1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors

Salameh, Bader A.; Cumpstey, Ian; Sundin, Anders; Leffler, Hakon; Nilsson, Ulf J.

doi:10.1016/j.bmc.2010.05.040

Cited by 98 publications

(80 citation statements)

References 36 publications

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“…galactoside derivatives were synthesized using the same synthetic strategy and described a few years later (40). Interestingly, the derivative having a 1-naphthyl moiety on the 1,2,3-triazole core was determined as the best candidate with a K d of 120 µM against galectin-3 using the same biological assay.…”

Section: Se23mentioning

confidence: 99%

Synthetic Inhibitors of Galectins: Structures and Syntheses

Denavit

Lainé

Tremblay

et al. 2018

Trends in Glycoscience and Glycotechnology

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The recent discovery of the critical involvement of galectins in cancer progression, and in inflammatory and immune responses, has raised this family of β-D-galactoside-binding proteins to the rank of high-priority drug targets by the scientific community. This report will highlight the relevance of glycochemistry toward the efficient development of synthetic galectins inhibitors with high affinity and selectivity, as small molecules or multivalent glycoconjugates.

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Section: Se23mentioning

confidence: 99%

Synthetic Inhibitors of Galectins: Structures and Syntheses

Denavit

Lainé

Tremblay

et al. 2018

Trends in Glycoscience and Glycotechnology

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“…Some specific ligands with high affinity for the single galectin CRDs are mentioned in Table 1. The recognition of galactose is common for all galectins but the interaction with the monosaccharide alone is very weak (Carlsson et al, 2007;Knibbs et al, 1993;Salameh et al, 2010). Disaccharides containing galactose -glycosidic bound to GlcNAc, Glc or GalNAc are bound with significantly increased affinities.…”

Section: Comparison Of Different Common Assaysmentioning

confidence: 99%

Galectins: Structures, Binding Properties and Function in Cell Adhesion

Römer¹,

Elling²

2011

Biomaterials - Physics and Chemistry

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“…15 Nevertheless, few 3-deoxy-3-triazolyl-and 3-deoxy-triazolylmetyl-derivatives of furanoses have been studied as glycosidase inhibitors, 16,17 but 3-deoxy-3-triazolyl-galactopyranose derivatives have proved to be excellent galectin inhibitors 18,19 with enhanced binding affinities if used as dimeric structures. 20 Here we aimed to develop a user-friendly synthesis of novel C(3)-modified galactohybrids and to determine their affinities towards galectin-1 and galectin-3. The latter are involved in various pathological pathways (e.g.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

Mackeviča¹,

Ostrovskis²,

Leffler³

et al. 2014

Arkivoc

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Here a synthesis of novel galactose-1,2,3-triazole conjugates is described. The title compounds were obtained from 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-galactofuranose via a copper catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction. It was demonstrated that the title compounds in their isopropylidene-protected form tend to chelate copper. The copper content can be diminished to 10 ppm by successive treatment with EDTA and Na 2 S followed by chromatographic purification. Acidic hydrolysis of the acetonide protecting groups provided water soluble galactohybrids that were tested for their affinity towards galectin-1 and galectin-3. The trimeric galactohybrid exhibited a 160-fold preference for galectin-3 binding with K d 50 μM. One of the obtained disaccharides was characterized by X-ray analysis.

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1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors

Cited by 98 publications

References 36 publications

Synthetic Inhibitors of Galectins: Structures and Syntheses

Synthetic Inhibitors of Galectins: Structures and Syntheses

Galectins: Structures, Binding Properties and Function in Cell Adhesion

Synthesis of 1,2,3-triazole-linked galactohybrids and their inhibitory activities on galectins

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