1,1-di-tert-butyl 3-(6-((2,3-dimethylbut-2-enoyl)oxy)hexyl) butane-1,1,3-tricarboxylate | 1362862-17-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,1-di-tert-butyl 3-(6-((2,3-dimethylbut-2-enoyl)oxy)hexyl) butane-1,1,3-tricarboxylate
• CAS: 1362862-17-6
• 化学式: C₂₅H₄₂O₈
• 分子量: 470.604
• InChiKey: QKQSVCDXMDGSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  33.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  丙二酸二叔丁酯 、 1,6-己二醇二甲基丙烯酸酯 在 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 1,1-di-tert-butyl 3-(6-((2,3-dimethylbut-2-enoyl)oxy)hexyl) butane-1,1,3-tricarboxylate
  参考文献：
  名称：

  Block Copolymer Micelles with Pendant Bifunctional Chelator for Platinum Drugs: Effect of Spacer Length on the Viability of Tumor Cells

  摘要：

  Three monomers with 1,3-dicarboxylate functional groups but varying spacer lengths were synthesized via carbon Michael addition using malonate esters and ethylene-(MAETC), butylene- (MABTC), and hexylene (MAHTC) glycol dimethacrylate, respectively. Poly[oligo-(ethylene glycol) methylether methacrylate] (POEGMEMA) was prepared in the presence of a RAFT (reversible addition-fragmentation chain transfer) agent, followed by chain extension with the prepared monomers to generate three different block copolymers (BP-E80, BP-B82, and BP-H79) with similar numbers of repeating units, but various spacer lengths as distinguishing features. Conjugation with platinum drugs created macromolecular platinum drugs resembling carboplatin. The amphiphilic natures of these Pt-containing block copolymers led to the formation micelles in solution. The rate of drug release of all micelles was similar, but a noticeable difference was the increasing stability of the micelle against dissociation with increasing spacer length. The platinum conjugated polymer showed high activity against A549, OVCAR3, and SKOV3 cancer cell lines exceeding the activity of carboplatin., but only the micelle based on the longest spacer had IC50 values as low as cisplatin. Cellular uptake studies identified a better micelle uptake with increasing micelle stability as a possible reason for lower IC50 values. The clonogenic assay revealed that micelles loaded with platinum drugs, in contrast to low molecular weight carboplatin, have not only better activity within the frame of a 72 h cell viability study, but also display a longer lasting effect by preventing the colony formation A549 for more than 10 days.

  DOI：

  10.1021/bm2017299