Abstract
A series of O2 and O3-derivatized methyl beta-d-talopyranosides were synthesized and evaluated in vitro as inhibitors of the galactose-binding galectin-1, -2, -3, -4 (N- and C-terminal domains), 8 (N-terminal domain), and 9 (N-terminal domain). Galectin-4C and 8N were found to prefer the d-talopyranose configuration to the natural ligand d-galactopyranose configuration. Derivatization at talose O2 and/or O3 provided selective submillimolar inhibitors for these two galectins.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Benzoates / chemistry*
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Binding Sites
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Galactose / chemistry
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Galectin 1 / chemistry
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Galectin 3 / chemistry
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Galectin 4 / chemistry*
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Galectins / chemistry*
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Glycosides / chemistry*
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Humans
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Lactones / chemistry*
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Ligands
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Models, Chemical
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Protein Engineering / methods
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Protein Structure, Tertiary
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Pyrans / chemistry
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Spectrometry, Fluorescence / methods
Substances
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Benzoates
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Galectin 1
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Galectin 3
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Galectin 4
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Galectins
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Glycosides
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L-talo-gamma-lactone
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LGALS8 protein, human
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LGALS9 protein, human
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Lactones
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Ligands
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Pyrans
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methyl 2-O-acetyl-3-O-toluoyltalopyranoside
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Galactose