4-Fluorophenylundecanoyl-α-galactosylceramide (7DW8-5)

Cat. No. AG-CN2-0519-M001



 Size:  1mg  /   (500 µg, Ask inquiry)

 

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.

 

Description
   

• 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.

 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)

14. Zhao, M., Svensson, M. N. D., Venken, K., Chawla, A., Liang, S., Engel, I., ... & Kronenberg, M. (2018). Altered thymic differentiation and modulation of arthritis by invariant NKT cells expressing mutant ZAP70. Nature Communications, 9(1), 2627.

15. Lang, G. A., Norman, K., Amadou Amani, S., Shadid, T. M., Ballard, J. D., & Lang, M. L. (2022). Use of a Clostridioides difficile murine immunization and challenge model to evaluate single and combination vaccine adjuvants consisting of alum and NKT cell-activating ligands. Frontiers in Immunology, 12, 818734.