N-(9-(2-((2-((2-bromo-2-methylpropanoyl)oxy)ethoxy)carbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride | 1279694-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: N-(9-(2-((2-((2-bromo-2-methylpropanoyl)oxy)ethoxy)carbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride
• CAS: 1279694-09-5
• 化学式: C₃₄H₄₀BrN₂O₅*Cl
• 分子量: 672.059
• InChiKey: USEUZADMXKGITB-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  43.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  罗丹明B 、 ATRP 羟基引发剂 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以65%的产率得到N-(9-(2-((2-((2-bromo-2-methylpropanoyl)oxy)ethoxy)carbonyl)phenyl)-6-(diethylamino)-3H-xanthen-3-ylidene)-N-ethylethanaminium chloride
  参考文献：
  名称：

  Effect of Chain Length on Cytotoxicity and Endocytosis of Cationic Polymers

  摘要：

  We investigated the effect of chain length on the cytotoxicity and endocytosis of rhodamine B end-labeled cationic linear poly(2-(N,N-dimethylamino)ethyl methacrylate) (RhB-PDMAEMA) polymers [M-w = (1.1-4.8) x 10(4) g/mol and M-w/M-n similar to 1.2], which were synthesized via atom transfer radical polymerization by using rhodamine B-based initiator. The 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT), lactate dehydrogenase (LDH), and caspase-3/7 assays revealed that the cytotoxicity and cellular membrane disruption of HepG2 cells induced by PD/vIAEMA depend on both the polymer concentration and chain length, and the apoptosis depends on chain length at the concentration of 37.6 mu g/mL. In the concentration range 10-110 mu g/mL, PDMAEMA chains with different lengths are cytotoxic to HepC2 cells by different mechanisms. Namely, (1) for short PDMAEMA chains [M = (1.1-1.7) x 10(4) g/mol] the cytotoxicity, membrane disruption, and apoptosis are very low, independent of the chain length; (2) in the medium range (1.7 X 10(4) < M-w < 3.9 x 10(4) g/mol), the cytotoxicity increases with the chain length and polymer concentration, mainly due to the cooperative effect of membrane disruption and apoptosis; and (3) for long chains [M-w = (3.9-4.8) x 10(4) g/mol], they are very disruptive to the cellular membrane, pro-apoptotic, and able to enter the cytoplasm and nucleus faster than short chains, as revealed by the real-time confocal laser scanning microscopy images, and their much higher cytotoxicity is independent of the PDMAEMA chain length.

  DOI：

  10.1021/ma102498g