alpha-Galactosylceramide
Product Code: AG-CN2-0013
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0013-C250 | 250 ug | £120.00 |
Quantity:
| AG-CN2-0013-M001 | 1 mg | £180.00 |
Quantity:
| AG-CN2-0013-M005 | 5 mg | £690.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Blue Ice
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
alpha-Gal-Cer; KRN7000
Appearance:
White to off-white solid.
CAS:
158021-47-7
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Aliquot into glass vials.
InChi:
1S/C50H51NO9.24H/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2;;;;;;;;;;;;;;;;;;;;;;;;/h1,42-44,46-50,52-53,55-58H,4,6,8,10,12,14,16,28,30,32,34,36,38-41H2,2H3,(H,51,54);;;;;;;;;;;;;;;;;;;;;;;;/t42-,43?,44+,46-,47-,48-,49+,50-;;;;;;;;;;;;;;;;;;;;;;;;/m0............/s1
InChiKey:
LSUQVAFARUJTHS-ABBGRRHVSA-N
Long Description:
Chemical. CAS: 158021-47-7. Formula: C50H99NO9. MW: 858.3. Synthetic. Originally isolated from the marine sponge Angelas mauritianus. Immunostimulant. Potent stimulator of natural killer T (NKT) cells. Specific ligand of the lipid-binding MHC class I-like protein CD1d in human and mouse NKT cells. Protects against LPS-induced shock. Potent antitumor compound.
MDL:
MFCD00939559
Molecular Formula:
C50H99NO9
Molecular Weight:
858.3
Package Type:
Vial
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].
Purity:
>96% (NMR)
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
Solubility Chemicals:
Soluble in pyridine. Solubilization in Tween20 or PBS for cell culture use see online protocol.
Source / Host:
Synthetic. Originally isolated from the marine sponge Agelas mauritianus.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
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) | alpha-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)