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A Selective Galactose–Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model

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    A Selective Galactose–Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model
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    † Indian Institute of Science Education and Research-Kolkata (IISER) Kolkata, Mohanpur Campus, P.O. BCKV Campus Main Office, Mohanpur, Nadia 741246, India
    ‡ Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, SE-221 00 Lund, Sweden
    § MRC Centre for Inflammation Research, The Queen’s Medical Research Institute, University of Edinburgh, Edinburgh EH16 4TJ, U.K.
    ∥ Institute for Glycomics, Griffith University, Gold Coast Campus, Parklands Southport, Queensland 4222, Australia
    ⊥ Department of Laboratory Medicine, Section MIG, Lund University, BMC-C1228b, Klinikgatan 28, SE-221 84 Lund, Sweden
    # Department of Respiratory Medicine and Allergy, Kings College, Denmark Hill Campus, Bessemer Road, London SE5 9RS, U.K.
    ∇ Galecto Biotech ApS, COBIS, Ole Maaloes vej 3, Copenhagen N, DK-2200, Denmark
    *Phone: +46 46 2228218. Fax: +46 46 2228209. E-mail: [email protected]
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2016, 59, 17, 8141–8147
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    https://doi.org/10.1021/acs.jmedchem.6b00957
    Published August 8, 2016
    Copyright © 2016 American Chemical Society
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    Abstract

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    Synthesis of doubly 3-O-coumarylmethyl-substituted thiodigalactosides from bis-3-O-propargyl-thiodigalactoside resulted in highly selective and high affinity galectin-3 inhibitors. Mutant studies, structural analysis, and molecular modeling revealed that the coumaryl substituents stack onto arginine side chains. One inhibitor displayed efficacy in a murine model of bleomycin-induced lung fibrosis similar to that of a known nonselective galectin-1/galectin-3 inhibitor, which strongly suggests that blocking galectin-3 glycan recognition is an important antifibrotic drug target.

    Copyright © 2016 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jmedchem.6b00957.

    • Expression constructs, expression, and purification of recombinant galectins, competitive fluorescence polarization experiments determining galectin affinities, protein expression and crystallization, X-ray data collection and structure determination, in vivo experimental details, NMR spectra (1H and 13C) for compounds 5–7, and associated references (PDF)

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    Atomic coordinates and experimental data for the crystal structures of galectin-3 with bound 12 (PDB code 5EXO) will be released upon article publication.

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    Cite this: J. Med. Chem. 2016, 59, 17, 8141–8147
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jmedchem.6b00957
    Published August 8, 2016
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