Synthesis and Cell Imaging of a Near-Infrared Fast Responsive Hydrogen Sulfide Fluorescent Probe

doi:10.19894/j.issn.1000-0518.240220

Chinese Journal of Applied Chemistry ›› 2025, Vol. 42 ›› Issue (2): 192-200.DOI: 10.19894/j.issn.1000-0518.240220

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Synthesis and Cell Imaging of a Near-Infrared Fast Responsive Hydrogen Sulfide Fluorescent Probe

Chang-Jiang GAO, Xin HUANG, Ya-Yang TIAN, Hai-Feng YU(), Xiao-Bo WANG()

School of Pharmacy，Xianning Medical College，Hubei University of Science and Technology，Xianning 437100，China

Received:2024-07-18 Accepted:2024-12-23 Published:2025-02-01 Online:2025-03-14
Contact: Hai-Feng YU,Xiao-Bo WANG
About author:eas7on@163.com
yu_hf090556@163.com；
Supported by:
Xianning Natural Science Foundation(2023ZRKX087)

1. .pdf(505KB)

Abstract

Abstract:

Based on the formation of CuS， a fluorescent probe of H₂S containing BODIPY， Mito-BPN-Cu， was designed and synthesized. The study of photophysical properties show that the maximum absorption peak and the maximum emission wavelength are 694 nm and 805 nm respectively. Mito-BPN-Cu shows high selectivity for hydrogen sulfide and has an extremely fast response speed （within 10 seconds）. In both pure acetonitrile and V（acetonitrile）∶V（water）=1∶1 solvent systems， Mito-BPN-Cu has high sensitivity to H₂S， and the detection limit in the latter solvent system reaches 0.56 μmol/L. Mito-BPN-Cu showed low cytotoxicity， and the survival rate of HCT116 cells was still greater than 80% at 48 h and even the concentration of the probe was 150 μmol/L. In addition， the probe can specifically target mitochondria with a Pearson correlation coefficient of 0.92. In view of the above advantages of the probe， Mito-BPN-Cu was successfully used for fluorescence imaging of hydrogen sulfide in HCT116 cells.

Key words: Hydrogen sulfide, Fluorescent imaging, Mitochondrial targetable, Near-infrared

CLC Number:

O614.1

Chang-Jiang GAO, Xin HUANG, Ya-Yang TIAN, Hai-Feng YU, Xiao-Bo WANG. Synthesis and Cell Imaging of a Near-Infrared Fast Responsive Hydrogen Sulfide Fluorescent Probe[J]. Chinese Journal of Applied Chemistry, 2025, 42(2): 192-200.

Figures/Tables 8

Fig.1 Synthesis route of Mito-BPN-Cu

Fig.2 （A） UV-Vis absorption spectra of Mito-BPN-Cu in different solvents； Fluorescence emission spectra of Mito-BPN-Cu in different solvents （B） and in pure acetonitrile system （C）， respectively

Fig.3 Bar plots of fluorescence intensity ratios I/I0 before and after the addition of H2S and its competing substances to the Mito- BPN-Cu acetonitrile solution

Fig.4 （A）Temporal plot of fluorescence intensity in reaction of the probe with DTT （100 μmol/L）；（B）Temporal plot of fluorescence intensity after reaction of the probe with L-Cys （100 μmol/L）；（C） Temporal plot of fluorescence intensity after probe and Na2S （100 μmol/L）

Fig.5 （A） Fluorescence emission spectrum of H2S-titrated Mito-BPN-Cu （acetonitrile solvent）；（B） Linear plot of H2S-titrated Mito-BPN-Cu（acetonitrile solvent）；（C） Fluorescence emission spectra of H2S-titrated Mito-BPN-Cu （V（acetonitrile）∶V（water）=1∶1）；（D） H2S titration Mito-BPN-Cu （V（acetonitrile）∶V（water ）=1∶1） of the linear diagram

Fig.6 The cytotoxicity of Mito-BPN-Cu against HCT116 cells

Fig.7 Probe Mito-BPN-Cu in HCT116 cell mitochondria in the positioning fluorescent

Fig.8 Cell imaging of H2S by probe Mito-BPN-Cu

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Synthesis and Cell Imaging of a Near-Infrared Fast Responsive Hydrogen Sulfide Fluorescent Probe

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