dioleyl 3-bromopropylphosphonate | 1064147-35-8

• 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: dioleyl 3-bromopropylphosphonate
• 英文别名: di(Z)-octadec-9-enyl 3-bromopropylphosphonate；(Z)-1-[3-bromopropyl-[(Z)-octadec-9-enoxy]phosphoryl]oxyoctadec-9-ene
• CAS: 1064147-35-8
• 化学式: C₃₉H₇₆BrO₃P
• 分子量: 703.908
• InChiKey: RJDVEFHRYQIMAE-CLFAGFIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.4
• 重原子数：
  44
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  dioleyl 3-bromopropylphosphonate 在 N-甲基吗啉 、 sodium carbonate 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 di(Z)-octadec-9-enyl 1-(4-((6-amino-2-(butylamino)-8-hydroxy-9H-purin-9-yl)methyl)phenyl)-1-oxo-2,6,11,15-tetraazaoctadecan-18-ylphosphonate
  参考文献：
  名称：

  Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids

  摘要：

  公开号：

  EP2674170B1
• 作为产物：
  描述：

  油醇 、 3-bromopropyl dichlorophosphine 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以54%的产率得到dioleyl 3-bromopropylphosphonate
  参考文献：
  名称：

  Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids

  摘要：

  公开号：

  EP2674170B1

文献信息

• 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.
• 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.
• US9458184B2
  申请人：——

  公开号：US9458184B2

  公开（公告）日：2016-10-04
• Novel compositions of TLR7 and/or TLR8 agonists conjugated to lipids
  申请人：Invivogen

  公开号：EP2674170B1

  公开（公告）日：2014-11-19