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Fluorescent probe for detecting hydrogen sulfide in cells, method for preparing fluorescent probe and application thereof

A fluorescent probe, hydrogen sulfide technology, applied in the field of analytical chemistry, to achieve the effect of cheap raw materials, low preparation cost, and simple and easy synthesis process

Inactive Publication Date: 2019-05-10
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the lack of fast response and selective hydrogen sulfide detection probes at present, the present invention provides a fluorescent probe for detecting intracellular hydrogen sulfide, which has fast response speed and strong anti-interference ability

Method used

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  • Fluorescent probe for detecting hydrogen sulfide in cells, method for preparing fluorescent probe and application thereof
  • Fluorescent probe for detecting hydrogen sulfide in cells, method for preparing fluorescent probe and application thereof
  • Fluorescent probe for detecting hydrogen sulfide in cells, method for preparing fluorescent probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Synthesis of Fluorescent Probes

[0033] (1) Add 4-ethynylbenzonitrile (1 mmol), 4-bromo-2-hydroxybenzaldehyde (1 mmol), triphenylphosphine (0.02mmol), [1,1-bis(diphenylphosphine Base) Ferrocene] Palladium dichloride (0.02 mmol) was dissolved in triethylamine, after stirring for 10 min, cuprous iodide (0.04 mmol) was added to the reaction system, and heated to reflux at 90°C for 2 hours under the protection of nitrogen , using petroleum ether:ethyl acetate=5:1v / v as the eluent, separated and purified by column chromatography to obtain compound 1: ;

[0034] (2) Dissolve compound 1 (0.3 mmol), 2,4-dinitrofluorobenzene (0.35 mmol) and N,N-diisopropylethylamine (0.3 mmol) in 10 mL of dichloromethane, at room temperature The reaction was stirred for 6 hours, and the target product was obtained by separation and purification by column chromatography with petroleum ether:ethyl acetate=2:1v / v as eluent. 1 H NMR spectrum see figure 1 .

Embodiment 2

[0035] Example 2 Fluorescent probes for different concentrations of Na 2 S's response

[0036] The probe obtained in Example 1 was dissolved in ethanol, and then diluted with PBS to form a 5 μM probe buffer solution (containing 10% ethanol, pH 7.4). Take 22 parts of the above probe solution, add Na 2 The concentration of S solution is: 0, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 120, 130, 150, 170, 190, 210, 230, 260, 280, 290, 300 μM, followed by fluorescence detection (λ Ex = 405 nm); calculate the relative fluorescence intensity in each system; the probe has different concentrations of Na 2 S responds as figure 2 Shown: the maximum fluorescence intensity peak is at 510 nm, with Na 2 The fluorescence intensity increased gradually with the increase of S solution concentration. Take Na 2 When the concentration of S is 0, 10, 20, 30, and 40 μM, the concentration of the detected substance is the abscissa, and the corresponding fluorescence intensity at 510 nm (I 510nm ...

Embodiment 3

[0037] Example 3 Selectivity of fluorescent probes to different substances

[0038] The probe obtained in Example 1 was dissolved in ethanol, and then diluted with PBS to form a 5 μM probe buffer solution (containing 10% ethanol, pH 7.4). Take 22 parts of the above probe solution with a volume of 4 mL, add 20 μL of PBS solutions of different substances with a concentration of 40 mM, and then perform fluorescence scanning (λ Ex = 405 nm); calculate the relative fluorescence intensity in each system; take the corresponding fluorescence intensity at 510 nm (I 510nm ) is the ordinate, and the histogram of the response of the probe to different substances is obtained, such as Figure 4 Shown, among them, 1-22 are respectively blank, Al 3+ 、 Ba 2+ , Ca 2+ 、Co 2+ 、Cu 2+ , Cys, F - , glucose, GSH, H 2 o 2 , HClO, Hcy, I - , Mg 2+ , MnO 2 、Ni 2+ , Sn 2+ , SO 3 2- , VC, Zn 2+ 、Na 2 S. It can be seen that the fluorescent probe is only sensitive to the addition of Na ...

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Abstract

The invention provides a fluorescent probe for detecting hydrogen sulfide in cells, a method for preparing the fluorescent probe and application thereof. A chemical structural formula of the fluorescent probe is shown. Reaction can be carried out on 2,4-dinitrofluorobenzene and reaction products of 4-ethynylbenzonitrile and 4-bromine-2-hydroxybenzaldehyde to obtain the fluorescent probe. The hydrogen sulfide in solution or the cells or organisms can be detected by the fluorescent probe by the aid of fluorescence. The fluorescent probe, the method and the application have the advantages that the fluorescent probe can be obtained by means of chemical synthesis, synthesis processes are simple and feasible, raw materials are inexpensive and are easily available, and accordingly the fluorescentprobe is low in preparation cost; the fluorescent probe is high in specificity, and interference due to other components can be prevented in detection procedures; the fluorescent probe is short in response time, high in sensitivity and excellent in fluorescence emission spectral characteristic, and the hydrogen sulfide in the cells can be quickly and accurately detected by the fluorescent probe;the fluorescent probe has a broad application prospect in research on the influence of the hydrogen sulfide in the biological cells on physiological and pathological procedures.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting intracellular hydrogen sulfide and an application thereof. Background technique [0002] Hydrogen sulfide (H 2 S) together with nitric oxide (NO) and carbon monoxide (CO) are regarded as important gas signal molecules in life, H 2 The biosynthesis of S is mainly catalyzed by three enzymes, cystathionine β synthase (CBS), cystathionine γ lyase (CSE) and 3-mercaptopyruvate sulfotransferase (3-MST). Produced from L-cysteine ​​(Cys) in the heart, brain, liver and kidneys. The results of the study showed that H 2 S plays an important role in regulating the physiological and pathological processes of the myocardium, participating in the relaxation of blood vessels, angiogenesis, regulation of inflammation, regulation of blood pressure and regulation of the nervous system. Endogenous H 2 S can protect cells under oxidative ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C255/56C07C253/30G01N21/64
Inventor 林伟英卢雅如董宝利张楠宋文辉
Owner UNIV OF JINAN
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