26993-30-6 Usage
Description
Sphingosine-1-phosphate (S1P) is the product of phosphorylation of sphingosine by sphingosine kinase that is secreted from cells and acts as an agonist at S1P receptors. It increases intracellular calcium levels in TAg-Jurkat cells expressing S1P1 and Gqi5, which allows for phospholipase C stimulation by Gi proteins, when used at a concentration of 200 nM, as well as in TAg-Jurkat cells expressing S1P2 and S1P3 receptors (EC50s = 8 and 11 nM, respectively). Intra- and extracellular levels of S1P vary spatially allowing it to function as an autocrine or paracrine factor, respectively, and dysregulation of S1P levels are associated with various disease states, such as inflammation and autoimmunity. S1P has a wide variety of effects, including an involvement in cell growth, angiogenesis, immunity, and neuroprotection.
Chemical Properties
Off-White to Grey Powder
Uses
Different sources of media describe the Uses of 26993-30-6 differently. You can refer to the following data:
1. A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cel
l metastasis and inflammatory processes; mobilizes intracellular calcium stores; decreases cellular cAMP; activates phospholipase D; does not inhibitprotein kinase C.
2. A ligand for EDG-1 and EDG-3 and activator of GPR3, GPR6, and GPR12.
3. A putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes. It mobilizes intracellular calcium stores, decreases cellular cAMP, activates phospholipase D and does not inhibitprotein kinase C.
4. D-erythro-Dihydrosphingosine-1-phosphate is a saturated analog of D-erythro-Sphingosine-1-phosphate a putative lipid second messenger; found to inhibit cellular mobility of melanoma cells at very low concentrations with no toxic effects thereby making it a possible agent for prevention of tumor cell metastasis and inflammatory processes.
Definition
ChEBI: A phosphosphingolipid that consists of sphingosine having a phospho group attached at position 1
General Description
Sphingosine-1-phosphate (S1P), a sphingolipid, is an important cellular metabolite and signaling lipid in animal cells. It has also been found in yeasts and plants. Sphingosine kinases (SPKs) catalyzes the synthesis of S1P from spingosine and regulates S1P levels. It is the end product of ceramide catabolism and is metabolized to phosphoethanolamine and hexadecenal by S1P lyase. S1P is produced in endothelial cells.
Biological Activity
Endogenous second messenger involved in the control of cell proliferation and motility, and Ca 2+ mobilization. Acts as an agonist at sphingosine-1-phosphate receptors, S1P 1-5 . Effectors regulated include p38 MAP kinase, PLC, adenylyl cyclase, myosin light chain phosphatase and focal adhesion kinase.
Biochem/physiol Actions
A lipid second messenger that binds to S1P1 and S1P3 receptors. Mobilizes intracellular Ca2+ stores and decreases cellular cAMP. Activates phospholipase D. S1P stimulates the migration of endothelial cells but inhibits the migration of other cell types. Induces angiogenesis.
References
1) Spiegel and Milstien (2003)?Sphingosine-1-phosphate: an enigmatic signaling lipid; Nat. Rev. Mol. Cell Biol.,?4?397
2) Rosen?et al. (2009)?Sphingosine-1-phosphate receptor signaling; Annu. Rev .Biochem.,?78?743
3) Maceyka?et al. (2012)?Sphingosine-1-phosphate signaling and its role in disease; Trends Cell Biol.,?22?50
Check Digit Verification of cas no
The CAS Registry Mumber 26993-30-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,6,9,9 and 3 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 26993-30:
(7*2)+(6*6)+(5*9)+(4*9)+(3*3)+(2*3)+(1*0)=146
146 % 10 = 6
So 26993-30-6 is a valid CAS Registry Number.
InChI:InChI=1/C18H38NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1
26993-30-6Relevant articles and documents
A facile regioselective synthesis of sphingosine 1-phosphate and ceramide 1-phosphate
Szulc,Hannun,Bielawska
, p. 7821 - 7824 (2000)
A novel regioselective synthesis of D-erythro-sphingosine 1-phosphate and D-erythro-ceramide 1-phosphate is described. The synthesis is based upon (1) in situ oxidative phosphorylation of the primary hydroxyl group in N-Boc-D-erythro-sphingosine utilizing trimethyl phosphite and carbon tetrabromide in pyridine, (2) chemoselective deprotection of the 1-O-phosphate and/or 2-amino groups with trimethylsilyl bromide or chloride, and (3) introduction of the fatty acid moiety into sphingosine 1-phosphate dimethyl ester via base-catalyzed N-acylation. (C) 2000 Elsevier Science Ltd.
4'-HALOGEN CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO
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Page/Page column 290, (2019/10/01)
Disclosed are halogen containing nucleotide and nucleoside therapeutic compositions and uses related thereto. In certain embodiments, the disclosure relates to the treatment or prophylaxis of viral infections. Such viral infections can include tongaviridae, bunyaviridae, arenaviridae, coronaviridae, flaviviridae, picornaviridae, Eastern, Western, and Venezuelan Equine Encephalitis (EEE, WEE and VEE, respectively), Chikungunya fever (CHIK), Ebola, Influenza, RSV, and Zika virus infections.
NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO
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Page/Page column 145, (2017/09/27)
This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.
