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Quick, highly selective and ultra-sensitive hypobromous acid fluorescence probe

A technology of sulfonic acid groups and compounds, applied in fluorescence/phosphorescence, luminescent materials, and material analysis through optical means, can solve the problems of insufficient response speed, insufficient selectivity, and insufficient sensitivity, and achieve rapid reaction and synthesis Simple and stable effect

Inactive Publication Date: 2018-10-02
李新元
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems with the currently reported and fluorescent probes, including insufficient selectivity, insufficient sensitivity, insufficient response speed, and complex synthesis.

Method used

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  • Quick, highly selective and ultra-sensitive hypobromous acid fluorescence probe
  • Quick, highly selective and ultra-sensitive hypobromous acid fluorescence probe
  • Quick, highly selective and ultra-sensitive hypobromous acid fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035]

[0036] (Scheme 1) Dissolve 232mg (1mmol) of 4-chloro-1,8-naphthalene anhydride in 15mL of ethanol, then add 130mg (1mmol) of 2-aminoethylmorpholine, then stir and react at 85°C for 6h, after the reaction Ethanol was evaporated to dryness to obtain the crude product. Finally, a mixed system of dichloromethane and methanol (75:1, v / v) was used for column chromatography to obtain 235.3 mg of a white pure product with a yield of 65%.

[0037] Dissolve 344 mg (1 mmol) of the fluorophore compound in 15 mL of ethylene glycol methyl ether, then add 183.24 mg (3 mmol) of monoethanolamine, then stir and react at 140°C for 12 hours, and spin evaporate to dryness of ethylene glycol methyl ether after the reaction is complete to obtain crude product. Finally, a mixed system of dichloromethane and methanol (50:1, v / v) was used for column chromatography to obtain 305.8 mg of a yellow pure product with a yield of 58%.

[0038] (Scheme 2) Dissolve 232mg (1mmol) of 4-c...

Embodiment 2

[0046] figure 1 It is the change graph of the fluorescence spectrum of the hypobromous acid fluorescent probe (5 μM) after adding hypobromous acid (0-10 μM). It can be clearly seen from the figure that with the increase of the concentration of hypobromous acid added, the fluorescence intensity at 550 nm of the solution gradually decreases. Moreover, it can be seen from the illustration that the change of the fluorescence intensity at 550 nm has a good linear relationship with the concentration of the added hypobromous acid, which proves that the fluorescent probe can be used for quantitative analysis of hypobromous acid.

Embodiment 3

[0048] figure 2 It is the graph showing the change of fluorescence spectrum with time after adding hypobromous acid fluorescent probe (5 μM) to hypobromous acid (5 μM). It can be clearly seen from the figure that when hypobromous acid is added, the detected fluorescence intensity is instantly quenched and reaches the plateau, which shows that the probe reacts rapidly with hypobromous acid and can provide a rapid analysis method for the determination of hypobromous acid.

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Abstract

The invention relates to a quick, highly selective and ultra-sensitive hypobromous acid fluorescence probe. In particular, the probe is a 4-amino-1,8-naphthalimide compound and can serve as the hypobromous acid fluorescence probe for hypobromous acid detection. The probe can achieve at least one of the following technical effects that probe can highly selectively identify hypobromous acid, quicklyrespond to hypobromous acid, highly sensitively analyze hypobromous acid and achieve hypobromous acid analysis, is stable in property, can be stored and used for a long term, and has higher interference resistance.

Description

technical field [0001] The invention relates to a 4-amino-1,8-naphthalimide compound used as a hypobromous acid fluorescent probe, which can quickly perform ultrasensitive and selective identification of the hypobromous acid and measure the concentration of the hypobromous acid in a sample. Background technique [0002] Hypobromous acid is considered a bromine species (RBS) among reactive endogenous reactant species. It has long been considered a key component of the neutrophil host defense system. Macrophages and eosinophils can utilize eosinophil peroxidase (EPO), hydrogen peroxide (H 2 o 2 ) reacts with bromide (Br-) to release HOBr. HOBr is critical for immune responses that can lead to host tissue damage as well as arthritis, cardiovascular disease, cancer, asthma, neurodegenerative diseases, kidney disease, cystic fibrosis, and inflammatory bowel disease. However, detection of HOBr in vivo faces many challenges because HOBr is only produced in solution, with pK at ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029C09K2211/1033G01N21/6428G01N2021/6439
Inventor 李新元朱宝存
Owner 李新元
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