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Sphingosine-1-phosphate

Catalog No.GC17004

Sphingosine-1-phosphate Chemical Structure

An agonist of S1P1-5 receptors and a ligand of GPR3, GPR6 and GPR12

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Background

Sphingosine-1-phosphate is an endogenous second messenger that involved in cell proliferation and survival and is a ligand for S1PR1 [1] [2].

Sphingosine-1-phosphate receptor 1 (S1PR1), also known as endothelial differentiation gene 1 (EDG1), is a G-protein-coupled receptor for sphingosine-1-phosphate (S1P) and is involved in regulating endothelial cell cytoskeletal structure, capillary-like network formation, migration and vascular maturation.

Sphingosine-1-phosphate is an endogenous second messenger and a ligand for S1PR1. In endothelial cells, S1P (1-20 µM) induced EDG-l-dependent morphogenesis. In HEK293EDG-1 cells, S1P bound to S1PR1 with Kd value of 8.1 nM in a time-dependent way. In cells transfected with EDG-l, S1P activated ERK-1 and ERK-2 via EDG-1. S1P existed in platelets and released through platelet activation [2]. In human embryonic kidney (HEK) cells, S1P significantly increased [Ca2+]i with EC50 value of 2 nM in a pertussis toxin-sensitive way and inhibited cAMP accumulation induced by forskolin. Also, S1P increased the binding of guanosine 5’-3-O-(thio)triphosphate to cell membranes. In guinea pig atrial myocytes, S1P at the extracellular face activated Gi protein-regulated inwardly rectifying potassium channels [3]. S1P inhibited programmed cell death mediated by ceramide [4].

References:
[1].  Olivera A, Spiegel S. Sphingosine-1-phosphate as second messenger in cell proliferation induced by PDGF and FCS mitogens. Nature, 1993, 365(6446): 557-560.
[2].  Lee MJ, Van Brocklyn JR, Thangada S, et al. Sphingosine-1-phosphate as a ligand for the G protein-coupled receptor EDG-1. Science, 1998, 279(5356): 1552-1555.
[3].  van Koppen C, Meyer zu Heringdorf M, Laser KT, et al. Activation of a high affinity Gi protein-coupled plasma membrane receptor by sphingosine-1-phosphate. J Biol Chem, 1996, 271(4): 2082-2087.
[4].  Cuvillier O, Pirianov G, Kleuser B, et al. Suppression of ceramide-mediated programmed cell death by sphingosine-1-phosphate. Nature, 1996, 381(6585): 800-803.

Chemical Properties

Cas No. 26993-30-6 SDF
Synonyms 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 2-8°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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