vitamin E mesylate | 1261156-27-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: vitamin E mesylate
• 英文别名: 2-(4,8,12-trimethyltridecyl)-2,5,7,8-tetramethyl-chroman-6-ylmethanesulfonate；O-mesyl-α-tocopherol
• CAS: 1261156-27-7
• 化学式: C₃₀H₅₂O₄S
• 分子量: 508.806
• InChiKey: WZTZUZFHVKLZLK-IQLGONJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  35.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  vitamin E mesylate 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 146.0h， 生成
  参考文献：
  名称：

  Design, Synthesis, and inVitro Transfection Biology of Novel Tocopherol Based Monocationic Lipids: A Structure−Activity Investigation

  摘要：

  Herein, we report on the design, synthesis, and in vitro gene delivery efficacies of five novel tocopherol based cationic lipids (1-5) in transfecting CHO, B16F10, A-549, and HepG2 cells. The in vitro gene transfer efficiencies of lipids (1-5) were evaluated by both beta-galactosidase reporter gene expression and inverted fluorescent microscopic experiments. The results of the present structure activity investigation convincingly demonstrate that the tocopherol based lipid with three hydroxyl groups in its headgroup region showed 4-fold better transfection efficiency than the commercial formulation. The results also demonstrate that these tocopherol based lipids may be targeted to liver. Transfection efficiency of all the relevant lipids was maintained even when the serum was present during the transfection conditions. The results indicated that the designed systems are quite capable of transferring the DNA into all four types of cells studied with low or no toxicity.

  DOI：

  10.1021/jm100704u
• 作为产物：
  描述：

  甲基磺酰氯 、 天然维生素E 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85.1%的产率得到vitamin E mesylate
  参考文献：
  名称：

  生育酚基阳离子脂质头基区域中的氮杂糖部分的羟基官能团对体外基因转染效率的巨大影响

  摘要：

  阳离子脂质已被有效地用作非病毒载体，用于将多核酸输送到细胞质中。特别地，在头部基团区域具有羟基的脂质通过氢键和静电相互作用促进多核酸与DNA的带负电荷的磷酸基团的牢固结合，从而调节转染效率。在这方面，我们设计并合成了两种阳离子脂质，分别是基于氮杂糖首基的阳离子脂质（Toc-Aza）和基于非氮杂糖基的阳离子脂质（Toc-Pyr）。众所周知的共脂质1,2-二油酰基-sn-甘油-3-磷酸乙醇胺（DOPE）用于配制脂质体和脂质复合物，对它们的生物学特性进行了流体动力学直径，整体表面电荷和DNA结合的表征。三种细胞系，即HEK-293，CHO和HepG2，用于细胞活力测定和体外转染研究。体外转染研究表明，基于氮杂糖头基团的阳离子脂质（Toc-Aza）和氮杂糖头基团上的无羟基阳离子脂质（吡咯烷基）（Toc-Pyr）在2：2时显示对比转染效率。在所有研究的三个细胞系中电荷比为1。Toc-Aza的活性比T

  DOI：

  10.1039/d0nj03717f

文献信息

• Synthesis of triphenylphosphonium vitamin E derivatives as mitochondria-targeted antioxidants
  作者：Victoria J.A. Jameson、Helena M. Cochemé、Angela Logan、Lyall R. Hanton、Robin A.J. Smith、Michael P. Murphy

  DOI：10.1016/j.tet.2015.09.014

  日期：2015.11

  A series of mitochondria-targeted antioxidants comprising a lipophilic triphenylphosphonium cation attached to the antioxidant chroman moiety of vitamin E by an alkyl linker have been prepared. The synthesis of a series of mitochondria-targeted vitamin E derivatives with a range of alkyl linkers gave compounds of different hydrophobicities. This work will enable the dependence of antioxidant defence on hydrophobicity to be determined in vivo. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.