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MedKoo Cat#: 598849 | Name: Liga 20

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Liga 20 is a semisynthetic GM1 ganglioside with N-dichloroacetylsphingosine; about ten times more potent than the natural GM2 in protecting neurons in culture against glutamate toxicity.

Chemical Structure

Liga 20
Liga 20
CAS#126586-85-4

Theoretical Analysis

MedKoo Cat#: 598849

Name: Liga 20

CAS#: 126586-85-4

Chemical Formula: C57H97Cl2N3O31

Exact Mass: 1389.5483

Molecular Weight: 1391.29

Elemental Analysis: C, 49.21; H, 7.03; Cl, 5.10; N, 3.02; O, 35.65

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Liga 20; Liga-20; Liga20;
IUPAC/Chemical Name
(2S,4R,5R,6S)-5-acetamido-2-(((2R,3S,4R,5S,6R)-3-(((2S,3S,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-(((2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4R,5S,6R)-6-(((2R,3S,E)-2-(2,2-dichloroacetamido)-3-hydroxyoctadec-4-en-1-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-5-hydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-2-carboxylic acid
InChi Key
CQCBGDOXLXRPIU-XXDAVWNGSA-N
InChi Code
InChI=1S/C57H97Cl2N3O31/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(70)27(62-51(81)50(58)59)24-84-53-43(79)41(77)45(33(22-66)87-53)89-55-44(80)49(93-57(56(82)83)18-29(71)35(60-25(2)68)48(92-57)37(73)30(72)19-63)46(34(23-67)88-55)90-52-36(61-26(3)69)47(39(75)32(21-65)85-52)91-54-42(78)40(76)38(74)31(20-64)86-54/h16-17,27-50,52-55,63-67,70-80H,4-15,18-24H2,1-3H3,(H,60,68)(H,61,69)(H,62,81)(H,82,83)/b17-16+/t27-,28+,29-,30-,31-,32-,33-,34-,35-,36+,37-,38+,39+,40+,41-,42+,43+,44+,45+,46+,47-,48+,49-,52+,53-,54-,55-,57+/m1/s1
SMILES Code
CC(N[C@@H]1[C@H](O)C[C@@](O[C@@H]1[C@H](O)[C@H](O)CO)(C(O)=O)O[C@@H]2[C@H](O)[C@H](O[C@H](CO)[C@@H]2O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4[C@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)[C@@H]3NC(C)=O)O[C@@H]5[C@H](O)[C@H](O)[C@H](OC[C@H]([C@H](/C=C/CCCCCCCCCCCCC)O)NC(C(Cl)Cl)=O)O[C@@H]5CO)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,391.29 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
1: Schneider JS, DiStefano L. LIGA 20 increases striatal dopamine levels in aged MPTP-treated mice refractory to GM1 ganglioside treatment. Neuroreport. 1993 Nov 18;5(2):103-4. PubMed PMID: 8110995. 2: Wu G, Lu ZH, Wang J, Wang Y, Xie X, Meyenhofer MF, Ledeen RW. Enhanced susceptibility to kainate-induced seizures, neuronal apoptosis, and death in mice lacking gangliotetraose gangliosides: protection with LIGA 20, a membrane-permeant analog of GM1. J Neurosci. 2005 Nov 23;25(47):11014-22. PubMed PMID: 16306414. 3: Wu G, Lu ZH, Xie X, Li L, Ledeen RW. Mutant NG108-15 cells (NG-CR72) deficient in GM1 synthase respond aberrantly to axonogenic stimuli and are vulnerable to calcium-induced apoptosis: they are rescued with LIGA-20. J Neurochem. 2001 Feb;76(3):690-702. PubMed PMID: 11158239. 4: Hadaczek P, Wu G, Sharma N, Ciesielska A, Bankiewicz K, Davidow AL, Lu ZH, Forsayeth J, Ledeen RW. GDNF signaling implemented by GM1 ganglioside; failure in Parkinson's disease and GM1-deficient murine model. Exp Neurol. 2015 Jan;263:177-89. doi: 10.1016/j.expneurol.2014.10.010. Epub 2014 Oct 23. PubMed PMID: 25448159. 5: Schneider JS, Distefano L. Response of the damaged dopamine system to GM1 and semisynthetic gangliosides: effects of dose and extent of lesion. Neuropharmacology. 1995 May;34(5):489-93. PubMed PMID: 7566482. 6: Schneider JS, DiStefano L. Oral administration of semisynthetic sphingolipids promotes recovery of striatal dopamine concentrations in a murine model of parkinsonism. Neurology. 1994 Apr;44(4):748-50. PubMed PMID: 8164837. 7: Pitto M, Miglio A, Kirschner G, Leon A, Ghidoni R. Metabolism of semisynthetic single-chain GM1 derivatives in cerebellar granule cells in culture. Neurochem Res. 1991 Nov;16(11):1187-92. PubMed PMID: 1815134. 8: Saito M, Saito M, Berg MJ, Guidotti A, Marks N. Gangliosides attenuate ethanol-induced apoptosis in rat cerebellar granule neurons. Neurochem Res. 1999 Sep;24(9):1107-15. PubMed PMID: 10485581. 9: Hatini V, DiNardo S. Distinct signals generate repeating striped pattern in the embryonic parasegment. Mol Cell. 2001 Jan;7(1):151-60. PubMed PMID: 11172720. 10: Saito M, Guidotti A, Berg MJ, Marks N. The semisynthetic glycosphingolipid LIGA20 potently protects neurons against apoptosis. Ann N Y Acad Sci. 1998 Jun 19;845:253-62. PubMed PMID: 9668359. 11: Rabin SJ, Bachis A, Mocchetti I. Gangliosides activate Trk receptors by inducing the release of neurotrophins. J Biol Chem. 2002 Dec 20;277(51):49466-72. Epub 2002 Oct 17. PubMed PMID: 12388556. 12: Marks N, Berg MJ, Guidotti A, Saito M. Activation of caspase-3 and apoptosis in cerebellar granule cells. J Neurosci Res. 1998 May 1;52(3):334-41. PubMed PMID: 9590441. 13: Polo A, Kirschner G, Guidotti A, Costa E. Brain content of glycosphingolipids after oral administration of monosialogangliosides GM1 and LIGA20 to rats. Mol Chem Neuropathol. 1994 Jan;21(1):41-53. PubMed PMID: 7910019. 14: Bachis A, Mocchetti I. Semisynthetic sphingoglycolipid LIGA20 is neuroprotective against human immunodeficiency virus-gp120-mediated apoptosis. J Neurosci Res. 2006 Apr;83(5):890-6. PubMed PMID: 16477610. 15: Saito M, Mao RF, Wang R, Vadasz C, Saito M. Effects of gangliosides on ethanol-induced neurodegeneration in the developing mouse brain. Alcohol Clin Exp Res. 2007 Apr;31(4):665-74. PubMed PMID: 17374046. 16: Wu G, Lu ZH, Xie X, Ledeen RW. Susceptibility of cerebellar granule neurons from GM2/GD2 synthase-null mice to apoptosis induced by glutamate excitotoxicity and elevated KCl: rescue by GM1 and LIGA20. Glycoconj J. 2004;21(6):305-13. PubMed PMID: 15514479. 17: Kharlamov A, Zivkovic I, Polo A, Armstrong DM, Costa E, Guidotti A. LIGA20, a lyso derivative of ganglioside GM1, given orally after cortical thrombosis reduces infarct size and associated cognition deficit. Proc Natl Acad Sci U S A. 1994 Jul 5;91(14):6303-7. PubMed PMID: 8022776; PubMed Central PMCID: PMC44189. 18: Lipartiti M, Lazzaro A, Manev H. Ganglioside derivative LIGA20 reduces NMDA neurotoxicity in neonatal rat brain. Neuroreport. 1992 Oct;3(10):919-21. PubMed PMID: 1421099. 19: Skaper SD, Fadda E, Facci L, Manev H. A semisynthetic glycosphingolipid (LIGA20) reduces 2,4, 5-trihydroxyphenylalanine neurotoxicity in primary neuronal cultures. Eur J Pharmacol. 1993 Oct 12;243(1):91-3. PubMed PMID: 8253129. 20: Seren MS, Lazzaro A, Yang CL, Canella R, Bassan M, Zanoni R, Manev H. Orally administered glycolipid derivative LIGA20 reduces infarct volume and behavioral impairment after focal cerebral ischemia. J Pharmacol Exp Ther. 1994 Jan;268(1):460-5. PubMed PMID: 8301588.