| Identification | Back Directory | [Name]
C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z)) | [CAS]
151057-28-2 | [Synonyms]
C24:1 3&rsquo
N-Tetracosenoyl-(cis-15)-sulfatide
-sulfo Galactosylceramide (d18:1/24:1(15Z))
C24:1 3'-sulfo Galactosylceramide (d18:1/24:1(15Z))
15-Tetracosenamide, N-[(1S,2R,3E)-2-hydroxy-1-[[(3-O-sulfo-β-D-galactopyranosyl)oxy]methyl]-3-heptadecen-1-yl]-, (15Z)- | [Molecular Formula]
C48H91NO11S | [MOL File]
151057-28-2.mol | [Molecular Weight]
890.3 |
| Hazard Information | Back Directory | [Description]
C24:1 3’-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It is the predominate sulfatide species in mature myelin, and it accumulates at a higher rate than C24 3’-sulfo galactosylceramide in rat cerebellum from seven to 32 days of age when active myelination occurs.1 It interacts with C-type lectins and immunoglobulin-like receptors with the highest affinity for LMIR5.2 It induces production of MCP-1 in basophils but not mast cells and increases the activation of NFAT in a reporter assay via LMIR5. C24:1 3’-sulfo Galactosylceramide is an immunodominant species in myelin, is bound by CD1d in vitro, and increases proliferation in isolated mouse splenocytes.3 It reduces symptoms and increases survival in a mouse model of chronic relapsing-remitting experimental autoimmune encephalomyelitis (EAE) when used at a dose of 20 μg.4 It also decreases the number of inflammatory lesions and infiltrating mononuclear cells in the lumbar spinal cord of EAE mice. As this product is derived from a natural source, there may be variations in the sphingoid backbone. | [Uses]
Sulfo galactosylceramide (N-Nervonoyl Sulfatide; C24:1 Sulfatide) is a glycolipid and the major sulfolipid species in mature myelin. Sulfo galactosylceramide interacts with C-type lectins and immunoglobulin-like receptors, with the highest affinity for LMIR5. Sulfo galactosylceramide induces MCP-1 production by basophils but not mast cells, and increases NFAT activation via LMIR5. Sulfo galactosylceramide alleviates symptoms and improves survival in a mouse model of chronic relapsing-remitting experimental autoimmune encephalomyelitis (EAE), and reduces inflammatory lesions and the number of infiltrating mononuclear cells in the lumbar spinal cord of EAE mice. | [Definition]
ChEBI: 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine is an N-acyl-beta-D-galactosylsphingosine having a sulfo group at the 3-position on the galactose ring and (15Z)-tetracos-15-enoyl as the N-acyl group. It has a role as an epitope. It is a galactosylceramide sulfate and a N-acyl-beta-D-galactosylsphingosine. It is a conjugate acid of a 1-(3-O-sulfo-beta-D-galactosyl)-N-[(15Z)-tetracos-15-enoyl]sphingosine(1-). | [References]
1. Marbois, B.N., Faull, K.F., Fluharty, A.L., et al. Analysis of sulfatide from rat cerebellum and multiple sclerosis white matter by negative ion electrospray mass spectrometry Biochim. Biophys. Acta 1484(1),59-70(2000).
2. Phongsisay, V., Iizasa, E., Hara, H., et al. 3-O-sulfo-β-D-galactose moiety of endogenous sulfoglycolipids is a potential ligand for immunoglobulin-like receptor LMIR5 Mol. Immunol. 63(2),595-599(2015).
3. Zajonc, D.M., Maricic, I., Wu, D., et al. Structural basis for CD1d presentation of a sulfatide derived from myelin and its implications for autoimmunity J. Exp. Med. 202(11),1517-1526(2005).
4. Maricic, I., Halder, R., Bischof, F., et al. Dendritic cells and anergic type I NKT cells play a crucial role in sulfatide-mediated immune regulation in experimental autoimmune encephalomyelitis J. Immunol. 193(3),1035-1046(2014). |
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Enzo Biochem Inc
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