A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg2+ and Its Multiple Applications

doi:10.6023/cjoc202206007

Abstract

A fluorescent probe HMI-Hg²⁺ was designed and synthesized to recognize Hg²⁺ in dimethyl sulfoxide (DMSO)/ phosphate buffer solution (PBS) (V∶V=5∶5, pH=10.17). HMI-Hg²⁺ recognized Hg²⁺ through the fluorescence signal strengthen, and solution color shifted within a few seconds. Spectral experiments confirmed the advantages of the probe with high selectivity and sensitivity to Hg²⁺. The detection limit was calculated to be 0.22 μmol/L. HMI-Hg²⁺ has excellent detection consequences in water samples and seafood samples (fish, shrimp and scallop). Moreover, HMI-Hg²⁺ can be applied for the cell imaging of Hg²⁺ in MCF-7 and has mitochondria-targeted capabilities.

Key words: fluorescent probe, Hg²⁺, seafood sample, cell imaging

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Hongwei Tang, Chao Wang, Keli Zhong, Shuhua Hou, Lijun Tang, Yanjiang Bian. A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 712-717.

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Fig. & Tab. 14

Scheme 1. Synthesis of probe HMI-Hg2+

Figure 1. UV absorption spectra changes after metal ions (10 μmol/L) added to HMI-Hg2+ in DMSO/PBS (V∶V=5∶5, pH=10.17) solution (Inset: color changes of HMI-Hg2+ before and after addition of Hg2+ under sunlight)

Figure 2. Color changes of HMI-Hg2+ solution upon the addition of various metal ions under sunlight 0, HMI-Hg2+; 1, Ba2+; 2, Fe2+; 3, Fe3+; 4, Mn2+; 5, Mg2+; 6, Hg2+; 7, Cu2+; 8, Zn2+; 9, Al3+; 10, Na+; 11, Cd2+; 12, Ni2+; 13, Ca2+; 14, Co2+; 15, Cr3+; 16, Pb2+; 17, K+; 18, Ag+.

Figure 3. Fluorescence intensity changes after all kinds of ions (12 μmol/L) added to HMI-Hg2+ Inset: fluorescence color changes of HMI-Hg2+ before and after addition of Hg2+ under UV lamp irradiation at 365 nm. λex=455 nm, λem=585 nm.

Figure 4. (a) Fluorescence intensity changes of HMI-Hg2+ after Hg2+ (0~12 μmol/L) gradually added and (b) linear relationship between the concentration of Hg2+ (0~12 μmol/L) added to HMI-Hg2+ and fluorescence intensity (λem=585 nm)

Figure 5. Fluorescence intensity changes when other ions (12 μmol/L) added to HMI-Hg2+ and Hg2+ (12 μmol/L) further added (λem=585 nm)

Scheme 2. Proposed mechanism of probe HMI-Hg2+ to Hg2+

Figure 6. TLC plate tracer under 365 nm irradiation (a) Compound HMI-CHO; (b) probe HMI-Hg2+; (c) reaction mixture of HMI-Hg2+ with Hg2+.

Figure 7. Comparison of partial 1H NMR spectra of isolated product from reaction of HMI-Hg2+ with Hg2+, compound HMI-CHO and HMI-Hg2+ in DMSO-d6

Sample	Added/ (μmol•L^-1)	Found/ (μmol•L^-1)	RSD (n=3)/%	Recovery/%
Lake water	1 2 3	1.06 1.82 3.22	4.77 3.99 8.24	100.6 93.7 107.2
Tap water	1 2 3	0.93 2.12 3.08	5.33 4.20 1.52	93.4 106.4 102.6

Table 1. Detection results of Hg2+ in water samples

Sample	Added/ (μmol•L^-1)	Found/ (μmol•L^-1)	RSD (n=3)/%	Recovery/%
Fish	2 4 6	2.03 4.08 6.02	1.11 3.11 0.85	101.3 102.0 100.4
Shrimp	2 4 6	1.92 4.01 5.87	2.72 3.34 1.91	96.2 100.2 97.9
Scallop	2 4 6	2.01 4.09 5.88	0.74 0.28 1.18	100.4 102.2 97.9

Table 2. Detection results of Hg2+ in seafood samples

Figure 8. Fluorescence images of MCF-7 cells incubated with HMI-Hg2+ (10 μmol/L) and different concentrations of Hg2+ (0, 10, 30, 50 and 100 μmol/L) Left: bright field image; middle: green channel image; right: merge field image.

Figure 9. Colocalization experiments of HMI-Hg2+ and Mito- Tracker Green FM in MCF-7 cells (A) Bright field image; (B) Red channel image (from HMI-Hg2+, the emission was collected at 585 nm with red pseudocolor); (C) Green channel image (from Mito-Tracker Green FM); (D) Merge image of (B) and (C); (E) Intensity distribution of fluorescence intensity changes in red and green channels of MCF-7 cells stained with HMI-Hg2+ and Mito-Tracker Green FM; (F) Intensities of green and red channels Scatter plot.

Figure 10. Picture of HMI-Hg2+ test strips with different concentrations of Hg2+ under UV light irradiation (365 nm)

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一种裸眼和荧光双通道快速检测Hg²⁺的探针及其多种应用

A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications

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一种裸眼和荧光双通道快速检测Hg2+的探针及其多种应用