SEW 2871

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Cat.No. 2284 - SEW 2871 | C20H10F6N2OS | CAS No. 256414-75-2
Description: Cell-permeable, selective S1P1 receptor agonist
Chemical Name: 5-[4-Phenyl-5-(trifluoromethyl)thiophen-2-yl]-3-[3-(trifluoromethyl)phenyl]1,2,4-oxadiazole
Purity: ≥99% (HPLC)
Datasheet
Citations (6)
Reviews
Literature

Biological Activity

Novel, potent and selective sphingosine-1-phosphate 1 (S1P1) receptor agonist. Activates S1P1 receptor with an EC50 of 13 nM, but does not activate S1P2, S1P3, S1P4 or S1P5 receptors at concentrations up to 10 μM. Cell-permeable and active in vivo.

Technical Data

M. Wt 440.36
Formula C20H10F6N2OS
Storage Store at RT
Purity ≥99% (HPLC)
CAS Number 256414-75-2
PubChem ID 4077460
InChI Key OYMNPJXKQVTQTR-UHFFFAOYSA-N
Smiles FC(F)(F)C1=C(C=C(S1)C1=NC(=NO1)C1=CC(=CC=C1)C(F)(F)F)C1=CC=CC=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 8.81 20
ethanol 8.81 20

Preparing Stock Solutions

The following data is based on the product molecular weight 440.36. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.2 mM 11.35 mL 56.77 mL 113.54 mL
1 mM 2.27 mL 11.35 mL 22.71 mL
2 mM 1.14 mL 5.68 mL 11.35 mL
10 mM 0.23 mL 1.14 mL 2.27 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Hale et al (2004) A rational utilization of high-throughput screening affords selective, orally bioavailable 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonists. J.Med.Chem. 47 6662 PMID: 15615513

Sanna et al (2004) Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate. J.Biol.Chem. 279 13839 PMID: 14732717

Bolick et al (2005) Sphingosine-1-phosphate prevents tumor necrosis factor-α-mediated monocyte adhesion to aortic endothelium in mice. Arterioscler.Thromb.Vasc.Biol. 25 976 PMID: 15761190


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Keywords: SEW 2871, SEW 2871 supplier, Cell-permeable, selective, S1P1, receptors, agonists, EDG1, sphingosine-1-phosphate, SEW2871, Sphingosine-1-phosphate, Receptors, 2284, Tocris Bioscience

6 Citations for SEW 2871

Citations are publications that use Tocris products. Selected citations for SEW 2871 include:

Matsushima-Nishiwaki et al (2018) Sphingosine 1-phosphate (S1P) reduces hepatocyte growth factor-induced migration of hepatocellular carcinoma cells via S1P receptor 2. PLoS One 13 e0209050 PMID: 30543684

Zhang et al (2010) Sphingosine-1-phosphate prevents permeability increases via activation of endothelial sphingosine-1-phosphate receptor 1 in rat venules. Am J Nephrol 299 H1494 PMID: 20729401

Kim et al (2010) Isoflurane protects human kidney proximal tubule cells against necrosis via sphingosine kinase and sphingosine-1-phosphate generation. Cardiovasc Res 31 353 PMID: 20234131

Frias et al (2010) Native and reconstituted HDL protect cardiomyocytes from doxorubicin-induced apoptosis. Nature 85 118 PMID: 19700468

Beckham et al (2012) Acid ceramidase-mediated production of sphingosine 1-phosphate promotes prostate cancer invasion through upregulation of cathepsin B. Int J Cancer 131 2034 PMID: 22322590

O'Sullivan et al (2014) Sphingosine 1-phosphate (S1P) induced interleukin-8 (IL-8) release is mediated by S1P receptor 2 and nuclear factor κB in BEAS-2B cells. PLoS One 9 e95566 PMID: 24743449


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