N-omega-CD3-Octadecanoyl-D-erythro-sphingosine-1-phosphate/N-omega-CD3-十八烷酰基-D-红-鞘氨醇-1-磷酸盐

Specifications

• Catalog #:2206

• Scientific Name:N-omega-CD₃-Octadecanoyl-D-erythro-sphingosine-1-phosphate

• Common Name:C18:0-D₃-Ceramide-1-phosphate; N-Stearoyl-D₃-C1P

• Empirical Formula:C₃₆H₆₉D₃NO₆P

• SDS:View Safety Data Sheet

• Data Sheet:View Data Sheet

• Formula Weight:649

• Unit:1 mg

• Solvent:none

• Source:synthetic

• Purity:98+%

• Analytical Methods:TLC, identity confirmed by MS

• Solubility:chloroform/methanol/acetic acid, 60:15:25; chloroform/methanol/7.5M ammonium hydroxide 80:20:4

• Physical Appearance:solid

• Storage:-20℃

• Dry Ice:No

• Hazardous:No

Description

Application Notes:

这种氘化神经酰胺-1-磷酸盐是理想的质谱标准和体内和体外研究。神经酰胺-1-磷酸是哺乳动物细胞中几种重要的磷脂类物质之一，它是由神经酰胺激酶磷酸化产生的。神经酰胺-1-磷酸因其重要的细胞功能，如在炎症中的作用，作为一种新型的第二信使，并参与细胞吞噬、钾离子通道功能、炎症反应、细胞存活和肿瘤发生等过程，目前备受关注。神经酰胺-1-磷酸的第一个被报道的生物作用是其刺激DNA合成和细胞分裂的能力。神经酰胺-1-磷酸也被发现是有丝分裂成纤维细胞和巨噬细胞。神经酰胺-1-磷酸的有丝分裂作用依赖于其通过NADPH氧化酶在细胞内刺激巨噬细胞产生活性氧的能力。该酶位于PKC-α和cPLA(2)-α的下游。神经酰胺-1-磷酸酯的另一个重要功能是促进细胞存活。神经酰胺-1-磷酸刺激磷脂酰肌醇3-激酶(PI3-K)/蛋白激酶B (PKB)通路，这是生长因子促进细胞存活的主要机制。神经酰胺-1-磷酸可能通过刺激PI3-K/PKB/NFkappaB通路来阻断细胞凋亡，从而维持抗凋亡Bcl-X(L)的产生。基于这些和之前的研究结果，有人提出抑制酸性鞘磷脂酶和随后降低的神经酰胺水平可以通过刺激PI3-K/PKB通路来促进细胞存活。

This deuterated ceramide-1-phosphate is ideal as a mass spectrometry standard and for in vivo and in vitro investigations. Ceramide-1-phosphate is one of several important phosphosphingolipids in mammalian cells and it is generated by the phosphorylation of ceramide by the enzyme ceramide kinase. Ceramide-1-phosphate is currently attracting much attention in research due to its important cellular functions like its role in inflammation, as a novel second messenger, and its involvement in cellular processes like phagocytosis, potassium channel function, inflammatory responses, cell survival, and tumorigenesis. The first reported biological action of ceramide-1-phosphate was its ability to stimulate DNA synthesis and cell division. Ceramide-1-phosphate was also found to be mitogenic for both fibroblasts and macrophages. The mitogenic effect of ceramide-1-phosphate is dependent on its intracellular ability to stimulate reactive oxygen specie production in macrophages via the enzyme NADPH oxidase. This enzyme is downstream of PKC-α and cPLA(2)-α in this pathway. Another important function of ceramide-1-phophate is its promotion of cell survival. Ceramide-1-phosphate stimulates the phosphatidylinositol 3-kinase (PI3-K)/protein kinase B (PKB) pathway, a major mechanism whereby growth factors promote cell survival. It is probable that ceramide-1-phosphate blocks apoptosis by stimulating the PI3-K/PKB/NFkappaB pathway and thereby maintaining the production of antiapoptotic Bcl-X(L). Based on these and previous findings it has been proposed that the inhibition of acid sphingomyelinase and the subsequent decrease in ceramide levels would allow cell signaling through stimulation of the PI3-K/PKB pathway to promote cell survival.

References:
1. E. Kooijman et al. Structure of Ceramide-1-Phosphate at the Air-Water Solution Interface in the Absence and Presence of Ca2+. Journal of Biophysics, Vol. 96(6), pp. 2204-2215, 2009
2. R. Stahelin et al. Ceramide-1-phosphate Binds Group IVA Cytosolic Phospholipase a2 via a Novel Site in the C2 Domain. The Journal of Biological Chemistry, Vol. 282(28) pp. 20467-20474, 2007
3. Arana, L. et al. Generation of reactive oxygen species (ROS) is a key factor for stimulation of macrophage proliferation by ceramide 1-phosphate. Exp. Cell Res., Vol. 318(4) pp. 350-360, 2012
4. Gómez-Muñoz A. et al. Ceramide-1-phosphate promotes cell survival through activation of the phosphatidylinositol 3-kinase/protein kinase B pathway. FEBS Lett., Vol. 579(17) pp. 3744-3750, 2005