Development and in vitro Profiling of Dual FXR/LTA4H Modulators

ChemMedChem. 2021 Aug 5;16(15):2366-2374. doi: 10.1002/cmdc.202100118. Epub 2021 May 24.

Abstract

Designed polypharmacology presents as an attractive strategy to increase therapeutic efficacy in multi-factorial diseases by a directed modulation of multiple involved targets with a single molecule. Such an approach appears particularly suitable in non-alcoholic steatohepatitis (NASH) which involves hepatic steatosis, inflammation and fibrosis as pathological hallmarks. Among various potential pharmacodynamic mechanisms, activation of the farnesoid X receptor (FXRa) and inhibition of leukotriene A4 hydrolase (LTA4Hi) hold promise to counteract NASH according to preclinical and clinical observations. We have developed dual FXR/LTA4H modulators as pharmacological tools, enabling evaluation of this polypharmacology concept to treat NASH and related pathologies. The optimized FXRa/LTA4Hi exhibits well-balanced dual activity on the intended targets with sub-micromolar potency and is highly selective over related nuclear receptors and enzymes rendering it suitable as tool to probe synergies of dual FXR/LTA4H targeting.

Keywords: farnesoid X receptor; leukotriene A4 hydrolase; non-alcoholic fatty liver disease; non-alcoholic steatohepatitis; polypharmacology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chenodeoxycholic Acid / analogs & derivatives*
  • Chenodeoxycholic Acid / chemical synthesis
  • Chenodeoxycholic Acid / chemistry
  • Chenodeoxycholic Acid / pharmacology
  • Drug Development*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Epoxide Hydrolases / antagonists & inhibitors*
  • Epoxide Hydrolases / metabolism
  • Humans
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology*
  • Molecular Structure
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / metabolism

Substances

  • Enzyme Inhibitors
  • Isoxazoles
  • Receptors, Cytoplasmic and Nuclear
  • obeticholic acid
  • farnesoid X-activated receptor
  • Chenodeoxycholic Acid
  • Epoxide Hydrolases
  • GW 4064
  • leukotriene A4 hydrolase