S3944

SEW2871

Name: SEW2871
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24724607

UNSPSC Code:

12352211

MDL number:

MFCD00096600

Product Name

SEW2871, ≥98% (HPLC), solid

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

SMILES string

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

InChI key

OYMNPJXKQVTQTR-UHFFFAOYSA-N

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

Quality Level

100

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

Novel, selective human sphingosine-1-phosphate subtype 1 (S1P1) receptor agonist.

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.

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

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

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Involvement of Sphingosine 1-Phosphate in Palmitate-Induced Non-Alcoholic Fatty Liver Disease.

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

Sphingosine-1-phosphate receptor 1 activation in astrocytes contributes to neuropathic pain.

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

S1P1-selective agonist SEW2871 exacerbates reperfusion arrhythmias.

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

Sphingosine-1-phosphate (S1P) induces potent anti-inflammatory effects in vitro and in vivo by S1P receptor 4-mediated suppression of 5-lipoxygenase activity.

Jasmin Fettel et al.

FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 33(2), 1711-1726 (2018-09-07)

Sphingosine-1-phosphate (S1P) is involved in the regulation of important cellular processes, including immune-cell trafficking and proliferation. Altered S1P signaling is strongly associated with inflammation, cancer progression, and atherosclerosis; however, the mechanisms underlying its pathophysiologic effects are only partially understood. This

Recruitment of mesenchymal stem cells and macrophages by dual release of stromal cell-derived factor-1 and a macrophage recruitment agent enhances wound closure.

Yang-Hee Kim et al.

Journal of biomedical materials research. Part A, 104(4), 942-956 (2015-12-26)

In this study, the wound closure of mouse skin defects was examined in terms of recruitment of mesenchymal stem cells (MSC) and macrophages. For the cells recruitment, stromal derived factor-1 (SDF-1) of a MSC recruitment agent and sphingosine-1 phosphate agonist

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