D-erythro-Sphingosine-1-phosphateA ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12

D-erythro-Sphingosine-1-phosphate (CAS 26993-30-6)

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Synonym: (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(Dihydrogen phosphate); Sphingosine-1-phosphate
Application: A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12
CAS Number: 26993-30-6
Purity: ≥95%
Molecular Weight: 379.48
Molecular Formula: C18H38NO5P
* Refer to Certificate of Analysis for lot specific data (including water content).
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D-erythro-Sphingosine-1-phosphate(S1P) is a polar sphingolipid metabolite which regulates diverse cellular responses including cell growth, survival and migration. S1P was reported to stimulate DNA synthesis and cell division in quiescent cultures of Swiss 3T3 fibroblasts and to trigger the dual signal transduction pathways of calcium mobilization and PC-PLD (phospholipase D) activation. S1P serves as a second messenger for intracellular calcium mobilization in U-937 cells (sc-2239) and decreases cellular cAMP. Recent studies show that S1P is a G-protein-coupled receptor (GPCR) ligand for the EDG-1 family, including EDG-1, -3, -5, -6 and -8. This bioactive lipid mediator has been shown to stimulate the ERK pathway and to also counteract the ceramide-induced activation of stress-activated protein kinase (SAPK/JNK). Researchers have also found that S1P is a strong inhibitor of cell motility and phagokinesis in B16 melanoma cells. Additionally, it induces rapid and transient tyrosine phosphorylation of epidermal growth factor receptor (EGFR) and c-Met in gastric cancer cells. S1P has also been known as a tumor-promoting lipid. Suggested to be an activator of GPR3, GPR6, and GPR12. D-erythro-Sphingosine-1-phosphate is an activator of EDG-1, EDG-3, EDG-2, EDG-4 and EDG-5.


References

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Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in 0.3M NaOH (~4 mg/ml). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
179-189° C
Refractive Index :
n20D 1.50
IC50 :
Sphingosine 1-phosphate receptor Edg-1 : IC50 = 0.78 nM (human); Sphingosine 1-phosphate receptor Edg-8: IC50 = 2 nM (human); Sphingosine 1-phosphate receptor Edg-6: IC50 = 1.04 nM (human); Sphingosine 1-phosphate receptor Edg-3 : IC50 = 0.92 nM (human)
pK Values :
pKa: 1.76, pKb: 9.8
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
RG2260500
PubChem CID :
5283560
MDL Number :
MFCD00270077
SMILES :
CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O

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D-erythro-Sphingosine-1-phosphate  Product Citations

See how others have used D-erythro-Sphingosine-1-phosphate. Click on the entry to view the PubMed entry .

Citations 1 to 4 of 4 total

PMID: # 17255471  Novgorodov, AS. et al. 2007. FASEB J. 21: 1503-1514.

PMID: # 16926156  El-Shewy, HM. et al. 2006. J. Biol. Chem. 281: 31399-31407.

PMID: # 15377653  Argraves, KM. et al. 2004. J. Biol. Chem. 279: 50580-50590.

PMID: # 12855693  Pettus, BJ. et al. 2003. J. Biol. Chem. 278: 38206-38213.

Citations 1 to 4 of 4 total
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Rated 5 out of 5 by from Novgorodov et al Novgorodov et al. (PubMed ID 17255471) found D-erythro-Sphingosine-1-phosphate to be a specific and potent inhibitor of integrin-mediated oligodendrocyte precursor cell (OPC) migration. -SCBT Publication Review
Date published: 2015-05-27
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