A New Turn-On Fluorescent Chemosensor for Selective Detection of Al3+ Based on a Purine Schiff Base and Its Cell Imaging

doi:10.6023/cjoc202112002

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (6): 1706-1712.DOI: 10.6023/cjoc202112002 Previous Articles Next Articles

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基于嘌呤席夫碱荧光探针检测Al³⁺及细胞实验应用

鞠立鑫, 邵琦, 陆临川, 陆鸿飞^*()

江苏科技大学环境与化学工程学院江苏镇江 212100

收稿日期:2021-12-02 修回日期:2022-01-13 发布日期:2022-03-21
通讯作者: 陆鸿飞
基金资助:
镇江市重点研发计划(SH2020009); 江苏科技大学资助项目.

A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging

Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu()

School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212100

Received:2021-12-02 Revised:2022-01-13 Published:2022-03-21
Contact: Hongfei Lu
Supported by:
Key Research & Development Project of Zhenjiang City(SH2020009); Jiangsu University of Science and Technology.

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Abstract

A new “turn-on” fluorescent probe (E)-2-((2-(8,9-di(naphthalen-1-yl)-9H-purin-6-yl)hydrazono)methyl)-5-(diethylamino)phenol (DNHP) for detecting Al³⁺ was designed, synthesized and evaluated based on purine schiff base. DNHP exhibited remarkable selectivity and rapid response towards Al³⁺ in MeOH/H₂O (V∶V=9∶1, pH=7.4), accompanying with a fluorescent color change from yellow to bright blue. A good linear relationship (R²=0.98367) was obtained between the emission intensity of DNHP and the concentration of Al³⁺ (2~6 µmol/L) with a detection limit of 588 nmol/L. The sensing mechanism of DNHP to Al³⁺ was investigated through the Job’s plot, ¹H NMR and density functional theory (DFT) study. More importantly, the sensor DNHP exhibits permeability and could be successfully applied for detection of intracellular cadmium ions in living HepG-2 cells.

Key words: fluorescent sensor, purine, aluminum, practical application

Cite this article

Lixin Ju, Qi Shao, Linchuan Lu, Hongfei Lu. A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1706-1712.

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Fig. & Tab. 11

Scheme 1. Synthetic route of DNHP

Figure 1. (a) Fluorescence emission spectra of DNHP (10 μmol/L) in the presence of different metal ions (5.0 equiv.) and (b) UV-Vis absorption (left) and fluorescence spectra (right) of DNHP (red line) and DNHP-Al3+ (black line) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mol/L)

Figure 2. Fluorescence response of DNHP (10 μmol/L) to addition of 5.0 equiv. of other metal ions (the blank bar portion) and the mixture of 5.0 equiv. of other metal ions with 5.0 equiv. of Al3+ (the red bar portion, left to right: Co2+, Pd2+, Ni2+, Cu2+, Cr3+, Zn2+, Cu+, Mn2+, Mg2+, Ba2+, Pb2+, Fe3+, Sn2+, Fe2+, K+, Ca2+, Na+, Ag+, Hg2+ and Cd2+)

Figure 3. Fluorescence changes of DNHP (10 μmol/L) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mmol/L) with the addition of Al3+ (0~6 equiv.) (Inset: photographic fluorescence images of DNHP and DNHP-Al3+. Excitation is at 380 nm; Emission is at 468 nm)

Figure 4. Effect of pH on the fluorescence intensity at 468 nm of DNHP (10 μmol/L) in the absence and presence of 5 equiv. of Al3+

Figure 5. Time profile of DNHP (10 μmol/L) in the presence of Al3+ (5 equiv., 50 μmol/L) in MeOH/H2O solution (V∶V=9∶1, pH 7.4, HEPES buffer, 0.2 mmol/L)

Figure 6. Job’s plot between DNHP+Al3+ and Al3+ in MeOH/H2O buffer solution

Figure 7. Fluorescence color changes of test strips for Al3+ at different concentrations under a UV lamp

Figure 8. HOMO and LUMO distributions of DNHP and DNHP-Al3+ complex

Figure 9. Cytotoxic nature of DNHP in HepG-2 cells

Figure 10. Fluorescence imaging of DNHP (8 μmol/L) in HepG-2 cells in the absence and presence of Al3+ (20 μmol/L)

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基于嘌呤席夫碱荧光探针检测Al³⁺及细胞实验应用

A New Turn-On Fluorescent Chemosensor for Selective Detection of Al³⁺ Based on a Purine Schiff Base and Its Cell Imaging

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基于嘌呤席夫碱荧光探针检测Al3+及细胞实验应用