810205P
Avanti
NBD Sphingosine
omega(7-nitro-2-1,3-benzoxadiazol-4-yl)(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol, powder
Synonym(s):
D-erythro-Sphingosine-N-NBD
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About This Item
Empirical Formula (Hill Notation):
C24H39N5O5
CAS Number:
Molecular Weight:
477.60
UNSPSC Code:
12352211
NACRES:
NA.25
Recommended Products
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 250 μg (810205P-250ug)
pkg of 1 × 50 μg (810205P-50ug)
manufacturer/tradename
Avanti Polar Lipids 810205P
shipped in
dry ice
storage temp.
−20°C
SMILES string
OC[C@@](N)([H])[C@]([H])(O)/C=C/CCCCCCCCCCCCCNC1=CC=C([N+]([O-])=O)C2=NON=C21
General description
Sphingosine is the most bioactive sphingoid and a constituent of cell membrane. NBD sphingosine is a derivative of sphingosine tagged with the fluorophore, 7-nitro-2-1,3-benzoxadiazol-4-yl (NBD) group.
Application
NBD Sphingosine or omega(7-nitro-2-1,3-benzoxadiazol-4-yl)(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol has been used to measure sphingosine kinase 1 (SPHK1) and sphingosine kinase 2 (SPK2) activity. NBD Sphingosine may be used as a negative control to determine the binding of Atg12-Atg5 conjugate with phosphatidylethanolamine(PE)-containing liposomes and to label sphingosine kinase 1 (SphK1) to determine its role in endocytic membrane trafficking.
Biochem/physiol Actions
Sphingosine is the precursor of ceramide. It plays a major role as a selective inhibitor of protein kinase C.
Packaging
5 mL Amber Glass Screw Cap Vial (810205P-250UG)
5ML Amber Glass Screw Cap Vial (810205P-50UG)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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Sphingosine kinase 2 activates autophagy and protects neurons against ischemic injury through interaction with Bcl-2 via its putative BH3 domain
Song DD, et al.
Cell Death & Disease, 8(7), e2912-e2912 (2017)
F-Xabier Contreras et al.
Biophysical journal, 90(11), 4085-4092 (2006-03-15)
Sphingosine, at 5-15 mol % total lipids, remarkably increases the permeability to aqueous solutes of liposomal and erythrocyte ghost membranes. The increased permeability cannot be interpreted in terms of leakage occurring at the early stages of a putative membrane solubilization
Dan-Dan Song et al.
Cell death & disease, 8(7), e2912-e2912 (2017-07-07)
Our previous findings suggest that sphingosine kinase 2 (SPK2) mediates ischemic tolerance and autophagy in cerebral preconditioning. The aim of this study was to determine by which mechanism SPK2 activates autophagy in neural cells. In both primary murine cortical neurons
Sphingosine increases the permeability of model and cell membranes
Contreras FX, et al.
Biophysical Journal, 90(11), 4085-4092 (2006)
Santiago Lima et al.
The Journal of biological chemistry, 292(8), 3074-3088 (2017-01-05)
The balance between cholesterol and sphingolipids within the plasma membrane has long been implicated in endocytic membrane trafficking. However, in contrast to cholesterol functions, little is still known about the roles of sphingolipids and their metabolites. Perturbing the cholesterol/sphingomyelin balance
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