SMILES string
[H][C@](/C=C/CCCCCCCCCCCCC)(O)[C@@]([H])(NC(CCCCCCCCCCCCCCCCC)=O)COP([O-])(OCC[N+](C)(C)C)=O
InChI
1S/C41H83N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1
InChI key
LKQLRGMMMAHREN-YJFXYUILSA-N
description
Sphingomyelin (Brain, Porcine)
assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 g (860062P-1g), pkg of 1 × 200 mg (860062P-200mg), pkg of 1 × 25 mg (860062P-25mg), pkg of 1 × 500 mg (860062P-500mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand
lipid type
sphingolipids
shipped in
dry ice
storage temp.
−20°C
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General description
作为细胞膜的主要成分，鞘磷脂在神经细胞（髓鞘）膜和红细胞膜中的浓度特别高。以前认为，它是因鞘氨醇碱基的2-酰胺基、3-羟基和4,5-反式双键介导的分子间相互作用而具有与磷脂酰胆碱功能相似的纯结构作用。但是，现在人们认识到，鞘磷脂对胆固醇具有高亲和力，这两种脂质在液体无序相中紧密堆积成液体有序结构域，形成脂质筏。这些膜微结构域被认为是调节蛋白质定位和相互作用的信号转导平台。但是，鞘磷脂不仅是会影响信号传导的脂质筏成分，它还是神经酰胺和其他鞘脂代谢（包括鞘磷脂循环或鞘脂网络）产物的前体。
鞘磷脂和相关脂质
鞘磷脂和相关脂质
Application
脑SM适用于：
- 可作为高效液相色谱-电喷雾串联质谱（HPLC-ESI-MS/MS）的标准品
- 作为Hela细胞空泡化的补充
- 脂质体的制备
Packaging
20 mL透明玻璃螺旋盖小瓶（860062P-500mg）
5 mL棕色玻璃螺旋盖小瓶（860062P-200mg）
5 mL棕色玻璃螺旋盖小瓶（860062P-25mg）
60 mL棕色广口螺旋盖玻璃瓶（860062P-1g）
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
存储类别
11 - Combustible Solids
Sphingomyelin functions as a novel receptor for Helicobacter pylori VacA
Gupta VR, et al.
PLoS Pathogens, 4(5), e1000073-e1000073 (2008)
Lipid raft components cholesterol and sphingomyelin increase H+/OH- permeability of phosphatidylcholine membranes
Gensure R H, et al.
The Biochemical Journal, 398(3), 485-495 (2006)
Distinct disruptions in Land's cycle remodeling of glycerophosphocholines in murine cortex mark symptomatic onset and progression in two Alzheimer's disease mouse models
Granger M W, et al.
Journal of Neurochemistry (2018)
Yusuke Sato et al.
Acta biomaterialia, 102, 341-350 (2019-11-17)
Despite the fact that small-sized lipid nanoparticles (LNPs) are important for improved tissue penetration and efficient drug delivery, their poor stability and intracellular trafficking significantly hinders their use as potent small-sized LNPs. It has been reported that both the diffusion
Sphingomyelin metabolism at the plasma membrane: implications for bioactive sphingolipids.
Milhas D, et al.
Febs Letters, 584, 1887-1894 (2010)
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