磷脂酰乙醇胺(牛脑) | 383907-18-4

• 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: 磷脂酰乙醇胺(牛脑)
• 英文名称: β-Oleoyl-γ-stearoyl-L-α-glycerophosphoryl-aethanolamin
• 英文别名: 1-Stearoyl-2-oleoyl-phosphatidylethanolamin；1-Stearoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine；2-azaniumylethyl (2R)-2-[(9Z)-octadec-9-enoyloxy]-3-(stearoyloxy)propyl phosphate；2-azaniumylethyl [(2R)-3-octadecanoyloxy-2-[(Z)-octadec-9-enoyl]oxypropyl] phosphate
• CAS: 383907-18-4
• 化学式: C₄₁H₈₀NO₈P
• 分子量: 746.062
• InChiKey: JQKOHRZNEOQNJE-DJEJVYNPSA-N

物化性质

• 物理描述：
  Solid
• 碰撞截面：
  277.02 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  51
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  磷脂酰乙醇胺(牛脑) 、 L-丝氨酸 生成 1-Stearoyl-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：

  1-stearoyl-2-oleoyl-sn-glycero-3-phospho-(N-triphenylmethyl)-ethanolamine 以 三氟乙酸 为溶剂， 以72%的产率得到磷脂酰乙醇胺(牛脑)
  参考文献：
  名称：

  Derivatives of glycerophosphocholine and glycerophosphoethanolamine,

  摘要：

  该发明涉及一般式##STR1##的新三苯甲基衍生物，其中T代表一个未取代或单取代或多取代的C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.6 -烷氧基或卤素的三苯甲基基团，基团R.sub.1、R.sub.2和R.sub.3要么相同且各代表一个甲基基团，要么不同，在这种情况下，基团R.sub.1、R.sub.2和R.sub.3中的两个始终代表氢，第三个基团代表一个未取代或单取代或多取代的C.sub.1 -C.sub.6 -烷基、C.sub.1 -C.sub.6 -烷氧基或卤素的三苯甲基基团，还涉及它们的制备方法，以及它们用于制备化学定义的纯对映体1,2-二酰基-sn-甘油-3-磷酰胆碱和1,2-二酰基-sn-甘油-3-磷酸乙醇胺，这些化合物在甘油的1和2位置独立地被不同的酰基基团取代。

  公开号：

  US04622180A1

文献信息

• Amine Cationic Lipids and Uses Thereof
  申请人：Dicerna Pharmaceuticals, Inc.

  公开号：US20140371293A1

  公开（公告）日：2014-12-18

  The present invention relates to lipid compounds and uses thereof. In particular, the compounds include a class of cationic lipids having an amine moiety, such as an amino-amine or an amino-amide moiety. The lipid compounds are useful for in vivo or in vitro delivery of one or more agents (e.g., a polyanionic payload or an antisense payload, such as an RNAi agent).

  本发明涉及脂质化合物及其用途。具体而言，这些化合物包括一类具有胺基团的阳离子脂质，例如氨基-胺或氨基-酰胺基团。这些脂质化合物可用于体内或体外传递一个或多个药物（例如，多聚阴离子荷载物或反义荷载物，如RNAi药物）。
• [EN] BIODEGRADABLE AMINO-ESTER NANOMATERIALS FOR NUCLEIC ACID DELIVERY<br/>[FR] NANOMATÉRIAUX D'AMINO-ESTER BIODÉGRADABLES POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2017176974A1

  公开（公告）日：2017-10-12

  The present disclosure relates to a series of biodegradable amino-ester lipid-like nanoparticles. In some embodiments, the biodegradable amino-ester lipid-like nanoparticles are used in methods for the delivery of nucleic acids.

  本公开涉及一系列可生物降解的氨基酯脂类纳米粒子。在某些实施例中，这些可生物降解的氨基酯脂类纳米粒子用于核酸递送方法。
• Discovery of a lysophospholipid acyltransferase family essential for membrane asymmetry and diversity
  作者：Daisuke Hishikawa、Hideo Shindou、Saori Kobayashi、Hiroki Nakanishi、Ryo Taguchi、Takao Shimizu

  DOI：10.1073/pnas.0712245105

  日期：2008.2.26

  All organisms consist of cells that are enclosed by a cell membrane containing bipolar lipids and proteins. Glycerophospholipids are important not only as structural and functional components of cellular membrane but also as precursors of various lipid mediators. Polyunsaturated fatty acids comprising arachidonic acid or eicosapentaenoic acid are located at sn -2 position, but not at sn -1 position of glycerophospholipids in an asymmetrical manner. In addition to the asymmetry, the membrane diversity is important for membrane fluidity and curvature. To explain the asymmetrical distribution of fatty acids, the rapid turnover of sn -2 position was proposed in 1958 by Lands [Lands WE (1958) Metabolism of glycerolipides: A comparison of lecithin and triglyceride synthesis. J Biol Chem 231:883–888]. However, the molecular mechanisms and biological significance of the asymmetry remained unknown. Here, we describe a putative enzyme superfamily consisting mainly of three gene families, which catalyzes the transfer of acyl-CoAs to lysophospholipids to produce different classes of phospholipids. Among them, we characterized three important enzymes with different substrate specificities and tissue distributions; one, termed lysophosphatidylcholine acyltransferase-3 (a mammalian homologue of Drosophila nessy critical for embryogenesis), prefers arachidonoyl-CoA, and the other two enzymes incorporate oleoyl-CoAs to lysophosphatidylethanolamine and lysophosphatidylserine. Thus, we propose that the membrane diversity is produced by the concerted and overlapped reactions with multiple enzymes that recognize both the polar head group of glycerophospholipids and various acyl-CoAs. Our findings constitute a critical milestone for our understanding about how membrane diversity and asymmetry are established and their biological significance.

  所有生物体都由细胞组成，这些细胞被包含双极脂质和蛋白质的细胞膜所包围。甘油磷脂不仅作为细胞膜的结构和功能组成部分，还是各种脂质介质的前体。由花生四烯酸或二十碳五烯酸组成的多不饱和脂肪酸位于甘油磷脂的不对称的sn-2位置，而不是sn-1位置。除了不对称性外，膜的多样性对于膜的流动性和曲率也很重要。为了解释脂肪酸的不对称分布，1958年Lands提出了sn-2位置的快速周转。然而，不对称性的分子机制和生物学意义仍然未知。在这里，我们描述了一个潜在的酶超家族，主要由三个基因家族组成，它们催化酰基辅酶A转移至溶血磷脂，以产生不同类别的磷脂。其中，我们表征了三种具有不同底物特异性和组织分布的重要酶；一种被称为溶血磷脂酰转移酶-3（果蝇nessy的哺乳动物同源物，对胚胎发育至关重要），更喜欢花生四烯酰辅酶A，而另外两种酶则将油酰辅酶A并入到溶血磷脂酰乙醇胺和溶血磷脂酰丝氨酸中。因此，我们提出，膜的多样性是由多个酶的协同和重叠反应产生的，这些酶识别甘油磷脂的极性头基和各种酰基辅酶A。我们的发现对于我们理解膜的多样性和不对称性的建立及其生物学意义构成了一个关键的里程碑。
• 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。
• Compositions and methods for enhancing contrast in imaging
  申请人：Marval Biosciences, Inc.

  公开号：EP2578237A1

  公开（公告）日：2013-04-10

  Example compositions of liposomes with hydrophilic polymers on their surface, and containing relatively high concentrations of contrast- enhancing agents for computed tomography are provided. Example pharmaceutical compositions of such liposomes, when administered to a subject, provide for increased contrast of extended duration, as measured by computed tomography, in the bloodstream and other tissues of the subject. Also provided are example methods for making liposomes containing high concentrations of contrast-enhancing agents, and example methods for using the compositions.

  本发明提供了一些脂质体组合物实例，这些脂质体表面具有亲水性聚合物，并含有相对高浓度的计算机断层扫描造影剂。这种脂质体的药物组合物范例在给受试者用药时，可使受试者血液和其他组织中的对比度增加，持续时间延长，如计算机断层扫描所测。此外，还提供了制造含有高浓度造影剂的脂质体的示例方法，以及使用这些组合物的示例方法。