alpha-Galactosylceramide, NKT cell stimulator (ab144262)

Overview

  • Product name

    alpha-Galactosylceramide, NKT cell stimulator
  • Description

    Potent NKT cell stimulator. Selective CD1d ligand.
  • Biological description

    Potent NKT cell stimulator. Selective CD1d ligand. Stimulates lymphocyte proliferation and enhances antibody production. Shows antiangiogenic, antitumor and potent immunoregulatory effects in vivo.
  • Purity

    > 96%
  • CAS Number

    158021-47-7
  • Chemical structure

    Chemical Structure

Properties

  • Chemical name

    N-[(2S,3S,4R)-3,4-Dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
  • Molecular weight

    858.32
  • Molecular formula

    C50H99NO9
  • PubChem identifier

    2826713
  • Storage instructions

    Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.
  • Handling

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

  • SMILES

    CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O
  • Source

    Synthetic

References

This product has been referenced in:

  • Nur H  et al. Stimulation of invariant natural killer T cells by a-Galactosylceramide activates the JAK-STAT pathway in endothelial cells and reduces angiogenesis in the 5T33 multiple myeloma model. Br J Haematol 167:651-63 (2014). Read more (PubMed: 25142285) »
  • Chen Q & Ross AC a-Galactosylceramide stimulates splenic lymphocyte proliferation in vitro and increases antibody production in vivo in late neonatal-age mice. Clin Exp Immunol : (2014). Read more (PubMed: 25178151) »
  • Saubermann LJ  et al. Activation of natural killer T cells by alpha-galactosylceramide in the presence of CD1d provides protection against colitis in mice. Gastroenterology 119:119-28 (2000). Read more (PubMed: 10889161) »
See all 2 Publications for this product

Customer reviews and Q&As

Question
Answer



In general I can confirm that the reconstitution of alpha-GalCer is quiet challenging. The lack of solubility is an inherent property of the molecule.
It has been described as insoluble in water, methanol, ethanol or other organic solvents, very slightly soluble in tetrahydrofuran and slightly soluble in pyridine.

Pyridine is often used to solubilize compounds that are not very soluble. However, pyridine as solvent is not suitable for cell culture applications. Below are protocols that worked for researchers in the past.




Different solubilization protocols for α-Galactosylceramide:



1) Tween20 and Sodium chloride - Heat - Sonicate

- Dissolve alpha;-GalCer in 0.5% Tween20, 0.9% NaCl solution.

- Heat to 85oC until solution turns cloudy.

- Take out of water bath und keep at RT.

- Solution will become clear quickly.

- In case some particles are left, sonicate (important: sonication has to be performed in glass vial, it

does not work in plastic Eppendorf tube!) and filter afterwards with 2 um filter.



2) Tween20 and PBS Heat Sonicate

- Dissolve alpha-GalCer in 0.2mg/ml PBS containing 0.5% Tween20 (warm up and sonicate 2 hrs. at 37oC).

- The solution can be more a suspension then a clear solution.

- In case some particles are left, warm up and sonicate (important: sonication has to be performed in glass vial, it does not work in plastic Eppendorf tube!).

- For sonication no interval is recommended, just use a conventional water bath sonicator at standard amplitude.



3) DMSO - Heat - Sonicate

- Dissolve alpha-GalCer in DMSO at the concentration of 1mg/ml with heating at 80oC for several minutes.

- Sonication for 2 h.

- The solution of 1mg/ml in DMSO can be further diluted in PBS.



4) 2 Steps: Chloroform:Methanol Evaporation DMSO, PBS or Tween20 - Heat - Sonicate

- Dissolve alpha-GalCer in a mixture of chloroform:methanol (2:1).

- Aliquot into reasonable aliquots for the experiment.

- Evaporate the solvent using a gentle stream of nitrogen so that you have a thin, dry film of material at the bottom of the vial.

- Add either DMSO or PBS + 0.5% Tween20 to achieve your final concentration.

- Some heating and sonication might be necessary.

- The thin film of compound generated by the evaporation step allows greater access of the compound to the solvent and better dissolution.


5) 5.6% sucrose, 0.75% L-histidine and 0.5% Tween20 -Heat - Sonicate

- Dissolve alpha-GalCer in 5.6% sucrose, 0.75% L-histidine and 0.5% Tween20

- Heat at 80oC for several minutes and sonicate.


IMPORTANT: alpha-GalCer can be stored in solution in glass vials at 4o;C or -20°C, and is stable for ˜3 months also when dissolved!

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