Introduction of Nonacidic Side Chains on 6-Ethylcholane Scaffolds in the Identification of Potent Bile Acid Receptor Agonists with Improved Pharmacokinetic Properties

Molecules. 2019 Mar 16;24(6):1043. doi: 10.3390/molecules24061043.

Abstract

As a cellular bile acid sensor, farnesoid X receptor (FXR) and the membrane G-coupled receptor (GPBAR1) participate in maintaining bile acid, lipid, and glucose homeostasis. To date, several selective and dual agonists have been developed as promising pharmacological approach to metabolic disorders, with most of them possessing an acidic conjugable function that might compromise their pharmacokinetic distribution. Here, guided by docking calculations, nonacidic 6-ethyl cholane derivatives have been prepared. In vitro pharmacological characterization resulted in the identification of bile acid receptor modulators with improved pharmacokinetic properties.

Keywords: FXR agonists; bile acid receptors; medicinal chemistry; steroidal scaffolds.

MeSH terms

  • Bile Acids and Salts / metabolism
  • Cholanes / chemical synthesis
  • Cholanes / chemistry*
  • Cholanes / pharmacokinetics
  • Glucose / metabolism
  • HEK293 Cells
  • Hep G2 Cells
  • Humans
  • Lipid Metabolism / drug effects
  • Metabolic Diseases / drug therapy*
  • Metabolic Diseases / metabolism
  • Metabolic Diseases / pathology
  • Molecular Docking Simulation
  • Molecular Structure
  • Protein Conformation / drug effects
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, G-Protein-Coupled / metabolism
  • Structure-Activity Relationship

Substances

  • Bile Acids and Salts
  • Cholanes
  • GPBAR1 protein, human
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, G-Protein-Coupled
  • farnesoid X-activated receptor
  • Glucose