Enhanced fluorescent probe and preparation method and application thereof

A fluorescent probe and enhanced technology, applied in the field of enhanced fluorescent probes and their preparation, can solve the problems of poor water solubility, difficult preservation of azoreductase, and the need to add a large amount of organic solvent for testing, and achieves high sensitivity, high sensitivity, and high sensitivity. High accuracy and good water solubility

Active Publication Date: 2016-11-16
SOUTH CHINA UNIV OF TECH
View PDF3 Cites 16 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing fluorescence method (for example, published paper Chem.Commun., 2012, 48, 6393–6395) uses cyclohexane to graft two molecules of dansylamide, and fixes it with an azo bond to prevent its conformational change, thus preparing The detection system of azo reductase, because azo reductase is not easy to store, there is no commercial channel to provide, they use sodium dithionite to simulate the action of azo reductase, react with azo group, so that the azo bond breaks, Cyclohexane undergoes a boat-like and chair-like conformational transformation, the original excimer fluorescence of dansylamide at 552nm is weakened, and the fluorescence of the monomer at 448nm is enhanced, thus realizing the ratiometric fluorescence detection of azoreductase ; but this system cannot track the release of enteri

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Enhanced fluorescent probe and preparation method and application thereof
  • Enhanced fluorescent probe and preparation method and application thereof
  • Enhanced fluorescent probe and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] (1) 3g of 4-methyl-benzenesulfonyl chloride (15.8mmol) was dissolved in 8mL of dichloromethane, and was added dropwise to 9.48g of ethylenediamine (158mmol) under conditions of ice bath and nitrogen protection, and the resulting mixture The solution was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was extracted three times with dichloromethane and potassium carbonate aqueous solution, and the organic phase was collected, dried over magnesium sulfate, and filtered; the resulting solid was purified by silica gel chromatography (eluent used was dichloromethane / methanol , V / V=8:1), the organic solvent was removed by rotary evaporation to obtain solid N-(2-amino-ethyl)-4-methyl-benzenesulfonamide. It was characterized by H NMR spectroscopy: 1 H NMR (400MHz, CD 3 OD-d 4 ,δppm):7.65-7.69ppm(d,2H), 7.37-7.42ppm(d,2H), 2.66-2.71ppm(t,2H), 2.47-2.52ppm(m,4H), 2.35-2.41ppm(s ,3H). Among them, 2.36ppm is the characteristic peak ...

Embodiment 2

[0048] (1) Take 3.6g of 4-methyl-benzenesulfonyl chloride (18.94mmol) and dissolve it in 18.94mL of dichloromethane, and add it dropwise to 11.5g of ethylenediamine (191.3mmol) under the conditions of ice bath and nitrogen protection , and the resulting mixed solution was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was extracted three times with dichloromethane and potassium carbonate aqueous solution, and the organic phase was collected, dried over magnesium sulfate, and filtered; the resulting solid was purified by silica gel chromatography (eluent used was dichloromethane / methanol, V / V=8:1), the organic solvent was removed by rotary evaporation to obtain solid N-(2-amino-ethyl)-4-methyl-benzenesulfonamide. Take the N-(2-amino-ethyl)-4-methyl-benzenesulfonamide solid (516mg, 2.4mmol) obtained above and dissolve it in 4-bromo-1,8-naphthalic anhydride (664mg, 2.4mmol) In 30mL of ethanol, stir to dissolve it completely; the re...

Embodiment 3

[0054] (1) 4.7g of 4-methyl-benzenesulfonyl chloride (24.5mmol) was dissolved in 49mL of dichloromethane, and was added dropwise to 14.96g of ethylenediamine (249.9mmol) under conditions of ice bath and nitrogen protection, The resulting mixed solution was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was extracted three times with dichloromethane and potassium carbonate aqueous solution, and the organic phase was collected, dried over magnesium sulfate, and filtered; the resulting solid was purified by silica gel chromatography (eluent used was dichloromethane / methanol, V / V=8:1), the organic solvent was removed by rotary evaporation to obtain solid N-(2-amino-ethyl)-4-methyl-benzenesulfonamide. Take N-(2-amino-ethyl)-4-methyl-benzenesulfonamide (671mg, 3.12mmol) and 4-bromo-1,8-naphthalic anhydride (863mg, 3.12mmol) obtained above were dissolved in In 46.8mL of ethanol, stir to dissolve it completely; the resulting solution wa...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention belongs to the technical field of fluorescence detection materials and discloses an enhanced fluorescent probe and a preparation method and application thereof. The fluorescent probe is 5-{4-[3-(2-{2-[2-(toluene-4-sulfamine)-ethyl]-1H-benzo(de)isoquinoline-1,3(2 H)-diketone-6-amino}-ethylamino)-propoxy]-phenylazo}-2-hydroxybenzoic acid and has a molecular structural formula shown in a formula (1). The probe compound is prepared from visible light excited and emitted fluorescent chromophore naphthalimides and an azo reductase recognition group 5-aminosalicylic acid azobenzene derivative. The probe compound not only has better water solubility, but also is high in accuracy when being used for azo reductase detection, is convenient to use and can simultaneously trace release of anti-inflammatory drugs such as 5-aminosalicylic acid and provide a supplementary means for diagnosis and treatment of colitis.

Description

technical field [0001] The invention belongs to the technical field of fluorescence detection materials, and in particular relates to an enhanced fluorescent probe and its preparation method and application. Background technique [0002] Azoreductase is an oxidoreductase that can reduce azo complexes to aromatic amine products; it widely exists in bacterial flora and is used to decompose organic matter to provide nutrients for survival. At present, azo dyes are widely used in industries such as printing and dyeing, food and cosmetics. The residual azo dye components discharged in the wastewater will seriously affect the passage of light to the water and the growth of aquatic organisms, and destroy the ecological balance of the water body. Therefore, there is widespread interest in treating residual azo dyes and the like in wastewater by using appropriate amounts of bacterial azoreductase. Not only that, cells will express azoreductase, nitroreductase and other oxidoreducta...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07D221/14C09K11/06C12Q1/26
CPCC07D221/14C09K11/06C09K2211/1029C12Q1/26
Inventor 吴水珠黄靖谢惠婷武英龙曾钫
Owner SOUTH CHINA UNIV OF TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap