| 1373559-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• CAS: 1373559-05-7
• 化学式: C₉₅H₁₄₃N₁₅O₂₄
• 分子量: 1879.27
• InChiKey: JAHQJMDHNUJFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.29
• 重原子数：
  134.0
• 可旋转键数：
  21.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  482.02
• 氢给体数：
  10.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以100%的产率得到5-guanidinium-25,26,27,28-tetrakis(3-guanidiniumpropoxy)calix[4]arene pentachloride
  参考文献：
  名称：

  Lower Rim Guanidinocalix[4]arenes: Macrocyclic Nonviral Vectors for Cell Transfection

  摘要：

  Guanidinium groups were introduced through a spacer at the lower rim of calix[4]arenes in the cone conformation to give new potential nonviral vectors for gene delivery. Several structural modifications were explored, such as the presence or absence of a macrocyclic scaffold, lipophilicity of the backbone, length of the spacer, and nature of the charged groups, in order to better understand the factors which affect the DNA condensation ability and transfection efficiency of these derivatives. The most interesting compound was a calix[4]arene unsubstituted at the upper rim and having four guanidinium groups linked at the lower rim through a three carbon atom spacer. This compound, when formulated with DOPE, showed low toxicity and transfection efficiency higher than the commercially available lipofectamine LTX in the treatment of human Rhabdomiosarcoma and Vero cells. Most of the investigated compounds showed a tendency to self-aggregate in pure water or in the presence of salts, as evidenced by NMR and AFM studies, and it was found that the ability to condense DNA plasmids in nanometric globules is a necessary but not sufficient condition for transfection. The superiority of macrocyclic vectors over linear Gemini-type analogues and of guanidinium compared to other ammonium head groups in determining the biological activity of the vectors was also ascertained.

  DOI：

  10.1021/bc2006829
• 作为产物：
  描述：

  1,3-二-BOC-2-(三氟甲基磺酰)胍 、 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Lower Rim Guanidinocalix[4]arenes: Macrocyclic Nonviral Vectors for Cell Transfection

  摘要：

  Guanidinium groups were introduced through a spacer at the lower rim of calix[4]arenes in the cone conformation to give new potential nonviral vectors for gene delivery. Several structural modifications were explored, such as the presence or absence of a macrocyclic scaffold, lipophilicity of the backbone, length of the spacer, and nature of the charged groups, in order to better understand the factors which affect the DNA condensation ability and transfection efficiency of these derivatives. The most interesting compound was a calix[4]arene unsubstituted at the upper rim and having four guanidinium groups linked at the lower rim through a three carbon atom spacer. This compound, when formulated with DOPE, showed low toxicity and transfection efficiency higher than the commercially available lipofectamine LTX in the treatment of human Rhabdomiosarcoma and Vero cells. Most of the investigated compounds showed a tendency to self-aggregate in pure water or in the presence of salts, as evidenced by NMR and AFM studies, and it was found that the ability to condense DNA plasmids in nanometric globules is a necessary but not sufficient condition for transfection. The superiority of macrocyclic vectors over linear Gemini-type analogues and of guanidinium compared to other ammonium head groups in determining the biological activity of the vectors was also ascertained.

  DOI：

  10.1021/bc2006829