Literature DB >> 32005415

A novel series of cysteine-dependent, allosteric inverse agonists of the nuclear receptor RORγt.

Xin Jiang1, Irina Dulubova1, Scott A Reisman1, Martha Hotema1, Chun-Yue I Lee1, Liping Liu1, Lyndsey McCauley1, Isaac Trevino1, Deborah A Ferguson1, Yigitcan Eken2, Angela K Wilson2, W Christian Wigley1, Melean Visnick3.   

Abstract

Inhibition of the nuclear receptor Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) is a promising strategy for the treatment of autoimmune diseases. In this paper, we describe a series of allosteric, cysteine-dependent, inverse agonists of RORγt. Site-directed mutagenesis and molecular dynamics simulations are supportive of a mechanism of action through specific binding to Cys476 on alpha helix 11 of the ligand binding domain (LBD). Representative compounds in the series selectively inhibit RORγt, potently suppress interleukin-17A (IL-17A) production by human CD4+ T cells, and inhibit T helper 17 (Th17) differentiation from human naïve CD4+ T cells. The advanced compound 13 is orally bioavailable and active at a dose of 3 mg/kg in a murine collagen-induced model of rheumatoid arthritis. Collectively, these data are supportive of the development of compound 13 in autoimmune diseases.
Copyright © 2020 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Allosteric NR modulator; Autoimmune disease; IL-17; Molecular dynamics simulations; RORgγt inverse agonists; Th17 cell differentiation

Mesh:

Substances:

Year:  2020        PMID: 32005415     DOI: 10.1016/j.bmcl.2020.126967

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  6 in total

1.  Structure-Activity Relationship Studies of Trisubstituted Isoxazoles as Selective Allosteric Ligands for the Retinoic-Acid-Receptor-Related Orphan Receptor γt.

Authors:  Femke A Meijer; Annet O W M Saris; Richard G Doveston; Guido J M Oerlemans; Rens M J M de Vries; Bente A Somsen; Anke Unger; Bert Klebl; Christian Ottmann; Peter J Cossar; Luc Brunsveld
Journal:  J Med Chem       Date:  2021-05-19       Impact factor: 7.446

Review 2.  RORγ Structural Plasticity and Druggability.

Authors:  Mian Huang; Shelby Bolin; Hannah Miller; Ho Leung Ng
Journal:  Int J Mol Sci       Date:  2020-07-27       Impact factor: 5.923

3.  Elucidation of an Allosteric Mode of Action for a Thienopyrazole RORγt Inverse Agonist.

Authors:  Rens M J M de Vries; Richard G Doveston; Femke A Meijer; Luc Brunsveld
Journal:  ChemMedChem       Date:  2020-03-12       Impact factor: 3.466

4.  Cooperativity between the orthosteric and allosteric ligand binding sites of RORγt.

Authors:  Rens M J M de Vries; Femke A Meijer; Richard G Doveston; Iris A Leijten-van de Gevel; Luc Brunsveld
Journal:  Proc Natl Acad Sci U S A       Date:  2021-02-09       Impact factor: 11.205

5.  Covalent Occlusion of the RORγt Ligand Binding Pocket Allows Unambiguous Targeting of an Allosteric Site.

Authors:  Femke A Meijer; Maxime C M van den Oetelaar; Richard G Doveston; Ella N R Sampers; Luc Brunsveld
Journal:  ACS Med Chem Lett       Date:  2021-03-08       Impact factor: 4.345

6.  SAMPL7: Host-guest binding prediction by molecular dynamics and quantum mechanics.

Authors:  Yiğitcan Eken; Nuno M S Almeida; Cong Wang; Angela K Wilson
Journal:  J Comput Aided Mol Des       Date:  2020-11-05       Impact factor: 3.686

  6 in total

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