4-Fluorophenylundecanoyl-alpha-galactosylceramide
| Code | Size | Price |
|---|
| AG-CN2-0519-C500 | 500 ug | £280.00 |
Quantity:
| AG-CN2-0519-M001 | 1 mg | £420.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
BLUE ICE
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
7DW8-5; (2S,3S,4R)-1-O-(alpha-D-Galactopyranosyl)-N-(11-(4-fluorophenyl)undeaconyl)-2-amino-1,3,4-octadecanetriol
Appearance:
Off-white solid.
CAS:
1056025-00-3
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Aliquot into gl
InChi:
InChI=1S/C41H72FNO9/c1-2-3-4-5-6-7-8-9-10-14-17-20-23-34(45)37(47)33(30-51-41-40(50)39(49)38(48)35(29-44)52-41)43-36(46)24-21-18-15-12-11-13-16-19-22-31-25-27-32(42)28-26-31/h25-28,33-35,37-41,44-45,47-50H,2-24,29-30H2,1H3,(H,43,46)/t33-,34?,35+,37-,38-,39-,40+,41-/m0/s1
InChiKey:
GIXLTJURKGIRDL-KDGVDGCMSA-N
Long Description:
Chemical. CAS: 1056025-00-3. Formula: C41H72FNO9. MW: 742. . Glycolipid derivative of alpha-GalCer. Potent stimulator of invariant natural killer T (iNKT) cells (140-fold lower EC50 compared to alpha-GalCer). Specific ligand (strongest binding affinity) of the lipid-binding MHC class I-like protein CD1d in human and mouse NKT cells with. Show to induce secretion of key cytokines such as IFN-gamma and IL-12, and activate autologous dendritic cells, as well as binding to CD1d and the invariant T cell receptor (invTCR). Potent vaccine adjuvant (~100 times stronger than alpha-GalCer) that can harness and amplify the immunotherapeutic potential of NKT cells to treat certain microbial infections such as malaria and HIV. Potential immunotherapeutic to treat cancer, infectious diseases and autoimmune diseases.
Molecular Formula:
C41H72FNO9
Molecular Weight:
742
Other data:
NOTE: This glycolipid compound can be challenging in terms of solubility. A DMSO solution in phosphate buffered saline (PBS) with 10% Tween-20 or -80 remained clear at 4°C for 7 days. The same DMSO solution in PBS with 5% Tween-80 remained clear at 4°C for 5 days. After more than 20 days at 4°C the samples become a "gel-like" substance, except the solution in PBS with 10% Tween-80 which remained clear with some floats.
Package Type:
Vial
Product Description:
Glycolipid derivative of alpha-GalCer. Potent stimulator of invariant natural killer T (iNKT) cells (140-fold lower EC50 compared to alpha-GalCer). Specific ligand (strongest binding affinity) of the lipid-binding MHC class I-like protein CD1d in human and mouse NKT cells with. Show to induce secretion of key cytokines such as IFN-gamma and IL-12, and activate autologous dendritic cells, as well as binding to CD1d and the invariant T cell receptor (invTCR). Potent vaccine adjuvant (~100 times stronger than alpha-GalCer) that can harness and amplify the immunotherapeutic potential of NKT cells to treat certain microbial infections such as malaria and HIV. Potential immunotherapeutic to treat cancer, infectious diseases and autoimmune diseases.
Purity:
>95% (1H-NMR, 13C-NMR and TLC (CH2Cl2/MeOH 85:15)
SMILES:
O[C@H]1[C@@H](O)[C@@H](CO)O[C@H](OC[C@@H]([C@@H]([C@@H](CCCCCCCCCCCCCC)O)O)NC(CCCCCCCCCCC2=CC=C(F)C=C2)=O)[C@@H]1O
Solubility Chemicals:
Soluble in DMSO.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Quantitative microarray analysis of intact glycolipid-CD1d interaction and correlation with cell-based cytokine production: P.H. Liang, et al.; JACS 130, 12348 (2008) | Design of a potent CD1d-binding NKT cell ligand as a vaccine adjuvant: X. Li, et al.; PNAS 107, 13010 (2010) | In vivo protection provided by a synthetic new alpha-galactosyl ceramide analog against bacterial and viral infections in murine models: K.H. Lin, et al.; Antimicrob. Agents Chemother. 54, 4129 (2010) | Clinical development of a novel CD1d-binding NKT cell ligand as a vaccine adjuvant: N.N. Padte, et al.; Clin. Immunol. 140, 142 (2011) (Review) | A glycolipid adjuvant, 7DW8-5, enhances CD8+ T cell responses induced by an adenovirus-vectored malaria vaccine in non-human primates: N.N. Padte, et al.; PLoS One 8, e78407 (2013) | Effective cancer vaccine platform based on attenuated salmonella and a type III secretion system: X. Xu, et al.; Cancer Res. 74, 6260 (2014) | Improving Mycobacterium bovis bacillus Calmette-Guerin as a vaccine delivery vector for viral antigens by incorporation of glycolipid activators of NKT cells: M.M. Venkataswamy, et al.; PLoS One 9, e108383 (2014) | Colocalization of a CD1d-Binding Glycolipid with a Radiation-Attenuated Sporozoite Vaccine in Lymph Node-Resident Dendritic Cells for a Robust Adjuvant Effect: X. Li, et al.; J. Immunol. 195, 2710 (2015) | Lipid and Carbohydrate Modifications of alpha-Galactosylceramide Differently Influence Mouse and Human Type I Natural Killer T Cell Activation: A. Birkholz, et al.; J. Biol. Chem. 290, 17206 (2015) | Co-administration of alpha-GalCer analog and TLR4 agonist induces robust CD8(+) T-cell responses to PyCS protein and WT-1 antigen and activates memory-like effector NKT cells: J.G. Coelho-Dos-Reis, et al.; Clin. Immunol. 168, 6 (2016) | A potent adjuvant effect of a CD1d-binding NKT cell ligand in human immune system mice: X. Li, et al.; Expert. Rev. Vaccines 16, 73 (2017) | Co-localization of a CD1d-binding glycolipid with an adenovirus-based malaria vaccine for a potent adjuvant effect: X. Li, et al.; Vaccine 35, 3171 (2017) | Retinoic acid induction of CD1d expression primes chronic lymphocytic leukemia B cells for killing by CD8+ invariant natural killer T cells: Y.G. Ghnewa, et al.; Clin. Immunol. 183, 91 (2017)