1,2-二己酰卵磷脂 | 34506-67-7

• 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: 1,2-二己酰卵磷脂
• 中文别名: 1,2-二己酰-Sn-甘油-3-磷酰胆碱
• 英文名称: 1,2-dihexanoyl-sn-phosphatidylcholine
• 英文别名: 1,2-dihexanoyl-sn-glycero-3-phosphocholine；dihexanoylphosphatidylcholine；1,2-dihexanoyl-sn-glycero-3-phosphatidylcholine；[(2R)-2,3-di(hexanoyloxy)propyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 34506-67-7
• 化学式: C₂₀H₄₀NO₈P
• 分子量: 453.513
• InChiKey: DVZARZBAWHITHR-GOSISDBHSA-N

物化性质

• 溶解度：
  DMF：>20mg/mL； DMSO：> 7 mg/mL；乙醇：>30mg/mL； PBS（pH 7.2）：> 250 μg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 危险品运输编号：
  UN 1888 6.1/PG 3
• 海关编码：
  2923900090
• WGK Germany：
  3
• 储存条件：
  -20°C

制备方法与用途

1,2-二己酰基-sn-甘油-3-磷酸胆碱是一种生物化学试剂，可以作为生物材料或有机化合物应用于生命科学的相关研究中。

反应信息

• 作为反应物：
  描述：

  1,2-二己酰卵磷脂 在 水 作用下， 以 various solvent(s) 为溶剂， 生成 1-己酰基-2-羟基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  Secretory phospholipase A2-α from Arabidopsis thaliana: functional parameters and substrate preference

  摘要：

  The secretory phospholipase A(2)-alpha from Arabidopsis thaliana (AtsPLA(2)-alpha), being one of the first plant sPLA(2)s obtained in purified state, has been characterised with respect to substrate preference and optimum conditions of catalysis. The optima of pH, temperature, and calcium concentration were similar to the parameters of secretory PLA(2)s from animals. However, substrate preferences markedly differed. In contrast to pancreatic PLA(2)s, AtsPLA(2)-alpha preferred zwitterionic phospholipids, and showed lower activity toward anionic phospholipids. In substrates with two identical fatty acid chains, AtsPLA(2)-alpha showed optimum activity toward phospholipids with decanoyl groups. In substrates with palmitoyl groups in sn-1 position, acyl chains with higher degree of unsaturation in sn-2 position were preferred, excluding arachidonic acid, showing the evolutionary adaptation of the enzyme to substrate composition in plants. Km values for short chain phospholipids were comparable to sPLA(2)s from animals, whereas k(cat) values were much smaller and interfacial activation was less important. (C) 2007 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2007.07.001
• 作为产物：
  描述：

  己酸 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 双氧水 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 38.75h， 生成 1,2-二己酰卵磷脂
  参考文献：
  名称：

  General Method for the Synthesis of Phospholipid Derivatives of 1,2-O-Diacyl-sn-Glycerols

  摘要：

  An efficient phosphite coupling protocol is described for the syntheses of the major classes of phospholipids that are derived from 1,2-O-diacyl-sn-glycerols and analogues thereof. The symmetrical diacyl glycerols 10c,d were prepared by straightforward acylation of 3-O-benzyl-sn-glycerol (7) with the appropriate carboxylic acid in the presence of dicyclohexylcarbodiimide (DCC) and 4-(dimethylamino)pyridine (DMAP). A simple method for preparing saturated and unstaturated mixed 1,2-O-diacyl-sn-glycerols was then devised that involved stepwise acylation of 7 with different alkyl carboxylic acids and debenzylation this procedure is exemplified by the preparation of 10a,b. The 1,2-O-diacyl-sn-glycerols 10a-d were then coupled with suitably protected lipid head groups employing reactive alkyl or aryl dichlorophosphites to give intermediate phosphite triesters in high overall yields. Oxidation or sulfurization of these phosphites proceeded smoothly to give the corresponding phosphate or phosphorothioate triesters, deprotection of which then provided the phosphatidylcholines 16 and 17, the phosphatidylethanolamine 20, the phosphatidylserine 28, and the phosphatidylinositols 37 and 38. Preparation of 37 and 38 required the invention of an improved method for resolving the isopropylidene-protected D-myo-inositol derivative 33. This phosphite coupling procedure was modified to assemble phospholipids bearing-polyunsaturated acyl side chains at the sn-2-position as exemplified by the preparation of the phosphatidylethanolamine 26. The one-pot phosphite coupling procedure is also applicable to the syntheses of a variety of other biologically interesting phospholipid analogues. For example, the phosphatidylinositol analogues 49-51, in which the hydroxyl group at C(2) of the inositol ring has been modified, were prepared in excellent overall yields by conjoining the 1,2-O-diacyl-sn-glycerol 10c with the protected inositol derivatives 44, 45, and 48. Phospholipid analogues that contain other replacements of the phosphate group including phosphoramidates and thiophosphates maybe prepared as evidenced by the syntheses of 56 and 61 in which the sn-3 oxygen atom of the 1,2-O-diacyl-sn-glycerol moiety is replaced with an N-benzyl group or a sulfur atom, respectively.

  DOI：

  10.1021/jo00096a023

文献信息

• [EN] NEUROTENSIN RECEPTOR BINDING CONJUGATES AND FORMULATIONS THEREOF<br/>[FR] CONJUGUÉS DE LIAISON AU RÉCEPTEUR DE LA NEUROTENSINE ET FORMULATIONS ASSOCIÉES
  申请人：TARVEDA THERAPEUTICS INC

  公开号：WO2017180834A1

  公开（公告）日：2017-10-19

  Conjugates of an active agent attached to a neurotensin receptor-binding targeting moiety via a linker have been designed. Nanoparticles and microparticles comprising such conjugates can provide improved temporospatial delivery of the active agent and/or improved biodistribution. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer or other diseases.

  已设计出将活性剂与神经肽受体结合靶向基团通过连接剂连接的共轭物。包含这种共轭物的纳米颗粒和微粒可以提供改善活性剂的时间空间传递和/或改善生物分布的效果。提供了制备这些共轭物、颗粒和其配方的方法。提供了将这些配方用于治疗或预防癌症或其他疾病的方法，例如向需要的受试者施用这些配方的方法。
• Targeted Conjugates Encapsulated in Particles and Formulations Thereof
  申请人：Blend Therapeutics, Inc.

  公开号：US20140187501A1

  公开（公告）日：2014-07-03

  Particles, including nanoparticles and microparticles, and pharmaceutical formulations thereof, containing conjugates of an active agent such as a therapeutic, prophylactic, or diagnostic agent attached to a targeting moiety via a linker have been designed which can provide improved temporospatial delivery of the active agent and/or improved biodistribution. Methods of making the conjugates, the particles, and the formulations thereof are provided. Methods of administering the formulations to a subject in need thereof are provided, for example, to treat or prevent cancer or infectious diseases.

  包括纳米颗粒和微粒在内的微粒子以及其药物配方，其中含有活性剂的共轭物，例如治疗、预防或诊断剂，通过连接体连接到靶向基团，已经设计出来，可以提供改善活性剂的时间空间传递和/或改善生物分布的效果。提供了制备共轭物、微粒子和其配方的方法。提供了将这些配方用于需要的受试者的方法，例如用于治疗或预防癌症或传染病。
• Methods of treating conditions associated with an EDG-4 receptor
  申请人：Solow-Cordero David

  公开号：US20050113283A1

  公开（公告）日：2005-05-26

  The present invention provides a method of modulating an Edg-4 receptor mediated biological activity in a cell. A cell expressing the Edg-4 receptor is contacted with a modulator of an Edg-4 receptor sufficient to modulate the Edg-4 receptor mediated biological activity. In another aspect, the present invention provides a method for modulating an Edg-4 receptor mediated biological activity in a subject. A therapeutically effective amount of a modulator of the Edg-4 receptor is administered to the subject.

  本发明提供了一种调节细胞中Edg-4受体介导的生物活性的方法。将表达Edg-4受体的细胞与足以调节Edg-4受体介导的生物活性的调节剂接触。在另一个方面，本发明提供了一种调节受体Edg-4介导的生物活性的方法。向受体施用治疗有效量的Edg-4受体调节剂。
• 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。
• Enzymatic synthesis of a modified phospholipid and its evaluation as a substrate for B. cereus phospholipase C
  作者：Stephen F. Martin、Paul J. Hergenrother

  DOI：10.1016/s0960-894x(98)00071-7

  日期：1998.3

  The novel phospholipid 2, which bears a tert-butyl moiety in place of the natural trimethyl ammonium group of phosphatidylcholine, has been enzymatically synthesized via a transphosphatidylation reaction mediated by phospholipase D. The change from the choline headgroup in 1 to the tert-butyl group in 2 reduced the efficiency of hydrolysis by the phosphatidylcholine-preferring phospholipase C from Bacillus

  通过磷脂酶D介导的反式磷脂酰化反应，通过酶促合成了新型磷脂2，该磷脂具有一个叔丁基部分来代替磷脂酰胆碱的天然三甲基铵基团。 2中的方法将蜡状芽孢杆菌中偏爱磷脂酰胆碱的磷脂酶C的水解效率降低了10倍以上（3）。