N-3-[3-(methacryloylamino)propyl]-7-(diethylamino)coumarine-3-carboxamide | 1264740-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-3-[3-(methacryloylamino)propyl]-7-(diethylamino)coumarine-3-carboxamide
• CAS: 1264740-48-8
• 化学式: C₂₁H₂₇N₃O₄
• 分子量: 385.463
• InChiKey: IKBMFDJKCRVJCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  7-(二乙胺基)-2-氧代-2-苯并吡喃-3-羧酸N-琥珀酰亚胺酯 、 N-(3-aminopropyl)methacrylamide 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-3-[3-(methacryloylamino)propyl]-7-(diethylamino)coumarine-3-carboxamide
  参考文献：
  名称：

  Removable Nanocoatings for siRNA Polyplexes

  摘要：

  To assist in overcoming the inherent instability of nucleic add-containing polyplexes in physiological solutions, we have here set out to develop removable nanocoatings For modifying the surface of siRNA-based nanoparticles. Here, N-(2-hydroxypropyl)methacrylamide (HPMA) based copolymers containing carbonylthiazolidine-2-thione (TT) reactive groups in their side chains bound via disulfide spacers to the polymeric backbone were synthesized, and these copolymers were used to coat the surface of polyplexes formed by the self-assembly of anti-Luciferase siRNA with the polycations polyethylene imine (PEI) and poly(HPMA)-grafted poly(L-lysine) (GPL). The coating process was monitored by analyzing changes in the weight-average molecular weight (M-w), the hydrodynamic radius (R-h), and the zeta-potential (zeta) of the polyplexes, using both static (SLS) and dynamic (DLS) light scattering methods. The outlined methods resulted in the attachment of, on average, 28 polymer molecules to the surface of the polyplexes, forming a similar to 5-nm-thick hydrophilic stealth coating. Initial efforts to develop RGD-targeted coated polyplexes are also described. Atomic force microscopy (AFM) showed an angular polyplex structure and confirmed the narrow size distribution of the coated nanoparticles. The stability of the polymer-coated and uncoated polyplexes was evaluated by gel electrophoresis and by turbidity measurements, and it was found that modifying the surface of the siRNA-containing polyplexes substantially improved their stability in physiological solutions. Using polymer-coated GPL-based polyplexes containing anti-Luciferase siRNA, we finally also obtained some initial proof-of-principle for time- and concentration-dependent target-specific gene silencing, suggesting that these systems hold significant potential for further in vitro and in vivo evaluation.

  DOI：

  10.1021/bc100197e