1-(1Z-十八碳烯基)-2-油酰基-sn-甘油-3-磷酸乙醇胺 | 144371-68-6

• 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-(1Z-十八碳烯基)-2-油酰基-sn-甘油-3-磷酸乙醇胺
• 英文名称: 1-O-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine
• 英文别名: 1-(1Z-octadecenyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoethanolamine；1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoethanolamine；PE 18:1/18:1；2-azaniumylethyl (2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(1Z)-octadec-1-en-1-yloxy]propyl phosphate；2-azaniumylethyl [(2R)-3-[(Z)-octadec-1-enoxy]-2-[(Z)-octadec-9-enoyl]oxypropyl] phosphate
• CAS: 144371-68-6
• 化学式: C₄₁H₈₀NO₇P
• 分子量: 730.062
• InChiKey: XVYPOHCSLJZFED-QZEVRULJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  50
• 可旋转键数：
  41
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(1Z-十八碳烯基)-2-油酰基-sn-甘油-3-磷酸乙醇胺 、 L-丝氨酸 生成 1-(1Z-octadecenyl)-2-oleoyl-sn-glycero-3-phosphoserine(1-) 、 2-amino-ethanol; protonated form
  参考文献：
  名称：

  Phosphatidylserine synthase 2: high efficiency for synthesizing phosphatidylserine containing docosahexaenoic acid

  摘要：

  Phosphatidylserine (PS), the major anionic phospholipid in eukaryotic cell membranes, is synthesized by the integral membrane enzymes PS synthase 1 (PSS1) and 2 (PSS2). PSS2 is highly expressed in specific tissues, such as brain and testis, where docosahexaenoic acid (DHA, 22:6n-3) is also highly enriched. The purpose of this work was to characterize the hydrocarbon-chain preference of PSS2 to gain insight on the specialized role of PSS2 in PS accumulation in the DHA-abundant tissues. Flag-tagged PSS2 was expressed in HEK cells and immunopurified in a functionally active form. Purified PSS2 utilized both PE plasmalogen and diacyl PE as substrates. Nevertheless, the latter was six times better utilized, indicating the importance of an ester linkage at the sn-1 position. Although no sn-1 fatty acyl preference was noted, PSS2 exhibited significant preference toward DHA compared with 18:1 or 20:4 at the sn-2 position. Preferential production of DHA-containing PS (DHA-PS) was consistently observed with PSS2 purified from a variety of cell lines as well as with microsomes from mutant cells in which PS synthesis relies primarily on PSS2.(jlr) These findings suggest that PSS2 may play a key role in PS accumulation in brain and testis through high activity toward DHA-containing substrates that are abundant in these tissues.-Kimura, A. K., and H.-Y. Kim. Phosphatidylserine synthase 2: high efficiency for synthesizing phosphatidylserine containing docosahexaenoic acid. J. Lipid Res. 2013. 54: 214-222.

  DOI：

  10.1194/jlr.m031989
• 作为产物：
  描述：

  Phosphatidylethanolamine-(O-18:0/18:1(9Z)) 、 铁燧石 、 氢(+1)阳离子 、 氧气 生成 1-(1Z-十八碳烯基)-2-油酰基-sn-甘油-3-磷酸乙醇胺 、 铁阳离子 、 水
  参考文献：
  名称：

  细菌光反应揭示了一种用于人缩醛磷脂合成的孤儿去饱和酶

  摘要：

  远亲有助于发现动物酶 除了形成包裹细胞的膜外，脂质也是重要的信号分子。含有乙烯基醚键的缩醛磷脂是动物体内​​丰富的脂类。这些脂质是如何从具有烷基醚键的前体合成的，一直是个谜。加列戈-加西亚等人。在社会细菌 Myxococcus xanthus 中发现了一种酶 CarF，它产生缩醛磷脂，用于单线态氧的信号通路，单线态氧是光氧化应激的标志物。然后他们表明，动物同源物可以催化细菌和人类细胞中缩醛磷脂合成的最后一步，从而解决了动物中缩醛磷脂的来源。科学，这个问题 p。探索了动物和社会细菌中的 128 种纤溶酶原生物合成酶。缩醛磷脂是具有标志性 sn-1 乙烯基醚键的甘油磷脂。这些脂质存在于动物和一些细菌中，并具有膜组织、信号传导和抗氧化作用。我们发现了对在细菌酶 CarF 中形成乙烯基醚键必不可少的等离子体乙醇胺去饱和酶活性，该酶是人类酶 TMEM189 的同系物。CarF 介导黄色粘球菌中光诱导

  DOI：

  10.1126/science.aay1436

文献信息

• Hetero-Diels–Alder Cycloaddition Reaction of Vinyl Ethers Enables Selective Fluorescent Labeling of Plasmalogens in Human Plasma Lipids
  作者：Yiwen Ding、Chu Zhang、Min Zhou、Yu Xiang、Aijun Tong

  DOI：10.1021/acs.joc.3c01380

  日期：2023.10.6

  challenge, we report an efficient hetero-Diels–Alder cycloaddition reaction between nonterminal vinyl ethers of Pls and o-quinolinone quinone methide probes under mild conditions. On the basis of this mechanism, a selective fluorescent labeling method for Pls is developed. The application of this method permits the exclusive derivatization of Pls over other human plasma lipids. The process also imparts labeled

  缩醛磷脂 (Pls) 是具有广泛生物学意义的含乙烯基醚甘油磷脂。它们的异常水平与神经系统疾病和心血管疾病有关。分析脂质样品中 Pls 的复杂性源于多种其他共存脂质种类，这强调了对 Pls 特异性标记反应的迫切需要。为了应对这一挑战，我们报告了在温和条件下 Pls 的非末端乙烯基醚与邻喹啉酮醌甲基化物探针之间的高效杂狄尔斯-阿尔德环加成反应。基于该机制，开发了Pls的选择性荧光标记方法。该方法的应用允许 Pls 相对于其他人血浆脂质进行独特的衍生化。该过程还赋予标记的 Pls 独特的荧光发射和色谱保留特性。通过将该方法与高效液相色谱相结合，我们能够从 10 种不同的人血浆样本中识别 Pls 的单独色谱特征。这种由 Pls 特异性标记反应支持的 Pls 特征分析技术在仪器方面具有成本效益且简单，表明其在与 Pls 异常相关的疾病的早期筛查和诊断方面具有广阔的潜力。
• Novel neutral (bio)material
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2444464A1

  公开（公告）日：2012-04-25

  The instant invention concerns - a method for preparing a material comprising the following steps of a) treating the support to obtain a layer having SiH function, b) grafting the SiH layer obtained in step a) with an alkene and a catalyst for covalently bonding the alkene to the coating, said alkene being non-terminal and/or having an hydrophilic part, and c) recovering a material comprising a support coated with a chain covalently grafted with Si-C bonds, - a material comprising a support, optionally comprising a polyhydrosiloxane layer, on which surface is covalently bonded a grafted chain, wherein the covalent bonding between the support and/or the polyhydrosiloxane and the chain is an Si-C bond, and the grafted chain is bonded through a non-terminal carbon, through more than one covalent bond and/or the chain is having at least one hydrophilic part, and - devices comprising such material.

  本发明涉及 - 一种制备材料的方法，包括以下步骤 a) 处理支持物以获得具有 SiH 功能的层；b) 将步骤 a) 中获得的 SiH 层与烯烃和催化剂接枝，以将烯烃共价键合到涂层上，所述烯烃为非末端烯烃和/或具有亲水部分；以及 c) 回收一种材料，该材料包括涂有共价键合的 Si-C 键接枝链的支持物、 - 一种材料，包括支撑体，可选择包括聚氢硅氧烷层，在支撑体表面共价键合了一条接枝链，其中支撑体和/或聚氢硅氧烷与链之间的共价键合是 Si-C 键，接枝链通过非末端碳键、通过一个以上的共价键和/或链具有至少一个亲水部分键合，以及 - 包括这种材料的装置。
• MICROFLUIDIC PRODUCTION OF BIOFUNCTIONALIZED GIANT UNILAMELLAR VESICLES FOR TARGETED INTRACELLULAR CARGO DELIVERY
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP3838266A1

  公开（公告）日：2021-06-23

  The present invention relates to a method for preparation of monodisperse cell-targeting giant unilamellar vesicles based on symmetrically division of a parent polymer shell-stabilized giant unilamellar vesicle into smaller polymer shell-stabilized giant unilamellar vesicles with a diameter smaller than 10 µm using a microfluidic splitting device. The inventive method allows preparation of differently charged giant unilamellar vesicles as well as bioligand- and PEG-conjugated giant unilamellar vesicles, which are useful for targeted cellular delivery at high efficiency and specificity. A further advantage of the present invention is that the giant unilamellar vesicles can deliver huge cargos such as drug releasing porous microparticles, high amounts of in vivo imaging probes, viruses, or up-and-coming DNA origami robots.

  本发明涉及一种制备单分散细胞靶向巨型单拉美米尔囊泡的方法，其基础是利用微流体分割装置将母体聚合物壳稳定巨型单拉美米尔囊泡对称分割成直径小于10微米的较小聚合物壳稳定巨型单拉美米尔囊泡。 本发明的方法可制备不同电荷的巨型单拉米分子囊泡以及生物配体和 PEG 共轭巨型单拉米分子囊泡，这些囊泡可用于高效、特异性的细胞靶向递送。本发明的另一个优点是，巨型单拉美拉尔囊泡可以输送巨大的载体，如释放药物的多孔微颗粒、大量的体内成像探针、病毒或新兴的 DNA 折纸机器人。
• BOTTOM-UP ASSEMBLY OF SYNTHETIC EXTRACELLULAR VESICLES
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP3858332A1

  公开（公告）日：2021-08-04

  The present invention relates to a method for producing synthetic extracellular vesicles comprising a lipid bilayer including at least two lipids, optionally one or more extracellular vesicle associated proteins, and optionally one or more nucleic acid molecules. The inventive synthetic extracellular vesicles are formed by emulsification using a mechanic emulsifier in the form of polymer shell stabilized synthetic extracellular vesicles. The inventive method allows producing synthetic extracellular vesicles miming the composition and function of natural extracellular vesicles. Therefore, synthetic extracellular vesicles with specific protein and nucleic acids compositions are also disclosed herein, as well as their therapeutic uses.

  本发明涉及一种生产合成细胞外囊泡的方法，该囊泡包括一个脂质双分子层，其中至少包括两种脂质、一种或多种细胞外囊泡相关蛋白，以及一种或多种核酸分子。本发明的合成细胞外囊泡是通过使用机械乳化剂乳化形成的聚合物壳稳定合成细胞外囊泡。本发明的方法可以生产出模拟天然细胞外囊泡成分和功能的合成细胞外囊泡。因此，本文还公开了具有特定蛋白质和核酸成分的合成细胞外囊泡及其治疗用途。
• Liposomal formulation of nonglycosidic ceramides and uses thereof
  申请人：LUDWIG INSTITUTE FOR CANCER RESEARCH LTD.

  公开号：US10039715B2

  公开（公告）日：2018-08-07

  The invention provides liposomes containing nonglycosidic ceramides within their bilayers, and compositions thereof. These liposomes activate murine iNKT cells and induce dendritic cell (DC) maturation, both in vitro and in vivo at an efficacy that is comparable to their corresponding soluble nonglycosidic ceramides. Also provided are methods for treating diseases using the liposomes and compositions of the invention.

  本发明提供了在其双层内含有非糖苷类神经酰胺的脂质体及其组合物。这些脂质体可在体外和体内激活小鼠 iNKT 细胞并诱导树突状细胞（DC）成熟，其功效与相应的可溶性非糖苷神经酰胺相当。此外，还提供了使用本发明脂质体和组合物治疗疾病的方法。