Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators

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Documents

  • Ulven, Elisabeth Rexen
  • Tezz Quon
  • Eugenia Sergeev
  • Natasja Barki
  • Matjaz Brvar
  • Brian D Hudson
  • Palash Dutta
  • Anders Højgaard Hansen
  • Line Ø Bielefeldt
  • Andrew B Tobin
  • Christine J McKenzie
  • Graeme Milligan
  • Ulven, Trond

Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 μM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 μM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

Original languageEnglish
JournalJournal of Medicinal Chemistry
Volume63
Issue number7
Pages (from-to)3577-3595
Number of pages19
ISSN0022-2623
DOIs
Publication statusPublished - 9 Apr 2020

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