5,11,17,23-tetrachloromethyl-25,26,27,28-tetrakis(n-hexyloxy)-calix[4]arene | 823219-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetrachloromethyl-25,26,27,28-tetrakis(n-hexyloxy)-calix[4]arene
• 英文别名: 5,11,17,23-tetrachloromethyl-25,26,27,28-tetrahexyloxycalix[4]arene；5,11,17,23-Tetrakis(chloromethyl)-25,26,27,28-tetrahexoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene
• CAS: 823219-78-9
• 化学式: C₅₆H₇₆Cl₄O₄
• 分子量: 955.029
• InChiKey: XRAYOGFNAQGXLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.5
• 重原子数：
  64
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrachloromethyl-25,26,27,28-tetrakis(n-hexyloxy)-calix[4]arene 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以95%的产率得到5,11,17,23-tetraazidomethyl-25,26,27,28-tetrakis(n-hexyloxy)-calix[4]arene
  参考文献：
  名称：

  Cyclodextrin- and calixarene-based polycationic amphiphiles as gene delivery systems: a structure–activity relationship study

  摘要：

  多头/多尾部的面部两性分子建立在环糊精（CD）和杯芳烃（CA）支架上，是单分散基因传递系统的典范示例。

  DOI：

  10.1039/c4ob02204a
• 作为产物：
  描述：

  溴己烷 在 四氯化锡 、 sodium hydroxide 作用下， 以 氯仿 、 水 、 二甲基亚砜 为溶剂， 反应 0.75h， 生成 5,11,17,23-tetrachloromethyl-25,26,27,28-tetrakis(n-hexyloxy)-calix[4]arene
  参考文献：
  名称：

  Cationic amphiphilic calixarenes to compact DNA into small nanoparticles for gene delivery

  摘要：

  带有较长烷基链的阳离子两性卡立克酮对细胞毒性较小，它们的病毒大小的DNA纳米颗粒表现出更高的转染效率。

  DOI：

  10.1039/c4nj01395f

文献信息

• Phosphatase-responsive amphiphilic calixarene assembly
  作者：Yi-Xuan Wang、Dong-Sheng Guo、Yu Cao、Yu Liu

  DOI：10.1039/c3ra40453f

  日期：——

  A phosphatase-responsive supramolecular amphiphilic assembly was fabricated as an operationally targeted drug delivery carrier based on the host–guest complexation of amphiphilic calixarene with adenosine triphosphate (ATP). Remarkably, the complexation of calixarene with ATP lowers its critical aggregation concentration pronouncedly to form hollow spherical nanoparticles, which are identified by the combination of atomic force microscopy, high-resolution transmission electron microscopy and scanning electron microscopy. Moreover, the spherical assembly is efficiently responsive to phosphatase that is overexpressed in many tumor cells, and therefore the present system may have potential application in drug delivery systems.

  基于两亲性杯芳烃与三磷酸腺苷（ATP）的宿主-客体络合，我们制备了一种磷酸酶响应型超分子两亲性组装体，作为操作靶向药物递送载体。值得注意的是，杯芳烃与ATP的络合使其临界聚集浓度显著降低，形成中空球形纳米颗粒，并通过原子力显微镜、高分辨率透射电子显微镜和扫描电子显微镜的组合进行识别。此外，球形组装体对许多肿瘤细胞中过度表达的磷酸酶具有高效的响应性，因此本系统可能具有在药物递送系统中的潜在应用。
• A Stimulus-Responsive Shape-Persistent Micelle Bearing a Calix[4]arene Building Block: Reversible pH-Dependent Transition between Spherical and Cylindrical Forms
  作者：Shota Fujii、Yusuke Sanada、Tomoki Nishimura、Isamu Akiba、Kazuo Sakurai、Naoto Yagi、Efstratios Mylonas

  DOI：10.1021/la2037668

  日期：2012.2.14

  A series of cationic calix[4]arene-based lipids with alkyl chains of varying length were newly synthesized, and the ones with propyl and hexyl tails, denoted by CaL[4]C3 and C6, respectively, were found to form spherical micelles at low pH (protonated state of the amine headgroup). Upon deprotonation with increasing pH, CaL[4]C3 showed a sphere-to-cylinder transition, while CaL[4]C6 changed from sphere, to cylinder, to monolayer vesicle. Synchrotron small-angle X-ray scattering (SAXS) patterns from both spherical and cylindrical CaL[4]C3 micelles exhibited a sharp intensity minimum, indicating shape monodispersity. The monodispersity of the CaL[4]C3 spherical micelles was further confirmed by analytical ultracentrifugation (AUC). SAXS, AUC, and static light scattering agreeingly indicated an aggregation number of 6. In contrast, CaL[4]C6 exhibited polydispersity with an average aggregation number of 12. When the number of carbons of the alkyl chain was increased to 9 (CaL[4]C9), cylinder formed at low pH, while at high pH, no clear morphology could be observed. The present results indicate that a very precise combination of tail length, head volume, and rigidity of the building block is required to produce shape-persistent micelles and that the shape-persistence can be maintained upon a structural transition. An attempt to reconstruct a molecular model for the spherical CaL[4]C3 micelle was made With an ab initio shape determining program.