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Sphingosine-1-phosphate (Synonyms: Sphingosine-1-phosphate (d18:1); S1P (d18:1); Sphingosine-1-Phosphoric Acid)

Catalog No.GC17004 Copy One-Click Copy Product Info

Sphingosine-1-phosphate est un produit métabolique des sphingolipides de la membrane cellulaire.

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Sphingosine-1-phosphate Chemical Structure

Cas No.: 26993-30-6

Taille Prix Stock Qté
1mg
131,00 $US
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Description of Sphingosine-1-phosphate

Sphingosine-1-phosphate est un produit métabolique des sphingolipides de la membrane cellulaire. Il est lié à des chaperons extracellulaires, enrichi dans les fluides circulatoires et se lie aux récepteurs Sphingosine-1-phosphate couplés aux protéines G (Sphingosine 1-phosphateRs) utilisés pour réguler le développement embryonnaire, la fonction des organes postnatals et les maladies.[1]

In vitro, le traitement avec 200 et 400 μM de Sphingosine-1-phosphate dans des échantillons corticaux ovariens humains a montré une diminution dose-dépendante de l'expression protéique de la caspase-3 clivée par western blot et du nombre de follicules apoptotiques positifs pour la caspase-3 clivée par immunohistochimie.[2] In vitro, avec 0.1-10 μM de Sphingosine-1-phosphate de manière concentration-dépendante a évoqué la génération de potentiel d'action (PA) par des enregistrements électrophysiologiques de fibres uniques.[3] De plus, en utilisant des expériences d'imagerie Ca2+, Sphingosine-1-phosphate à 1 μM peut provoquer une augmentation transitoire du Ca2+ intracellulaire dans les astrocytes, suivie d'une élévation soutenue.[4]

In vivo, la superfusion de 0.001-10 μM de Sphingosine-1-phosphate a provoqué une vasoconstriction des microvaisseaux préglomérulaires, principalement des artérioles afférentes, de manière concentration-dépendante.[5] Une expérience in vivo a montré que l'injection intraveineuse de 10 mg/kg de Sphingosine-1-phosphate chez la souris causait une rigidité immédiate et la mort.[6] Chez les beagles mâles, le traitement intraveineux avec 85 μg/kg de Sphingosine-1-phosphate a diminué la formation de Q(s)/Q(t) (32%), ainsi que la présence de protéines (72%) et de neutrophiles (95%) dans le liquide BAL par rapport aux témoins ayant reçu le véhicule. Cependant, Sphingosine-1-phosphate a augmenté la production systémique induite par le LPS de trois cytokines inflammatoires, TNF-alpha (6 fois), KC (1,2 fois) et IL-6 (3 fois), sans entraîner de dysfonctionnement d'organe terminal.[7]

References:
[1]Cartier A, et al. Sphingosine 1-phosphate: Lipid signaling in pathology and therapy. Science. 2019 Oct 18;366(6463):eaar5551.
[2]Guzel Y, et al. Sphingosine-1-phosphate protects human ovarian follicles from apoptosis in vitro. Eur J Obstet Gynecol Reprod Biol. 2018 Mar;222:19-24.
[3]Patil MJ, et al. Sphingosine-1-phosphate activates mouse vagal airway afferent C-fibres via Sphingosine 1-phosphateR3 receptors. J Physiol. 2019 Apr;597(7):2007-2019.
[4]Shirakawa H, et al. Sphingosine-1-phosphate induces Ca2+ signaling and CXCL1 release via TRPC6 channel in astrocytes. Glia. 2017 Jun;65(6):1005-1016.
[5]Guan Z, et al. Sphingosine-1-phosphate evokes unique segment-specific vasoconstriction of the renal microvasculature. J Am Soc Nephrol. 2014 Aug;25(8):1774-85.
[6]Igarashi Y, et al. Sphingosine 1-phosphate is a blood constituent released from activated platelets, possibly playing a variety of physiological and pathophysiological roles. Acta Biochim Pol. 1998;45(2):299-309.
[7]Szczepaniak WS,et al. Sphingosine 1-phosphate rescues canine LPS-induced acute lung injury and alters systemic inflammatory cytokine production in vivo. Transl Res. 2008 Nov;152(5):213-24.

Protocol of Sphingosine-1-phosphate

Cell experiment [1]:

Cell lines

SH-SY5Y cells

Preparation Method

SH-SY5Y cells were cultured in DMEM medium supplemented with 10% fetal bovine serum, 1% penicillin-streptomycin, and 1% glutamine in a humidified incubator containing 5% CO2 at 37°C. Cells were exposed to OGD for 3h, followed by 16h of recovery, with or without Sphingosine-1-phosphate (0, 0.1, 0.5, and 1μM), and cell viability was measured.

Reaction Conditions

0, 0.1, 0.5, and 1µM; 19h

Applications

Sphingosine-1-phosphate treatment enhanced the cell viability of SH-SY5Y cells under OGD conditions in a dose-dependent manner.
Animal experiment [2]:

Animal models

Male C57BL/6 mice

Preparation Method

Male C57BL/6 mice (8-week-old) were maintained in a controlled environment at 22-24°C and 60% relative humidity under a 12h light/dark cycle, and were given free access to food and water. Mice were fasted overnight before the experiment but had free access to water. Mice were anesthetized with 3% isoflurane and the abdomen was shaved and rinsed with 70% isopropanol solution. Anesthesia was maintained using 1% isoflurane and body temperature was maintained at 37°C using a heating pad. A midline laparotomy was made and, using a dissecting microscope, the superior mesenteric artery (SMA) as well as the collateral branch from the celiac axis were identified and occluded with nontraumatic vascular clamps. After 45 min of ischemia, the SMA was re-perfused. Then the abdomen was closed. Ischemia was determined by the existence of pulseless or pale color of the small intestine. The return of pulse and restoration of pink color were assumed to be due to the reperfusion of the intestine. In the sham-operated group, the SMA and collateral branches from the celiac axis were identified but were not occluded. Mice were randomized to three groups: (1) sham-operated mice (sham group; n=8), (2) mice exposed to SMA occlusion for 45min followed by reperfusion for 6h (I/R group; n=8), or (3) mice exposed to I/R that received Sphingosine-1-phosphate (I/R+S1P group; n=8). As soon as the abdomen was closed, Sphingosine-1-phosphate (100μg/kg; dissolved in 0.9% saline solution) was administered by intraperitoneal injection. An equal volume of saline was administered to the sham group and I/R group as a vehicle. After 6-h reperfusion, the lung tissues of the mice were collected for analysis.

Dosage form

100μg/kg; once; i.p.

Applications

Sphingosine-1-phosphate markedly attenuated I/R-induced lung injury, manifested by the improvement of histological changes and significant decreases of lung water content.

References:

[1] Agudo-López A, Miguel B G, Fernández I, et al. Involvement of mitochondria on neuroprotective effect of sphingosine-1-phosphate in cell death in an in vitro model of brain ischemia[J]. Neuroscience letters, 2010, 470(2): 130-133.

[2] Ding R, Han J, Tian Y, et al. Sphingosine-1-phosphate attenuates lung injury induced by intestinal ischemia/reperfusion in mice: role of inducible nitric-oxide synthase[J]. Inflammation, 2012, 35(1): 158-166.

Chemical Properties of Sphingosine-1-phosphate

Cas No. 26993-30-6 SDF
Synonymes Sphingosine-1-phosphate (d18:1); S1P (d18:1); Sphingosine-1-Phosphoric Acid
Chemical Name (2S,3R,E)-2-amino-3-hydroxyoctadec-4-en-1-yl dihydrogen phosphate
Canonical SMILES O[C@H](/C=C/CCCCCCCCCCCCC)[C@H](COP(O)(O)=O)N
Formula C18H38NO5P M.Wt 379.5
Solubility 0.3M NaOH: 4 mg/ml,DMF: <50 µg/ml,DMSO: <50 µg/ml,PBS pH 7.2: <50 µg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Sphingosine-1-phosphate

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1 mg 5 mg 10 mg
1 mM 2.635 mL 13.1752 mL 26.3505 mL
5 mM 527 μL 2.635 mL 5.2701 mL
10 mM 263.5 μL 1.3175 mL 2.635 mL
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