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S3944

SEW2871

Name: SEW2871
Brand: SIGMA

≥98% (HPLC), solid

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):

C₂₀H₁₀F₆N₂OS

Numéro CAS:

256414-75-2

Poids moléculaire :

440.36

Numéro MDL:

MFCD00096600

Code UNSPSC :

12352211

ID de substance PubChem :

24724607

Nomenclature NACRES :

NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Conditions de stockage

protect from light

Couleur

white

Pf

94.5-95.3 °C

Solubilité

DMSO: ≥10 mg/mL
H₂O: insoluble

Température de stockage

2-8°C

Chaîne SMILES

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

Clé InChI

OYMNPJXKQVTQTR-UHFFFAOYSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Conditionnement

Light sensitive.

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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

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 (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

Differential Tolerance to FTY720-Induced Antinociception in Acute Thermal and Nerve Injury Mouse Pain Models: Role of Sphingosine-1-Phosphate Receptor Adaptation.

Laura J Sim-Selley et al.

The Journal of pharmacology and experimental therapeutics, 366(3), 509-518 (2018-06-28)

The immunomodulatory prodrug 2-amino-2-(2-[4-octylphenyl]ethyl)-1,3-propanediol (FTY720), which acts as an agonist for sphingosine-1-phosphate (S1P) receptors (S1PR) when phosphorylated, is proposed as a novel pain therapeutic. In this study, we assessed FTY720-mediated antinociception in the radiant heat tail-flick test and in the

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