7-Methylation of Chenodeoxycholic Acid Derivatives Yields a Substantial Increase in TGR5 Receptor Potency

J Med Chem. 2019 Jul 25;62(14):6824-6830. doi: 10.1021/acs.jmedchem.9b00770. Epub 2019 Jul 3.

Abstract

TGR5 agonists are potential therapeutics for a variety of conditions including type 2 diabetes, obesity, and inflammatory bowel disease. After screening a library of chenodeoxycholic acid (CDCA) derivatives, it was determined that a range of modifications could be made to the acid moiety of CDCA which significantly increased TGR5 agonist potency. Surprisingly, methylation of the 7-hydroxyl of CDCA led to a further dramatic increase in potency, allowing the identification of 5.6 nM TGR5 agonist 17.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cell Line
  • Chenodeoxycholic Acid / analogs & derivatives*
  • Chenodeoxycholic Acid / pharmacology*
  • Cyclic AMP / metabolism
  • Drug Discovery
  • Humans
  • Methylation
  • Molecular Docking Simulation
  • Receptors, G-Protein-Coupled / agonists*
  • Receptors, G-Protein-Coupled / metabolism

Substances

  • GPBAR1 protein, human
  • Receptors, G-Protein-Coupled
  • Chenodeoxycholic Acid
  • Cyclic AMP