ditetradecyl 2-bromoethylphosphonate | 263765-32-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ditetradecyl 2-bromoethylphosphonate
• 英文别名: 1-[2-Bromoethyl(tetradecoxy)phosphoryl]oxytetradecane
• CAS: 263765-32-8
• 化学式: C₃₀H₆₂BrO₃P
• 分子量: 581.698
• InChiKey: HCUDHUMNOVCKLN-UHFFFAOYSA-N

物化性质

• 沸点：
  593.1±33.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  35
• 可旋转键数：
  30
• 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：

  ditetradecyl 2-bromoethylphosphonate 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 144.0h， 生成
  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：

  十四醇 、 (2-bromoethyl)phosphonic dichloride 在 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 ditetradecyl 2-bromoethylphosphonate
  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

文献信息

• Novel lipophilic compounds having affinity with nucleic acids and therapeutical uses thereof
  申请人：——

  公开号：US20010056074A1

  公开（公告）日：2001-12-27

  The invention consists of a compound of the general formula (I) below: 1 Wherein A, R1, R2, R3, R4 and X are as disclosed in the specification. The invention also relates to the therapeutical uses of this compound, particularly for gene therapy.

  本发明包括以下通式(I)的化合物： 1 其中 A、R1、R2、R3、R4 和 X 如说明书中所公开。 本发明还涉及该化合物的治疗用途，特别是用于基因治疗。
• 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.