Discovery of GPR183 Agonists Based on an Antagonist Scaffold

  • Viktoria M. S. Kjær
    Department of Biomedical Sciences Faculty of Health and Medical Sciences University of Copenhagen Blegdamsvej 3B 2200 Copenhagen Denmark
  • Loukas Ieremias
    Department of Drug Design and Pharmacology Faculty of Health and Medical Sciences University of Copenhagen Jagtvej 162 2100 Copenhagen Denmark
  • Viktorija Daugvilaite
    Department of Biomedical Sciences Faculty of Health and Medical Sciences University of Copenhagen Blegdamsvej 3B 2200 Copenhagen Denmark
  • Michael Lückmann
    Novo Nordisk Foundation Center for Basic Metabolic Research University of Copenhagen Maersk Tower Blegdamsvej 3B 2200 Copenhagen Denmark
  • Thomas M. Frimurer
    Novo Nordisk Foundation Center for Basic Metabolic Research University of Copenhagen Maersk Tower Blegdamsvej 3B 2200 Copenhagen Denmark
  • Trond Ulven
    Department of Drug Design and Pharmacology Faculty of Health and Medical Sciences University of Copenhagen Jagtvej 162 2100 Copenhagen Denmark
  • Mette M. Rosenkilde
    Department of Biomedical Sciences Faculty of Health and Medical Sciences University of Copenhagen Blegdamsvej 3B 2200 Copenhagen Denmark
  • Jon Våbenø
    Helgeland Hospital Trust Prestmarkveien 1 8800 Sandnessjøen Norway

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説明

<jats:title>Abstract</jats:title><jats:p>The G protein‐coupled receptor GPR183/EBI2, which is activated by oxysterols, is a therapeutic target for inflammatory and metabolic diseases where both antagonists and agonists are of potential interest. Using the piperazine diamide core of the known GPR183 antagonist (<jats:italic>E</jats:italic>)‐3‐(4‐bromophenyl)‐1‐(4‐(4‐methoxybenzoyl)piperazin‐1‐yl)prop‐2‐en‐1‐one (NIBR189) as starting point, we identified and sourced 79 structurally related compounds that were commercially available. <jats:italic>In vitro</jats:italic> screening of this compound collection using a Ca<jats:sup>2+</jats:sup> mobilization assay resulted in the identification of 10 compounds with agonist properties. To enable establishment of initial structure‐activity relationship trends, these were supplemented with five in‐house compounds, two of which were also shown to be GPR183 agonists. Taken together, our findings suggest that the agonist activity of this compound series is dictated by the substitution pattern of one of the two distal phenyl rings, which functions as a molecular efficacy‐switch.</jats:p>

収録刊行物

  • ChemMedChem

    ChemMedChem 16 (17), 2623-2627, 2021-08-03

    Wiley

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