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Fluorescent probe and preparation method thereof, and applications of fluorescent probe in detection of tyrosinase

A fluorescent probe and reaction technology, applied in the field of analysis and detection, can solve the problems that fluorescent probes are easily interfered by external factors, are not suitable for accurate detection of tyrosinase, and have poor detection sensitivity of fluorescent probes, and achieve an intuitive detection mode. , Improve the detection accuracy and accuracy, and facilitate the effect of popularization and application

Active Publication Date: 2018-01-19
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The obvious disadvantages of this method are low sensitivity and high detection limit
Chinese patent (application number: 201610663952.0) prepared a cyanine-based small molecule probe, which can generate a strong fluorescent signal. In the presence of tyrosinase, the probe is added and irradiated by 670nm excitation light , can emit fluorescence in the wavelength range of 700-720nm, thereby realizing the fluorescence-enhanced detection of tyrosinase; but the detection sensitivity of this fluorescent probe is not good, and its synthesis steps are cumbersome, so it is not suitable for accurate detection of tyrosinase
Research papers (Analytical chemical, 2016, 88, 4557-4564) reported a fluorescent probe based on naphthalene dicarboxamide derivatives, which has almost no fluorescence at 550nm; when there is tyrosinase in the system, Oxygen oxidizes the phenolic hydroxyl group in the probe molecule to benzoquinone, and then rearranges the intramolecular charge, releasing the fluorescent naphthalene dicarboxamide derivative resorufin. Under the irradiation of 425nm laser, the probe molecule The fluorescent probe emits green fluorescence, which realizes the fluorescence recovery detection of tyrosinase; however, the fluorescent probe is easily interfered by external factors, and it is difficult to achieve accurate analysis of the enzyme.

Method used

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  • Fluorescent probe and preparation method thereof, and applications of fluorescent probe in detection of tyrosinase
  • Fluorescent probe and preparation method thereof, and applications of fluorescent probe in detection of tyrosinase
  • Fluorescent probe and preparation method thereof, and applications of fluorescent probe in detection of tyrosinase

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] (1) Dissolve 1.0g of 4-aminophenol and 0.936g of imidazole in tetrahydrofuran, add 1.797g of tert-butyldimethylchlorosilane, stir rapidly to form a white precipitate, continue to react for 30 minutes, remove the solvent by rotary evaporation, wash with water, Then extract with ethyl acetate, the gained organic layer is washed with water and saturated sodium chloride solution, the organic phase is dried again, and the organic solvent is removed by rotary evaporation, and the obtained solid is purified by silica gel column chromatography (petroleum ether: ethyl acetate, V / V =10:1), obtain colorless viscous product 4-(tert-butyldimethylsilaoxy)aniline 1.842g (yield rate is 90.0%); This product is characterized by proton nuclear magnetic resonance spectrum, nuclear magnetic resonance The resonance spectrum is as figure 2 shown;

[0048] (2) Dissolve 0.210g of 4-(tert-butyldimethylsilyloxy)aniline and 1.117g of triphosgene in 15ml of dichloromethane, and add 959μl of N,N-d...

Embodiment 2

[0055] (1) Dissolve 1.0g of 4-aminophenol and 0.967g of imidazole in tetrahydrofuran, add 1.866g of tert-butyldimethylchlorosilane, stir rapidly to form a white precipitate, continue the reaction for 45 minutes, and remove the solvent by rotary evaporation to obtain a solid Purified by silica gel column chromatography (petroleum ether: ethyl acetate, V / V=10:1), to obtain a colorless viscous product 4-(tert-butyldimethylsilyloxy)aniline 1.887g (yield was 92.2%);

[0056] (2) Dissolve 0.210g of 4-(tert-butyldimethylsilyloxy)aniline and 1.117g of triphosgene in 15ml of dichloromethane, and add 959μl of N,N-diiso The organic solution of propylethylamine was first reacted at low temperature for 1 hour, then reacted at room temperature for 2.5 hours, and spin-dried under reduced pressure to obtain a reaction intermediate product;

[0057] (3) Under the protection of inert gas, dissolve 0.470g 9-[bis(3-methoxy-3-propionyl)amino]-5H-benzo[α]phenoxazine-5-imine salt in Add 180 μl of tr...

Embodiment 3

[0061] (1) Dissolve 1.0g of 4-aminophenol and 0.998g of imidazole in tetrahydrofuran, add 1.932g of tert-butyldimethylsilyl chloride, stir rapidly to form a white precipitate, continue the reaction for 1 hour, and remove the solvent by rotary evaporation to obtain a solid Purified by silica gel column chromatography (petroleum ether: ethyl acetate, V / V=10:1), to obtain a colorless viscous product 4-(tert-butyldimethylsilyloxy)aniline 1.862g (yield is 91.1%);

[0062] (2) Dissolve 0.210g of 4-(tert-butyldimethylsilyloxy)aniline and 1.117g of triphosgene in 20ml of dichloromethane, and add 959μl of N,N-diiso The organic solution of propylethylamine was first reacted at low temperature for 1 hour, then reacted at room temperature for 3 hours, and spin-dried under reduced pressure to obtain a reaction intermediate product;

[0063] (3) Under the protection of inert gas, dissolve 0.490g 9-[bis(3-methoxy-3-propionyl)amino]-5H-benzo[α]phenoxazine-5-imine salt in Add 188 μl of triet...

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Abstract

The invention belongs to the technical field of analysis and detection, and discloses a fluorescent probe and a preparation method thereof, and applications of the fluorescent probe in detection of tyrosinase, wherein the system of the fluorescent probe is named 3,3'-({5-[3-(4-hydroxyphenyl)ureido]-5H-benzo[a]phenoxazin-9-yl}azanediyl)methyl dipropionate, and the structure formula is represented by a formula (I). According to the present invention, the fluorescent probe compound can be used for the qualitative and quantitative analysis of tyrosinase, and has advantages of good detection precision, good accuracy and good anti-interference property. The formula (I) is defined in the specification.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, and in particular relates to a fluorescent probe, a preparation method thereof and an application in tyrosinase detection. Background technique [0002] Tyrosinase, also known as polyphenol oxidase, is a metalloenzyme that contains two copper ions in its active center, which are respectively combined with histidine in the enzyme molecule. Tyrosinase widely exists in animals, plants and microorganisms. It is called tyrosinase in animals and microorganisms, and it is generally called polyphenol oxidase in plants. Tyrosinase from different sources will have different physical and chemical properties. In plants, tyrosinase plays an important role in the synthesis of L-dopa, phenols, lignin and other substances. Also, tyrosinase has a lot to do with the browning of fruits and vegetables. Therefore, it is of great significance to study the detection and regulation of tyrosinase activi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38C09K11/06G01N21/64
Inventor 曾钫成家添占晨越吴水珠
Owner SOUTH CHINA UNIV OF TECH
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