2-(2-bromoethyl)-6-(butylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1485222-11-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-bromoethyl)-6-(butylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• CAS: 1485222-11-4
• 化学式: C₁₈H₁₉BrN₂O₂
• 分子量: 375.265
• InChiKey: QULCWMQQVCVFTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromoethyl)-6-(butylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 sodium azide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以59.4%的产率得到2-(2-azidoethyl)-6-(butylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer

  摘要：

  In this work, we presented a naphthalimide-rhodamine based fluorescence resonance energy transfer system (FRET) NR1 as a ratiometric and intracellular pH probe, in which 1,2,3-triazole was identified as an ideal bridge and biocompatibility. It could selectively monitor pH variations in methanol/HEPES solution at room temperature. When the pH changed from 6.20 to 2.00, both the fluorescence intensities at 580 nm and the intensity ratios, R (I-580 nm/I-538 nm) increased, which allowed the detection of pH changes by both normal fluorescence and ratiometric fluorescence methods. The observation is consistent with the increased FRET from the 1,8-naphthalimide (donor) to the ring-opened, colored form of rhodamine (acceptor). Moreover, as NR1 is lysosomal with low cytotoxicity, it will be helpful for investigating the pivotal role of H+ in a biological context, especially in lysosomes through direct intracellular imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.032
• 作为产物：
  描述：

  4-n-butylamino-9-(2-hydroxyethyl)-1,8-naphthalimide 在 三溴化磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以23.8%的产率得到2-(2-bromoethyl)-6-(butylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer

  摘要：

  In this work, we presented a naphthalimide-rhodamine based fluorescence resonance energy transfer system (FRET) NR1 as a ratiometric and intracellular pH probe, in which 1,2,3-triazole was identified as an ideal bridge and biocompatibility. It could selectively monitor pH variations in methanol/HEPES solution at room temperature. When the pH changed from 6.20 to 2.00, both the fluorescence intensities at 580 nm and the intensity ratios, R (I-580 nm/I-538 nm) increased, which allowed the detection of pH changes by both normal fluorescence and ratiometric fluorescence methods. The observation is consistent with the increased FRET from the 1,8-naphthalimide (donor) to the ring-opened, colored form of rhodamine (acceptor). Moreover, as NR1 is lysosomal with low cytotoxicity, it will be helpful for investigating the pivotal role of H+ in a biological context, especially in lysosomes through direct intracellular imaging. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.032

文献信息

• Photophysical properties and bioimaging application of an aminonaphthalimide-squaraine non-conjugated system
  作者：Vladimir Stamentović、Daniel Collado、Ezequiel Perez-Inestrosa

  DOI：10.1016/j.saa.2021.120546

  日期：2022.2

  650–700 nm region that could operate via energy transfer (ET) between covalently linked naphthalimide and squaraine chromophores. The photophysical properties of the new fluorescent system were explored with the aim of understanding the ET in one- and two-photon excitation modes. The spectroscopic techniques employed in the characterization includes; absorption, fluorescence, quantum yields and fluorescence

  设计并合成了一种氨基萘二甲酰亚胺-方酸胺非共轭体系，目的是在 650-700 nm 区域制备荧光分子，该荧光分子可以通过共价连接的萘二甲酰亚胺和方酸胺发色团之间的能量转移 (ET) 进行操作。探索了新荧光系统的光物理特性，目的是了解单光子和双光子激发模式下的 ET。表征中采用的光谱技术包括：不同溶剂中的吸收、荧光、量子产率和荧光寿命测量。使用单光子和双光子激发荧光评估溶剂极性对 ET 效率的影响。将非共轭系统的光学行为与其单独的方酸和萘二甲酰亚胺部分进行比较。TPA ) 高于 4200 GM。最后，在 N13 小胶质细胞中证明了该分子在单光子和双光子激发模式下荧光成像的适用性。在体外和体内共焦显微镜的研究表明，非共轭系统中有效地积累在细胞质中暗示它可能被用作亚细胞探针。