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Submit ReviewSphingosine-1-phosphate
Description: Endogenous agonist at S1P1-5
Chemical Name: (E)-D-erythro-2-amino-1-(dihydrogenphosphate)-4-octadecene-1,3-diol
Purity: ≥98% (HPLC)
Biological Activity for Sphingosine-1-phosphate
Sphingosine-1-phosphate is an endogenous second messenger involved in the control of cell proliferation and motility, and Ca2+ mobilization. Acts as an agonist at sphingosine-1-phosphate receptors (S1P1-5) and as an activator of GPR3, GPR6 and GPR12. Effectors regulated include p38 MAP kinase, PLC, adenylyl cyclase, myosin light chain phosphatase and focal adhesion kinase. Also activates VRAC-mediated transport of 2'3'-cyclic-GMP-AMP (cGAMP).
Technical Data for Sphingosine-1-phosphate
| M. Wt | 379.48 |
| Formula | C18H38NO5P |
| Storage | Store at +4°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 26993-30-6 |
| PubChem ID | 5283560 |
| InChI Key | DUYSYHSSBDVJSM-KRWOKUGFSA-N |
| Smiles | O[C@H](/C=C/CCCCCCCCCCCCC)[C@@H](N)COP(O)(O)=O |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Product Datasheets for Sphingosine-1-phosphate
References for Sphingosine-1-phosphate
References are publications that support the biological activity of the product.
Essler et al (2002) Sphingosine 1-phosphate dynamically regulates myosin light chain phosphatase activity in human endothelial cells. Cell.Signal. 14 607 PMID: 11955953
Pyne and Pyne (2000) Sphingosine 1-phosphate signalling via the endothelial differentiation gene family of G-protein-coupled receptors. Pharmacol.Ther. 88 115 PMID: 11150592
Uhlenbrock et al (2002) Sphingosine 1-phosphate is a ligand of the human gpr3, gpr6 and gpr12 family of constitutively active G protein-coupled receptors. Cell.Signal. 14 941 PMID: 12220620
van Koppen et al (1996) Activation of a high affinity Gi protein-coupled plasma membrane receptor by sphingosine-1-phosphate. J.Biol.Chem. 271 2082 PMID: 8567663
Morstein et al (2019) Optical control of sphingosine-1-phosphate formation and function. Nat.Chem 15 623 PMID: 31036923
Lahey et al (2020) LRRC8A:C/E heteromeric channels are ubiquitous transporters of cGAMP. Mol.Cell. 80 1 PMID: 33171122
If you know of a relevant reference for Sphingosine-1-phosphate, please let us know.
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Keywords: Sphingosine-1-phosphate, Sphingosine-1-phosphate supplier, Endogenous, agonists, S1P1, S1P2, S1P3, S1P4, S1P5, Receptors, EDG, Sphingosine-1-Phosphate, GPR3, GPR6, GPR12, cGAMP, transports, transporters, VRAC, LRRC8, Sphingosine-1-phosphate, STING-Dependent, Signaling, 1370, Tocris Bioscience
10 Citations for Sphingosine-1-phosphate
Citations are publications that use Tocris products. Selected citations for Sphingosine-1-phosphate include:
Evseenko et al (2013) Lysophosphatidic acid mediates myeloid differentiation within the human bone marrow microenvironment. PLoS One 8 e63718 PMID: 23696850
Hu et al (2016) Hemovascular Progenitors in the Kidney Require Sphingosine-1-Phosphate Receptor 1 for Vascular Development. J Am Soc Nephrol 27 1984 PMID: 26534925
Pierre et al (2004) PAM mediates sustained inhibition of cAMP signaling by sphingosine-1-phosphate. EMBO J 23 3031 PMID: 15257286
Simula et al (2018) Drp1 Controls Effective T Cell Immune-Surveillance by Regulating T Cell Migration, Proliferation, and cMyc-Dependent Metabolic Reprogramming. Cell Rep 25 3059 PMID: 30540939
Camp et al (2016) Dynamic mass redistribution reveals diverging importance of PDZ-ligands for G protein-coupled receptor pharmacodynamics. Pharmacol Res 105 13 PMID: 26773201
Kho et al (2015) Application of xCELLigence RTCA Biosensor Technology for Revealing the Profile and Window of Drug Responsiveness in Real Time. Mol Pain 5 199 PMID: 25893878
Hill et al (2018) The signaling lipid sphingosine 1-phosphate regulates mechanical pain. Elife 7 PMID: 29561262
Krispin et al (2018) Growth Differentiation Factor 6 Promotes Vascular Stability by Restraining Vascular Endothelial Growth Factor Signaling. Arterioscler Thromb Vasc Biol 38 353 PMID: 29284606
Hübner et al (2018) Wnt/β-catenin signaling regulates VE-cadherin-mediated anastomosis of brain capillaries by counteracting S1pr1 signaling. Nat Commun 9 4860 PMID: 30451830
Hannedouche et al (2013) Identification of the C3a receptor (C3AR1) as the target of the VGF-derived peptide TLQP-21 in rodent cells. Biosensors (Basel) 288 27434 PMID: 23940034
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