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Merck

S4257

Sigma-Aldrich

鞘氨醇磷酸胆碱

≥98%, powder

别名:

(2S,3R,4E)-2-氨基-4-十八碳烯-3-羟基-1-磷酸胆碱, 2-[[[(2-氨基-3-羟基-4-十八碳烯基)氧基]羟基-亚膦酰基]氧基] -N,N,N-三甲基乙胺 内盐, D-赤式-鞘氨醇磷酸胆碱, Lyso SM (d18:1), 溶鞘磷脂

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About This Item

经验公式(希尔记法):
C23H49N2O5P
CAS号:
分子量:
464.62
Beilstein:
7342520
MDL號碼:
分類程式碼代碼:
12352211
PubChem物質ID:
NACRES:
NA.77

品質等級

化驗

≥98%

形狀

powder

顏色

light yellow

溶解度

chloroform/methanol (2:1): complete 10 mg/ml, clear to slightly hazy, colorless to light yellow

儲存溫度

−20°C

SMILES 字串

[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(N)COP([O-])(OCC[N+](C)(C)C)=O

InChI

1S/C23H49N2O5P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)22(24)21-30-31(27,28)29-20-19-25(2,3)4/h17-18,22-23,26H,5-16,19-21,24H2,1-4H3/b18-17+/t22-,23+/m0/s1

InChI 密鑰

JLVSPVFPBBFMBE-HXSWCURESA-N

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應用

目前已研究了鞘氨醇磷酸胆碱对小鼠小脑颗粒神经元和PC-12细胞的神经营养作用。

生化/生理作用

鞘氨醇磷酸胆碱(SPC)是一种介导细胞内和细胞外信号传导的生物活性脂质。它通过不依赖IP3的途径从细胞内储存物中调动Ca2+。它刺激CCL2生成,可能有助于动脉粥样硬化病情发展。SPC是内皮细胞分化基因受体3 (EDG3)的配体。

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)


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H Okamoto et al.
Biochemical and biophysical research communications, 260(1), 203-208 (1999-06-25)
AGR16/H218/EDG5 and EDG1 are functional receptors for lysosphingolipids, whereas EDG2 and EGD4 are receptors for lysophosphatidic acid (LPA). The present study demonstrates that EDG3, the yet poorly defined member of the EDG family G protein-coupled receptors, shows identical agonist specificity
Naoko Konno et al.
Biochemical and biophysical research communications, 364(1), 163-168 (2007-10-16)
Sphingosylphosphorylcholine (SPC) is a choline-containing naturally occurring derivative of sphingolipid involved in various biological processes. Here we show that SPC displays neurotrophic effects in cerebellar granule neurons (CGNs) and in PC12 cells. When CGNs were cultured under non-depolarizing condition, they
A Uehara et al.
FEBS letters, 460(3), 467-471 (1999-11-11)
The effects of the lysosphingolipid, sphingosylphosphorylcholine (SPC), on the cardiac ryanodine receptor (RyR) were examined. The open probability of cardiac RyR incorporated in lipid bilayers was decreased by cytoplasmic, but not lumenal side application of micromolar concentrations of SPC. Modification
D Meyer zu Heringdorf et al.
FEBS letters, 410(1), 34-38 (1997-06-23)
Sphingolipid breakdown products are now being recognized to play a dual role in cellular signalling, acting as intracellular as well as extracellular signalling molecules. Both types of action may even be found with one sphingolipid species. The recent demonstration of
Ha Young Lee et al.
Journal of immunology (Baltimore, Md. : 1950), 186(7), 4347-4353 (2011-03-04)
Sphingosylphosphorylcholine (SPC) is a component of high-density lipoprotein particles. We investigated the functional role of SPC in HUVECs. SPC stimulation induced production of the CCL2 chemokine in a PTX-sensitive G-protein-dependent manner. SPC treatment caused the activation of NF-κB and AP-1

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