四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu2＋

doi:10.6023/cjoc202403043

摘要/Abstract

设计合成了一种四苯乙烯基酰胺类荧光探针TPE-Py, 并对其结构进行了表征. 通过荧光发射光谱和HeLa细胞成像实验研究了其金属离子识别性能. 结果表明: 探针TPE-Py对Cu^2＋具有较好的选择性和灵敏性, 在H₂O/THF (V∶ V=9∶1)溶液中对Cu^2＋显示出荧光淬灭效应, 且不受其他金属离子干扰. 细胞成像实验表明, 探针TPE-Py可以检测细胞脂滴中的Cu^2＋.

关键词: 聚集诱导发光, 荧光探针, 离子识别, 细胞成像

The fluorescent probe TPE-Py was designed and synthesized, and its structure was confirmed by NMR and HRMS. The recognition properties of probe TPE-Py for metal ions have been studied through fluorescence spectrophotometry and cell imaging experiments in HeLa cells. The results showed that TPE-Py had good selectivity and sensitivity for Cu^2＋. Among various metal ions, TPE-Py only showed exclusive fluorescence turn-off sensing on Cu^2＋ in H₂O/THF (V∶V=9∶1). The results of cell imaging experiments showed that the probe TPE-Py could detect Cu^2＋ in lipid droplets of cells.

Key words: aggregation-induced emission, fluorescent sensor, ion recognition, cell imaging

引用此文

苏小龙, 李健鹏, 刘孟鑫, 邹莉, 杨得锁, 冯海涛. 四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu^2＋[J]. 有机化学, 2024, 44(8): 2581-2587.

Xiaolong Su, Jianpeng Li, Mengxin Liu, Li Zou, Desuo Yang, Haitao Feng. Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2581-2587.

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图/表 8

图1. (A) TPE-Py (10 μmol/L)的荧光光谱随四氢呋喃中水分数的变化而变化和(B) 480 nm处的荧光强度相对于水分数的曲线(λex=330 nm)

Figure 1. (A) Fluorescence spectra of TPE-Py (10 μmo/L) in THF/H2O mixture with different H2O fractions, and (B) relative fluorescence intensity in different THF/H2O mixtures at 480 nm (λex=330 nm)

图2. (A)探针TPE-Py对不同金属离子(10 μmol/L)选择性、(B)探针TPE-Py-Cu2＋的干扰性研究(λex=330 nm, c=10 μmol/L)、(C)加入1 equiv.不同金属离子后探针TPE-Py (10 μmol/L)溶液的荧光照片

Figure 2. (A) Selectivity of probe TPE-Py for different metal ions (10 μmol/L), (B) interference study of probe TPE-Py-Cu2＋ (λex=330 nm, c=10 μmol/L), and (C) fluorescent photos of probe TPE-Py (10 μmol/L) after addition 1 equiv. of different metal ion

图3. (A)探针TPE-Py在H2O/THF (V∶V=9∶1)中与Cu2＋的荧光光谱变化和(B) 480 nm处TPE-Py的荧光强度与Cu2＋浓度之间的线性关系

Figure 3. (A) Fluorescence spectrum change of TPE-Py with Cu2＋ in H2O/THF (V∶V=9∶1), and (B) linear relationship between fluorescence intensity of TPE-Py and Cu2＋ concentration at 480 nm

图4. (A)探针TPE-Py与Cu2＋的Job曲线图和(B)探针TPE-Py与Cu2＋之间可能的配位模式

Figure 4. (A) Job plot of probe TPE-Py and Cu2＋, and (B) possible coordination modes between TPE-Py and Cu2＋

图5. 在H2O/THF (V∶V=9∶1)中的(A, C) TPE-Py和(B, D) TPE-Py＋Cu2＋的SEM图像

Figure 5. SEM images of (A, C) TPE-Py and (B, D) TPE-Py＋Cu2＋ in H2O/THF (V∶V=9∶1)

图6. 用不同浓度的TPE-Py处理的HeLa细胞的存活率

Figure 6. Viability of HeLa cells treated with different concentrations of TPE-Py

图7. (A) HeLa细胞与10 μmol/L TPE-Py-NPs的荧光图像和(B) HeLa细胞与10 μmol/L TPE-Py-NPs＋10 μmol/L Cu2＋的荧光图像

Figure 7. (A) Fluorescence image of HeLa cells with 10 μmol/L TPE-Py-NPs, and (B) fluorescence image of HeLa cells with 10 μmol/L TPE-Py-NPs＋10 μmol/L Cu2＋ Bright field transmission images (A1, B1), fluorescence dark field transmission images (A2, B2), and superimposed field transmission images (A3, B3).

图8. (A)探针TPE-Py的晶体结构图和(B)探针TPE-Py的中的π-π堆积及与溶剂分子间的氢键作用

Figure 8. (A) Crystal structure diagram of probe TPE-Py, and (B) π-π stacking in probe TPE-Py and hydrogen bonding with solvent molecules

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