Water-soluble hydrogen sulfide fluorescent probe, preparation method thereof and application thereof in detection of water sulfide and cell hydrogen sulfide

A fluorescent probe and hydrogen sulfide technology, applied in the field of analysis and detection, can solve the problems of poor biocompatibility, high detection cost, and high detection limit, and achieve the effects of good biocompatibility, good water solubility, and low detection limit

Active Publication Date: 2019-08-23
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the detection methods of hydrogen sulfide mainly include methylene blue spectrophotometry, gas chromatography, ion electrode method, etc. These methods have the disadvantages of complicated operation, high detection cost, high detection limit and poor biocompatibility.

Method used

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  • Water-soluble hydrogen sulfide fluorescent probe, preparation method thereof and application thereof in detection of water sulfide and cell hydrogen sulfide
  • Water-soluble hydrogen sulfide fluorescent probe, preparation method thereof and application thereof in detection of water sulfide and cell hydrogen sulfide
  • Water-soluble hydrogen sulfide fluorescent probe, preparation method thereof and application thereof in detection of water sulfide and cell hydrogen sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Preparation N-(5-trimethylsilylethynyl quinoline-8-amino) benzamide

[0030]

[0031] 0.1 mmol of N-(5-iodoquinoline-8-amino) benzamide shown in formula I, 0.2 mmol of trimethylsilyl acetylene, 0.04 mmol of bistriphenylphosphine palladium dichloride, 0.015 mmol of CuI, three Add 0.3ml of ethylamine to 15ml of tetrahydrofuran solution, under nitrogen protection, stir and heat up to 50°C for 12h. After the reaction, add saturated aqueous NaCl solution to the reaction solution, extract with ethyl acetate, and dry the organic phase over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation, and the crude product was separated by column chromatography, using ethyl acetate:petroleum ether as the mobile phase at a ratio of 1:50, to obtain 28 mg of the compound represented by formula II.

[0032] 1 H NMR (400MHz, DMSO) δ10.73(s, 1H), 9.04(dd, J=4.2, 1.5Hz, 1H), 8.73(d, J=8.1Hz, 1H), 8.59(dd, J=8.4, 1.5Hz,1H),8.10–7.99(m,...

Embodiment 2

[0033] Embodiment 2: Preparation of N-(5-trimethylsilylethynyl quinoline-8-amino) benzamide

[0034]

[0035]0.1 mmol of N-(5-iodoquinoline-8-amino) benzamide shown in formula I, 0.3 mmol of trimethylsilyl acetylene, 0.05 mmol of bistriphenylphosphine palladium dichloride, 0.015 mmol of CuI, three Add 0.5ml of ethylamine to 15ml of tetrahydrofuran solution, under nitrogen protection, stir and raise the temperature to 70°C for 12h. After the reaction, add saturated aqueous NaCl solution to the reaction solution, extract with ethyl acetate, and dry the organic phase over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation, and the crude product was separated by column chromatography, using ethyl acetate:petroleum ether at a ratio of 1:50 as the mobile phase, to obtain 31 mg of the compound represented by formula II.

Embodiment 3

[0036] Embodiment 3: Preparation N-(5-ethynyl quinoline-8-amino) benzamide

[0037]

[0038] Add 0.1mmol of N-(5-trimethylsilylethynylquinoline-8-amino)benzamide represented by formula II and 0.4mmol of KOH into 25ml of methanol solution, stir and heat to 40°C, and react for 12h. , add saturated aqueous NaCl solution to the reaction solution, extract with ethyl acetate, dry the organic phase through anhydrous magnesium sulfate, filter, remove the solvent through rotary evaporation, and separate the crude product through column chromatography, ethyl acetate:petroleum ether is 1:50 As the mobile phase, 18 mg of the compound represented by formula III was obtained.

[0039] 1 H NMR (400MHz, DMSO) δ10.76(s, 1H), 9.06(dd, J=4.2, 1.5Hz, 1H), 8.74(d, J=8.1Hz, 1H), 8.65(dd, J=8.4, 1.5Hz,1H),8.13–8.01(m,2H),7.91(d,J=8.1Hz,1H),7.83(dd,J=8.4,4.2Hz,1H),7.73–7.60(m,3H), 4.68(s,1H). 13 C NMR (101MHz, DMSO) δ165.12, 150.24, 138.26, 135.52, 134.96, 134.63, 132.83, 132.60, 129.56, 128.4...

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PUM

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Abstract

The invention discloses a water-soluble hydrogen sulfide fluorescent probe, a preparation method thereof, application of the water-soluble hydrogen sulfide fluorescent probe in water sulfide detectionand application of the water-soluble hydrogen sulfide fluorescent probe in cell hydrogen sulfide detection. The water-soluble hydrogen sulfide fluorescent probe has a structural formula as shown in aformula VI, wherein the substance in the formula VI is glucose, or galactose, or allose, or altrose, or mannose, or talose. The water-soluble hydrogen sulfide fluorescent probe has the advantages ofgood water solubility, low detection limit, high detection sensitivity and the like. The fluorescent probe is successfully applied to water sulfide detection, has good water sulfide detection performance, and achieves a good detection effect. The fluorescent probe is also successfully applied to the detection of cell hydrogen sulfide, and has a good detection effect.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, in particular to a water-soluble hydrogen sulfide fluorescent probe, a preparation method thereof, and its application in water quality sulfide detection and cell hydrogen sulfide detection. Background technique [0002] Hydrogen sulfide is an important gas signal molecule, which can effectively remove hydrogen peroxide, superoxide anion, etc., and plays an important role in the life activities of organisms. However, the concentration of hydrogen sulfide in the body needs to be kept within a certain range, too little will cause diseases such as Alzheimer's disease, Huntington's disease, chronic heart disease or heart failure, too much will directly cause Crohn's disease, periodontitis , Irritable bowel syndrome and other diseases. At the same time, hydrogen sulfide is very soluble in water, which has an important impact on aquatic organisms and has become the "first killer of aqua...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/056C07H1/00C09K11/06G01N21/64
CPCC07H1/00C07H19/056C09K11/06C09K2211/1029C09K2211/1059C09K2211/1088G01N21/6428G01N21/643G01N2021/6417
Inventor 杜奎金卉敏窦言东沈大冬沈润溥章鹏飞
Owner SHAOXING UNIVERSITY
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