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Thiodigalactoside (TDG) 51555-87-4

Thiodigalactoside (TDG) 51555-87-4

CAS No.: 51555-87-4

Thiodigalactoside (TDG) is an orally bioactive and potent galectin (GAL) inhibitor (antagonist) with Kds of 24 μM and 4
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Thiodigalactoside (TDG) is an orally bioactive and potent galectin (GAL) inhibitor (antagonist) with Kds of 24 μM and 49 μM for GAL-1 and GAL-3, respectively. Thiodigalactoside is a nonmetabolizable disaccharide with anti-inflammatory and anticancer activities. Thiodigalactoside significantly reduces weight gain in diet-induced obese rats.

Physicochemical Properties


Molecular Formula C12H22O10S
Molecular Weight 358.36
Exact Mass 358.093
CAS # 51555-87-4
PubChem CID 119138
Appearance White to off-white solid powder
LogP -3.4
Hydrogen Bond Donor Count 8
Hydrogen Bond Acceptor Count 11
Rotatable Bond Count 4
Heavy Atom Count 23
Complexity 353
Defined Atom Stereocenter Count 10
SMILES

C([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)S[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)O)O

InChi Key SYKYBMOFPMXDRQ-ZFDCCPEWSA-N
InChi Code

InChI=1S/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+/m1/s1
Chemical Name

(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyloxane-3,4,5-triol
HS Tariff Code 2934.99.9001
Storage

Powder-20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity


Targets Kd: 24 μM (GAL1) and 49 μM (GAL3)[1]
ln Vitro Based on TG content and Oil Red O (ORO) staining, thiodigalactoside (TDG; 250 and 500 μM) shows dose-dependent decrease of fat accumulation[1].
ln Vivo Thiodigalactoside (TDG; 5 mg/kg; IP; once weekly for 5 weeks) significantly reduces the amount of body weight increase that is caused by a high fat diet[2]. In comparison to IP, thiodigalactoside (5 mg/kg; oral; daily or weekly for 5 weeks) produced a smaller reduction in body weight gain[2].
Animal Protocol Animal/Disease Models: Fiveweeks old SD (Sprague-Dawley) male rats[2]
Doses: 5 mg/kg
Route of Administration: IP; once per week for 5 weeks
Experimental Results: Resulted in dramatic inhibition of HFD-induced body weight gain by inhibiting adipogenesis and lipogensis as well as by increasing expression of the proteins associated with thermogenesis and energy expenditure.
References

[1]. 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.

[2]. Small-Molecule ONC201/TIC10 Targets Chemotherapy-Resistant Colorectal Cancer Stem-like Cells in an Akt/Foxo3a/TRAIL-Dependent Manner. Cancer Res. 2015 Apr 1;75(7):1423-32.

Additional Infomation Thiodigalactoside is a solid. This compound belongs to the dihexoses. These are disaccharides containing two hexose carbohydrates. This medication is known to target galectin-1, heat-labile enterotoxin b chain, neurocan core protein, and lactose permease.

Solubility Data


Solubility (In Vitro) H2O: 100 mg/mL (279.05 mM)
Solubility (In Vivo) Solubility in Formulation 1: 100 mg/mL (279.05 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.7905 mL 13.9525 mL 27.9049 mL
5 mM 0.5581 mL 2.7905 mL 5.5810 mL
10 mM 0.2790 mL 1.3952 mL 2.7905 mL
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.