Thiodigalactoside
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MedKoo CAT#: 585238

CAS#: 80441-61-8

Description: Thiodigalactoside is a potent inhibitor of galectin-1 that suppress tumor growth by inhibiting multiple cancer enhancing activities of galectin-1, including immune cell dysregulation, angiogenesis and protection against oxidative stress.

Chemical Structure

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Thiodigalactoside
CAS# 80441-61-8
Instruction

Theoretical Analysis

MedKoo Cat#: 585238
Name: Thiodigalactoside
CAS#: 80441-61-8
Chemical Formula: C12H22O10S
Exact Mass: 358.09
Molecular Weight: 358.358
Elemental Analysis: C, 40.22; H, 6.19; O, 44.65; S, 8.95

Price and Availability

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25mg USD 220
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Synonym: Thiodigalactoside; Galsgal; GBTGP; Tdg cpd

IUPAC/Chemical Name: beta-D-Galactopyranoside, D-galactosyl 1-thio-

InChi Key: SYKYBMOFPMXDRQ-VVLLKYQZSA-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

SMILES Code: O[C@H]([C@H]([C@H]([C@@H](CO)O1)O)O)[C@@H]1SC2[C@@H]([C@H]([C@H]([C@@H](CO)O2)O)O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 358.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: van Hattum H, Branderhorst HM, Moret EE, Nilsson UJ, Leffler H, Pieters RJ. 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. doi: 10.1021/jm301677r. Epub 2013 Jan 23. PubMed PMID: 23281927.

2: Delaine T, Cumpstey I, Ingrassia L, Le Mercier M, Okechukwu P, Leffler H, Kiss R, Nilsson UJ. 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. doi: 10.1021/jm801077j. PubMed PMID: 19053747.

3: Laaf D, Bojarová P, Elling L, Křen V. Galectin-Carbohydrate Interactions in Biomedicine and Biotechnology. Trends Biotechnol. 2019 Apr;37(4):402-415. doi: 10.1016/j.tibtech.2018.10.001. Epub 2018 Nov 6. Review. PubMed PMID: 30413271.

4: Parray HA, Yun JW. Proteomic Identification of Target Proteins of Thiodigalactoside in White Adipose Tissue from Diet-Induced Obese Rats. Int J Mol Sci. 2015 Jun 25;16(7):14441-63. doi: 10.3390/ijms160714441. PubMed PMID: 26121299; PubMed Central PMCID: PMC4519851.

5: Cagnoni AJ, Kovensky J, Uhrig ML. Design and synthesis of hydrolytically stable multivalent ligands bearing thiodigalactoside analogues for peanut lectin and human galectin-3 binding. J Org Chem. 2014 Jul 18;79(14):6456-67. doi: 10.1021/jo500883v. Epub 2014 Jun 25. PubMed PMID: 24937526.

6: Mukherjee R, Kim SW, Park T, Choi MS, Yun JW. Targeted inhibition of galectin 1 by thiodigalactoside dramatically reduces body weight gain in diet-induced obese rats. Int J Obes (Lond). 2015 Sep;39(9):1349-58. doi: 10.1038/ijo.2015.74. Epub 2015 Apr 29. PubMed PMID: 25920776.

7: Eelkema JA, O'Donnell MA, Brooker RJ. An analysis of lactose permease "sugar specificity" mutations which also affect the coupling between proton and lactose transport. II. Second site revertants of the thiodigalactoside-dependent proton leak by the Val177/Asn319 permease. J Biol Chem. 1991 Mar 5;266(7):4139-44. PubMed PMID: 1999408.

8: Salameh BA, Cumpstey I, Sundin A, Leffler H, Nilsson UJ. 1H-1,2,3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors. Bioorg Med Chem. 2010 Jul 15;18(14):5367-78. doi: 10.1016/j.bmc.2010.05.040. Epub 2010 May 20. PubMed PMID: 20538469.

9: Ito K, Scott SA, Cutler S, Dong LF, Neuzil J, Blanchard H, Ralph SJ. Thiodigalactoside inhibits murine cancers by concurrently blocking effects of galectin-1 on immune dysregulation, angiogenesis and protection against oxidative stress. Angiogenesis. 2011 Sep;14(3):293-307. doi: 10.1007/s10456-011-9213-5. Epub 2011 Apr 27. PubMed PMID: 21523436; PubMed Central PMCID: PMC3155035.

10: van Scherpenzeel M, Moret EE, Ballell L, Liskamp RM, Nilsson UJ, Leffler H, Pieters RJ. Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3. Chembiochem. 2009 Jul 6;10(10):1724-33. doi: 10.1002/cbic.200900198. PubMed PMID: 19492387.

11: Franco PJ, Eelkema JA, Brooker RJ. Isolation and characterization of thiodigalactoside-resistant mutants of the lactose permease which possess an enhanced recognition for maltose. J Biol Chem. 1989 Sep 25;264(27):15988-92. PubMed PMID: 2674122.

12: Kuo P, Bratman SV, Shultz DB, von Eyben R, Chan C, Wang Z, Say C, Gupta A, Loo BW Jr, Giaccia AJ, Koong AC, Diehn M, Le QT. Galectin-1 mediates radiation-related lymphopenia and attenuates NSCLC radiation response. Clin Cancer Res. 2014 Nov 1;20(21):5558-69. doi: 10.1158/1078-0432.CCR-14-1138. Epub 2014 Sep 4. PubMed PMID: 25189484; PubMed Central PMCID: PMC4216761.

13: Astorgues-Xerri L, Riveiro ME, Tijeras-Raballand A, Serova M, Neuzillet C, Albert S, Raymond E, Faivre S. Unraveling galectin-1 as a novel therapeutic target for cancer. Cancer Treat Rev. 2014 Mar;40(2):307-19. doi: 10.1016/j.ctrv.2013.07.007. Epub 2013 Aug 1. Review. PubMed PMID: 23953240.

14: Abramson J, Smirnova I, Kasho V, Verner G, Kaback HR, Iwata S. Structure and mechanism of the lactose permease of Escherichia coli. Science. 2003 Aug 1;301(5633):610-5. PubMed PMID: 12893935.

15: Chan YC, Lin HY, Tu Z, Kuo YH, Hsu SD, Lin CH. Dissecting the Structure-Activity Relationship of Galectin-Ligand Interactions. Int J Mol Sci. 2018 Jan 29;19(2). pii: E392. doi: 10.3390/ijms19020392. Review. PubMed PMID: 29382172; PubMed Central PMCID: PMC5855614.

16: Kaufman SJ, Lawless ML. Thiodigalactoside binding lectin and skeletal myogenesis. Differentiation. 1980 Feb;16(1):41-8. PubMed PMID: 7000605.

17: Varma PV, Frunchak YN, Evanson JE, Milos NC. Defective development of the craniofacial/digestive complex of Xenopus laevis after treatment with endogenous galactoside-binding lectin or its hapten inhibitor thiodigalactoside. J Craniofac Genet Dev Biol. 1994 Jul-Sep;14(3):177-91. PubMed PMID: 7852546.

18: Cumpstey I, Sundin A, Leffler H, Nilsson UJ. C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions. Angew Chem Int Ed Engl. 2005 Aug 12;44(32):5110-2. PubMed PMID: 16007713.

19: Patterson RJ, Haudek KC, Voss PG, Wang JL. Examination of the role of galectins in pre-mRNA splicing. Methods Mol Biol. 2015;1207:431-49. doi: 10.1007/978-1-4939-1396-1_28. PubMed PMID: 25253157.

20: Ito K, Stannard K, Gabutero E, Clark AM, Neo SY, Onturk S, Blanchard H, Ralph SJ. Galectin-1 as a potent target for cancer therapy: role in the tumor microenvironment. Cancer Metastasis Rev. 2012 Dec;31(3-4):763-78. doi: 10.1007/s10555-012-9388-2. Review. PubMed PMID: 22706847.