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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

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

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

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 Code

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
Lysosomal lipid storage diseases
Schulze H and Sandhoff K
Cold Spring Harbor Perspectives in Biology, 3(6), a004804-a004804 (2011)
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