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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:
799268-47-6
Molecular Weight:
477.60
UNSPSC Code:
12352211
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 250 μg (810205P-250ug)
pkg of 1 × 50 μg (810205P-50ug)

manufacturer/tradename

Avanti Research™ - A Croda Brand 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)
Sphingosine increases the permeability of model and cell membranes
Contreras FX, et al.
Biophysical Journal, 90(11), 4085-4092 (2006)
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
TP53 is required for BECN1-and ATG5-dependent cell death induced by sphingosine kinase 1 inhibition
Lim S, et al.
Autophagy, 14(6), 942-957 (2018)
Santiago Lima et al.
Autophagy, 14(6), 942-957 (2018-01-26)
The bioactive sphingolipid metabolite sphingosine-1-phosphate (S1P) and the enzyme that produces it, SPHK1 (sphingosine kinase 1), regulate many processes important for the etiology of cancer. It has been suggested that SPHK1 levels are regulated by the tumor suppressor protein TP53
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