CN-121990942-A - Fluorescent probe for detecting hydrogen sulfide, preparation method thereof and biological imaging application

CN121990942ACN 121990942 ACN121990942 ACN 121990942ACN-121990942-A

Abstract

The invention relates to a fluorescent probe for detecting hydrogen sulfide, a preparation method thereof and biological imaging application, wherein the fluorescent probe (S) is prepared by adding absolute ethyl alcohol into p-phenylenediamine, refluxing and dissolving the solution (solution A) in heating at 80 ℃, dissolving salicylaldehyde in a proper amount of absolute ethyl alcohol (solution B), dripping the solution B into the solution A, keeping the heating and refluxing at 80 ℃ in the whole process, continuously stirring, refluxing for 2 hours, and filtering to obtain a light yellow solid, namely the fluorescent probe (S). The fluorescent probe can specifically identify hydrogen sulfide (H 2 S) under the interference of common ions, has strong anti-interference capability and high sensitivity, and can be used for the real-time monitoring and fluorescent imaging of endogenous H 2 S of cell and mouse tumors.

Inventors

ZHANG ZIYI
ZHU BINGQING
GU GUOLONG
WANG JIN
GAO YUTING
WU JIE
TANG WEIZHEN
JIN CHAO
LI ZHE
Meng Wuwei
DAI JUNYI
YU LU

Assignees

盐城师范学院

Dates

Publication Date: 20260508
Application Date: 20260201

Claims (7)

1. A fluorescent probe for detecting hydrogen sulfide, a preparation method thereof and biological imaging application relate to the application of the probe in the aspect of specifically recognizing hydrogen sulfide molecules. The fluorescent probe has the following structural formula: 。
2. use according to claim 1, wherein hydrogen sulphide is selectively identifiable in an aqueous cationic solution.
3. Use according to claim 1, wherein hydrogen sulphide is selectively identifiable in an aqueous anionic solution.
4. Use according to claim 1, wherein hydrogen sulphide is selectively identifiable in an amino acid solution.
5. The use according to claim 1, wherein hydrogen sulphide is selectively identifiable in biologically active molecules.
6. The use according to claim 1 for fluorescence imaging of endogenous hydrogen sulfide in cancer cells.
7. The use according to claim 1, for real-time fluorescence imaging of mouse tumors.

Description

Fluorescent probe for detecting hydrogen sulfide, preparation method thereof and biological imaging application Technical Field The invention relates to the technical field of biological analysis and detection, in particular to a fluorescent probe for detecting hydrogen sulfide, a preparation method of the fluorescent probe and application of the fluorescent probe in biological imaging. Background Hydrogen sulfide (H 2 S) has traditionally been considered a toxic gas with malodorous odors, and recent studies have demonstrated that it is a third endogenous gas transmitter, playing a vital regulatory role in biological processes and pathological mechanisms (Zhang Peng, et al Journal of Cardiovascular Pharmacology, 2021, 2). In mammals, H 2 S can be synthesized endogenously by three enzymes, cystathionine beta-synthase (CBS), cystathionine gamma-lyase (CSE), and 3-thioglycolate sulfotransferase (3-MST). Recent studies have shown that abnormal changes in H 2 S concentration in organisms are closely related to the occurrence and development of a variety of diseases, including but not limited to neurodegenerative diseases, atherosclerosis, diabetes and various types of cancer (Zhou Guijuan, et al. Chinese science: life sciences, 2023, 10). Based on the method, an H 2 S instantaneous detection method with high specificity and high sensitivity is established, accurate and rapid detection of H 2 S in a biological sample is realized, and important theoretical research value and practical application significance are achieved. Disclosure of Invention In view of the defects in the prior art, the invention provides a symmetrical Schiff base fluorescent probe, a preparation method and application thereof, and the fluorescent probe can detect H 2 S more efficiently and sensitively. The invention takes p-phenylenediamine as raw material, and makes it and salicylaldehyde take condensation reaction, connect salicylaldehyde structure at both ends of p-phenylenediamine, thus form symmetrical Schiff base fluorescent probe (hereinafter referred to as probe S) with symmetry, this probe can be used for the detection of exogenous H 2 S, its structural formula is as follows: the synthesis method of the fluorescent probe (S) specifically comprises the following steps: p-phenylenediamine is placed in a round-bottomed flask, absolute ethanol solution is added, and heating reflux is carried out at 80 ℃ to obtain solution A; preparing corresponding salicylaldehyde, placing the salicylaldehyde into a beaker, and adding a proper amount of absolute ethyl alcohol to dissolve the salicylaldehyde into a homogeneous solution to serve as a solution B; Dropwise adding the solution B into the solution A, heating and refluxing at 80 ℃ in the whole process, continuously stirring, and refluxing for 2-4 hours to obtain a light yellow precipitate crude product; and (3) carrying out reduced pressure suction filtration on the light yellow precipitate crude product, placing a filter cake in absolute methanol for washing, carrying out reduced pressure suction filtration, and repeating the steps for three times to obtain pure light yellow solid, namely the symmetrical Schiff base fluorescent probe (S). The invention provides a method for detecting endogenous or exogenous hydrogen sulfide by using a fluorescent probe (S), which comprises the specific steps of preparing the fluorescent probe (S) into a solution with DMF or DMSO, wherein the concentration is 5.0X10 -5 mol/L, preparing H 2 S into deionized water, the concentration is 2.0X10 -2 mol/L, preparing the solution D, mixing the solution D with the solution C according to a certain proportion, detecting the mixed solution by adopting a fluorescence spectrum method, and comparing whether the stock solution has fluorescence. The preparation method of the symmetrical Schiff base fluorescent probe (S) is simple and convenient, the raw material cost is low, the one-step synthesis can be realized, the purity can reach 99%, the specific recognition H 2 S can be generated to generate a fluorescent effect, and compared with the common single-side fluorescent probe, the symmetrical Schiff base fluorescent probe (S) has the advantages of higher selectivity, higher sensitivity and strong anti-interference capability. In application, the symmetrical Schiff base fluorescent probe (S) can be widely applied to biological imaging detection of H 2 S, and a novel technical scheme is provided for rapid and accurate detection of H 2 S. Drawings FIG. 1 is a graph showing the change of fluorescence value of a fluorescent probe (S) with H 2 S concentration; FIG. 2 is a standard graph of fluorescence values of fluorescent probes (S) as a function of H 2 S concentration; FIG. 3 is a graph showing fluorescence emission spectra of a fluorescent probe (S) for selectively recognizing H 2 S in a cation; FIG. 4 is a graph showing fluorescence emission spectra of a fluorescent probe (S) for selectively recognizing H 2 S in anions; FIG