溶血磷脂酰胆碱(鸡蛋) | 17364-16-8

• 物质功能分类: 生物化工 - 生化试剂
• 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: 溶血磷脂酰胆碱(鸡蛋)
• 中文别名: 棕榈酰溶血卵磷脂；1-棕榈酰-RAC-甘油-3-磷酰胆碱；1-十六酰-SN-丙三醇-磷酸胆碱；1-十六酰-sn-丙三醇-磷酸胆碱；十六酰-SN-丙三醇-磷酸胆碱；1-棕榈酰溶血磷脂酰胆碱
• 英文名称: 1-palmitoyl-sn-glycero-3-phosphocholine
• 英文别名: lyso PC 16:0；LPC 16:0；1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine；16:0 lyso-PC；lysoPC(16:0/0:0)；PC (16:0/0:0)；[(2R)-3-hexadecanoyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 17364-16-8；97281-36-2
• 化学式: C₂₄H₅₀NO₇P
• 分子量: 495.637
• InChiKey: ASWBNKHCZGQVJV-HSZRJFAPSA-N

物化性质

• 熔点：
  253 °C
• 溶解度：
  氯仿（微溶）、甲醇（微溶、加热）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途

1-十六酰-SN-丙三醇-磷酸胆碱可用于研究生物膜的性质、细胞信号传导、细胞凋亡以及药物传递等相关领域。

反应信息

• 作为反应物：
  描述：

  溶血磷脂酰胆碱(鸡蛋) 在 氨基-Α-环糊精 、 水 作用下， 以 aq. buffer 为溶剂， 反应 72.0h， 生成 棕榈酸
  参考文献：
  名称：

  Lipase mimetic cyclodextrins

  摘要：

  脂肪酶类似物环糊精（CD）可以在生理条件下选择性水解天然的溶血磷脂酰甘油（GPLs）。

  DOI：

  10.1039/d0sc05711h
• 作为产物：
  描述：

  甘磷酸胆碱 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 2.5h， 生成 溶血磷脂酰胆碱(鸡蛋)
  参考文献：
  名称：

  Syntheses and antiproliferative activities of novel phosphatidylcholines containing dehydroepiandrosterone moieties

  摘要：

  Dehydroepiandrosterone (DHEA) is a natural hormone with many beneficial properties including an anticancer activity. Unfortunately, DHEA is unstable in the body and exhibits cytotoxicity against healthy cells. In this study, a series of new phosphocholines containing DHEA at sn-1 and/or sn-2 positions were prepared. Succinic acid was used as a linker between the active drug and sn-glycero-3-phosphocholine. All the compounds were evaluated in vitro for their antiproliferative activities against four cell lines: Balb/3T3, HL-60, B16, and LNCaP. The results showed that phosphocholines With DHEA at sn-1 and/or sn-2 positions did not have cytotoxic effects on the normal cell line (Balb/3T3). Mixed-chain phospholipids with DHEA and fatty acid residues showed the highest activity against tumor cell lines. The most active compound, tic, showed a moderate cytotoxic effect against the HL-60 and B16 cell lines. (C) 2017 Published by Elsevier Inc.

  DOI：

  10.1016/j.steroids.2016.12.015

文献信息

• Phospholipidic Colchicinoids as Promising Prodrugs Incorporated into Enzyme-Responsive Liposomes: Chemical, Biophysical, and Enzymological Aspects
  作者：Ekaterina S. Shchegravina、Daria S. Tretiakova、Anna S. Alekseeva、Timur R. Galimzyanov、Yuri N. Utkin、Yuri A. Ermakov、Elena V. Svirshchevskaya、Vadim V. Negrebetsky、Natalia Yu. Karpechenko、Valery P. Chernikov、Natalia R. Onishchenko、Elena L. Vodovozova、Alexey Yu. Fedorov、Ivan A. Boldyrev

  DOI：10.1021/acs.bioconjchem.9b00051

  日期：2019.4.17

  Enzyme-responsive liposomes release their cargo in response to pathologically increased levels of enzymes at the target site. We report herein an assembly of phospholipase A2-responsive liposomes based on colchicinoid lipid prodrugs incorporated into lipid bilayer of the nanosized vesicles. The liposomes were constructed to addresses two important issues: (i) the lipid prodrugs were designed to fit the structure of the enzyme binding site; and (ii) the concept of lateral pressure profile was used to design lipid prodrugs that introduce almost no distortions into the lipid bilayer packing, thus ensuring that corresponding liposomes are stable. The colchicinoid agents exhibit antiproliferative activity in subnanomolar range of concentrations.

  酶响应性脂质体能够在靶部位病理状态下酶水平升高时释放其载荷。本研究报告了一种基于秋水仙素类脂质前药，并将其整合到纳米级囊泡脂双层中的磷脂酶A2响应性脂质体的组装方法。这些脂质体的设计旨在解决两个重要问题：（i）脂质前药的结构被设计为与酶的结合位点相匹配；以及（ii）利用侧向压力分布的概念设计脂质前药，这些前药在脂双层排列中引入的畸变几乎为零，从而确保相应的脂质体是稳定的。秋水仙素类药物在亚纳摩尔浓度的范围内表现出抗增殖活性。
• Polymerization of supramolecular assemblies: Comparison of lamellar and inverted hexagonal phases
  作者：Warunee Srisiri、Youn-Sik Lee、Thomas M. Sisson、Bruce Bondurant、David F. O'Brien

  DOI：10.1016/s0040-4020(97)00969-1

  日期：1997.11

  extended this strategy to successfully polymerize the inverted hexagonal (HII) phase. This report is the first comparison of radical chain polymerizations in lamellar and HII phases. The number average degree of polymerization of polymers obtained in both lamellar and HII phases depended strongly on the initiation chemistry, but were insensitive to the lipid phases. The immediate benefit of these studies

  自从1980年代初首次报道水合双层的聚合反应以来，已经成功地使用了多种可聚合基团和脂质。在探索用于层状相聚合的各种策略中，一种特别有用的方法依赖于合适的可聚合两亲物的设计，该两亲物在水合作用时可形成组装体，然后可在保留结构的情况下进行聚合。我们最近扩展了此策略，以成功地聚合倒六角形（H II）相。该报告是层状和H II相中自由基链聚合的首次比较。层状和H II中获得的聚合物的数均聚合度相对引发化学反应的依赖性很大，但对脂质相不敏感。这些研究的直接好处是，可以在两个阶段广泛改变聚合物的大小，以获得不同的材料性能。
• Tin-mediated synthesis of lyso-phospholipids
  作者：Ezio Fasoli、Alberto Arnone、Antonio Caligiuri、Paola D'Arrigo、Lorenzo de Ferra、Stefano Servi

  DOI：10.1039/b604636c

  日期：——

  acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso-phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed.

  从相应的二醇，甘油磷酰基胆碱和3-磷酸甘油中，选择性地且高收率地制备了1-O-酰基-sn-甘油-3-磷酸胆碱和1-O-酰基-sn-甘油-3-磷酸。由二醇开始，在2-丙醇中通过与二烷基氧化锡反应制备活化的锡缩酮。在相同的溶剂中用长链脂肪酸氯化物酰化中间体，从而以高收率和完全的区域选择性得到相应的1-酰基-溶血磷脂。讨论了锡介导的酰化反应的催化性质和溶剂的相关性。
• Synthesis and Biological Evaluation of Novel Phosphatidylcholine Analogues Containing Monoterpene Acids as Potent Antiproliferative Agents
  作者：Anna Gliszczyńska、Natalia Niezgoda、Witold Gładkowski、Marta Czarnecka、Marta Świtalska、Joanna Wietrzyk

  DOI：10.1371/journal.pone.0157278

  日期：——

  The synthesis of novel phosphatidylcholines with geranic and citronellic acids in sn-1 and sn-2 positions is described. The structured phospholipids were obtained in high yields (59–87%) and evaluated in vitro for their cytotoxic activity against several cancer cell lines of different origin: MV4-11, A-549, MCF-7, LOVO, LOVO/DX, HepG2 and also towards non-cancer cell line BALB/3T3 (normal mice fibroblasts). The phosphatidylcholines modified with monoterpene acid showed a significantly higher antiproliferative activity than free monoterpene acids. The highest activity was observed for the terpene-phospholipids containing the isoprenoid acids in sn-1 position of phosphatidylcholine and palmitic acid in sn-2.

  报道了在sn-1和sn-2位置上含有香叶酸和香茅酸的新型磷脂酰胆碱的合成。这些结构化磷脂以高产率（59-87%）获得，并在体外对其对几种不同来源的癌细胞系的细胞毒性活性进行了评估：MV4-11、A-549、MCF-7、LOVO、LOVO/DX、HepG2，以及对非癌细胞系BALB/3T3（正常小鼠成纤维细胞）。与游离单萜酸相比，修饰有单萜酸的磷脂酰胆碱显示出显著更高的抗增殖活性。含有磷脂酰胆碱sn-1位置上的异戊二烯酸和sn-2位置上的棕榈酸的萜类磷脂显示出最高的活性。
• γ-Ray irradiation of liposomes of polymerizable phospholipids containing octadeca-2,4-dienoyl groups and characterization of the irradiated liposomes
  作者：Kazuhiro Akama、Yoshihiro Yano、Satoru Tokuyama、Fumio Hosoi、Hideki Omichi

  DOI：10.1039/a908732j

  日期：——

  The synthesis of a variety of polymerizable phospholipids containing the octadeca-2,4-dienoyl moiety on 2-acyl chains and the characteristics of liposomes containing those phospholipids of the γ-irradiation are described. We synthesized three different polymerizable phosphocholines that have different 1-acyl chain lengths with the octadeca-2,4-dienoyl moiety on the 2-acyl chain: myristoyl (MODPC), palmitoyl (PODPC) and stearoyl (SODPC). The liposomes were prepared by extrusion through polycarbonate filters with a pore size of 0.2 µm, and were polymerized by γ-irradiation with various dose rates. The polymerization rate increased in the order SODPC > MODPC > PODPC. The mechanism of the polymerization of SODPC was the same as that of 1,2-bis-[(E,E)-octadeca-2,4-dienoyl]-sn-glycero-3-phosphocholine (DODPC), but differed from that of MODPC and PODPC. Freeze–thaw testing was used to evaluate the stability of the polymerizable liposomes. The MODPC liposome was more stable than other monofunctional liposomes. For similar irradiation, the polymerization behavior of the liposomes was significantly affected by the 1-acyl length.

  本文描述了含有十八碳-2,4-二烯酰基团在2-酰基链上的多种可聚合磷脂的合成以及含有这些磷脂的脂质体在γ辐照下的特性。我们合成了三种不同类型的可聚合磷脂酰胆碱，它们具有不同长度的1-酰基链和2-酰基链上的十八碳-2,4-二烯酰基团：肉豆蔻酰（MODPC）、棕榈酰（PODPC）和硬脂酰（SODPC）。脂质体通过0.2微米孔径的聚碳酸酯滤器挤压制备，并通过不同剂量率的γ辐照进行聚合。聚合速率按SODPC > MODPC > PODPC的顺序增加。SODPC的聚合机制与1,2-双[(E,E)-十八碳-2,4-二烯酰]-sn-甘油-3-磷脂酰胆碱（DODPC）相同，但与MODPC和PODPC不同。通过冷冻-解冻测试评估了可聚合脂质体的稳定性。MODPC脂质体比其他单功能脂质体更稳定。对于类似的辐照，脂质体的聚合行为受到1-酰基长度的显著影响。