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D-erythro-Sphingosine (synthetic) (Synonyms: (-)Sphingosine, DerythroSphingosine C18)

Katalog-Nr.GC17591

D-erythro-Sphingosin (synthetisch) (Erythrosphingosin) ist ein sehr potenter Aktivator der p32-Kinase mit einem EC50 von 8 μM und hemmt die Proteinkinase C (PKC). D-erythro-Sphingosin (synthetisch) (Erythrosphingosin) ist ebenfalls ein PP2A-Aktivator.

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D-erythro-Sphingosine (synthetic) Chemische Struktur

Cas No.: 123-78-4

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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Kinase experiment [1]:

Preparation Method

The protein-kinase assay was carried out in a total volume of 50µL containing 5µL of sphingosine (D-erythro-sphingosine) suspension (or ethanol solution), 5µL of other effectors, 20µL Mg2+/ATP solution (100mM Tris/HCl, pH 7.4, 25mM MgCl2, 62.5µM ATP and 62.5µCi/mL [32P]ATP) and 20µL of diluted cytosol (8-12µg of protein per sample).

Reaction Conditions

0-100µM D-erythro-sphingosine

Applications

When D-erythro-sphingosine was added to cytosolic extracts of Jurkat T cells, it caused a concentration-dependent phosphorylation of a p32 protein, suggesting that a p32-sphingosine-activated protein kinase was being activated. D-erythro-Sphingosine caused an approx.4-fold increase in p32 phosphorylation, with maximal effects observed at a concentration of 10µM of sphingosine. The EC50 for D-erythro-sphingosine was 8µM.

Cell experiment [2]:

Cell lines

HEK293 cells

Preparation Method

D-erythro-Sphingosine were diluted from 20mM stock solutions in ethanol.

Reaction Conditions

20µM D-erythro-Sphingosine

Applications

Extracellular application of D-erythro-Sphingosine induced an increase in [Ca2+]i in TRPM3-transfected HEK293 cells within 20 to 30s after start of application. In fura-2 quench experiments using 200µM Mn2+, the spontaneous activity of TRPM3-transfected HEK293 cells was enhanced after application of D-erythro-Sphingosine. The concentration of D-erythro-Sphingosine for half-maximal activation of TRPM3 was 12µM obtained from increases in [Ca2+]i. Application of D-erythro-Sphingosine as well as application of hypotonic extracellular solution each produced increases in [Ca2+]i with comparable amplitudes in individual cells.

References:

[1]. Pushkareva MYu, Bielawska A, et al. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid bases and inhibition by non-esterified fatty acids. Biochem J. 1993;294 ( Pt 3)(Pt 3):699-703.

[2]. Grimm C, Kraft R, et al. Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected] [published correction appears in Mol Pharmacol. 2005 Apr;67(4):1382]. Mol Pharmacol. 2005;67(3):798-805.

Background

D-erythro-sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 value of 8μM[1]. D-erythro-Sphingosine is also a PP2A agonist[2]. D-erythro-sphingosine has been shown to inhibit protein kinase C[3].

D-erythro-sphingosine activated TRPM3 variant containing 1325 aa, independently of PKC inhibition, formation of S1P, or intracellular Ca2+ store depletion[4]. D-erythro-sphingosine lowered the levels of HMG-CoA reductase activity in CHO-K1 cells[5]. D-erythro-sphingosine significantly inhibited mastoparan-, but not Na3VO4-, stimulated arachidonic acid release in PC12 cells. Production of prostaglandin F was suppressed by D-erythro-sphingosine (10 μM) in PC12 cells. D-erythro-sphingosine, directly inhibited cytosolic phospholipase A activity[6]. A p32-sphingosine-activated protein kinase responded to low concentrations of D-erythro-sphingosine with an initial activation observed at 2.5μM and a peak activity at 10-20μM. This kinase showed a modest specificity for D-erythro-sphingosine over other sphingosine stereoisomers, and a preference for sphingosines over dihydro-sphingosines[1]

D-erythro-sphingosine was identified as one of the most influential factors in ASB-induced nephrotoxicity[7]

References:
[1]. Pushkareva MYu, Bielawska A, et al. Regulation of sphingosine-activated protein kinases: selectivity of activation by sphingoid bases and inhibition by non-esterified fatty acids. Biochem J. 1993;294 ( Pt 3)(Pt 3):699-703.
[2]. Cheng P, Chen K, et al. Protein phosphatase 2A (PP2A) activation promotes axonal growth and recovery in the CNS. J Neurol Sci. 2015;359(1-2):48-56.
[3]. Pham VT, Joo JE, et al. A concise synthesis of a promising protein kinase C inhibitor: D-erythro-sphingosine. Arch Pharm Res. 2007;30(1):22-27.
[4]. Grimm C, Kraft R, et al. Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected] [published correction appears in Mol Pharmacol. 2005 Apr;67(4):1382]. Mol Pharmacol. 2005;67(3):798-805.
[5]. Pinkerton FD, Kisic A, et al. D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells. Biochem Biophys Res Commun. 1993;190(1):63-69.
[6]. Nakamura H, Hirabayashi T, et al. Inhibition of arachidonic acid release and cytosolic phospholipase A2 alpha activity by D-erythro-sphingosine. Eur J Pharmacol. 2004;484(1):9-17.
[7]. Xu JD, Xing WM, et al. Metabolic changes in the urine of andrographolide sodium bisulfite-treated rats. Hum Exp Toxicol. 2016;35(2):162-169.

Chemical Properties

Cas No. 123-78-4 SDF
Überlieferungen (-)Sphingosine, DerythroSphingosine C18
Chemical Name (2S,3R,E)-2-aminooctadec-4-ene-1,3-diol
Canonical SMILES O[C@H](/C=C/CCCCCCCCCCCCC)[C@H](CO)N
Formula C18H37NO2 M.Wt 299.5
Löslichkeit ≥ 14.9mg/mL in Ethanol Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 3.3389 mL 16.6945 mL 33.389 mL
5 mM 0.6678 mL 3.3389 mL 6.6778 mL
10 mM 0.3339 mL 1.6694 mL 3.3389 mL
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