(4-(2-(di-(2-pycolyl)amino)acetyl)amino-N-butyl-1,8-naphthalimide)zinc(II) | 1204576-08-8

• 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-(2-(di-(2-pycolyl)amino)acetyl)amino-N-butyl-1,8-naphthalimide)zinc(II)
• 英文别名: [(ZTRS)Zn](2+)
• CAS: 1204576-08-8
• 化学式: C₃₀H₂₉N₅O₃Zn
• 分子量: 572.982
• InChiKey: DLQZCJNJKGIUJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为产物：
  描述：

  锌 、 ZTRS 以 H₂O 为溶剂， 生成 (4-(2-(di-(2-pycolyl)amino)acetyl)amino-N-butyl-1,8-naphthalimide)zinc(II)
  参考文献：
  名称：

  Zn²⁺-Triggered Amide Tautomerization Produces a Highly Zn²⁺-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor

  摘要：

  It is still a significant challenge to develop a Zn2+-selective fluorescent sensor with the ability to exclude the interference of some heavy and transition metal (HTM) ions such as Fe2+, Co2+, Ni2+, Cu2+, Cd2+, and Hg2+. Herein, we report a novel amide-containing receptor for Zn2+, combined with a naphthalimide fluorophore, termed ZTRS. The fluorescence, absorption detection, NMR, and IR studies indicated that ZTRS bound Zn2+ in an imidic acid tautomeric form of the amide/di-2-picolylamine receptor in aqueous solution, while most other HTM ions were bound to the sensor in an amide tautomeric form. Due to this differential binding mode, ZTRS showed excellent selectivity for Zn2+ over most competitive HTM ions with an enhanced fluorescence (22-fold) as well as a red-shift in emission from 483 to 514 nm. Interestingly, the ZTRS/Cd2+ complex showed an enhanced (21-fold) blue-shift in emission from 483 to 446 nm. Therefore, ZTRS discriminated in vitro and in vivo Zn2+ and Cd2+ with green and blue fluorescence, respectively. Due to the stronger affinity, Zn2+ could be ratiometrically detected in vitro and in vivo with a large emission wavelength shift from 446 to 514 nm via a Cd2+ displacement approach. ZTRS was also successfully used to image intracellular Zn2+ ions in the presence of iron ions. Finally, we applied ZTRS to detect zinc ions during the development of living zebrafish embryos.

  DOI：

  10.1021/ja907334j