heptakis[6-(2-tert-butoxycarbonylaminoethylthio)-6-deoxy]cyclomaltoheptaose | 1002752-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: heptakis[6-(2-tert-butoxycarbonylaminoethylthio)-6-deoxy]cyclomaltoheptaose
• CAS: 1002752-75-1
• 化学式: C₉₁H₁₆₁N₇O₄₂S₇
• 分子量: 2249.76
• InChiKey: MDXWMPXLLCFSQH-OJPCCTPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  147.0
• 可旋转键数：
  35.0
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  680.75
• 氢给体数：
  21.0
• 氢受体数：
  49.0

反应信息

• 作为反应物：
  描述：

  己酸酐 、 heptakis[6-(2-tert-butoxycarbonylaminoethylthio)-6-deoxy]cyclomaltoheptaose 在 吡啶 、 4-二甲氨基吡啶 、 甲醇 作用下， 反应 8.0h， 以80%的产率得到C₁₆₉H₂₉₁N₇O₅₅S₇
  参考文献：
  名称：

  Insights in cellular uptake mechanisms of pDNA–polycationic amphiphilic cyclodextrin nanoparticles (CDplexes)

  摘要：

  It is generally recognized that the major obstacle to efficient gene delivery is cellular internalization and endosomal escape of the DNA. Recently, we have developed a modular strategy for the preparation of well-defined polycationic amphiphilic cyclodextrins (paCDs) capable of complexing and compacting DNA into homogeneous nanoparticles (<70 nm). Since paCDs resemble both cationic polymers and cationic lipids, it is conceivable that the corresponding pDNA-paCD nanoparticles (CDplexes) might use the cell internalization and endosomal escape mechanisms described for both lipoplexes and polyplexes. To verify this hypothesis, we have now investigated the uptake and transfection efficiencies of CDplexes in the presence of several inhibitors of endocytosis, namely chlorpromazine, genistein, dynasore and methylated beta-cyclodextrin (MbCD). Our data show that CDplexes obtained from paCD 1, which ranks among the most efficient paCD gene vectors reported up to date, are internalized by both clathrin-dependent (CDE) and clathrin-independent endocytosis (CIE), both processes being cholesterol- and dynamin-dependent. We observed that the largest fraction of gene complexes is taken up via CDE, but this fraction is less relevant for transfection. The smaller fraction that is internalized via the CIE pathway is predominantly responsible for successful transfection. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2010.01.016
• 作为产物：
  描述：

  2-叔丁氧羰基氨基乙硫醇 、 七(6-溴-6-脱氧)-beta-环糊精 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以99%的产率得到heptakis[6-(2-tert-butoxycarbonylaminoethylthio)-6-deoxy]cyclomaltoheptaose
  参考文献：
  名称：

  Insights in cellular uptake mechanisms of pDNA–polycationic amphiphilic cyclodextrin nanoparticles (CDplexes)

  摘要：

  It is generally recognized that the major obstacle to efficient gene delivery is cellular internalization and endosomal escape of the DNA. Recently, we have developed a modular strategy for the preparation of well-defined polycationic amphiphilic cyclodextrins (paCDs) capable of complexing and compacting DNA into homogeneous nanoparticles (<70 nm). Since paCDs resemble both cationic polymers and cationic lipids, it is conceivable that the corresponding pDNA-paCD nanoparticles (CDplexes) might use the cell internalization and endosomal escape mechanisms described for both lipoplexes and polyplexes. To verify this hypothesis, we have now investigated the uptake and transfection efficiencies of CDplexes in the presence of several inhibitors of endocytosis, namely chlorpromazine, genistein, dynasore and methylated beta-cyclodextrin (MbCD). Our data show that CDplexes obtained from paCD 1, which ranks among the most efficient paCD gene vectors reported up to date, are internalized by both clathrin-dependent (CDE) and clathrin-independent endocytosis (CIE), both processes being cholesterol- and dynamin-dependent. We observed that the largest fraction of gene complexes is taken up via CDE, but this fraction is less relevant for transfection. The smaller fraction that is internalized via the CIE pathway is predominantly responsible for successful transfection. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jconrel.2010.01.016