Bile acid derivatives as ligands of the farnesoid X receptor. Synthesis, evaluation, and structure-activity relationship of a series of body and side chain modified analogues of chenodeoxycholic acid

J Med Chem. 2004 Aug 26;47(18):4559-69. doi: 10.1021/jm049904b.

Abstract

The farnesoid X receptor (FXR) is activated by endogenous bile acids (BAs) and plays a variety of physiological roles related to modulation of gene transcription. In particular, FXR positively regulates the cholesterol catabolism while feedback inhibits the BA synthesis by repressing the expression of the CYP7A and CYP8B genes. We have previously shown that 6alpha-ethyl-CDCA (6ECDCA) is a potent and selective FXR agonist. In this paper we report an extensive structure-activity relationship for a series of synthetic bile acids. Our results indicate that the 6alpha position plays a fundamental role in determining affinity and that the side chain of BA is amenable to a variety of chemical modification. Although none of the new derivatives is more potent than 6ECDCA, we show here that a wide variability in efficacy, from full agonists to partial antagonists, can be obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bile Acids and Salts / chemical synthesis*
  • Bile Acids and Salts / metabolism
  • Bile Acids and Salts / pharmacology
  • Chenodeoxycholic Acid / analogs & derivatives*
  • Chenodeoxycholic Acid / pharmacology
  • DNA-Binding Proteins / agonists*
  • DNA-Binding Proteins / metabolism
  • Humans
  • Ligands
  • Protein Binding
  • Receptors, Cytoplasmic and Nuclear
  • Structure-Activity Relationship
  • Transcription Factors / agonists*
  • Transcription Factors / metabolism

Substances

  • Bile Acids and Salts
  • DNA-Binding Proteins
  • Ligands
  • Receptors, Cytoplasmic and Nuclear
  • Transcription Factors
  • farnesoid X-activated receptor
  • Chenodeoxycholic Acid