AdipoGen Life Sciences

α-Galactosylceramide

Name: α-Galactosylceramide
Brand: AdipoGen Life Sciences
SKU: AG-CN2-0013
Price: 190.00 CHF
Availability: InStock

As low as CHF 130.00

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AG-CN2-0013-C250250 µgCHF 130.00

AG-CN2-0013-M0011 mgCHF 190.00

AG-CN2-0013-M0055 mgCHF 760.00

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Specifications / Handling

More Information
Product Details
Synonyms	KRN7000; α-Gal-Cer; αGalCer; alphaGalCer; α-GC
Product Type	Chemical
Properties
Formula	C₅₀H₉₉NO₉
MW	858.3
CAS	158021-47-7
Source/Host Chemicals	Synthetic. Originally isolated from the marine sponge Agelas mauritianus.
Purity Chemicals	≥98% (NMR, TLC (CHCl3/MeOH 85:15))
Appearance	White to off-white solid.
Solubility	Soluble in pyridine. Solubilization in Tween20 or PBS for cell culture use see online protocol.
Identity	Identity determined by ¹H-NMR.
Declaration	Manufactured by AdipoGen. Not sold in Japan.
InChi Key	LSUQVAFARUJTHS-ABBGRRHVSA-N
Smiles	[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].[H].CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](COC1OC(CO)C(O)C(O)C1O)NC(=O)CC#CC#CC#CC#CC#CC#CC#CC#CC#CC#CC#CC#C
Shipping and Handling
Shipping	BLUE ICE
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Aliquot into glass vials.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
Protocols	Download PDF
Safety Data Sheet	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Scientific Background Information

Product Description

Immunostimulant [1, 2, 3].
Potent stimulator of natural killer T (NKT) cells [4, 5].
Specific ligand of the lipid-binding MHC class I-like protein CD1d in human and mouse NKT cells [5].
Protects against LPS-induced shock [7].
Potent antitumor compound [2, 6, 8].

Product-specific References

Synthesis of alpha-, beta-monoglycosylceramides and four diastereomers of an alpha-galactosylceramide: M. Morita, et al.; Bioorg. Med. Chem. Lett. 5, 699 (1995)
Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties: K. Motoki, et al.; Biol. Pharm. Bull. 18, 1487 (1995)
Immunostimulatory activities of monoglycosylated alpha-D-pyranosylceramides: A. Uchimura, et al.; Bioorg. Med. Chem. 5, 2245 (1997)
Activation of natural killer T cells by alpha-galactosylceramide rapidly induces the full maturation of dendritic cells in vivo and thereby acts as an adjuvant for combined CD4 and CD8 T cell immunity to a coadministered protein: Fujii S, et al.; J. Exp. Med. 198, 267 (2003)
Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides: K.O. Yu, et al.; PNAS 102, 3383 (2005)
A phase I study of alpha-galactosylceramide (KRN7000)-pulsed dendritic cells in patients with advanced and recurrent non-small cell lung cancer: A. Ishikawa, et al.; Clin. Cancer Res. 11, 1910 (2005)
Pivotal advance: alpha-galactosylceramide induces protection against lipopolysaccharide-induced shock: G. Sireci, et al.; J. Leukoc. Biol. 81, 607 (2007)
α-Galactosylceramide activates antitumor immunity against liver tumor: T. Tatsumi, et al.; Hepatol. Res. 41, 160 (2011)
Deletion of CD1d in adipocytes aggravates adipose tissue inflammation and insulin resistance in obesity: J.Y. Huh, et al.; Diabetes 66, 835 (2017)
Migration, Distribution, and Safety Evaluation of Specific Phenotypic and Functional Mouse Spleen-Derived Invariant Natural Killer T2 Cells after Adoptive Infusion: Mediators Inflamm. 5170123 (2021)
Unique adipose tissue invariant natural killer T cell subpopulations control adipocyte turnover in mice: S.M. Han, et al.; Nature Commun. 14, 8512 (2023)

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