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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
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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 enteritis drugs at the same time, and the water solubility is not good, so a large amount of organic solvents need to be added for the test
As another example, the method for fluorescence-enhanced detection of azoreductase (for example, published a paper Chem.Commun., 2013, 49, 8815--8817), synthesized a fluorescent probe that azotized rhodamine 110 amino, the The probe molecule basically has no fluorescence emission at 520nm. When the azoreductase mimic sodium dithionite reacts with it, the original azo bond is reduced to an amino group and becomes a rhodamine 110 structure. At 520nm, the fluorescence intensity increased significantly, realizing the fluorescence-enhanced detection of azoreductase; but this system cannot track the release of enteritis drugs at the same time, and the water solubility is not good

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  • 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
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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...

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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

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Application Information

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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
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