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  • Aromatic heterocycle galectin-1 interactions for selective single-digit nM affinity ligands

    Author(s)
    Peterson, Kristoffer
    Collins, Patrick M
    Huang, Xiaoli
    Kahl-Knutsson, Barbro
    Essen, Sofia
    Zetterberg, Fredrik R
    Oredsson, Stina
    Leffler, Hakon
    Blanchard, Helen
    Nilsson, Ulf J
    Griffith University Author(s)
    Collins, Patrick
    Blanchard, Helen
    Year published
    2018
    Metadata
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    Abstract
    A series of 3-triazole-thiogalactosides and 3,3′-triazole-thiodigalactosides substituted with different five-membered heterocycles at the C-4 triazole position were found to have high selectivity for galectin-1. Initial studies on the 3-triazole-thiogalactosides indicated that five membered heterocycles in general gave increased affinity for galectin-1 and improved selectivity over galectin-3. The selectivity profile was similar for thiodigalactosides exemplified by 3,3′ substituted thien-3-yltriazole and thiazol-2-yltriazole, both having single-digit nM galectin-1 affinity and almost 10-fold galectin-1 selectivity. The ...
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    A series of 3-triazole-thiogalactosides and 3,3′-triazole-thiodigalactosides substituted with different five-membered heterocycles at the C-4 triazole position were found to have high selectivity for galectin-1. Initial studies on the 3-triazole-thiogalactosides indicated that five membered heterocycles in general gave increased affinity for galectin-1 and improved selectivity over galectin-3. The selectivity profile was similar for thiodigalactosides exemplified by 3,3′ substituted thien-3-yltriazole and thiazol-2-yltriazole, both having single-digit nM galectin-1 affinity and almost 10-fold galectin-1 selectivity. The binding interactions of a thiodigalactoside based galectin-1 inhibitor with two thien-3-yltriazole moieties were studied with X-ray crystallography. One of the thiophene moieties was positioned deeper into the pocket than previously reported phenyltriazoles and formed close contacts with Val31, Ser29, Gly124, and Asp123. The affinity and structural analysis thus revealed that steric and electronic optimization of five-membered aromatic heterocycle binding in a narrow galectin-1 subsite confers high affinity and selectivity.
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    Journal Title
    RSC Advances
    Volume
    8
    DOI
    https://doi.org/10.1039/c8ra04389b
    Subject
    Chemical sciences
    Other chemical sciences not elsewhere classified
    Aromatic heterocycle galectin-1
    Single-digit nM affinity ligands
    Thiophene moieties
    Publication URI
    http://hdl.handle.net/10072/381721
    Collection
    • Journal articles

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