α-Galactosylceramide

CHF 160.00
In stock
AG-CN2-0013-C250250 µgCHF 160.00
AG-CN2-0013-M0011 mgCHF 390.00
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Product Details
Synonyms α-Gal-Cer; KRN7000
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 ≥96% (NMR)
Appearance 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
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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 References
    1. Synthesis of alpha-, beta-monoglycosylceramides and four diastereomers of an alpha-galactosylceramide: M. Morita, et al.; Bioorg. Med. Chem. Lett. 5, 699 (1995)
    2. Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties: K. Motoki, et al.; Biol. Pharm. Bull. 18, 1487 (1995)
    3. Immunostimulatory activities of monoglycosylated alpha-D-pyranosylceramides: A. Uchimura, et al.; Bioorg. Med. Chem. 5, 2245 (1997)
    4. 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)
    5. Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides: K.O. Yu, et al.; PNAS 102, 3383 (2005)
    6. 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)
    7. Pivotal advance: alpha-galactosylceramide induces protection against lipopolysaccharide-induced shock: G. Sireci, et al.; J. Leukoc. Biol. 81, 607 (2007)
    8. α-Galactosylceramide activates antitumor immunity against liver tumor: T. Tatsumi, et al.; Hepatol. Res. 41, 160 (2011)
    9. Deletion of CD1d in adipocytes aggravates adipose tissue inflammation and insulin resistance in obesity: J.Y. Huh, et al.; Diabetes 66, 835 (2017)
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