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Merck
CN

810220P

Avanti

C6-NBD Galactosyl Ceramide

Avanti Research™ - A Croda Brand

Synonym(s):

N-[6-[(7-nitro-2-1,3-benzoxadiazol-4-yl)amino]hexanoyl]-D-galactosyl-β1-1′-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C36H59N5O11
CAS Number:
170212-26-7
Molecular Weight:
737.88
MDL number:
MFCD03453619
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

C6-NBD Galactosyl Ceramide, Avanti Research™ - A Croda Brand 810220P, powder

SMILES string

[N+](=O)([O-])c1c2n[o]nc2c(cc1)NCCCCCC(=O)N[C@H]([C@H](O)\C=C\CCCCCCCCCCCCC)CO[C@@H]3O[C@@H]([C@@H]([C@@H]([C@H]3O)O)O)CO

InChI

1S/C36H59N5O11/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-28(43)26(24-50-36-35(47)34(46)33(45)29(23-42)51-36)38-30(44)19-16-14-17-22-37-25-20-21-27(41(48)49)32-31(25)39-52-40-32/h15,18,20-21,26,28-29,33-37,42-43,45-47H,2-14,16-17,19,22-24H2,1H3,(H,38,44)/b18-15

InChI key

ZYEQNDHFYIPTAY-LFUFHFQKSA-N

assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 250 μg (810220P-250ug)

manufacturer/tradename

Avanti Research™ - A Croda Brand 810220P

shipped in

dry ice

storage temp.

−20°C

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General description

C6-NBD Galactosyl Ceramide is a fluorescent analog of the sphingolipid, galactosyl ceramide. Its fluorescent property is due to presence of NBD (2-(4-nitro-2,1,3-benzoxadiazol-7-yl) aminoethyl) group.

Application

C6-NBD Galactosyl Ceramide is suitable for use as a substrate in neutral β-glycosylceramidase (GCase) activity assay.

Biochem/physiol Actions

Galactosyl ceramide is also known as galactocerebroside and is produced in the lumen of the endoplasmic reticulum. Galactosyl ceramide is a vaccine adjuvant, it stimulates natural killer T (NKT) cells to increase secretion of T helper type 1 (Th1) and T-helper type 2 (TH2) cytokines. Galactosyl ceramide accumulation in excess is responsible for diseases such as Krabbe′s disease. Galactocerebroside is a precursor of 3′-sulfo-galactosylceramide, a vital sulfoglycolipid found in the brain and other organs.

Packaging

5 mL Amber Glass Screw Cap Vial (810220P-250ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class

11 - Combustible Solids

Regulatory Information

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Distinct APCs explain the cytokine bias of $\alpha$-galactosylceramide variants in vivo
Bai LC, et al.
Journal of immunology (Baltimore, Md. : 1950), 188(7), 3053-3061 (2012)
Bernadette Breiden et al.
Annual review of biochemistry, 88, 461-485 (2019-06-22)
Glycosphingolipids are cell-type-specific components of the outer leaflet of mammalian plasma membranes. Gangliosides, sialic acid-containing glycosphingolipids, are especially enriched on neuronal surfaces. As amphi-philic molecules, they comprise a hydrophilic oligosaccharide chain attached to a hydrophobic membrane anchor, ceramide. Whereas glycosphingolipid
Fluorescent and Luminescent Probes for Biological Activity (1999)
Li Bai et al.
Journal of immunology (Baltimore, Md. : 1950), 188(7), 3053-3061 (2012-03-07)
α-Galactosylceramide represents a new class of vaccine adjuvants and immunomodulators that stimulate NKT cells to secrete Th1 and Th2 cytokines. Synthetic variants with short or unsaturated acyl chains exhibit a striking Th2 bias in vivo but no evidence of defect
Yanfeng Chen et al.
Neuromolecular medicine, 12(4), 306-319 (2010-08-04)
Sphingolipids (SP) are a complex class of molecules found in essentially all eukaryotes and some prokaryotes and viruses where they influence membrane structure, intracellular signaling, and interactions with the extracellular environment. Because of the combinatorial nature of their biosynthesis, there
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