Synthesis and biological evaluation of novel 4-hydroxytamoxifen analogs as estrogen-related receptor gamma inverse agonists

Eur J Med Chem. 2016 Sep 14:120:338-52. doi: 10.1016/j.ejmech.2016.04.076. Epub 2016 May 9.

Abstract

Estrogen-related receptor gamma (ERRγ) has recently been recognized as an attractive target for treating inflammation, cancer, and metabolic disorders. Herein, we discovered and demonstrated the in vitro pharmacology as well as the absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of chemical entities that could act as highly selective inverse agonists for ERRγ. The results were comparable to those for GSK5182 (4), a leading ERRγ inverse agonist ligand. Briefly, the half-maximal inhibitory concentration (IC50) range of the synthesized compounds for ERRγ was 0.1-10 μM. Impressively, compound 24e exhibited potency comparable to 4 but was more selective for ERRγ over three other subtypes: ERRα, ERRβ, and estrogen receptor α. Furthermore, compound 24e exhibited a superior in vitro ADMET profile compared to the other compounds. Thus, the newly synthesized class of ERRγ inverse agonists could be lead candidates for developing clinical therapies for ERRγ-related disorders.

Keywords: ADMET; ERRγ inverse agonist; GSK5182; Nuclear receptor.

MeSH terms

  • Drug Inverse Agonism*
  • Humans
  • Inhibitory Concentration 50
  • Ligands
  • Receptors, Estrogen / antagonists & inhibitors*
  • Small Molecule Libraries / chemical synthesis
  • Structure-Activity Relationship
  • Tamoxifen / analogs & derivatives*
  • Tamoxifen / chemical synthesis
  • Tamoxifen / pharmacokinetics
  • Tamoxifen / pharmacology

Substances

  • ESRRG protein, human
  • Ligands
  • Receptors, Estrogen
  • Small Molecule Libraries
  • Tamoxifen
  • afimoxifene