A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury

doi:10.6023/cjoc202301003

Abstract

The fluorescent probe for the detection of overexpressed ClO^－ in acute lung injury is required to have high selectivity against other reactive species. A hydroxybenzo[g]coumarin, NaphCou, was synthesized as a ratiometric fluorescent probe to detect ClO^－ with ultra-high selectivity, a fast response, long-wavelength emissions (from green to red) and large Stokes shifts (from 107 nm to 155 nm). Using probe NaphCou as a fluorescence sensing tool, the lipopolysaccharide (LPS)-induced acute lung injury in mouse model was investigated by monitoring the hypochlorous acid concentration variation.

Key words: acute lung injury, hypochlorous acid, fluorescent probe, ratiometric measurement

Cite this article

Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.

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Fig. & Tab. 9

Scheme 1. Synthetic route of probe NaphCou

Scheme 2. Proposed sensing mechanism of 7-hydroxycoumarin and probe NaphCou towards ClO－ at pH 7.4

Figure 1. Absorption (a) and emission (b) spectra of probe NaphCou (10.0 μmol/L) without (black line) and with (red line) of ClO－ (120.0 μmol/L) Insets: color (a) and fluorescence (b) images of probe NaphCou (10.0 μmol/L) with/without of ClO－ (120.0 μmol/L).

Figure 2. Emission spectra (a) and the fluorescence intensity ratio (I640 nm/I507 nm) (b) of probe NaphCou (10.0 μmol/L) with ClO－ (0~12 equiv.) and parallel tests 3 times Inset: the linear relationship between the ratio of I640 nm/I507 nm and the concentration of ClO－

Figure 3. Ratio of I640 nm/I507 nm vs time after 4.0, 8.0 and 12.0 equiv. of ClO－ were added into the solution of probe NaphCou

Figure 4. (a) Emission spectra of probe NaphCou (10.0 μmol/L) with various interferential analytes. (b) The ratio of I640 nm/I507 nm of probe NaphCou (10.0 μmol/L) in response to ClO－ in the presence of other interfering analytes 1, blank; 2, HO?; 3, 1O2; 4, H2O2; 5, KO2; 6, NO?; 7, ONOO－; 8, ROO?; 9, TBHP; 10, t-BuO?; 11, $\text{O}_{\text{2}}^{}$; 12, BrO－; 13, H2S; 14, SO2.

Figure 5. Bright (the first column), fluorescence (the second and third columns) and merged (the fourth column) images of A549 cells Top row: cells incubated with probe NaphCou (10.0 μmol/L) for 30 min; bottom row: cells treated with ClO－ (120.0 μmol/L) for 30 min and then incubated with probe NaphCou (10.0 μmol/L) for 30 min. Emission was collected at 490~520 nm for the green channel and 620~650 nm for the red channel. λex=435~460 nm. Scale bar=50 μm.

Figure 6. Bright (the first column), fluorescence (the second and third columns) and merged (the fourth column) images and of zebrafish Top row: zebrafish incubated with probe NaphCou (10.0 μmol/L) for 30 min; bottom row: zebrafish treated with ClO－ (120.0 μmol/L) for 30 min and then incubated with probe NaphCou (10.0 μmol/L) for 30 min. Emission was collect at 490~520 nm for the green channel and 620~650 nm for the red channel. λex=435~460 nm. Scale bar=200 μm.

Figure 7. (A) Bright (the first column) and fluorescence (the second and third columns) images of lung histology slides of the normal (a~c) and ALI (d~f) mice treated with probe NaphCou (10.0 μmol/L) for 30 min. (B) Pathological changes of the lung tissue of normal and ALI mice (H&E staining) Scale bar=200 μm.

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