Thiodigalactoside
(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
Cas No.:51555-87-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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.
| 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 |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
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.