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Fluorescent probe for targeting detection of hydrogen sulfide in lysosome, and application thereof

A fluorescent probe, hydrogen sulfide technology, applied in the field of analytical chemistry, can solve the problems of many reaction steps, mild reaction conditions, difficult detection, etc., and achieve the effects of high specificity, low preparation cost and high sensitivity

Inactive Publication Date: 2019-08-20
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most detection of H 2 S probes are mainly directed against H in vitro and in the cytoplasm 2 detection of S, it is difficult to achieve endogenous H at the organelle level 2 Detection of S, especially lysosome-targeted H 2 Detection of S
Moreover, the existing preparation methods have problems such as many reaction steps and mild reaction conditions.

Method used

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  • Fluorescent probe for targeting detection of hydrogen sulfide in lysosome, and application thereof
  • Fluorescent probe for targeting detection of hydrogen sulfide in lysosome, and application thereof
  • Fluorescent probe for targeting detection of hydrogen sulfide in lysosome, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of Fluorescent Probes

[0030] (1) Combine coumarin-3-carboxylic acid (1 mmol), N-(2-aminoethyl)morpholine (1 mmol), 1-hydroxybenzotriazole (0.5 mmol), 1-(3- Dimethylaminopropyl)-3-ethylcarbodiimide (3 mmol), N,N-diisopropylethylamine (0.1 mL) and N,N-dimethylformamide (5 mL) were added to 25 mL one-necked flask, stirred at room temperature for 5 h. Use water-dichloromethane to carry out extraction, the compound 1 obtained after spin-drying;

[0031] (2) Compound 1 (0.6 mmol) and 2,4-dinitrobenzenesulfonyl chloride (1 mmol) were stirred in tetrahydrofuran (5 mL) at 75°C for 2.5 h, filtered with suction, and dried. The resulting solid was purified by column chromatography (dichloromethane:methanol=25:1 / v:v) to obtain a white product which was the fluorescent probe CMDN with a yield of 72%, and its HRMS spectrum was shown in figure 1 .

Embodiment 2

[0032] Example 2 Fluorescent probe pair S 2- the response to

[0033] Prepare in advance 13 5 mL portions of 10 μM probe buffer solution containing 20% ​​DMSO. Then add Na 2 S solution, so that its concentration is 0, 10, 20, 50, 80, 100, 150, 180, 200, 250, 300, 350, 400 and 450 μM. Then perform a fluorescence scan (λ ex = 405 nm); Calculate the fluorescence intensity in each system, the scanning results are as follows figure 2 : As the concentration increases, the fluorescence peak gradually increases.

Embodiment 3

[0034] Example 3 Selectivity of fluorescent probes to different ions

[0035] Prepare 30 parts of 2 mL of 10 μM probe buffer solution (containing 20% ​​DMSO, pH = 5), and then add 20 μL of 10 μM amino acids (Ser, Ala, Thr, Glu, Gln , Val, Asp, Leu, LLe, His, Gly and Arg), biothiols (Cys, GSH and Hcy) and other ions (NaF, NaCl, NaBr, NaI, AlCl 3 、KNO 3 , BaCl 2 , CaCl 2 、H 2 o 2 , HClO, MgCl 2 、Na 2 SO 3 and Na 2 S) etc. in PBS solution. Fluorescence detection is then performed (λ ex = 405 nm, λ em = 455 nm); calculate the fluorescence intensity in each system, and use the fluorescence intensity of the above substances as the vertical axis to make a histogram, such as image 3 Shown, where 1-30 are PBS, AlCl 3 , BaCl 2 , CaCl 2 , Ser, Ala, KCl, KI, KNO 3 , Thr, Glu, Gln, Val, Asp, Leu, LLe, His, Gly, Arg, NaF, NaCl, NaBr, NaI, MgCl 2 、Na 2 SO 3 , Cys, GSH, Hcy, Na 2 S. The results showed that the fluorescent probes for Na 2 The selectivity of S is much h...

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Abstract

The invention provides a fluorescent probe for detection of hydrogen sulfide. The fluorescent probe can be used to detect hydrosulfide ions or sulfions in solutions or cells. The fluorescent probe ofthe invention can be obtained by chemical synthesis, and a synthesis technology of the fluorescent probe has the advantages of simplicity, easiness in implementation, cheap and easily available raw materials, low preparation cost, and easiness in promotion. The fluorescent probe of the invention has the advantages of good targeting property to the lysosome, high sensitivity to the lysosome, good fluorescence emission spectrum characteristics (415-600 nm), realization of the quantitative detection of H2S in the cell lysosome by drawing a standard curve, and achieving of the purpose of rapidly and accurately detecting H2S in the cell lysosome. The fluorescent probe of the invention has a high specificity, is not prone to be interfered by other components in the corresponding H2S detection process, can be used for real-time detection of H2S in the living cell lysosome, and has a broad application prospect.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting hydrogen sulfide and an application thereof. Background technique [0002] Hydrogen sulfide (H 2 S) is a gas with a special smell, and its toxic pollution to the environment has been deeply studied. In addition, H 2 S is an important gas signal molecule, which is closely related to many important physiological and pathological processes. At the same time, H 2 S is the third endogenous gas signal molecule that can play a physiological role in the living body after carbon monoxide and nitric oxide. At physiological concentrations, H 2 S is involved in a series of physiological regulation processes, such as regulation of vascular tone, myocardial contraction, nerve conduction and insulin secretion, etc. Cells that cannot maintain their normal H 2 S concentration, it will cause diseases such as arterial and pulmonary h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/13C09K11/06G01N21/64
CPCC07D295/13C09K11/06C09K2211/1007C09K2211/1011C09K2211/1033G01N21/6428G01N21/643
Inventor 林伟英景新颖于法祺
Owner UNIV OF JINAN
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