α-Gal-Cer

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Additional Information

Product Data
Synonyms	α-Gal-Cer; KRN7000
Properties
Formula	C₅₀H₉₉NO₉
MW	858.3
Purity	≥96% (NMR)
Appearance	Off-white solid.
Solubility	Soluble in pyridine.
Identity	Identity determined by ¹H-NMR.
InChi Key	LSUQVAFARUJTHS-ABBGRRHVSA-N
Product Type	Chemical
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
MSDS	Download

Product Description

Synthetic. Originally isolated from the marine sponge Angelas mauritianus [1].
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].

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Product 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)

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