THIODIGALACTOSIDE Chemical Properties

Melting point:

>225°C (dec.)

storage temp. 

−20°C

solubility 

DMSO (Slightly)

form 

Solid

color 

White

Water Solubility 

H2O: 2mg/mL, clear

InChI

InChI=1/C12H22O10S/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5+,6+,7+,8+,9-,10-,11+,12?/s3

InChIKey

SYKYBMOFPMXDRQ-YSLNCGCNNA-N

SMILES

C1([C@H](O)[C@H]([C@@H](O)[C@@H](CO)O1)O)S[C@H]1[C@H](O)[C@H]([C@@H](O)[C@@H](CO)O1)O |&1:1,3,4,6,12,13,15,16,18,r|

Safety Information

WGK Germany 

3

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

THIODIGALACTOSIDE Usage And Synthesis

Description

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 K_d values between 24 and 78 μM. It is used to investigate the roles of these galectins in cell signaling and carcinogenesis.

Chemical Properties

White to off-white crystalline powder

Uses

Thiogdigalactosideis an inhibitor of galectin 1 which has an essential role in high-fat diet induced obesity development.

References

[1] ALI HASAN EBRAHIM. Galectins in cancer: carcinogenesis, diagnosis and therapy.[J]. Annals of translational medicine, 2014, 2 9: 88. DOI: 10.3978/j.issn.2305-5839.2014.09.12
[2] NANDOR GABOR THAN. Galectins: Double-edged Swords in the Cross-roads of Pregnancy Complications and Female Reproductive Tract Inflammation and Neoplasia.[J]. Journal of Pathology and Translational Medicine, 2015, 49 3: 181-208. DOI: 10.4132/jptm.2015.02.25
[3] BADER A. SALAMEH . 1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors[J]. Bioorganic & Medicinal Chemistry, 2010, 18 14: Pages 5367-5378. DOI: 10.1016/j.bmc.2010.05.040
[4] HILDE VAN HATTUM. Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1[J]. Journal of Medicinal Chemistry, 2013, 56 3: 1350-1354. DOI: 10.1021/jm301677r
[5] KOICHI ITO. Thiodigalactoside inhibits murine cancers by concurrently blocking effects of galectin-1 on immune dysregulation, angiogenesis and protection against oxidative stress[J]. Angiogenesis, 2011, 14 3: 293-307. DOI: 10.1007/s10456-011-9213-5
[6] PEIWEN KUO. Galectin-1 mediates radiation-related lymphopenia and attenuates NSCLC radiation response.[J]. Clinical Cancer Research, 2014, 20 21: 5558-5569. DOI: 10.1158/1078-0432.ccr-14-1138
[7] R MUKHERJEE. Targeted inhibition of galectin 1 by thiodigalactoside dramatically reduces body weight gain in diet-induced obese rats[J]. International Journal of Obesity, 2015, 39 9: 1349-1358. DOI: 10.1038/ijo.2015.74

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