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S3944

Sigma-Aldrich

SEW2871

≥98% (HPLC), solid

Synonym(s):

5-[4-Phenyl-5-(trifluoromethyl)-2-thienyl]-3-[3-(trifluoromethyl)phenyl]- 1,2,4-oxadiazole

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About This Item

Empirical Formula (Hill Notation):
C20H10F6N2OS
CAS Number:
256414-75-2
Molecular Weight:
440.36
MDL number:
MFCD00096600
UNSPSC Code:
12352211
PubChem Substance ID:
24724607
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

storage condition

protect from light

color

white

mp

94.5-95.3 °C

solubility

DMSO: ≥10 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

FC(F)(F)c1cccc(c1)-c2noc(n2)-c3cc(-c4ccccc4)c(s3)C(F)(F)F

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

InChI key

OYMNPJXKQVTQTR-UHFFFAOYSA-N

Gene Information

human ... S1PR1(1901) , S1PR2(9294) , S1PR3(1903) , S1PR4(8698) , S1PR5(53637)

Application

SEW2871 has been used as a sphingosine-1 phosphate (S1P) receptor agonist to determine the effects of reconstituting plasma apolipoprotein M (ApoM) /S1P on vascular permeability in mice.
SEW2871 was used to mimic the effects of sphingosine-1 phosphate in HUVECs to study the innate immunity rendered by long pentraxin 3.

Biochem/physiol Actions

SEW2871 is a selective agonist of spingosine-1 phosphate receptor. It exacerbates reperfusion arrhythmias by significantly prolonging the duration of ventricular tachycardia and ventricular fibrillation. SEW2871 modulates inflammatory reactions by influencing lymphocyte homing and cell migration. By the inhibition of proinflammatory molecules, SEW2871 reduces acute renal failure due to ischemia.
Novel, selective human sphingosine-1-phosphate subtype 1 (S1P1) receptor agonist.

Features and Benefits

This compound is featured on the Lysophospholipid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Packaging

Light sensitive.

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sphingosine 1-phosphate ≥98.0% (TLC)

Sigma-Aldrich

73914

Sphingosine 1-phosphate

Frdoos Al Fadel et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 40(6), 1637-1645 (2016-12-23)
Ectopic lipid accumulation in hepatocytes has been identified as a risk factor for the progression of liver fibrosis and is strongly associated with obesity. In particular, the saturated fatty acid palmitate is involved in initiation of liver fibrosis via formation
Zhoumou Chen et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(21), 10557-10562 (2019-05-10)
Neuropathic pain afflicts millions of individuals and represents a major health problem for which there is limited effective and safe therapy. Emerging literature links altered sphingolipid metabolism to nociceptive processing. However, the neuropharmacology of sphingolipid signaling in the central nervous
Yayoi T Tsukada et al.
Journal of cardiovascular pharmacology, 50(6), 660-669 (2007-12-20)
Sphingosine-1-phosphate (S1P) has been considered to play an important role in ischemia/reperfusion (I/R) injury. We used SEW2871 (SEW), a novel receptor-selective agonist for S1P1, to elucidate the role of S1P1 in myocardial I/R. Isolated perfused rat hearts exposed to S1P
David T Bolick et al.
Arteriosclerosis, thrombosis, and vascular biology, 25(5), 976-981 (2005-03-12)
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
Y-Hh Lien et al.
Kidney international, 69(9), 1601-1608 (2006-03-31)
The pathogenesis of renal ischemia/reperfusion (I/R) injury involves activating several signal transduction cascade systems in endothelial cells. Sphingosine 1-phospate (S1P) maintains endothelial cell integrity and inhibits lymphocyte egress via the specific S1P(1) receptor, and may play a role in reducing
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