α-Galactosylceramide

α-Galactosylceramide
Names
	IUPAC name N-[(2S,3S,4R)-1-(α-D-Galactopyranosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
	Systematic IUPAC name N-[(2S,3S,4R)-3,4-Dihydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadecan-2-yl]hexacosanamide
	Other names α-GalCer, KRN7000
Identifiers
CAS Number	158021-47-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	7326597
ChEBI	CHEBI:466659;
ChEMBL	ChEMBL384200;
PubChem CID	2826713;
UNII	WX671898JF ;
CompTox Dashboard (EPA)	DTXSID40935847 ;
	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/s1 Key: VQFKFAKEUMHBLV-BYSUZVQFSA-N;
	SMILES CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H]([C@@H](CCCCCCCCCCCCCC)O)O;
Properties
Chemical formula	C50H99NO9
Molar mass	858.340 g·mol−1
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 [77 °F], 100 kPa). Infobox references

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.[1]

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.[2]

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.[3]

References

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.
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.
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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[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.