4-Fluorophenylundecanoyl-α-galactosylceramide

CHF 350.00
In stock
AG-CN2-0519-C500500 µgCHF 350.00
AG-CN2-0519-M0011 mgCHF 530.00
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Product Details
Synonyms 7DW8-5; (2S,3S,4R)-1-O-(alpha-D-Galactopyranosyl)-N-(11-(4-fluorophenyl)undeaconyl)-2-amino-1,3,4-octadecanetriol
Product Type Chemical
Properties
Formula

C41H72FNO9

MW 742.0
CAS 1056025-00-3
Purity Chemicals ≥95% (1H-NMR, 13C-NMR and TLC (CH2Cl2/MeOH 85:15)
Appearance Off-white solid.
Solubility Soluble in DMSO.
Identity Identity determined by 1H-NMR and MS.
Other Product 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.

InChi Key GIXLTJURKGIRDL-KDGVDGCMSA-N
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
Shipping and Handling
Shipping BLUE ICE
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Aliquot into glass vials.
Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Glycolipid derivative of α-GalCer.
  • Potent stimulator of invariant natural killer T (iNKT) cells (140-fold lower EC50 compared to α-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-γ 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 α-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.
Product References
  1. Quantitative microarray analysis of intact glycolipid-CD1d interaction and correlation with cell-based cytokine production: P.H. Liang, et al.; JACS 130, 12348 (2008)
  2. Design of a potent CD1d-binding NKT cell ligand as a vaccine adjuvant: X. Li, et al.; PNAS 107, 13010 (2010)
  3. 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)
  4. 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)
  5. 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)
  6. Effective cancer vaccine platform based on attenuated salmonella and a type III secretion system: X. Xu, et al.; Cancer Res. 74, 6260 (2014)
  7. 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)
  8. 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)
  9. Lipid and Carbohydrate Modifications of α-Galactosylceramide Differently Influence Mouse and Human Type I Natural Killer T Cell Activation: A. Birkholz, et al.; J. Biol. Chem. 290, 17206 (2015)
  10. Co-administration of α-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)
  11. 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)
  12. 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)
  13. 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)
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