Chemistry:Alpha-Galactosylceramide
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| Names | |
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| IUPAC name
N-[(2S,3S,4R)-1-(α-D-Galactopyranosyloxy)-3,4-dihydroxyoctadecan-2-yl]hexacosanamide
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| Preferred 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
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| Identifiers | |
3D model (JSmol)
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| 7326597 | |
| ChEBI | |
| ChEMBL | |
PubChem CID
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| UNII | |
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| Properties | |
| 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 | |
alpha-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 et al. (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.
- ↑ Godfrey, Dale I.; Kronenberg, Mitchell (2004-11-15). "Going both ways: Immune regulation via CD1d-dependent NKT cells" (in en). Journal of Clinical Investigation 114 (10): 1379–1388. doi:10.1172/jci200423594. ISSN 0021-9738. PMID 15545985.
- ↑ Cerundolo, Vincenzo; Silk, Jonathan D.; Masri, S. Hajar; Salio, Mariolina (January 2009). "Harnessing invariant NKT cells in vaccination strategies" (in En). Nature Reviews Immunology 9 (1): 28–38. doi:10.1038/nri2451. ISSN 1474-1741. PMID 19079136.
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