7-(diethylamino)-2-oxo-N-tetradecyl-2H-chromene-3-carboxamide | 1334534-03-0

• 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: 7-(diethylamino)-2-oxo-N-tetradecyl-2H-chromene-3-carboxamide
• CAS: 1334534-03-0
• 化学式: C₂₈H₄₄N₂O₃
• 分子量: 456.669
• InChiKey: ULTHDQKWZPMDEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  33.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  62.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  十四胺 、 7-(二乙基氨基)香豆素-3-羧酸 在 N-甲基吗啉 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以81%的产率得到7-(diethylamino)-2-oxo-N-tetradecyl-2H-chromene-3-carboxamide
  参考文献：
  名称：

  A novel fluorescent probe for more effective monitoring of nanosized drug delivery systems within the cells

  摘要：

  To improve visualization of nanoparticles within the cells' compartments, we synthesized a coumarin based fluorescent derivative, tetradecyl diethylamino coumarin amid, 14-DACA. In this compound the coumarin chromophore is linked with a tetradecyl alkyl chain that contributes to lipophilicity and slightly amphiphilic character of this probe. 14-DACA exhibits good biocompatibility, its solubility and emission spectrum are not sensitive to changes in pH value. Solid lipid nanoparticles (SLN) labeled with 14-DACA (SLN-D) and frequently used 6-coumarin (SLN-C) were utilized to evaluate probes' properties in the trafficking and intracellular localization of nanoparticles. SLN-D were seen as distinct blue dots in the cellular environment in contrast to SLN-C which were hardly to recognize due to the self-quenching of 6-coumarin, its leakage and distribution in intracellular compartments. Spectra of 14-DACA indicated the possibility of spectral resolution from both green and red fluorophores allowing clear multicolor imaging of organelles in both fixed and living cells. The results showed valuableness of new probe for trafficking of the drug nanocarriers intracellularly in a kinetic and sensitive manner. Such studies are of great importance in investigations aimed to clarify subcellular targeted drug delivery, controlled release and even to identify toxicological changes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2011.06.046