GlpBio

D-erythro-Sphingosine (synthetic)

目录号: GC17591纯度: >98.00%同义词: 鞘氨醇; Erythrosphingosine; erythro-C18-Sphingosine; trans-4-Sphingenine
D-erythro-sphingosine (Erythrosphingosine) 是一种非常有效的 p32 激酶激活剂，EC50 值为 8μM。
D-erythro-Sphingosine (synthetic)
Cas No.: 123-78-4
规格价格库存数量操作
10mg¥585.00现货
1
10mM (in 1mL EtOH)询价现货
1
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产品描述 Description

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 F2α was suppressed by D-erythro-sphingosine (10 μM) in PC12 cells. D-erythro-sphingosine, directly inhibited cytosolic phospholipase A2α 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.

D-erythro-sphingosine (Erythrosphingosine) 是一种非常有效的 p32 激酶激活剂，EC50 值为 8μM[1]。 D-erythro-Sphingosine 也是一种 PP2A 激动剂[2]。 D-赤型鞘氨醇已被证明可抑制蛋白激酶 C[3]。

D-赤型鞘氨醇激活的 TRPM3 变体包含 1325 个氨基酸，独立于 PKC 抑制、S1P 形成或细胞内 Ca2+ 储存耗尽[4]。 D-赤型鞘氨醇降低 CHO-K1 细胞中 HMG-CoA 还原酶活性水平[5]。 D-erythro-sphingosine 显着抑制 PC12 细胞中 mastoparan- 而不是 Na3VO4- 刺激的花生四烯酸释放。 D-赤型鞘氨醇 (10 μM) 在 PC12 细胞中抑制前列腺素 F2α 的产生。 D-赤型鞘氨醇，直接抑制细胞溶质磷脂酶 A2α 活性[6]。 p32-鞘氨醇激活的蛋白激酶对低浓度的 D-赤型-鞘氨醇有反应，在 2.5μM 时观察到初始激活，在 10-20μM 时观察到峰值活性。该激酶显示出对 D-赤型-鞘氨醇的特异性优于其他鞘氨醇立体异构体，并且对鞘氨醇的偏好优于二氢-鞘氨醇[1]

D-赤型鞘氨醇被确定为 ASB 诱导的肾毒性中最有影响力的因素之一[7]

实验参考方法 Experimental Reference Method

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.

产品文档 Product Documents

Purity:>98.00%

化学性质Chemical Properties

CAS 号
123-78-4
同义词
鞘氨醇; Erythrosphingosine; erythro-C18-Sphingosine; trans-4-Sphingenine
化学名
(2S,3R,E)-2-aminooctadec-4-ene-1,3-diol
SMILES
O[C@H](/C=C/CCCCCCCCCCCCC)[C@H](CO)N
分子式
C18H37NO2
分子量
299.5 g/mol
溶解性
≥ 14.9mg/mL in Ethanol
保存条件
Store at -20°C
General tips
请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。
储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。
为了提高溶解度，请将管子加热至 37°C，然后在超声波浴中震荡一段时间。
Shipping Condition
评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备 RT，或根据请求配备蓝冰。

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