SEW 2871Cell-permeable, selective S1P1 receptor agonist CAS# 256414-75-2 |
- Laminin (925-933)
Catalog No.:BCC1015
CAS No.:110590-60-8
- Epidermal Growth Factor Receptor Peptide (985-996)
Catalog No.:BCC1014
CAS No.:96249-43-3
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 256414-75-2 | SDF | Download SDF |
| PubChem ID | 4077460 | Appearance | Powder |
| Formula | C20H10F6N2OS | M.Wt | 440.36 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 20 mM in DMSO and to 20 mM in ethanol | ||
| Chemical Name | 5-[4-phenyl-5-(trifluoromethyl)thiophen-2-yl]-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole | ||
| SMILES | C1=CC=C(C=C1)C2=C(SC(=C2)C3=NC(=NO3)C4=CC(=CC=C4)C(F)(F)F)C(F)(F)F | ||
| Standard InChIKey | OYMNPJXKQVTQTR-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C20H10F6N2OS/c21-19(22,23)13-8-4-7-12(9-13)17-27-18(29-28-17)15-10-14(11-5-2-1-3-6-11)16(30-15)20(24,25)26/h1-10H | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 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. |
SEW 2871 Dilution Calculator
SEW 2871 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2709 mL | 11.3543 mL | 22.7087 mL | 45.4174 mL | 56.7717 mL |
| 5 mM | 0.4542 mL | 2.2709 mL | 4.5417 mL | 9.0835 mL | 11.3543 mL |
| 10 mM | 0.2271 mL | 1.1354 mL | 2.2709 mL | 4.5417 mL | 5.6772 mL |
| 50 mM | 0.0454 mL | 0.2271 mL | 0.4542 mL | 0.9083 mL | 1.1354 mL |
| 100 mM | 0.0227 mL | 0.1135 mL | 0.2271 mL | 0.4542 mL | 0.5677 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
- BAY 41-2272
Catalog No.:BCC7932
CAS No.:256376-24-6
- 7beta-Acetoxytaxuspine C
Catalog No.:BCN7219
CAS No.:256347-91-8
- Delta-Tocotrienol
Catalog No.:BCN6696
CAS No.:25612-59-3
- 1,6,7-Trihydroxyxanthone
Catalog No.:BCN5124
CAS No.:25577-04-2
- Efetaal
Catalog No.:BCN8494
CAS No.:2556-10-7
- 7-Methoxy-4-methylcoumarin
Catalog No.:BCN6540
CAS No.:2555-28-4
- 1-(4-Hydroxybenzoyl)glucose
Catalog No.:BCN6900
CAS No.:25545-07-7
- Propidium iodide
Catalog No.:BCC8015
CAS No.:25535-16-4
- Mayumbine
Catalog No.:BCN5123
CAS No.:25532-45-0
- Z-Ile-Glu-Pro-Phe-Ome
Catalog No.:BCC5526
CAS No.:255257-97-4
- Isoferulic acid
Catalog No.:BCN5122
CAS No.:25522-33-2
- Ibotenic acid
Catalog No.:BCC6591
CAS No.:2552-55-8
- Schleicheol 1
Catalog No.:BCN4661
CAS No.:256445-66-6
- Schleicheol 2
Catalog No.:BCN5125
CAS No.:256445-68-8
- Ac2-12
Catalog No.:BCC5826
CAS No.:256447-08-2
- Preisocalamendiol
Catalog No.:BCN5126
CAS No.:25645-19-6
- Dactylorhin A
Catalog No.:BCN8217
CAS No.:256459-34-4
- Nantenine
Catalog No.:BCN7788
CAS No.:2565-01-7
- Aponorhyoscine
Catalog No.:BCN1871
CAS No.:25650-56-0
- Cannabigerol
Catalog No.:BCN5127
CAS No.:25654-31-3
- 3,2'-Dihydroxy-4,4'-dimethoxychalcone
Catalog No.:BCN7742
CAS No.:2567-65-9
- CCK Octapeptide, non-sulfated
Catalog No.:BCC5709
CAS No.:25679-24-7
- Cimiracemoside C
Catalog No.:BCN5128
CAS No.:256925-92-5
- HU 308
Catalog No.:BCC5971
CAS No.:256934-39-1
A selective sphingosine-1-phosphate receptor 1 agonist SEW-2871 aggravates gastric cancer by recruiting myeloid-derived suppressor cells.[Pubmed:29036438]
J Biochem. 2018 Jan 1;163(1):77-83.
The immune status of tumor microenvironment in gastric cancer is poorly understood, which limits the development of novel strategies in this field. Sphingosine-1-phosphate (S1P) acts as an immune modulator, but the role of S1P in gastric cancer is elusive. Here, we aim to investigate S1P receptor 1 (S1P1)-mediated effect of S1P in gastric cancer. We generated a xenograft mouse model and used SEW-2871, a S1P1 specific agonist to activate S1P1 signalling. Tumor-infiltrating lymphocytes (TILs) were isolated and analysed using flow cytometry. Chemokine expression of tumor cells was evaluated using quantitative real-time polymerase chain reaction. Myeloid-derived suppressor cells (MDSCs) migration was assessed using Transwell chambers. SEW-2871 promoted tumor growth in our mouse model, and induced a higher level of MDSC and a reduced level of CD8+CD69+ T cells within tumor. Consistently, the anti-tumoral function of cytotoxic T lymphocytes was impaired in mice with SEW-2871 treatment. Additionally, SEW-2871 enhanced expression of several MDSC recruitment-associated chemokines (CXCL12, CXCL5 and CCL2) in tumor cells. These chemokines facilitated MDSC migration by interaction with CCR2, CXCR2 and CXCR4. S1P1 signalling promoted gastric cancer by enhancing chemokine expression in tumor cells and recruiting MDSC to tumor microenvironment, which impaired anti-tumoral function of TILs.
Sphingosine-1-phosphate prevents tumor necrosis factor-{alpha}-mediated monocyte adhesion to aortic endothelium in mice.[Pubmed:15761190]
Arterioscler Thromb Vasc Biol. 2005 May;25(5):976-81.
OBJECTIVE: Endothelial activation and monocyte adhesion to endothelium are key events in inflammation. Sphingosine-1-phosphate (S1P) is a sphingolipid that binds to G protein-coupled receptors on endothelial cells (ECs). We examined the role of S1P in modulating endothelial activation and monocyte-EC interactions in vivo. METHODS AND RESULTS: We injected C57BL/6J mice intravenously with tumor necrosis factor (TNF)-alpha in the presence and absence of the S1P1 receptor agonist SEW2871 and examined monocyte adhesion. Aortas from TNF-alpha-injected mice had a 4-fold increase in the number of monocytes bound, whereas aortas from TNF-alpha plus SEW2871-treated mice had few monocytes bound (P<0.0001). Using siRNA, we found that inhibiting the S1P1 receptor in vascular ECs blocked the ability of S1P to prevent monocyte-EC interactions in response to TNF-alpha. We examined signaling pathways downstream of S1P1 and found that 100 nM S1P increased phosphorylation of Akt and decreased activation of c-jun. CONCLUSIONS: Thus, we provide the first evidence that S1P signaling through the endothelial S1P1 receptor protects the vasculature against TNF-alpha-mediated monocyte-EC interactions in vivo.
A rational utilization of high-throughput screening affords selective, orally bioavailable 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonists.[Pubmed:15615513]
J Med Chem. 2004 Dec 30;47(27):6662-5.
Moderately potent, selective S1P(1) receptor agonists identified from high-throughput screening have been adapted into lipophilic tails for a class of orally bioavailable amino acid-based S1P(1) agonists represented by 7. Many of the new compounds are potent S1P(1) agonists that select against the S1P(2), S1P(3), and S1P(4) (although not S1P(5)) receptor subtypes. Analogues 18 and 24 are highly orally bioavailable and possess excellent pharmacokinetic profiles in the rat, dog, and rhesus monkey.
Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate.[Pubmed:14732717]
J Biol Chem. 2004 Apr 2;279(14):13839-48.
Sphingosine 1-phosphate (S1P) influences heart rate, coronary artery caliber, endothelial integrity, and lymphocyte recirculation through five related high affinity G-protein-coupled receptors. Inhibition of lymphocyte recirculation by non-selective S1P receptor agonists produces clinical immunosuppression preventing transplant rejection but is associated with transient bradycardia. Understanding the contribution of individual receptors has been limited by the embryonic lethality of the S1P(1) knock-out and the unavailability of selective agonists or antagonists. A potent, S1P(1)-receptor selective agonist structurally unrelated to S1P was found to activate multiple signals triggered by S1P, including guanosine 5'-3-O-(thio)triphosphate binding, calcium flux, Akt and ERK1/2 phosphorylation, and stimulation of migration of S1P(1)- but not S1P(3)-expressing cells in vitro. The agonist also alters lymphocyte trafficking in vivo. Use of selective agonism together with deletant mice lacking S1P(3) receptor reveals that agonism of S1P(1) receptor alone is sufficient to control lymphocyte recirculation. Moreover, S1P(1) receptor agonist plasma levels are causally associated with induction and maintenance of lymphopenia. S1P(3), and not S1P(1), is directly implicated in sinus bradycardia. The sustained bradycardia induced by S1P receptor non-selective immunosuppressive agonists in wild-type mice is abolished in S1P(3)-/- mice, whereas S1P(1)-selective agonist does not produce bradycardia. Separation of receptor subtype usage for control of lymphocyte recirculation and heart rate may allow the identification of selective immunosuppressive S1P(1) receptor agonists with an enhanced therapeutic window. S1P(1)-selective agonists will be of broad utility in understanding cell functions in vitro, and vascular physiology in vivo, and the success of the chemical approach for S1P(1) suggests that selective tools for the resolution of function across this broad lipid receptor family are now possible.
