Identification of a nonsteroidal liver X receptor agonist through parallel array synthesis of tertiary amines

J Med Chem. 2002 May 9;45(10):1963-6. doi: 10.1021/jm0255116.

Abstract

A potent, selective, orally active LXR agonist was identified from focused libraries of tertiary amines. GW3965 (12) recruits the steroid receptor coactivator 1 to human LXRalpha in a cell-free ligand-sensing assay with an EC(50) of 125 nM and profiles as a full agonist on hLXRalpha and hLXRbeta in cell-based reporter gene assays with EC(50)'s of 190 and 30 nM, respectively. After oral dosing at 10 mg/kg to C57BL/6 mice, 12 increased expression of the reverse cholesterol transporter ABCA1 in the small intestine and peripheral macrophages and increased the plasma concentrations of HDL cholesterol by 30%. 12 will be a valuable chemical tool to investigate the role of LXR in the regulation of reverse cholesterol transport and lipid metabolism.

MeSH terms

  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters / metabolism
  • Administration, Oral
  • Amines / chemical synthesis*
  • Amines / chemistry
  • Amines / pharmacology
  • Animals
  • Biological Availability
  • Cell-Free System
  • Cholesterol / metabolism
  • Cholesterol, HDL / blood
  • DNA-Binding Proteins
  • Genes, Reporter
  • Humans
  • Intestine, Small / metabolism
  • Liver X Receptors
  • Macrophages / metabolism
  • Mice
  • Mice, Inbred C57BL
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Retinoic Acid / agonists*
  • Receptors, Thyroid Hormone / agonists*
  • Structure-Activity Relationship
  • Up-Regulation

Substances

  • ABCA1 protein, human
  • ATP Binding Cassette Transporter 1
  • ATP-Binding Cassette Transporters
  • Amines
  • Cholesterol, HDL
  • DNA-Binding Proteins
  • Liver X Receptors
  • NR1H3 protein, human
  • Nr1h3 protein, mouse
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, Retinoic Acid
  • Receptors, Thyroid Hormone
  • Cholesterol