Discovery of substituted maleimides as liver X receptor agonists and determination of a ligand-bound crystal structure

J Med Chem. 2005 Aug 25;48(17):5419-22. doi: 10.1021/jm050532w.

Abstract

Substituted 3-(phenylamino)-1H-pyrrole-2,5-diones were identified from a high throughput screen as inducers of human ATP binding cassette transporter A1 expression. Mechanism of action studies led to the identification of GSK3987 as an LXR ligand. GSK3987 recruits the steroid receptor coactivator-1 to human LXRalpha and LXRbeta with EC(50)s of 40 nM, profiles as an LXR agonist in functional assays, and activates LXR though a mechanism that is similar to first generation LXR agonists.

MeSH terms

  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters / biosynthesis
  • ATP-Binding Cassette Transporters / genetics
  • Aniline Compounds / chemical synthesis*
  • Aniline Compounds / chemistry
  • Aniline Compounds / pharmacology
  • Binding Sites
  • Cell Line
  • Crystallography, X-Ray
  • DNA-Binding Proteins / agonists*
  • DNA-Binding Proteins / chemistry
  • Genes, Reporter
  • Histone Acetyltransferases
  • Humans
  • Ligands
  • Liver X Receptors
  • Luciferases / genetics
  • Maleimides / chemical synthesis*
  • Maleimides / chemistry
  • Maleimides / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Monocytes / drug effects
  • Monocytes / metabolism
  • Nuclear Receptor Coactivator 1
  • Orphan Nuclear Receptors
  • Promoter Regions, Genetic
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / chemistry
  • Structure-Activity Relationship
  • Transcription Factors / metabolism
  • Up-Regulation

Substances

  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters
  • Aniline Compounds
  • DNA-Binding Proteins
  • GSK 3987
  • Ligands
  • Liver X Receptors
  • Maleimides
  • NR1H3 protein, human
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear
  • Transcription Factors
  • Luciferases
  • Histone Acetyltransferases
  • NCOA1 protein, human
  • Nuclear Receptor Coactivator 1