810205X
Avanti
NBD Sphingosine
omega(7-nitro-2-1,3-benzoxadiazol-4-yl)(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol, chloroform:methanol (8:2)
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Synonym(s):
D-erythro-Sphingosine-N-NBD
Empirical Formula (Hill Notation):
C24H39N5O5
Recommended Products
Assay
>99% (TLC)
form
liquid
packaging
pkg of 1 × 1 mL (810205X-250ug)
manufacturer/tradename
Avanti Polar Lipids 810205X
concentration
0.25 mg/mL (810205X-250ug)
shipped in
dry ice
storage temp.
−20°C
General description
Sphingosine is the most bioactive sphingoid with the common long chain base in sphingolipids. It is a constituent of the cell membrane. 7-nitro-2-1,3-benzoxadiazol-4-yl (NBD) sphingosine is a derivative of sphingosine attached with the fluorescent probe, 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 may be used:
- as a negative control to determine the binding of Atg12-Atg5 conjugate with phosphatidylethanolamine (PE)-containing liposomes
- to label sphingosine kinase 1 (SphK1) in order to determine its role in endocytic membrane trafficking
- to generate 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)-ceramide C16
Biochem/physiol Actions
Sphingosine serves as a precursor for ceramide. It is involved in the inhibition of protein kinase C in human platelets.
Packaging
5 mL Amber Glass Screw Cap Vial (810205X-250ug)
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 1 - STOT SE 3
Target Organs
Central nervous system
WGK
WGK 3
Flash Point(F)
>125.5 °F
Flash Point(C)
> 51.95 °C
Regulatory Information
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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
Sphingosine increases the permeability of model and cell membranes
Contreras FX, et al.
Biophysical Journal, 90(11), 4085-4092 (2006)
Body Mass Index in Multiple Sclerosis modulates ceramide-induced DNA methylation and disease course.
Kamilah Castro et al.
EBioMedicine, 43, 392-410 (2019-04-15)
Multiple Sclerosis (MS) results from genetic predisposition and environmental variables, including elevated Body Mass Index (BMI) in early life. This study addresses the effect of BMI on the epigenome of monocytes and disease course in MS. Fifty-four therapy-naive Relapsing Remitting
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
Eun A Ra et al.
Nature communications, 7, 11726-11726 (2016-05-25)
Autophagy is responsible for the bulk degradation of cytosolic constituents and plays an essential role in the intestinal epithelium by controlling beneficial host-bacterial relationships. Atg5 and Atg7 are thought to be critical for autophagy. However, Atg5- or Atg7-deficient cells still
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