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Sphingosine-1-phosphate

Catalog No.: GC17004

Sphingosine 1-phosphate is a metabolic product of cell membrane sphingolipids.

Sphingosine-1-phosphate Chemical Structure

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Background

Sphingosine 1-phosphate is a metabolic product of cell membrane sphingolipids. It is bound to extracellular chaperones, enriched in circulatory fluids and binds to G protein-coupled Sphingosine 1-phosphate receptors (Sphingosine 1-phosphateRs) used for regulating embryonic development, postnatal organ function and disease.[1]

In vitro, treatment with 200 and 400 μM Sphingosine 1-phosphate in human ovarian cortical samples in dose-dependent decrease in the protein expression of cleaved caspase-3 using western blot and in the number of apoptotic follicles stained positive for cleaved caspase-3 using immunohistochemistry.[2] In vitro, with 0.1-10 μM Sphingosine 1-phosphate in a concentration-dependent manner evoked action potential (AP) generation by single fibre electrophysiological recordings.[3] In addition, using Ca2+ imaging experiments, Sphingosine 1-phosphate at 1 μM can elicit a transient increase in intracellular Ca2+ in astrocytes, followed by sustained elevation.[4]

In vivo, superfusion of 0.001-10 μM Sphingosine 1-phosphate evoked in concentration-dependent manner vasoconstriction in preglomerular microvessels, predominantly afferent arterioles. [5] In vivo experiment it shown that injection 10 mg/kg sphingosine 1-phosphate intravenously in mice caused immediate rigor and death. [6] In male beagles, treatment with 85 ug/kg Sphingosine 1-phosphate intravenously decreased the formation of Q(s)/Q(t) (32%), and both the presence of protein (72%) and neutrophils (95%) in BAL fluid compared with vehicle controls. However, Sphingosine 1-phosphate increased the LPS-induced systemic production of three inflammatory cytokines, TNF-alpha (6-fold), KC (1.2-fold), and IL-6 (3-fold), without resulting in end-organ dysfunction.[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.

Chemical Properties

Cas No. 26993-30-6 SDF
Synonyms 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 379.48
Solubility ≤4 mg/ml in 0.3M NaOH Storage Store at -20°C
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.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Research Update

Sphingosine 1-phosphate: Lipid signaling in pathology and therapy

Sphingosine 1-phosphate (S1P), a metabolic product of cell membrane sphingolipids, is bound to extracellular chaperones, is enriched in circulatory fluids, and binds to G protein-coupled S1P receptors (S1PRs) to regulate embryonic development, postnatal organ function, and disease. S1PRs regulate essential processes such as adaptive immune cell trafficking, vascular development, and homeostasis. Moreover, S1PR signaling is a driver of multiple diseases. The past decade has witnessed an exponential growth in this field, in part because of multidisciplinary research focused on this lipid mediator and the application of S1PR-targeted drugs in clinical medicine. This has revealed fundamental principles of lysophospholipid mediator signaling that not only clarify the complex and wide ranging actions of S1P but also guide the development of therapeutics and translational directions in immunological, cardiovascular, neurological, inflammatory, and fibrotic diseases.

Modulation of sphingosine-1-phosphate in ulcerative colitis

Introduction: Sphingosine-1-phosphate (S1P) is a membrane-derived lysophospholipid signaling molecule implicated in various physiological and pathological processes, such as regulation of the immune, cardiovascular, pulmonary, and nervous systems and theoretical cancer-related risks, through extracellular activation of S1P1-5 receptors.Areas covered: S1P receptor agonism is a novel strategy for the treatment of UC targeting lymphocyte recirculation, through blockade of lymphocyte egress from lymph nodes. We conducted an extensive literature review on PUBMED on currently available data on molecular aspects of S1P modulation, the mechanisms of action of S1PR agonists (fingolimod, ozanimod, etrasimod, and KRP-203), and their potential efficacy and safety for the treatment of patients with ulcerative colitis.Expert opinion: Selective S1P modulators have emerged to enlarge the efficacy and safety profile of this class of agents. Phase 3 programs should add the potential body of evidence to prove their benefit for the management of UC patients.

Sphingosine 1-phosphate and inflammation

AbstractSphingosine 1-phosphate (S1P), a sphingolipid mediator, regulates various cellular functions via high-affinity G protein-coupled receptors, S1P1-5. The S1P-S1P receptor signaling system plays important roles in lymphocyte trafficking and maintenance of vascular integrity, thus contributing to the regulation of complex inflammatory processes. S1P is enriched in blood and lymph while maintained low in intracellular or interstitial fluids, creating a steep S1P gradient that is utilized to facilitate efficient egress of lymphocytes from lymphoid organs. Blockage of the S1P-S1P receptor signaling system results in a marked decrease in circulating lymphocytes because of a failure of lymphocyte egress from lymphoid organs. This provides a basis of immunomodulatory drugs targeting S1P1 receptor such as FTY720, an immunosuppressive drug approved in 2010 as the first oral treatment for relapsing-remitting multiple sclerosis. The S1P-S1P receptor signaling system also plays important roles in maintenance of vascular integrity since it suppresses sprouting angiogenesis and regulates vascular permeability. Dysfunction of the S1P-S1P receptor signaling system results in various vascular defects, such as exaggerated angiogenesis in developing retina and augmented inflammation due to increased permeability. Endothelial-specific deletion of S1P1 receptor in mice fed high-fat diet leads to increased formation of atherosclerotic lesions. This review highlights the importance of the S1P-S1P receptor signaling system in inflammatory processes. We also describe our recent findings regarding a specific S1P chaperone, apolipoprotein M, that anchors to high-density lipoprotein and contributes to shaping the endothelial-protective and anti-inflammatory properties of high-density lipoprotein.

Sphingosine-1-phosphate in acute exercise and training

Sphingosine-1-phosphate (S1P) is a bioactive sphingolipid found in all eukaryotic cells. Although it may function as an intracellular second messenger, most of its effects are induced extracellularly via activation of a family of five specific membrane receptors. Sphingosine-1-phosphate is enriched in plasma, where it is transported by high-density lipoprotein and albumin, as well as in erythrocytes and platelets which store and release large amounts of this sphingolipid. Sphingosine-1-phosphate regulates a host of cellular processes such as growth, proliferation, differentiation, migration, and apoptosis suppression. It was also shown to play an important role in skeletal muscle physiology and pathophysiology. In recent years, S1P metabolism in both muscle and blood was found to be modulated by exercise. In this review, we summarize the current knowledge on the effect of acute exercise and training on S1P metabolism, highlighting the role of this sphingolipid in skeletal muscle adaptation to physical effort.

Sphingosine 1-Phosphate Receptors in Cerebral Ischemia

Sphingosine 1-phosphate (S1P) is an important lipid biomolecule that exerts pleiotropic cellular actions as it binds to and activates its five G-protein-coupled receptors, S1P1-5. Through these receptors, S1P can mediate diverse biological activities in both healthy and diseased conditions. S1P is produced by S1P-producing enzymes, sphingosine kinases (SphK1 and SphK2), and is abundantly present in different organs, including the brain. The medically important roles of receptor-mediated S1P signaling are well characterized in multiple sclerosis because FTY720 (Gilenya?, Novartis), a non-selective S1P receptor modulator, is currently used as a treatment for this disease. In cerebral ischemia, its role is also notable because of FTY720's efficacy in both rodent models and human patients with cerebral ischemia. In particular, some of the S1P receptors, including S1P1, S1P2, and S1P3, have been identified as pathogenic players in cerebral ischemia. Other than these receptors, S1P itself and S1P-producing enzymes have been shown to play certain roles in cerebral ischemia. This review aims to compile the current updates and overviews about the roles of S1P signaling, along with a focus on S1P receptors in cerebral ischemia, based on recent studies that used in vivo rodent models of cerebral ischemia.

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