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α-Galactosylceramide

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α-Galactosylceramide
alpha-galactosylceramide
Names
IUPAC name N-hexacosanamide
Systematic IUPAC name N-oxy}octadecan-2-yl]hexacosanamide
Other names α-GalCer, KRN7000
Identifiers
CAS Number
3D model (JSmol)
Abbreviations α-GalCer
Beilstein Reference 7326597
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 973-258-3
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C50H99NO9/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/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42-,43+,44+,46-,47-,48-,49+,50-/m0/s1Key: VQFKFAKEUMHBLV-BYSUZVQFSA-N
SMILES
  • CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N(CO1((((O1)CO)O)O)O)((CCCCCCCCCCCCCC)O)O
Properties
Chemical formula C50H99NO9
Molar mass 858.340 g·mol
Appearance White powder
Melting point 189–190 °C (372–374 °F; 462–463 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

α-Galactosylceramide (α-GalCer, KRN7000) is a synthetic glycolipid derived from structure-activity relationship studies of galactosylceramides isolated from the marine sponge Agelas mauritianus. α-GalCer is a strong immunostimulant and shows potent anti-tumour activity in many in vivo models.

Immunostimulatory properties

α-GalCer is a potent activator of iNKT cells, and a model CD1d antigen. The invariant T cell receptor of the iNKT cell is able to bind the CD1d:glycolipid complex leading to iNKT cell activation in both mice and humans.

Adjuvant activity

In combination with a peptide antigen, α-GalCer is able to stimulate a strong immune response against the epitope. The CD1d:glycolipid:TCR interaction activates the iNKT cell which can then activate the dendritic cell. This causes the release of a range of cytokines and licenses the dendritic cell to activate a peptide-specific T cell response. This adjuvant acts through this cellular interaction, rather than through classic pattern recognition receptor pathways.

References

  1. Morita, Masahiro; Motoki, Kazuhiro; Akimoto, Kohji; Natori, Takenori; Sakai, Teruyuki; Sawa, Eiji; Yamaji, Kazuo; Koezuka, Yasuhiko; Kobayashi, Eiichi (1995-06-01). "Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice". Journal of Medicinal Chemistry. 38 (12): 2176–2187. doi:10.1021/jm00012a018. ISSN 0022-2623. PMID 7783149.
  2. Godfrey, Dale I.; Kronenberg, Mitchell (2004-11-15). "Going both ways: Immune regulation via CD1d-dependent NKT cells". Journal of Clinical Investigation. 114 (10): 1379–1388. doi:10.1172/jci200423594. ISSN 0021-9738. PMC 525753. PMID 15545985.
  3. Cerundolo, Vincenzo; Silk, Jonathan D.; Masri, S. Hajar; Salio, Mariolina (January 2009). "Harnessing invariant NKT cells in vaccination strategies". Nature Reviews Immunology. 9 (1): 28–38. doi:10.1038/nri2451. ISSN 1474-1741. PMID 19079136. S2CID 38675164.
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