive androstane receptor

Biochem Pharmacol. 2008 Nov 15;76(10):1288-97. doi: 10.1016/j.bcp.2008.08.014. Epub 2008 Aug 22.

Abstract

The constitutive androstane receptor (CAR; NR1I3) is a nuclear receptor responsible for the recognition of potentially toxic endo- and exogenous compounds whose elimination from the body is accelerated by the CAR-mediated inducible expression of metabolizing enzymes and transporters. Despite the importance of CAR, few human agonists are known so far. Following a sequential virtual screening procedure using a 3D pharmacophore and molecular docking approach, we identified 17 novel agonists that could activate human CAR in vitro and enhance its association with the nuclear receptor co-activator SRC1. Selected agonists also increased the expression of the human CAR target CYP2B6 mRNA in primary hepatocytes. Composed of substituted sulfonamides and thiazolidin-4-one derivatives, these agonists represent two novel chemotypes capable of human CAR activation, thus broadening the agonist spectrum of CAR.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cells, Cultured
  • Constitutive Androstane Receptor
  • Hepatocytes / drug effects
  • Hepatocytes / metabolism
  • Humans
  • Male
  • Middle Aged
  • Protein Binding / drug effects
  • Protein Binding / physiology
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / chemistry
  • Receptors, Cytoplasmic and Nuclear / metabolism*
  • Sulfonamides / chemistry*
  • Sulfonamides / metabolism*
  • Sulfonamides / pharmacology
  • Thiazolidines / chemistry*
  • Thiazolidines / metabolism*
  • Thiazolidines / pharmacology
  • Transcription Factors / agonists*
  • Transcription Factors / chemistry
  • Transcription Factors / metabolism*

Substances

  • Constitutive Androstane Receptor
  • NR1I3 protein, human
  • Receptors, Cytoplasmic and Nuclear
  • Sulfonamides
  • Thiazolidines
  • Transcription Factors