860492 | Sphingosine-1-Phosphate (d18:1)

D-erythro-sphingosine-1-phosphate


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1mg 860492P-1mg 860492P-1mg 1 x 1mg $219.23
5mg 860492P-5mg 860492P-5mg 1 x 5mg $617.05
25mg 860492P-25mg 860492P-25mg 1 x 25mg $1,590.00
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Sphingosine-1-Phosphate (d18:1)

Sphingosine-1-Phosphate (d18:1)

D-erythro-sphingosine-1-phosphate

Sphingosine-1-phosphate (S1P), a zwitterionic sphingolipid, is an important cellular metabolite and signalling lipid in animal cells. It has also been found in insects, yeasts and plants. You can find additional information on S1P at the following link:
Hygroscopic
No
Light Sensitive
No
Molecular Formula
C18H38NO5P
Percent Composition
C 56.97%, H 10.09%, N 3.69%, O 21.08%, P 8.16%
Purity
>99%
Stability
1 Year
Storage Temperature
-20°C
CAS Number
26993-30-6
CAS Registry Number is a Registered Trademark of the American Chemical Society
Formula Weight
379.472
Exact Mass
379.249
Synonyms
sphingosine d18 D erythro 2S,3R,4(E) 1-phosphate
(2S,3R,4E)-2-aminooctadec-4-ene-1,3-diol-1-Phosphate
(2S,3R,4E)-2-amino-1,3-octadec-4-enediol-1-Phosphate
S1P
sphing-4-enine-1-phosphate

Jakobi K, Beyer S, Koch A, Thomas D, Schwalm S, Zeuzem S, Pfeilschifter J, Grammatikos G. Sorafenib Treatment and Modulation of the Sphingolipid Pathway Affect Proliferation and Viability of Hepatocellular Carcinoma In Vitro. Int J Mol Sci. 2020 Mar 31;21(7):2409. doi: 10.3390/ijms21072409. PMID: 32244391; PMCID: PMC7177910.

PubMed ID: 32244391

Wing TT, Erikson DW, Burghardt RC, Bazer FW, Bayless KJ, Johnson GA. OPN binds alpha V integrin to promote endothelial progenitor cell incorporation into vasculature. Reproduction. 2020 Apr;159(4):465-478. doi: 10.1530/REP-19-0358. PMID: 31990676.

PubMed ID: 31990676

Vutukuri R, Koch A, Trautmann S, Schreiber Y, Thomas D, Mayser F, Meyer Zu Heringdorf D, Pfeilschifter J, Pfeilschifter W, Brunkhorst R. S1P d20:1, an endogenous modulator of S1P d18:1/S1P2 -dependent signaling. FASEB J. 2020 Jan 15:10.1096/fj.201902391R. doi: 10.1096/fj.201902391R. Epub ahead of print. PMID: 31944406.

PubMed ID: 31944406

Zeng Y, Liu X, Yan Z, Xie L. Sphingosine 1-phosphate regulates proliferation, cell cycle and apoptosis of hepatocellular carcinoma cells via syndecan-1. Prog Biophys Mol Biol. 2019 Nov;148:32-38. doi: 10.1016/j.pbiomolbio.2017.11.006. Epub 2017 Nov 24. PMID: 29180036.

PubMed ID: 29180036

Shimano K, Maeda Y, Kataoka H, Murase M, Mochizuki S, Utsumi H, Oshita K, Sugahara K. Amiselimod (MT-1303), a novel sphingosine 1-phosphate receptor-1 functional antagonist, inhibits progress of chronic colitis induced by transfer of CD4+CD45RBhigh T cells. PLoS One. 2019 Dec 5;14(12):e0226154. doi: 10.1371/journal.pone.0226154. PMID: 31805144; PMCID: PMC6894856.

PubMed ID: 31805144

Jeon S, Song J, Lee D, Kim GT, Park SH, Shin DY, Shin KO, Park K, Shim SM, Park TS. Inhibition of sphingosine 1-phosphate lyase activates human keratinocyte differentiation and attenuates psoriasis in mice. J Lipid Res. 2020 Jan;61(1):20-32. doi: 10.1194/jlr.RA119000254. Epub 2019 Nov 5.

PubMed ID: 31690639

Tran C, Heng B, Teo JD, Humphrey SJ, Qi Y, Couttas TA, Stefen H, Brettle M, Fath T, Guillemin GJ, Don AS. Sphingosine 1-phosphate but not Fingolimod protects neurons against excitotoxic cell death by inducing neurotrophic gene expression in astrocytes. J Neurochem. 2019 Nov 19:e14917. doi: 10.1111/jnc.14917. [Epub ahead of print]

PubMed ID: 31742704

Hu LL, Chang HM, Yi Y, Liu Y, Taylor EL, Zheng LP, Leung PCK. CCN2 Mediates S1P-Induced Upregulation of COX2 Expression in Human Granulosa-Lutein Cells. Cells. 2019 Nov 15;8(11). pii: E1445. doi: 10.3390/cells8111445.

PubMed ID: 31731760

Rivas DA, Rice NP, Ezzyat Y, McDonald DJ, Cooper BE, Fielding RA. Sphingosine-1-phosphate analog FTY720 reverses obesity but not age-induced anabolic resistance to muscle contraction. Am J Physiol Cell Physiol. 2019 Sep 1;317(3):C502-C512. doi: 10.1152/ajpcell.00455.2018. Epub 2019 Jun 26.

PubMed ID: 31241988

Klomp JE, Shaaya M, Matsche J, Rebiai R, Aaron JS, Collins KB, Huyot V, Gonzalez AM, Muller WA, Chew TL, Malik AB, Karginov AV. Time-Variant SRC Kinase Activation Determines Endothelial Permeability Response. Cell Chem Biol. 2019 Apr 25. pii: S2451-9456(19)30121-7. doi: 10.1016/j.chembiol.2019.04.007. [Epub ahead of print]

PubMed ID: 31130521

Byun J, Del Re DP, Zhai P, Ikeda S, Shirakabe A, Mizushima W, Miyamoto S, Brown JH, Sadoshima J. Yes-associated protein (YAP) mediates adaptive cardiac hypertrophy in response to pressure overload. J Biol Chem. 2019 Mar 8;294(10):3603-3617. doi: 10.1074/jbc.RA118.006123. Epub 2019 Jan 11.

PubMed ID: 30635403

Byun J, Del Re DP, Zhai P, Ikeda S, Shirakabe A, Mizushima W, Miyamoto S, Brown JH, Sadoshima J. Yes-Associated Protein (YAP) mediates adaptive cardiac hypertrophy in response to pressure overload. J Biol Chem. 2019 Jan 11. pii: jbc.RA118.006123. doi: 10.1074/jbc.RA118.006123. [Epub ahead of print]

PubMed ID: 30635403

Brunkhorst R, Pfeilschifter W, Rajkovic N, Pfeffer M, Fischer C, Korf HW, Christoffersen C, Trautmann S, Thomas D, Pfeilschifter J, Koch A. Diurnal regulation of sphingolipids in blood. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Mar;1864(3):304-311. doi: 10.1016/j.bbalip.2018.12.001. Epub 2018 Dec 15.

PubMed ID: 30557628

Abuhusain HJ, Matin A, Qiao Q, Shen H, Kain N, Day BW, Stringer BW, Daniels B, Laaksonen MA, Teo C, McDonald KL, Don AS. A metabolic shift favoring sphingosine 1-phosphate at the expense of ceramide controls glioblastoma angiogenesis. J Biol Chem. 2013 Dec 27;288(52):37355-64. doi: 10.1074/jbc.M113.494740. Epub 2013 Nov 21.

PubMed ID: 24265321

Allende ML, Sipe LM, Tuymetova G, Wilson-Henjum KL, Chen W, Proia RL. Sphingosine-1-phosphate phosphatase 1 regulates keratinocyte differentiation and epidermal homeostasis. J Biol Chem. 2013 Jun 21;288(25):18381-91. doi: 10.1074/jbc.M113.478420. Epub 2013 May 1.

PubMed ID: 23637227

Liang J, Nagahashi M, Kim EY, Harikumar KB, Yamada A, Huang WC, Hait NC, Allegood JC, Price MM, Avni D, Takabe K, Kordula T, Milstien S, Spiegel S. Sphingosine-1-phosphate links persistent STAT3 activation, chronic intestinal inflammation, and development of colitis-associated cancer. Cancer Cell. 2013 Jan 14;23(1):107-20. doi: 10.1016/j.ccr.2012.11.013. Epub 2012 Dec 27.

PubMed ID: 23273921

Karuna R, Park R, Othman A, Holleboom AG, Motazacker MM, Sutter I, Kuivenhoven JA, Rohrer L, Matile H, Hornemann T, Stoffel M, Rentsch KM, von Eckardstein A. Atherosclerosis. 2011 Dec;219(2):855-63. doi: 10.1016/j.atherosclerosis.2011.08.049. Epub 2011 Sep 6. Plasma levels of sphingosine-1-phosphate and apolipoprotein M in patients with monogenic disorders of HDL metabolism.

PubMed ID: 21944699

Sphingosine-1-Phosphate Solubility Protocol & Cell Delivery

Organic Solutions:
The solubility of stock solutions of sphingoid base 1-phosphates may be increased by the addition of dimethylamine.

Water Solutions:
Solubility of S1P is difficult using organic solvents so typically it is suspended in methanol to aliquot, the methanol dried and the residue dispersed using fatty acid free BSA solution.
A procedure for preparation of a S1P stock solution follows:

Stock Solution:
125µM Sphingosine-1-Phosphate in essentially fatty acid free Bovine Serum Albumin (BSA, 4mg/ml)

Preparation of Stock Solution:
Methanol Solution:

  • Add Sphingosine-1-phosphate to methanol:water 95:5 (0.5mg/ml)
  • Heat mixture (45°C-65°C methanol boiling point) and sonicate until Sphingosine-1-Phosphate is suspended (solutions are not clear - forms a slightly hazy suspention).
  • Transfer desired amounts of methanol:water stock solution to glass vessel.
  • Remove methanol:water solution using a stream of dry nitrogen.
  • Place glass vessel into a warm (approximately 50°C) water bath.
  • Rotate glass vessel during evaporation to make thin film of Sphingosine-1-phosphate on tube wall.
  • Store Sphingosine-1-Phosphate at -20°C in closed container. Maximum storage one year.


BSA Solution

  • Add enough BSA (4mg/ml) in water at 37°C to glass vessel containing Sphingosine-1-Phosphate to make a 125µM Sphingosine-1-Phosphate solution.
  • Incubate for 30 minutes and vortex occasionally.
  • Maximum storage three months.