bis(11-ferrocenylundecyl) dimethylammonium bromide | 173991-47-4

• 英文名称: bis(11-ferrocenylundecyl) dimethylammonium bromide
• 英文别名: bis(n-ferrocenylundecyl)dimethylammonium bromide；BFDMA
• CAS: 173991-47-4
• 化学式: Br*C₄₄H₆₈Fe₂N
• 分子量: 802.629
• InChiKey: LCZXQFJABSGARL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  bis(11-ferrocenylundecyl) dimethylammonium bromide 在 lithium sulfate 作用下， 以 水 为溶剂， 生成 BFDMA
  参考文献：
  名称：

  Redox-Based Control of the Transformation and Activation of siRNA Complexes in Extracellular Environments Using Ferrocenyl Lipids

  摘要：

  We report physical characterization and biological evaluation of complexes of small interfering RNA (siRNA) formed using a cationic lipid [bis(11-ferrocenylundecyl)dimethylammonium bromide (BFDMA)] containing redox-active ferrocenyl groups at the end of each hydrophobic tail. We demonstrate that control over the redox state of BFDMA can be used to influence key physical properties and control the activities of lipoplexes formed using siRNA-based constructs. Specifically, lipoplexes of siRNA and reduced BFDMA lead to high levels of sequence-specific gene silencing in cells, but lipoplexes formed using oxidized BFDMA do not. Lipoplexes of oxidized BFDMA can be activated in situ to induce high levels of silencing by addition of a chemical reducing agent, demonstrating a basis for external control over the activation/delivery of siRNA in cellular environments. Differences in activity arise from the inability of oxidized BFDMA to promote efficient internalization of siRNA; these differences also correlated to significant differences in the nanostructures of these lipoplexes (determined by cryo-TEM) and their zeta potentials as a function of oxidation state. These results are considered in view of recent studies characterizing the nanostructures, properties, and behaviors of lipoplexes formed using BFDMA and macromolecular plasmid DNA. We find that several key structural features and aspects of redox control observed for lipoplexes of plasmid DNA are maintained in complexes formed using smaller and more rigid siRNA. The ability to transform BFDMA in complex media presents opportunities to exert control over the nanostructures and behaviors of siRNA lipoplexes in ways not possible using conventional lipids. The approaches reported here could thus prove useful in both fundamental and applied contexts.

  DOI：

  10.1021/ja403546b
• 作为产物：
  描述：

  BFDMA 生成 bis(11-ferrocenylundecyl) dimethylammonium bromide
  参考文献：
  名称：

  Redox-Based Control of the Transformation and Activation of siRNA Complexes in Extracellular Environments Using Ferrocenyl Lipids

  摘要：

  We report physical characterization and biological evaluation of complexes of small interfering RNA (siRNA) formed using a cationic lipid [bis(11-ferrocenylundecyl)dimethylammonium bromide (BFDMA)] containing redox-active ferrocenyl groups at the end of each hydrophobic tail. We demonstrate that control over the redox state of BFDMA can be used to influence key physical properties and control the activities of lipoplexes formed using siRNA-based constructs. Specifically, lipoplexes of siRNA and reduced BFDMA lead to high levels of sequence-specific gene silencing in cells, but lipoplexes formed using oxidized BFDMA do not. Lipoplexes of oxidized BFDMA can be activated in situ to induce high levels of silencing by addition of a chemical reducing agent, demonstrating a basis for external control over the activation/delivery of siRNA in cellular environments. Differences in activity arise from the inability of oxidized BFDMA to promote efficient internalization of siRNA; these differences also correlated to significant differences in the nanostructures of these lipoplexes (determined by cryo-TEM) and their zeta potentials as a function of oxidation state. These results are considered in view of recent studies characterizing the nanostructures, properties, and behaviors of lipoplexes formed using BFDMA and macromolecular plasmid DNA. We find that several key structural features and aspects of redox control observed for lipoplexes of plasmid DNA are maintained in complexes formed using smaller and more rigid siRNA. The ability to transform BFDMA in complex media presents opportunities to exert control over the nanostructures and behaviors of siRNA lipoplexes in ways not possible using conventional lipids. The approaches reported here could thus prove useful in both fundamental and applied contexts.

  DOI：

  10.1021/ja403546b

文献信息

• Ferrocene-Containing Cationic Lipids: Influence of Redox State on Cell Transfection
  作者：Nicholas L. Abbott、Christopher M. Jewell、Melissa E. Hays、Yukishige Kondo、David M. Lynn

  DOI：10.1021/ja054038t

  日期：2005.8.24

  A ferrocene-containing, redox-active cationic lipid that can be transformed using electrochemical methods yields large differences in cell transfection depending on the oxidation state of the lipid. Expression of enhanced green fluorescent protein and firefly luciferase occurs at very high levels when DNA lipoplexes are formulated using the lipid in the reduced state. In contrast, transfection is negligible when oxidized lipid is used. These observations suggest the basis of a general method that could be used to transform inactive lipoplex formulations to an active form through the application of externally applied electrical potentials. The ability to activate lipoplexes toward transfection electrochemically and "on demand" could create new opportunities to deliver DNA in vitro and in vivo with both spatial and temporal control.