4-amino-N-(2-(2-acetoxyethoxy)ethyl)naphthalimide | 1018781-13-9

• 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-amino-N-(2-(2-acetoxyethoxy)ethyl)naphthalimide
• 英文别名: 4-amino-N-(2-(2-acetoxyethoxy)ethyl)-1,8-naphthalimide；2-[2-(6-Amino-1,3-dioxobenzo[de]isoquinolin-2-yl)ethoxy]ethyl acetate
• CAS: 1018781-13-9
• 化学式: C₁₈H₁₈N₂O₅
• 分子量: 342.351
• InChiKey: IZKVTULBVFZLGT-UHFFFAOYSA-N

物化性质

• 沸点：
  565.0±45.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-N-(2-(2-acetoxyethoxy)ethyl)naphthalimide 、 胆固醇甲酰氯 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以74.5%的产率得到
  参考文献：
  名称：

  Cholesteryl naphthalimide-based gelators: Their applications in the multiply visual sensing of CO2 based on an anion-induced strategy

  摘要：

  Several cholesteryl naphthalimide-derived compounds have been sythesized and developed as CO2 sensors. The derivatives, incorporating ether chains, were found to be capable of gelating various organic solvents, due to the modulation of the hydrophilicity/hydrophobility properties of them. The resulting organogels were well characterized by field emission scanning electron microscopy (FE-SEM), FT-IR spectroscopy, concentration- and temperature-dependent H-1 NMR spectra, and powder X-ray diffraction (PXRD). These gelators can be applied as fluorescent sensors for CO2 in DMSO solutions via the anion-triggered strategy. Furthermore, the resulting organogelation systems in DMSO could also provide visual sensing means for CO2 via the reversible solution-to-gel transition. Particularly, the re-gelation of DMSO induced by CO2 bubbling could be directly observed without the aid of the heating-and-cooling operation. And the reversible sensing process could be repeated several times with the excellent chemical stability of the gelation system after the repeated stimuli of fluoride anion, CO2 and N-2 with heating. These investigations indicate the developed organogelators own the applicable potential in the CO2 detection. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2017.07.067
• 作为产物：
  描述：

  过氧荧光素1 在 双氧水 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 4-amino-N-(2-(2-acetoxyethoxy)ethyl)naphthalimide
  参考文献：
  名称：

  通过荧光色度和亮度定量分析物的通用策略

  摘要：

  摘要利用荧光探针实现对分析物的定量分析，以实现一种快速，简便，精确的方法，是一个方便检测的目标，尤其是在原位。在本文中，我们报告了一种通常可用于通过荧光色度和发光度区分和定量分析物的方法。合成并测试了针对pH值，半胱氨酸，硫化氢，过氧化氢，钯和肼的七个代表性荧光探针。在不利用昂贵的仪器的情况下，采用便携式设备来响应不同的分析物而从荧光样品中收集照片数据。随后，在映射到CIE 1931 xyY标准色空间后，对照片图像进行数字处理以生成色度/发光度与浓度之间的校准曲线。良好的线性校准曲线和通过光谱技术对低误差的未知样品进行定量分析证明了该方法的可靠性。因此，我们展示了一种具有简单现场可构建/便携式设备的分析方法，有望在更多的荧光探针中应用

  DOI：

  10.1016/j.cclet.2020.07.012

文献信息

• FLUORESCENT PROBES FOR REACTIVE SULFUR SPECIES
  申请人：CHANG Christopher J.

  公开号：US20120329085A1

  公开（公告）日：2012-12-27

  The invention provides reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells.

  本发明提供了一种基于反应的荧光探针，用于活细胞中硫化氢的选择性成像。
• Generalizable synthesis of bioresponsive near-infrared fluorescent probes: sulfonated heptamethine cyanine prototype for imaging cell hypoxia
  作者：Kirk M. Atkinson、Janeala J. Morsby、Sai Shradha Reddy Kommidi、Bradley D. Smith

  DOI：10.1039/d1ob00426c

  日期：——

  bioresponsive near-infrared fluorescent probes with appended sulfonates that provide excellent physiochemical properties. A prototype version is triggered by nitroreductase enzyme to undergo self-immolative cleavage with a large enhancement in fluorescence signal at 780 nm and the probe enables microscopic imaging of cell hypoxia with “turn on” fluorescence. Near-infrared fluorescence imaging of hypoxia

  生物响应荧光成像的持续进步需要新型可激活荧光探针，这些探针可发射波长超过 740 nm 的近红外荧光。七次甲基花青染料 (Cy7) 具有合适的荧光特性，但创建可激活探针具有挑战性，因为 Cy7 染料具有自聚集和荧光猝灭的倾向。采用一种新的合成策略来创建一类可通用的亲水性生物响应性近红外荧光探针，其附加磺酸盐，可提供优异的理化性质。原型版本由硝基还原酶触发，进行自毁裂解，780 nm 处的荧光信号大幅增强，并且该探针能够通过“打开”荧光对细胞缺氧进行显微成像。缺氧的近红外荧光成像在生物医学研究和临床治疗的许多不同领域都有潜在用途。
• Naphthalimide-4-(4-nitrophenyl)thiosemicarbazide: A Fluorescent Probe for Simultaneous Monitoring of Viscosity and Nitric Oxide in Living Cells
  作者：Su Jung Kim、Sun Young Park、Shin A Yoon、Changshin Kim、Chulhun Kang、Min Hee Lee

  DOI：10.1021/acs.analchem.0c04019

  日期：2021.3.16

  Intracellular viscosity is a physicochemical factor that determines the outcomes of various biological processes, while nitric oxide (NO) is an essential signaling molecule that controls many cellular processes, including oxidative stress. Anticipating that both may be interrelated with a variety of pathologies, their simultaneous measurement would be highly valuable for the investigation of the pathological condition of cells. However, the development of a sensor for such simultaneous detection has not been attempted yet. Herein, we present the synthesis of naphthalimide-4-(4-nitrophenyl)thiosemicarbazide, probe 1, and its application to living cells under conditions of lipopolysaccharide or nystatin treatment, adopted as oxidative stress and altered intracellular viscosity models, respectively. The probe showed increased fluorescence in response to elevation of viscosity and NO levels at 470 and 550 nm, respectively, in the solution studies. When the probe was used for a confocal microscopic study of HeLa cells under stressed conditions, simultaneous monitoring of viscosity and NO level elevations was possible through fluorescence imaging using band-pass filters of 420–475 and 505–600 nm, respectively, upon excitation at a wavelength of 405 nm. Interestingly, both the cellular viscosity and NO levels increased together under lipopolysaccharide or nystatin treatment. Therefore, we suggest that probe 1 is a fluorescent chemical probe that enables the monitoring of alterations in intracellular viscosity and NO levels in living cells, which would be valuable in studies of various cellular damage models.

  细胞内粘度是决定各种生物过程结果的理化因素，而一氧化氮（NO）则是控制包括氧化应激在内的许多细胞过程的重要信号分子。由于这两种物质可能与多种病理现象相互关联，因此同时测量这两种物质对研究细胞的病理状态非常有价值。然而，目前还没有人尝试过开发一种传感器来进行这种同步检测。在此，我们介绍了萘二甲酰亚胺-4-（4-硝基苯基）硫代氨基甲酰肼（探针 1）的合成及其在脂多糖或囊菌素处理条件下活细胞中的应用，分别作为氧化应激模型和细胞内粘度改变模型。在溶液研究中，探针在 470 纳米和 550 纳米波长处的荧光分别随着粘度和 NO 水平的升高而增加。当使用该探针对受压条件下的 HeLa 细胞进行共聚焦显微镜研究时，在 405 纳米波长的激发下，使用波段分别为 420-475 纳米和 505-600 纳米的带通滤光片进行荧光成像，可以同时监测粘度和 NO 水平的升高。有趣的是，细胞粘度和 NO 含量在脂多糖或奈司他丁处理下同时升高。因此，我们认为探针 1 是一种荧光化学探针，可以监测活细胞中细胞内粘度和 NO 水平的变化，这对研究各种细胞损伤模型很有价值。
• An endoplasmic reticulum-selective ratiometric fluorescent probe for imaging a copper pool
  作者：Sun Young Park、Woori Kim、Sun-Hee Park、Jinhyoung Han、Jinju Lee、Chulhun Kang、Min Hee Lee

  DOI：10.1039/c7cc01430a

  日期：——

  Hydrazide-linked naphthalimides undergo copper ion-selective hydrolysis with concomitant ratiometric fluorescence change.

  “酰肼偶联的萘酰亚胺可以与铜离子选择性水解，并伴随比例荧光变化。”
• A New Prodrug-Derived Ratiometric Fluorescent Probe for Hypoxia: High Selectivity of Nitroreductase and Imaging in Tumor Cell
  作者：Lei Cui、Ye Zhong、Weiping Zhu、Yufang Xu、Qingshan Du、Xin Wang、Xuhong Qian、Yi Xiao

  DOI：10.1021/ol102975t

  日期：2011.3.4

  Based on the hypoxia prodrug moiety of p-nitrobenzyl, a selective ratiometric fluorescent sensor (RHP) for the detection of microenvironment hypoxia was designed and synthesized. RHP can be selectively activated by bioreductive enzymes (NTR) and results in an evident blue to green fluorescent emission wavelength change in both solution phases and in cell lines, which might be the first fluorescent ratiometric probe for hypoxia in solid tumors.