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A kind of flavone fluorescent dye and its preparation method and application

A technology of fluorescent dyes and flavonoids, applied in the field of fluorescent sensing, can solve the problems of poor photostability, inability to observe with long-term bioluminescent imaging, and easy photobleaching, etc., and achieve good photostability

Active Publication Date: 2021-04-13
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the object of the present invention is to provide a flavone fluorescent dye and its preparation method and application, aiming at solving the problem of poor photostability of the existing flavone fluorescent dye, which is prone to photobleaching and cannot be used for Problems of long-term bioluminescent imaging observation

Method used

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  • A kind of flavone fluorescent dye and its preparation method and application
  • A kind of flavone fluorescent dye and its preparation method and application
  • A kind of flavone fluorescent dye and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0067] Preparation of flavonoid fluorescent dye 2-(4-(cyclobutylamino)phenyl)-3-hydroxy-4hydro-chromen-4-one (APHC)

[0068] Add 10 millimoles of o-hydroxyacetophenone and 10 millimoles of p-iodobenzaldehyde into the reactor, add 30 milliliters of ethanol to dissolve, then add 30 milliliters of sodium hydroxide aqueous solution (mass concentration is 20%), and react at 70 degrees Celsius for 12 After one hour, the reaction system was placed in ice-water mixture to cool, and 10 mL of hydrogen peroxide (mass concentration was 30%) was added. After continuing the reaction for 5 h, the pH was neutralized to 5 with hydrochloric acid, and the precipitated solid was mixed with ethanol and water. Recrystallization in solution (water content is 50%wt) obtains pure product 3-hydroxy-2-(4-iodophenyl)-4 hydrogen-chromen-4-one;

[0069] Add 8 mmoles of 3-hydroxyl-2-(4-iodophenyl)-4 hydrogen-chromen-4-one and 24 mmoles of dimethyl sulfate into the reactor to protect 3-hydroxyl-2-(4- The hy...

Embodiment 2

[0072] Preparation of flavonoid-based fluorescent dye 2-(4-(cyclopropylamino)phenyl)-3-hydroxy-4hydro-chromen-4-one

[0073] Add 10 millimoles of o-hydroxyacetophenone and 10 millimoles of p-iodobenzaldehyde into the reactor, add 30 milliliters of ethanol to dissolve, then add 30 milliliters of sodium hydroxide aqueous solution (mass concentration is 20%), and react at 70 degrees Celsius for 12 After one hour, the reaction system was placed in ice-water mixture to cool, and 10 mL of hydrogen peroxide (mass concentration was 30%) was added. After continuing the reaction for 5 h, the pH was neutralized to 5 with hydrochloric acid, and the precipitated solid was mixed with ethanol and water. Recrystallization from solution (water content 50%wt) gave pure 3-hydroxy-2-(4-iodophenyl)-4hydro-chromen-4-one.

[0074] Add 8 mmoles of 3-hydroxyl-2-(4-iodophenyl)-4 hydrogen-chromen-4-one and 24 mmoles of dimethyl sulfate into the reactor to protect 3-hydroxyl-2-(4- The hydroxyl group on ...

Embodiment 3

[0077] Preparation of flavonoid fluorescent dye 2-(4-(cyclobutylamino)phenyl)-3-hydroxy-4hydro-chromen-4-one (APHC)

[0078] Add 10 millimoles of o-hydroxyacetophenone and 10 millimoles of p-iodobenzaldehyde into the reactor, add 30 milliliters of ethanol to dissolve, then add 30 milliliters of sodium hydroxide aqueous solution (mass concentration is 20%), and stir the reaction at 60 degrees Celsius After 12 hours, the reaction system was cooled in a mixed solution of ice and water, and 10 mL of hydrogen peroxide (mass concentration: 30%) was added. After continuing the reaction for 4 hours, the pH was neutralized to 5 with hydrochloric acid, and the precipitated solid was dissolved in ethanol and water. Recrystallization in the mixed solution (water content is 50%wt) to obtain pure product 3-hydroxyl-2-(4-iodophenyl)-4hydro-chromen-4-one;

[0079] Add 8 mmoles of 3-hydroxyl-2-(4-iodophenyl)-4 hydrogen-chromen-4-one and 24 mmoles of dimethyl sulfate into the reactor to protect...

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Abstract

The invention discloses a flavonoid fluorescent dye, a preparation method and application thereof. The general structural formula of the flavone fluorescent dye of the present invention is as follows: wherein, R is an aziridin-1-yl or azetidin-1-yl. The flavonoid-based fluorescent dye of the present invention is a fluorescent dye with good photostability, which can withstand long-term continuous irradiation of ultraviolet light without photobleaching, and is especially suitable for biological fluorescence imaging.

Description

technical field [0001] The invention relates to the field of fluorescent sensing, in particular to a flavonoid fluorescent dye and its preparation method and application. Background technique [0002] Due to its non-invasiveness, high sensitivity, fast response, and excellent spatio-temporal resolution, fluorescence imaging technology is widely used in the study of biological structure imaging and life dynamic process. The development of fluorescence imaging technology must rely on a variety of fluorescent dyes with excellent performance. Among them, small molecule fluorescent dyes have high tunability in optical properties and chemical structures, have little impact on biological dynamic processes, and are easy to functionalize and are widely used. Among them, flavonoids are natural structures existing in a class of plants and have good biocompatibility. In particular, flavonoid dyes with an electron donating-withdrawing structure have a high fluorescence quantum yield, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/10C09B57/00C09K11/06G01N21/64
CPCC07D405/10C09B57/00C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N2021/6439
Inventor 刘斌
Owner SHENZHEN UNIV
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