ditetradecyl 3-bromopropylphosphonate | 263765-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: ditetradecyl 3-bromopropylphosphonate
• 英文别名: 1-[3-Bromopropyl(tetradecoxy)phosphoryl]oxytetradecane
• CAS: 263765-34-0
• 化学式: C₃₁H₆₄BrO₃P
• 分子量: 595.725
• InChiKey: VUKIZVIZJFTLKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  36
• 可旋转键数：
  31
• 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：

  三甲基胂 、 ditetradecyl 3-bromopropylphosphonate 在 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 168000.0h， 以90%的产率得到EG356
  参考文献：
  名称：

  Cation Substitution in Cationic Phosphonolipids:  A New Concept To Improve Transfection Activity and Decrease Cellular Toxicity

  摘要：

  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.

  DOI：

  10.1021/jm000006z
• 作为产物：
  描述：

  十四醇 、 3-bromopropylphosphonyl dichloride 在 N,N-二异丙基乙胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以90%的产率得到ditetradecyl 3-bromopropylphosphonate
  参考文献：
  名称：

  Cation Substitution in Cationic Phosphonolipids:  A New Concept To Improve Transfection Activity and Decrease Cellular Toxicity

  摘要：

  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.

  DOI：

  10.1021/jm000006z

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。
• Cationic Phosphonolipids Containing Quaternary Phosphonium and Arsonium Groups for DNA Transfection with Good Efficiency and Low Cellular Toxicity**
  作者：Erwann Guénin、Anne-Cécile Hervé、Virginie Floch、Séverine Loisel、Jean-Jacques Yaouanc、Jean-Claude Clément、Claude Férec、Hervé des Abbayes

  DOI：10.1002/(sici)1521-3773(20000204)39:3<629::aid-anie629>3.0.co;2-k

  日期：2000.2.4
• Synthesis and evaluation of new phosphonolipid compounds for gene delivery
  作者：Angélique Durand Dal-Maso、Jérôme Dellacasagrande、Frédéric Legendre、Gérard Tiraby、Casimir Blonski、Pascal Hoffmann

  DOI：10.1016/j.ejmech.2007.11.002

  日期：2008.8

  The preparation of a series of novel water soluble cationic lipid derivatives possessing phosphonate ester groups linked to the para-position of N-methyl pyridinium moieties and bearing either identical or different alkyl chains is reported. The obtained phospholipids were tested for transfection efficiency into three different mammalian cell lines alone and in conjunction with diphytanoylphosphatidylethanolamine (DiPPE) or dioleylphosphatidylethanolamine (DOPE), using an assay adapted for 96-well microplates based on the detection of a colorimetric change caused by the production of a chromogen induced by expressed secreted human placental alkaline phosphatase. In our conditions, the highest transfection activities of cells HEK293 and hard-to-transfect cell lines B 16 and CHO were achieved with a 4-phosphonobutylpyridinium compound used at 1:5, 1: 10 or 3:6 DNA/lipid ratio bearing two myristyl chains in the presence of the fusogenic helper lipid DiPPE. (c) 2007 Elsevier Masson SAS. All rights reserved.
• 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.