Cinnamamides, Novel Liver X Receptor Antagonists that Inhibit Ligand-Induced Lipogenesis and Fatty Liver

J Pharmacol Exp Ther. 2015 Dec;355(3):362-9. doi: 10.1124/jpet.115.226738. Epub 2015 Sep 18.

Abstract

Liver X receptor (LXR) is a member of the nuclear receptor superfamily, and it regulates various biologic processes, including de novo lipogenesis, cholesterol metabolism, and inflammation. Selective inhibition of LXR may aid the treatment of nonalcoholic fatty liver diseases. In the present study, we evaluated the effects of three cinnamamide derivatives on ligand-induced LXRα activation and explored whether these derivatives could attenuate steatosis in mice. N-(4-trifluoromethylphenyl) 3,4-dimethoxycinnamamide (TFCA) decreased the luciferase activity in LXRE-tk-Luc-transfected cells and also suppressed ligand-induced lipid accumulation and expression of the lipogenic genes in murine hepatocytes. Furthermore, it significantly attenuated hepatic neutral lipid accumulation in a ligand-induced fatty liver mouse system. Modeling study indicated that TFCA inhibited activation of the LXRα ligand-binding domain by hydrogen bonding to Arg305 in the H5 region of that domain. It regulated the transcriptional control exerted by LXRα by influencing coregulator exchange; this process involves dissociation of the thyroid hormone receptor-associated proteins (TRAP)/DRIP coactivator and recruitment of the nuclear receptor corepressor. These results show that TFCA has the potential to attenuate ligand-induced lipogenesis and fatty liver by selectively inhibiting LXRα in the liver.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acid Phosphatase / genetics
  • Acid Phosphatase / metabolism
  • Adipogenesis
  • Animals
  • Cell Line
  • Cinnamates / pharmacology*
  • Fatty Liver / prevention & control*
  • Hepatocytes / drug effects
  • Hepatocytes / metabolism
  • Isoenzymes / genetics
  • Isoenzymes / metabolism
  • Ligands
  • Lipid Metabolism / drug effects
  • Lipogenesis / drug effects*
  • Liver X Receptors
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Orphan Nuclear Receptors / antagonists & inhibitors*
  • Tartrate-Resistant Acid Phosphatase
  • Transfection
  • Triglycerides / metabolism

Substances

  • Cinnamates
  • Isoenzymes
  • Ligands
  • Liver X Receptors
  • N-(4-trifluoromethylphenyl) 3,4-dimethoxycinnamamide
  • Nr1h3 protein, mouse
  • Orphan Nuclear Receptors
  • Triglycerides
  • Acid Phosphatase
  • Acp5 protein, mouse
  • Tartrate-Resistant Acid Phosphatase
  • cinnamamide