D-erythro-Sphingosine-1-phosphate CAS: 26993-30-6
MF: C18H38NO5P
MW: 379.48
A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.
  1. INICIO
  2. QUÍMICOS
  3. Protein-Interacting Inhibitors, Activators & Substrates
  4. Protein Activadores
  5. GPR12 Activadores
  6. D-erythro-Sphingosine-1-phosphate

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

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Nombres Alternativos: (2S,3R,4E)-2-Amino-4-octadecene-1,3-diol 1-(Dihydrogen phosphate); Sphingosine-1-phosphate
Solicitud: A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12
Número de CAS: 26993-30-6
Pureza: ≥95%
Peso Molecular: 379.48
Fórmula Molecular: C18H38NO5P
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
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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

1. Van Veldhoven, P.P., et al. 1989. J. Lipid Res. 30: 611-616. PMID: 2754341
2. Desai, N.N., et al. 1992. J. Biol. Chem. 267: 23122-23128. PMID: 1429659
3. Sadahira, Y., et al. 1992. Proc. Natl. Acad. Sci. U.S.A. 89: 9686-9690. PMID: 1409683
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5. Mattie, M., et al. 1994. J. Biol. Chem. 269: 3181-3188. PMID: 8106352
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9. Spiegel, S., et al. 2000. Biochim. Biophys. Acta. 1484: 107-116. PMID: 10760461
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12. Watterson, K.R., et al. 2005. Cell. Signal. 17: 289-298. PMID: 15567060

Apariencia :
Powder
Estado de Materia :
Solid
Solubilidad :
Soluble in 0.3M NaOH (~4 mg/ml). Insoluble in water.
ALMACENAMIENTO :
Store at -20° C
Punto de Fusión :
179-189° C
Indice de Refracción :
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)
Valores de pK :
pKa: 1.76, pKb: 9.8
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
3
RTECS :
RG2260500
PubChem CID :
5283560
Número MDL :
MFCD00270077
SMILES :
CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O

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Citaciones 1 a 5 de un total de 5

PMID: # 31455837  2019. Cancer Gene Ther.

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.

Citaciones 1 a 5 de un total de 5
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