1-O-棕榈基-2-花生酰基-sn-甘油-3-胆碱磷酸 | 86288-11-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 1-O-棕榈基-2-花生酰基-sn-甘油-3-胆碱磷酸
• 英文名称: 1-O-Hexadecyl-2-arachidonoyl-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-3-hexadecoxy-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 86288-11-1
• 化学式: C44H82NO7P
• 分子量: 768.1
• InChiKey: DUUSFCFZBREELS-WWBBCYQPSA-N

物化性质

• 闪点：
  14 °C
• 溶解度：
  酸性PBS：0.5mg/ml；碱性PBS：0.5mg/ml； DMF：10mg/mL； DMSO：2mg/mL；乙醇：1mg/mL； PBS pH 7.2：0.5 mg/mL
• 碰撞截面：
  297.2 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]
• 稳定性/保质期：
  按照规定使用和贮存的物品是不会分解的。

计算性质

• 辛醇/水分配系数(LogP)：
  13
• 重原子数：
  53
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险品标志：
  F,Xi
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3
• 安全说明：
  S16
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  1-O-棕榈基-2-花生酰基-sn-甘油-3-胆碱磷酸 、 水 生成 Arachidonate 、 1-O-十六烷基-SN-甘油基-3-胆碱磷酸 、 氢(+1)阳离子
  参考文献：
  名称：

  人胞质85 kDa磷脂酶A2的多种酶活性：水解反应和酰基转移至甘油。

  摘要：

  当在甘油存在下进行测定时，重组人85 kDa胞质磷脂酶A2（cPLA2）除了水解这些底物外，还催化了放射性标记的磷脂酰胆碱和脂肪酸的对位取代苯基酯的酰基链向甘油的转移。转酰化反应的产物是单酰基甘油（MAG），且酰基链主要被酯化（>或= 95％）为甘油的伯羟基（sn-1 / 3）；立体化学未知。通过为酶-底物复合物形成产物提供额外的机械途径，以及通过增加酶的固有水解和转酰化活性，甘油的浓度都加速了酶的转化。测定了sn-1 / 3-花生四烯酸单酰基甘油的明显酶水解，而sn-1 /3-α-亚麻酸-和sn-2-花生四烯酸单酰基甘油未检测到水解。1,3-丙二醇也可作为酶的酰基受体。cPLA2水解缺少sn-2羟基的溶血磷脂酰胆碱的类似物。该酶将水解rac-1-（花生四烯基，α-亚麻酸，棕榈酰）-2-O-十六烷基-甘油-3-磷酸胆碱脂质的sn-1-酰基链，并将该酰基链转移至甘油。因此，cPLA2具有磷脂

  DOI：

  10.1021/bi00024a004
• 作为产物：
  描述：

  arachidonoyl-CoA(4-) 、 1-O-十六烷基-SN-甘油基-3-胆碱磷酸 生成 1-O-棕榈基-2-花生酰基-sn-甘油-3-胆碱磷酸 、 coenzyme A
  参考文献：
  名称：

  Molecular Identification of a Novel Mammalian Brain Isoform of Acyl-CoA:Lysophospholipid Acyltransferase with Prominent Ethanolamine Lysophospholipid Acylating Activity, LPEAT2

  摘要：

  Acyl-CoA-dependent lysophospholipid acyltransferases play an important role in attaining the appropriate molecular species of phospholipids. A number of genes encoding these activities were recently identified. It has become clear that multiple genes can encode one enzymatic activity and that a given gene may encode multiple activities. Here we report the identification of a gene encoding a mammalian acyl-CoA-dependent lysophospholipid acyltransferase with prominent activity toward ethanolamine-containing lysophospholipids, which we termed acyl-CoA: lysophosphatidylethanolamine acyltransferase 2, LPEAT2 (previously annotated as AYTL3 or AGPAT7). LPEAT2 is predominantly expressed in brain, coinciding with an enrichment of phosphatidylethanolamine in this tissue. Ectopic expression of LPEAT2 in mammalian HEK293T cells led to a dramatic increase (up to 9-fold) in LPEAT activity when compared with cells transfected with empty vector or an unrelated acyltransferase. LPEAT2 also exhibited significant acyl-CoA-dependent acyltransferase activity toward 1-O-alkenyl-lysophosphatidylethanolamine, lysophosphatidylglycerol, 1-O-alkyl-lysophosphatidylcholine, lysophosphatidylserine, and lysophosphatidylcholine but lacked appreciable acylating activity toward glycerol 3-phosphate, lysophosphatidic acid, lysophosphatidylinositol, and diacylglycerol, demonstrating multiple but selective functions of LPEAT2 as an enzyme involved in phospholipid remodeling. LPEAT2 recognizes a broad range of medium and long chain fatty acyl-CoA, and its activity was not affected by Ca2+. When overexpressed in mammalian cells, LPEAT2 is localized to the endoplasmic reticulum. siRNA-mediated knockdown of LPEAT2 in HEK293T cells significantly decreased LPEAT and 1-alkenyl-LPEAT activities but did not affect other lysophospholipid acylating activities. These findings identify LPEAT2 as an important enzyme in the biosynthesis of ethanolamine-containing phospholipids, especially in brain.

  DOI：

  10.1074/jbc.m800364200

文献信息

• Functional associative coatings for nanoparticles
  申请人：Hainfeld James F.

  公开号：US20080089836A1

  公开（公告）日：2008-04-17

  Described herein are nanoparticles that are coated with a bilayer of molecules formed from surface binding molecules and amphiphatic molecules. The bilayer coating self assembles on the nanoparticles from readily available materials/molecules. The modular design of the bilayer coated nanoparticles provides a means for readily and efficiently optimizing the properties of the bilayer coated nanoparticle compositions. Also described herein are uses of such nanoparticles in medicine, laboratory techniques, industrial and commerical applications.

  本文描述了一种纳米颗粒，其表面涂覆有由表面结合分子和两亲分子形成的双层分子层。该双层涂层可以自组装在纳米颗粒上，使用易得的材料/分子。双层涂层纳米颗粒的模块化设计提供了一种方便和高效地优化其性质的方法。此外，本文还描述了这种纳米颗粒在医学、实验室技术、工业和商业应用中的用途。
• Oxidized lipids and uses thereof in the treatment of inflammatory diseases and disorders
  申请人：Harats Dror

  公开号：US20070099868A1

  公开（公告）日：2007-05-03

  Novel synthetic oxidized lipids and methods utilizing oxidized lipids for treating and preventing an inflammation associated with an endogenous oxidized lipid are provided.

  本发明提供了一种新型合成氧化脂质及利用氧化脂质治疗和预防与内源性氧化脂质相关的炎症的方法。
• Oxidized Lipids and Uses Thereof in the Treatment of Inflammatory Diseases and Disorders
  申请人：Harats Dror

  公开号：US20080261865A1

  公开（公告）日：2008-10-23

  Novel synthetic oxidized lipids and methods utilizing oxidized lipids for treating and preventing an inflammation associated with an endogenous oxidized lipid are provided.

  本发明提供了新型合成的氧化脂质以及利用氧化脂质治疗和预防与内源性氧化脂质相关的炎症的方法。
• OXIDIZED LIPIDS AND USES THEREOF IN THE TREATMENT OF INFLAMMATORY DISEASES AND DISORDERS
  申请人：HARATS Dror

  公开号：US20110189212A1

  公开（公告）日：2011-08-04

  Novel synthetic oxidized lipids and methods utilizing oxidized lipids for treating and preventing an inflammation associated with an endogenous oxidized lipid are provided.

  本发明提供了一种新型合成氧化脂质以及利用氧化脂质治疗和预防与内源性氧化脂质相关的炎症的方法。
• NANOPARTICLE-BASED DELIVERY SYSTEM WITH OXIDIZED PHOSPHOLIPIDS AS TARGETING LIGANDS FOR THE PREVENTION, DIAGNOSIS AND TREATMENT OF ATHEROSCLEROSIS
  申请人：WANG Shu

  公开号：US20140287024A1

  公开（公告）日：2014-09-25

  Disclosed are nanoparticle-based medicine/nutrient delivery system that are coated or incorporated with oxidized phospholipids as targeting ligands. Such delivery systems can specifically target macrophages, which are determinant cells in the aortic wall for atherosclerotic lesion development, to significantly increase bioavailability and specificity for the prevention, diagnosis and treatment of atherosclerosis.

  揭示了一种基于纳米颗粒的医药/营养素传递系统，其涂有或包含氧化磷脂作为靶向配体。这样的传递系统可以特异性地靶向巨噬细胞，它们是动脉壁上动脉粥样硬化病变发展的决定性细胞，从而显着增加生物利用度和特异性，用于预防、诊断和治疗动脉粥样硬化。