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ProductsBack/4-Fluorophenylundecanoyl-alpha-galactosylceramide [7DW8-5]
Chemical Structure
Chemical Structure
Chemical Structure

4-Fluorophenylundecanoyl-alpha-galactosylceramide [7DW8-5]

Research Use Only
AG-CN2-0519
AdipoGen Life Sciences
Estimated Purity>95%
DownloadMSDS
Product group Chemicals
Molecular Weight742
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    4-Fluorophenylundecanoyl-alpha-galactosylceramide [1056025-00-3]
  • Delivery Days Customer
    10
  • Certification
    Research Use Only
  • Estimated Purity
    >95%
  • Molecular Formula
    C41H72FNO9
  • Molecular Weight
    742
  • Scientific 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. - 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.
  • 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
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

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)