N-[2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-(octadecanoylamino)propyl]octadecanamide | 207273-85-6

• 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: N-[2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-(octadecanoylamino)propyl]octadecanamide
• CAS: 207273-85-6
• 化学式: C₄₈H₉₅N₄O₄P
• 分子量: 823.28
• InChiKey: GXAMBDAWMKUULA-UHFFFAOYSA-N

物化性质

• 沸点：
  841.4±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  17.1
• 重原子数：
  57
• 可旋转键数：
  44
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  十八烷酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 N-[2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-(octadecanoylamino)propyl]octadecanamide
  参考文献：
  名称：

  交联适体-脂质胶束在靶细胞识别中具有出色的稳定性和特异性

  摘要：

  DNA-脂质胶束 (DLM) 的特异性结合能力可以通过引入适体来增强。然而，基于两亲性 DLM 自组装的超分子胶束结构在某些条件下与细胞膜相互作用时预计会表现出较低的稳定性，这可能导致靶向癌细胞的选择性降低。我们在此报告了一种简单的交联策略，该策略依赖于甲基丙烯酰胺分支来连接适体和脂质片段。通过有效的光诱导聚合过程，共价连接的适体-脂质单元有助于稳定胶束结构并增强适体探针的稳定性，进一步提高所得纳米组件的靶向能力。除了开发一种简便的交联方法外，本研究还阐明了适体-脂质浓度与相应结合能力之间的关系。

  DOI：

  10.1002/anie.201804682

文献信息

• DNA-Based Micelles: Synthesis, Micellar Properties and Size-Dependent Cell Permeability
  作者：Haipeng Liu、Zhi Zhu、Huaizhi Kang、Yanrong Wu、Kwame Sefan、Weihong Tan

  DOI：10.1002/chem.200901546

  日期：2010.3.22

  three‐dimensional micellar nanostructures with a lipid core and a DNA corona. These hierarchical architectures are results of intermolecular hydrophobic interactions. Experimental testing further showed that these types of micelles have excellent thermal stability and their size can be fine‐tuned by changing the length of the DNA sequence. Moreover, in the micelle system, the molecular recognition properties of DNA

  基于分子自组装的功能纳米材料在生物医学和生物技术领域的应用前景广阔。然而，它们的功效可能是一个问题，可以通过精确控制尺寸、结构和功能来提高。这将需要能够生产单分散功能材料的分子工程设计，其特征在于尺寸、形状和化学结构的有益变化。为了应对这一挑战，我们设计并构建了一系列两亲性寡核苷酸分子。在水溶液中，由亲水性寡核苷酸与疏水性二酰基脂尾部共价连接组成的两亲性寡核苷酸分子自发地自组装成具有脂质核和 DNA 冠的单分散三维胶束纳米结构。这些分层结构是分子间疏水相互作用的结果。实验测试进一步表明，这些类型的胶束具有出色的热稳定性，并且可以通过改变 DNA 序列的长度来微调它们的大小。此外，在胶束系统中，DNA 的分子识别特性是完整的，因此，我们的 DNA 胶束可以与互补序列杂交，同时保持其结构完整性。重要的是，当与细胞膜相互作用时，高度带电的 DNA 胶束能够自行分解并插入细胞膜，通过内吞作用完成内
• Self-assembled hybrid nanoparticles for targeted co-delivery of two drugs into cancer cells
  作者：Fujian Huang、Mingxu You、Tao Chen、Guizhi Zhu、Haojun Liang、Weihong Tan

  DOI：10.1039/c3cc49003c

  日期：——

  A therapeutic aptamer–lipid–poly(lactide-co-glycolic acid) hybrid nanoparticle-based drug delivery system was prepared and characterized. This system can co-deliver two different drugs with distinct solubility and different anticancer mechanisms to target cancer cells with high specificity and efficiency.

  制备并表征了一种基于治疗性aptamer-脂质-聚（乳酸-共聚乙醇酸）混合纳米粒子的给药系统。该系统可联合递送两种具有不同溶解度和不同抗癌机制的药物，以高特异性和高效率靶向癌细胞。
• IMMUNOSTIMULATORY COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Massachusetts Institute of Technology

  公开号：US20130295129A1

  公开（公告）日：2013-11-07

  Lipid conjugates for enhanced delivery of cargo to the lymph nodes are disclosed. The lipid conjugates typically include three domains: a lipophilic domain that binds to albumin, a polar block domain, and a cargo such as a molecular adjuvant or immunostimulatory compound (such as an oligonucleotide) or antigenic peptide. Depending on the cargo, the length and compositions of the polar block can be tailored to push the equilibrium toward albumin binding, stable micelle formation, or cell insertion. The conjugates can be administered to a subject, for example, a subject with cancer or an infection, to induce or enhance a robust immune response in the subject.

  本发明公开了用于增强将载荷输送到淋巴结的脂质共轭物。脂质共轭物通常包括三个区域：一个与白蛋白结合的亲脂区、一个极性区块区域和一个载荷，例如分子佐剂或免疫刺激化合物（如寡核苷酸）或抗原肽。根据载荷，可以调整极性区块的长度和组成，以推动平衡向白蛋白结合、稳定的胶束形成或细胞插入。这些共轭物可以被给予一个受试者，例如一个患有癌症或感染的受试者，以诱导或增强受试者的强大免疫反应。
• Immunostimulatory compositions and methods of use thereof
  申请人：Massachusetts Institute of Technology

  公开号：US10029016B2

  公开（公告）日：2018-07-24

  Lipid conjugates for enhanced delivery of cargo to the lymph nodes are disclosed. The lipid conjugates typically include three domains: a lipophilic domain that binds to albumin, a polar block domain, and a cargo such as a molecular adjuvant or immunostimulatory compound (such as an oligonucleotide) or antigenic peptide. Depending on the cargo, the length and compositions of the polar block can be tailored to push the equilibrium toward albumin binding, stable micelle formation, or cell insertion. The conjugates can be administered to a subject, for example, a subject with cancer or an infection, to induce or enhance a robust immune response in the subject.

  本发明公开了用于加强向淋巴结输送货物的脂质共轭物。脂质共轭物通常包括三个结构域：与白蛋白结合的亲脂结构域、极性嵌段结构域和货物，如分子佐剂或免疫刺激化合物（如寡核苷酸）或抗原肽。根据载体的不同，极性区块的长度和成分也可进行调整，以促进白蛋白结合、稳定胶束形成或细胞插入的平衡。这些共轭物可施用给受试者，例如癌症患者或感染者，以诱导或增强受试者的强大免疫反应。
• Spherically Directed Synthesis and Enhanced Cellular Internalization of Metal-Crosslinked DNA Micelles
  作者：Yifan Lyu、Yian Guo、Ren Cai、Ruizi Peng、Chengyi Hong、Xigao Chen、Weijia Hou、Xiaowei Li、Jie Tan、Yuxiu Zou、Xiaobing Zhang、Qiaoling Liu、Weihong Tan

  DOI：10.1016/j.chempr.2019.02.004

  日期：2019.4

  Using spherically directed reduction of metal ions, a facile and universal method for in situ crosslinking of DNA micelles is described. By incorporating a series of specific template domains into lipid-DNA monomers, copper-, silver-, and gold-crosslinked DNA micelles are formed. By combining characterization results and simulation algorithms, accurate structural profiling of DNA micelles is achieved for the first time. The prepared metal-crosslinked DNA micelles show obvious merits, including one-step formation of core structure and ligand corona, facile size tunability, monodispersity, stability against salt-induced aggregation, high utilization of DNA ligand, mild synthesis conditions, and less time consumption and better internalization. Based on our spherically directed synthesis, metal-crosslinked DNA micelle flares were further prepared for effective intracellular imaging by integrating an aptamer-toehold strategy. In addition, we extended the strategy to cholesterol-based double-stranded DNA micelles, giving strong evidence that our method is not only universal but also flexible.