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Thiodigalactoside Sale

(Synonyms: D-吡喃半乳糖Β-D-硫代吡喃半乳糖苷,TDG) 目录号 : GC45040

A galectin-binding diglycan

Thiodigalactoside Chemical Structure

Cas No.:51555-87-4

规格 价格 库存 购买数量
25mg
¥599.00
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50mg
¥1,147.00
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100mg
¥1,679.00
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250mg
¥2,399.00
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产品描述

Galectins are a family of glycan-binding lectins with diverse regulatory roles in physiological processes. They have significant roles in inflammation and cancer. Thiodigalactoside is a diglycan that binds galectins-1, -3, -8, and -9 with Kd values between 24 and 78 µM. It is used to investigate the roles of these galectins in cell signaling and carcinogenesis.

Chemical Properties

Cas No. 51555-87-4 SDF
别名 D-吡喃半乳糖Β-D-硫代吡喃半乳糖苷,TDG
Canonical SMILES O[C@@H]1[C@H](O)[C@@H](O)[C@H](S[C@@]2([H])[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O2)O[C@@H]1CO
分子式 C12H22O10S 分子量 358.4
溶解度 DMF: 1 mg/ml,DMSO: 20 mg/ml,PBS (pH 7.2): 10 mg/ml 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.7902 mL 13.9509 mL 27.9018 mL
5 mM 0.558 mL 2.7902 mL 5.5804 mL
10 mM 0.279 mL 1.3951 mL 2.7902 mL
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Research Update

Synthesis of fluorinated Thiodigalactoside analogues

Carbohydr Res 2022 Jan;511:108481.PMID:34837848DOI:10.1016/j.carres.2021.108481.

In this work, we report the first synthesis of fluorinated Thiodigalactoside analogues. We used tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the elaboration of two monofluorinated heterodimers, one difluorinated homodimer, and one difluorinated heterodimer. Moreover, we also present an alternative synthesis of 3-deoxy-3-fluorogalactose and 4-deoxy-4-fluorogalactose from a common precursor. Finally, this small set of more stable Thiodigalactoside analogues could be interesting inhibitors of galactose-specific lectins.

Galectin-inhibitory Thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells

J Med Chem 2008 Dec 25;51(24):8109-14.PMID:19053747DOI:10.1021/jm801077j.

Aromatic 3,3'-diesters of Thiodigalactoside were synthesized in a rapid three-step sequence from commercially available Thiodigalactoside and evaluated as inhibitors of cancer- and immunity-related galectins. For each of galectins-1, -3, -7, and -9N-terminal domain, aromatic 3,3'-diesters of Thiodigalactoside were found to have affinities in the low micromolar range, which represents a 7-70 fold enhancement over Thiodigalactoside itself. No significant improvement was found for galectin-8 N-terminal domain. Two of the compounds were selected for testing in cell culture and were shown to have potent antimigratory effects on human PC-3 prostate and human A549 nonsmall-cell lung cancer cells.

Tuning the preference of thiodigalactoside- and lactosamine-based ligands to galectin-3 over galectin-1

J Med Chem 2013 Feb 14;56(3):1350-4.PMID:23281927DOI:10.1021/jm301677r.

Inhibitors for galectin-1 and -3 were synthesized from Thiodigalactoside and lactosamine by derivatization of the galactose C3. Introduction of 4-phenyl-1H-1,2,3-triazol-1-yl substituents at the Thiodigalactoside C3 by CuAAC, targeting arginine-arene interactions, increased the affinity to 13 nM but yielded little selectivity. The bulkier 4-(4-phenoxyphenyl)-1H-1,2,3-triazol-1-yl substituent, however, increased the preference for galectin-3 over galectin-1 to more than 200-fold. Modeling showed more arginine-arene interactions for galectin-3 than for galectin-1. Introducing 4-phenoxyaryl groups on lactosamine had a similar effect.

Hybrid ligands with calixarene and Thiodigalactoside groups: galectin binding and cytotoxicity

Org Chem Front 2019 Jul 12;6(16):2981-2990.PMID:34912566DOI:10.1039/c9qo00810a.

Galectins have diverse functions and are involved in many biological processes because of their complex intra- and extracellular activities. Selective and potent inhibitors for galectins will be valuable tools to investigate the biological functions of these proteins. Therefore, we describe here the synthesis of galectin inhibitors with a potential "chelate effect". These compounds are designed to bind to two different binding sites on galectins simultaneously. In this paper a series of asymmetric "hybrid" compounds are prepared, which combine two galectin ligands (1) a substituted Thiodigalactoside derivative and (2) an antagonist calixarene-based therapeutic agent. NMR spectroscopy was used to evaluate the interactions of these compounds with Galectin-1 and -3. In addition, cellular experiments were conducted to compare the cytotoxic effects of the hybrids with those of a calixarene derivative. While only the Thiodigalactoside part of the hybrids showed strong binding, the calixarene part was responsible for observed cytoxoxicity effects, suggesting that the calixarene moiety may also be addressing a non-galectin target.

Thiodigalactoside shows antitumour activity by beta-galactoside-binding protein and regulatory T cells inhibition in oral squamous cell carcinoma

Oral Dis 2016 Jul;22(5):445-53.PMID:27004748DOI:10.1111/odi.12479.

Objective: Thiodigalactoside (TDG), a synthetic inhibitor of β-galactoside-binding protein (β-GBP) suppresses tumour growth by inhibiting multiple cancer enhancing activities of β-GBP. Hence, we attempted to understand whether disruption of β-GBP functions and indirect inhibition of Treg cells by TDG affect the growth and establishment of oral cancer cells. Method: The growth, morphology, cell cycle regulation, apoptosis induction and angiogenesis of oral cancer cell lines (SCC-4, SCC-9, SCC-25) via MACS-purified Treg cells were performed by MTT, propidium iodide (PI) staining, annexin-V-binding assay and ELISA respectively. Results: Treatment with β-GBP showed growth-promoting effects on Tregs and oral cancer cells. However, the treatment with its inhibitor TDG resulted in inhibition of Treg subsets and also decreased the frequency of IL10(+) and IL35(+) Tregs indicating its immunomodulatory effects. Additionally, TDG treatment significantly (P < 0.001) inhibited the growth of OSCC cells with a concomitant induction of apoptosis, cell cycle arrest and anti-angiogenesis. Conclusion: It appears that TDG concurrently prevents many tumour-promoting effects of β-GBP in oral cancer cells possibly by Treg inhibition. This offers a preclinical proof of the concept that therapeutic targeting of β-GBP can overcome Treg -mediated tumour promotion and immunosuppression in oral cancer patients.