chloroditetradecyl phosphate | 181591-24-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: chloroditetradecyl phosphate
• 英文别名: 1-[Chloro(tetradecoxy)phosphoryl]oxytetradecane
• CAS: 181591-24-2
• 化学式: C₂₈H₅₈ClO₃P
• 分子量: 509.193
• InChiKey: VNWMDOFDDYCORG-UHFFFAOYSA-N

物化性质

• 沸点：
  558.4±19.0 °C(Predicted)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  33
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chloroditetradecyl phosphate 在 HX 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 EG373
  参考文献：
  名称：

  Cationic Phosphonolipids Containing Quaternary Phosphonium and Arsonium Groups for DNA Transfection with Good Efficiency and Low Cellular Toxicity**

  摘要：

  DOI：

  10.1002/(sici)1521-3773(20000204)39:3<629::aid-anie629>3.0.co;2-k
• 作为产物：
  描述：

  dimyristyl phosphite 在 四氯化碳 作用下， 生成 chloroditetradecyl phosphate
  参考文献：
  名称：

  New amphiphilic N-phosphoryl oligopeptides designed for gene delivery

  摘要：

  Gene therapy is a potent tool for the treatment of cancer and other gene defect diseases, which involves using DNA that encodes a functional, therapeutic gene to replace a mutated gene. However, the DNA transfection efficiency is restricted by its negative charges and low susceptibility to endonucleases which prevent them penetrating tissue and cellular membranes. Both viral and non-viral vectors have been used for gene delivery, but the former are limited by their immunogenicity, while the latter are less efficient than their viral counterpart. Cationic amphiphilic lipopeptides whose structures can be easily modified and transformed have been used as non-viral vectors in gene delivery system due to their low cytotoxicity and high transfection efficiency. In this study, a series of cationic amphiphilic N-phosphoryl oligopeptides with varied lengths of hydrophobic tails and oligopeptide headgroups (C12-K6, C14-K6, C16-K6, Chol-K6 and C12-H6) were synthesized and used as gene delivery vectors. The affinities, abilities to condense pDNA and transfection efficiencies of the K6-lipopeptides were better than those of the H6-lipopeptides. In addition, the hydrophobic chains of the lipopeptides also affected their transfection efficiencies. The K6-lipopeptide with a hydrophobic chain of twelve carbons (C12-K6) showed the highest transfection efficiency in all these synthetic lipopeptides. At an optimal P/N ratio of 20, C12-K6 showed comparable pDNA transfection efficiency to PEI-25k, a well-defined gene delivery vector, but the cytotoxicity of C12-K6 was much lower. With acceptable gene transfection efficiency and low cytotoxicity, this cationic amphiphilic lipopeptide will have promising applications in gene therapy. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2014.04.007

文献信息

• Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers
  作者：Stéphanie S. Le Corre、Mathieu Berchel、Nawal Belmadi、Caroline Denis、Jean-Pierre Haelters、Tony Le Gall、Pierre Lehn、Tristan Montier、Paul-Alain Jaffrès

  DOI：10.1039/c3ob42270d

  日期：——

  The synthesis of a series of new cationic lipids possessing two different lipid chains is detailed. The transfection efficacies have shown the interest to associate a phytanyl chain with either, a lauryl or oleyl chain.

  一系列新的阳离子脂质合成细节涉及具有两种不同脂肪链的脂质。转染效率表明将一种萜烯基链与月桂基链或油酸基链结合是有趣的。
• Cation Substitution in Cationic Phosphonolipids:  A New Concept To Improve Transfection Activity and Decrease Cellular Toxicity
  作者：Virginie Floch、Séverine Loisel、Erwann Guenin、Anne Cécile Hervé、Jean Claude Clément、Jean Jacques Yaouanc、Hervé des Abbayes、Claude Férec

  DOI：10.1021/jm000006z

  日期：2000.11.1

  Cationic lipids have been shown to be an-interesting alternative to viral vector-mediated gene delivery into in vitro and in vivo model applications. Prior studies have demonstrated that even minor structural modifications of the lipid hydrophobic domain or of the lipid polar domain result in significant changes in gene delivery efficiency. Previously, we developed a novel class of cationic lipids called cationic phosphonolipids and described the ability of these vectors to transfer DNA into different cell lines and in vivo. Up until now, in all new cationic lipids, nitrogen atoms have always carried the cationic or polycationic charge. Recently we have developed a new series of cationic phosphonolipids characterized by a cationic charge carried by a phosphorus or arsenic atom. In a second step, we have also examined the effects of the linker length between the cation and the hydrophobic domain as regards transfection activity. Transfection activities of this library of new cationic phosphonolipids were studied in vitro in different cell lines (HeLa, CFT1, K562) and in vivo using a luciferase reporter gene. A luminescent assay was carried out to assess luciferase expression. We demonstrated that cation substitution on the polar domain of cationic phosphonolipids (N --> P or As) results in significant increase in transfection activity for both in vitro and in vivo assays and decrease of cellular toxicity.