1,2-二-O-十八烷基-sn-甘油-3-磷酸胆碱 | 1188-85-8

• 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-O-十八烷基-sn-甘油-3-磷酸胆碱
• 英文名称: 1,2-di-O-octadecyl-sn-glycero-3-phosphatidylcholine
• 英文别名: (2R)-2,3-bis(octadecyloxy)propyl 2-(trimethylazaniumyl) ethyl phosphate；1,2-Di-o-octadecyl-sn-glycero-3-phosphocholine；[(2R)-2,3-dioctadecoxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 1188-85-8
• 化学式: C₄₄H₉₂NO₆P
• 分子量: 762.191
• InChiKey: HVVJCLFLKMGEIY-USYZEHPZSA-N

物化性质

• 熔点：
  205-210 °C(Solv: ethyl acetate (141-78-6))

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  52
• 可旋转键数：
  44
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2923900090

反应信息

• 作为产物：
  描述：

  1,2-o-二十八基-sn-甘油 在 三乙胺 作用下， 以 氯仿 、 水 、 异丙醇 、 乙腈 、 苯 为溶剂， 反应 40.0h， 生成 1,2-二-O-十八烷基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  具有末端全氟丁基的醚连接磷脂酰胆碱水合双层的热力学研究

  摘要：

  开发了具有不同烷基链长度 （di-O-F4-Cn-PCs， n = 14,16 和 18） 的新型末端含醚全氟丁基的末端全氟丁基磷脂酰胆碱作为稳定脂质体的可能材料，旨在用于膜蛋白的结构和功能分析。水合 di-O-F4-Cn-PC 双层热致变的差示扫描量热研究表明，与相应的非氟化 PCs、di-O-Cn-PCs相比，每个 di-O-F4-Cn-PC 的转变温度降低了 ~20 °C。另一方面，随着疏水链的伸长，过渡焓 （ΔH） 和熵 （ΔS） 呈线性增加。di-O-F4-Cn-PCs 和 di-O-Cn-PCs 之间 ΔH 和 ΔS 值与净烃链长度的比较强烈表明，在 di-O-F4-Cn-PC 膜的热致转变中，全氟丁基链段经历非常有限的结构变化;因此，烃段主要负责相变。

  DOI：

  10.1016/j.bbamem.2023.184261
• 作为试剂：
  描述：

  1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphoethanolamine-N-[4-(dipyrrometheneboron difluoride)butanoyl] 在 disodium citrate sesquihydrate 、 lysosomal phospholipase A₂ 、 1,2-二-O-十八烷基-sn-甘油-3-磷酸胆碱 、 bovine serum albumin 作用下， 反应 1.0h， 生成 、 1-lyso-palmitoyl-2-glutaroyl-sn-glycero-3-phosphoethanolamine-N-[4-(dipyrrometheneboron difluoride) butanoyl] 、 棕榈酸
  参考文献：
  名称：

  A fluorometric assay for lysosomal phospholipase A2 activity using fluorescence-labeled truncated oxidized phospholipid

  摘要：

  Lysosomal phospholipase A2 (LPLA2) is a key enzyme involved in the homeostasis of cellular phospholipids. Recently, LPLA2 was reported to preferentially degrade some truncated oxidized phospholipids at the sn-1 position. A commercially available, truncated oxidized phospholipid conjugated with a fluorescent dye, 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphoethanolamine-N- [4-(dipyrrometheneboron difluoride) butanoyl] (PGPE-BODIPY), was used to develop a specific assay for this enzyme. When recombinant mouse LPLA2 was incubated with liposomes consisting of l,2-O-octadecyl-sn-glycero-3-phosphocholine/PGPE-BODIPY under acidic conditions, PGPE-BODIPY was converted to palmitic acid and a polar BODIPY-product. After phase partitioning by chloroform/methanol, the polar BODIPY-product was recovered in the aqueous phase and identified as 1-lyso-PGPE-BODIPY. The formation of 1-lyso-PGPE-BODIPY was quantitatively determined by fluorescent measurements. The Km and Vmax values of the recombinant LPLA2 for PGPE-BODIPY were 5.64 mu M and 20.7 mu mol/min/ mg protein, respectively. Detectable activity against PGPE-BODIPY was present in LPLA2 deficient mouse sera, but the deacylase activity was completely suppressed by treatment with 4-(2-aminoethyl)benzenesulfonyl fluoride (AEBSF). AEBSF had no effect on LPLA2 activity. The LPLA2 activity of mouse serum pre-treated with AEBSF was specifically and quantitatively determined by this assay method. The PGPE-BODIPY and AEBSF based LPLA2 assay is convenient and can be used to measure LPLA2 activity in a variety of biological specimens.

  DOI：

  10.1016/j.ab.2018.03.024

文献信息

• Synthesis of 1,2-Di-<i>O</i>-alkyl-<i>sn</i>-glycero-3-phosphatidylcholine Using 2-Methoxyethoxymethyl and 2-(Trimethylsilyl)ethoxymethyl Protective Groups
  作者：Kiyoshi Yamauchi、Mitsuyoshi Hihara、Masayoshi Kinoshita

  DOI：10.1246/bcsj.60.2169

  日期：1987.6

  2-Methoxyethoxymethyl (MEM) and 2-(trimethylsilyl)ethoxymethyl (SEM) groups were used to protect the sn-3-OH of optically active glycerols in the synthesis of 1,2-di-O-octadecyl-sn-glycero-3-phosphatidylcholine. Both MEM and SEM protective groups had advantages of a classical benzyl group by virtue of (i) the facile preparation of 1,2-O-isopropylidene-3-O-(2-methoxyethoxymethyl)-sn-glycerol and its sn-3-O-SEM analog as starting materials and (ii) the rapid demasking of the MEM and SEM moieties in lipid precursors, especially by means of titanium tetrachloride.

  在合成1,2-二-O-十八烷基-sn-甘油-3-磷脂酰胆碱的过程中，使用了2-甲氧基乙氧基甲基（MEM）和2-（三甲基硅基）乙氧基甲基（SEM）保护基团来保护光学活性甘油的sn-3-OH。这两种保护基团具有经典苄基的优点，具体体现在：(i) 1,2-O-异丙烯基-3-O-(2-甲氧基乙氧基甲基)-sn-甘油及其sn-3-O-SEM类似物作为起始材料的制备方便；(ii) 在脂质前体中，特别是通过四氯化钛，MEM和SEM基团的快速去掩蔽。
• NOVEL 2'-METHYLIDENENUCLEOTIDE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PHARMACEUTICAL USE THEREOF
  申请人：Matsuda, Akira

  公开号：EP0690068A1

  公开（公告）日：1996-01-03

  A novel 2'-methylidenenucleotide compound represented by general formula (I) or a salt thereof, a process for producing the same, and a pharmaceutical use thereof. In said formula, R represents hydrogen or halogen; R¹ and R² represent each independently a fatty acid residue or a hydrocarbon residue; and R³ and R⁴ represent each independently hydrogen, halogen or alkyl. The compound and salts thereof have an excellent antitumor activity against mammals. More specifically, they have a remarkable activity of inhibiting growth of mouse tumors, cultured human tumor cells or human tumors transplanted to nude mice, and hence are efficacious in curing or inhibiting the recurrence of mammalian pulmonary cancer, digestive cancer, mamary cancer, head and neck cancers, gynecologic cancer, urologic cancer, leukemia, melanoma, lymphatic metastatic tumor, and so forth. Also they are useful as an antitumor drug because they have an increased bioavailability and are lowly toxic. Further they have the effects of persistent and increased activities.

  一种由通式(I)代表的新型 2'-亚甲基烯核苷酸化合物或其盐，一种生产该化合物的工艺及其药物用途。在所述式中，R 代表氢或卤素；R¹ 和 R² 各自独立地代表脂肪酸残基或烃残基；R³ 和 R⁴ 各自独立地代表氢、卤素或烷基。该化合物及其盐类对哺乳动物具有极佳的抗肿瘤活性。更具体地说，它们具有抑制小鼠肿瘤、培养的人类肿瘤细胞或移植到裸鼠身上的人类肿瘤生长的显著活性，因此在治疗或抑制哺乳动物肺癌、消化系统癌症、乳腺癌、头颈部癌症、妇科癌症、泌尿系统癌症、白血病、黑色素瘤、淋巴转移性肿瘤等方面具有疗效。此外，它们还可作为抗肿瘤药物，因为它们具有更高的生物利用度和低毒性。此外，它们还具有持续和增强活性的作用。
• FUNCTIONAL WOUND DRESSING
  申请人：Paul Hartmann AG

  公开号：EP3569261A1

  公开（公告）日：2019-11-20

  The invention relates to a functional wound dressing being able to detect and indicate the state of the wound, in particular with regard to infections for example caused by toxins produced by bacteria such Staphylococcus aureus and Pseudomonas aeruginosa. The present wound dressing can be used in moist wound healing and contains a substance being able to absorb wound exudate from the wound and to provide moisture to the wound.

  本发明涉及一种功能性伤口敷料，它能够检测和显示伤口的状态，尤其是由金黄色葡萄球菌和绿脓杆菌等细菌产生的毒素引起的感染。本伤口敷料可用于湿性伤口愈合，含有一种能够吸收伤口渗出物并为伤口提供水分的物质。
• 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。