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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)

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
MDL number:
MFCD00870345
UNSPSC Code:
12352211
NACRES:
NA.25

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (810205X-250ug)

manufacturer/tradename

Avanti Research™ - A Croda Brand 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.[1] 7-nitro-2-1,3-benzoxadiazol-4-yl (NBD) sphingosine is a derivative of sphingosine attached with the fluorescent probe, NBD group.[2]

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[3]
  • to label sphingosine kinase 1 (SphK1) in order to determine its role in endocytic membrane trafficking[4]
  • to generate 7-nitrobenz-2-oxa-1,3-diazol-4-yl (NBD)-ceramide C16[5]

Biochem/physiol Actions

Sphingosine serves as a precursor for ceramide. It is involved in the inhibition of protein kinase C in human platelets.[1]

Packaging

5 mL Amber Glass Screw Cap Vial (810205X-250ug)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

>125.5 °F

flash_point_c

> 51.95 °C

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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)
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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