3,3,4,4,5,5,6,6-octafluoro-1,8-diiodohexadecyl benzoate | 1208999-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,3,4,4,5,5,6,6-octafluoro-1,8-diiodohexadecyl benzoate
• CAS: 1208999-64-7
• 化学式: C₂₃H₂₈F₈I₂O₂
• 分子量: 742.27
• InChiKey: YHIVXZCUBJWLGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.48
• 重原子数：
  35.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,3,4,4,5,5,6,6-octafluoro-1,8-diiodohexadecyl benzoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以96%的产率得到3,3,4,4,5,5,6,6-octafluorohexadecyl benzoate
  参考文献：
  名称：

  “HFP” Fluorinated Cationic Lipids for Enhanced Lipoplex Stability and Gene Delivery

  摘要：

  Although a great number of cationic lipids have been designed and evaluated as gene delivery systems, there is still a need for improvement of nonviral vectors. Recently, cationic lipids incorporating terminal fluoroalkyl segments ("FHP" lipids) have been described to display remarkable transfection potency. Here, we describe the synthesis of a new family of fluorinated triblock cationic lipids in which a fluorous segment lays between the cationic and the lipophilic parts of the molecule ("HFP" lipids). The compounds were designed so their self-assembly would offer enhanced resistance toward the host's degradation mechanisms mediated by lipophilic insertion. Self-assembly properties of these cationic lipids were evaluated at the air-water interface where they collapse in a highly ordered liquid phase. The HFP lipids efficiently condense DNA, and the resulting lipoplexes display enhanced resistance to amphiphilic agents when compared to nonfluorinated or FHP cationic lipids. Transfection properties of the fluorinated vectors, alone or as mixtures with different helper lipids (DOPE and a fluorinated analogue of DOPE), were then investigated on different cell lines (BHK-21, HepG2, and HeLa) and compared to those of the reference cationic lipid DOTAP. Data show that impermeabilization of the lipidic phase by fluorous segments alter significantly the gene transfection activities. Remarkably, incorporation of DOPE within the lipoplexes provides the particles with high gene transfection activity without reducing their resistance to amphiphilic agents.

  DOI：

  10.1021/bc900469z
• 作为产物：
  描述：

  正癸烯 、 1,4-二碘全氟丁烷 、 苯甲酸乙烯酯 在 sodium dithionite 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 0.83h， 以29%的产率得到3,3,4,4,5,5,6,6-octafluoro-1,8-diiodohexadecyl benzoate
  参考文献：
  名称：

  “HFP” Fluorinated Cationic Lipids for Enhanced Lipoplex Stability and Gene Delivery

  摘要：

  Although a great number of cationic lipids have been designed and evaluated as gene delivery systems, there is still a need for improvement of nonviral vectors. Recently, cationic lipids incorporating terminal fluoroalkyl segments ("FHP" lipids) have been described to display remarkable transfection potency. Here, we describe the synthesis of a new family of fluorinated triblock cationic lipids in which a fluorous segment lays between the cationic and the lipophilic parts of the molecule ("HFP" lipids). The compounds were designed so their self-assembly would offer enhanced resistance toward the host's degradation mechanisms mediated by lipophilic insertion. Self-assembly properties of these cationic lipids were evaluated at the air-water interface where they collapse in a highly ordered liquid phase. The HFP lipids efficiently condense DNA, and the resulting lipoplexes display enhanced resistance to amphiphilic agents when compared to nonfluorinated or FHP cationic lipids. Transfection properties of the fluorinated vectors, alone or as mixtures with different helper lipids (DOPE and a fluorinated analogue of DOPE), were then investigated on different cell lines (BHK-21, HepG2, and HeLa) and compared to those of the reference cationic lipid DOTAP. Data show that impermeabilization of the lipidic phase by fluorous segments alter significantly the gene transfection activities. Remarkably, incorporation of DOPE within the lipoplexes provides the particles with high gene transfection activity without reducing their resistance to amphiphilic agents.

  DOI：

  10.1021/bc900469z