N-(2-morpholinoethyl)-4-nitro-1,8-naphthalimide | 1030665-78-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-morpholinoethyl)-4-nitro-1,8-naphthalimide
• 英文别名: morpholino-4-nitronaphthalic anhydride；N-(1-morpholinoethyl)-4-nitro-1,8-naphthalimide；2-(2-morpholin-4-ylethyl)-6-nitrobenzo[de]isoquinoline-1,3-dione
• CAS: 1030665-78-1
• 化学式: C₁₈H₁₇N₃O₅
• 分子量: 355.35
• InChiKey: ICPINGHORKMFDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.68
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  92.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-(2-morpholinoethyl)-4-nitro-1,8-naphthalimide 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以63%的产率得到6-amino-2-(2-morpholinoethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  A two-photon lysosome-targeted probe for endogenous formaldehyde in living cells

  摘要：

  一种基于ICT机制的双光子溶酶体靶向探针已经合成，并成功地用于在活细胞中监测和成像外源性和内源性甲醛，表现出优异的性能。

  DOI：

  10.1039/d2ra02672d
• 作为产物：
  描述：

  5-硝基苊 在 potassium dichromate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 N-(2-morpholinoethyl)-4-nitro-1,8-naphthalimide
  参考文献：
  名称：

  A two-photon lysosome-targeted probe for endogenous formaldehyde in living cells

  摘要：

  一种基于ICT机制的双光子溶酶体靶向探针已经合成，并成功地用于在活细胞中监测和成像外源性和内源性甲醛，表现出优异的性能。

  DOI：

  10.1039/d2ra02672d

文献信息

• A Lysosome-Targeting Fluorescence Off-On Probe for Imaging of Nitroreductase and Hypoxia in Live Cells
  作者：Jin Zhou、Wen Shi、Li-Hong Li、Qiu-Yu Gong、Xiao-Feng Wu、Xiao-Hua Li、Hui-Min Ma

  DOI：10.1002/asia.201600012

  日期：2016.10.6

  accompanied by a large fluorescence enhancement at a wavelength of 543 nm. The probe shows an accurate lysosome‐targeting ability with high selectivity and sensitivity to nitroreductase (detection limit: 2.2 ng mL−1). Notably, the probe has been used to image the change of lysosomal nitroreductase in live cells during hypoxia, revealing that the increase of nitroreductase in lysosomes may be smaller

  通过一步合成开发了一种靶向溶酶体的荧光关闭探针，用于检测溶酶体硝基还原酶和缺氧。该探针是通过将吗啉（一种溶酶体靶向单元）掺入4-硝基-1,8-萘二甲酰亚胺（作为荧光染料和硝基还原酶的特定底物）而构建的，其检测机理是基于硝基还原酶催化的探针还原到4-氨基-1,8-萘二甲酰亚胺，并在543 nm波长处有较大的荧光增强。该探针显示出精确的溶酶体靶向能力，对硝基还原酶具有很高的选择性和敏感性（检测限：2.2 ng mL -1）。值得注意的是，该探针已用于对缺氧期间活细胞中溶酶体硝基还原酶的变化进行成像，从而揭示了溶酶体中硝基还原酶的增加可能小于细胞质中。另外，预期该探针可用于研究溶酶体的酸性细胞器中的硝基还原酶的功能。
• A H2S-triggered two-photon ratiometric fluorescent theranostic prodrug for bio-imaging
  作者：Xianghua Wu、Yuxun Lu、Bo Liu、Yu Chen、Junfeng Zhang、Ying Zhou

  DOI：10.1016/j.cclet.2021.02.065

  日期：2021.8
• 4-Amino-1,8-naphthalimide-Based Tröger’s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds
  作者：Emma B. Veale、Daniel O. Frimannsson、Mark Lawler、Thorfinnur Gunnlaugsson

  DOI：10.1021/ol9013602

  日期：2009.9.17

  The synthesis and photophysical and biological Investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.
• Synthesis, Photophysical, and DNA Binding Studies of Fluorescent Tröger’s Base Derived 4-Amino-1,8-naphthalimide Supramolecular Clefts
  作者：Emma B. Veale、Thorfinnur Gunnlaugsson

  DOI：10.1021/jo1005697

  日期：2010.8.20

  The synthesis and characterization of three bis-1,8-naphthalimide-containing Trager's bases 1-3, formed from the corresponding 4-amino-1,8-naphthalimide precursors 7-9 in a single step, is described. The photophysical investigation of 1-3 and 7-9 was carried out in various organic solvents as well as in water and as a function of pH using UV/vis and fluorescence spectroscopy. As for their 4-amino-1,8-naphthalimide precursors 7-9, both the ground-state and excited-state characteristics of 1-3 were dependent on the polarity and the hydrogen-bonding ability of the solvent medium. The DNA-binding affinities of 1-3 were also studied in aqueous solution at pH 7.4, in the presence of calf-thymus DNA (ct-DNA), using various UV/vis absorption and fluorescence spectroscopic methods. These molecules exhibited significant DNA-binding ability, where large binding values K-b in the range of 10(6) M-1 were determined. Such strong binding to ct-DNA was maintained even in competitive media (50 and 160 mM NaCl) and was also found to be irreversible regardless of the concentration of the ionic strength. Thermal denaturation experiments also demonstrated that the interaction of 1-3 with ct-DNA gave rise to significant stabilization in the double-helical structure of DNA. The binding affinity of 1-3 for ct-DNA was also compared to that of their 4-amino-1,8-naphthalimide precursors 7-9, determined by fitting of data using "intrinsic" methods and ethidium bromide displacement assays. The latter method Oyes outstanding binding constants for 1-3 in the range of 10(7) M-1.