4-n-butylamino-9-(2-hydroxyethyl)-1,8-naphthalimide | 228406-71-1

• 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: 4-n-butylamino-9-(2-hydroxyethyl)-1,8-naphthalimide
• 英文别名: 4-n-butylamino-N-hydroxyethyl-1,8-naphthalimide；6-(Butylamino)-2-(2-hydroxyethyl)benzo[de]isoquinoline-1,3-dione
• CAS: 228406-71-1
• 化学式: C₁₈H₂₀N₂O₃
• 分子量: 312.368
• InChiKey: YWTPAPIQZDJIAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-n-butylamino-9-(2-hydroxyethyl)-1,8-naphthalimide 在 sodium azide 、 三溴化磷 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 28.0h， 生成 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-溴-1,8-萘二甲酸酐 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 4-n-butylamino-9-(2-hydroxyethyl)-1,8-naphthalimide
  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

• The synthesis and fluorescence of novel <i>N</i> ‐substituted‐1,8‐naphthylimides
  作者：Dongwu Yuan、Robert G Brown、John D Hepworth、Michael S Alexiou、John H. P. Tyman

  DOI：10.1002/jhet.5570450216

  日期：2008.3

  Abstractmagnified imageThe synthesis and characterisation of a series of novel 4‐acylamino and 4‐alkylamino‐N‐1,8‐naphthalimides is described. The UV‐visible absorption and emission properties of the compounds are reported. Significant solvent effects are noted for 4‐n‐butyl‐9‐n‐butyl‐1,8‐naphthylimide. The incorporation of acetyl and chloroacetyl groups into the 4‐substituent markedly increases the fluorescence quantum yield compared with 4‐alkylamino substituemnts.
• Synthesis and photophysical properties of vice-like 1,8-naphthalimide fluorescent sensor for sensitive detection of Mn2+ and Zn2+
  作者：Wo Nie、Jian Yang、Jiahui Wu、Liu Hu

  DOI：10.1016/j.jphotochem.2022.113951

  日期：2022.9
• A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer
  作者：Jiangli Fan、Chunying Lin、Honglin Li、Peng Zhan、Jingyun Wang、Shuang Cui、Mingming Hu、Guanghui Cheng、Xiaojun Peng

  DOI：10.1016/j.dyepig.2013.06.032

  日期：2013.12

  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.