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A kind of aminobenzopyranocyanine fluorescent dye and probe and its synthesis method and application

A pyranocyanine and fluorescent probe technology, applied in the fields of chemistry and biology, can solve the problems of difficult modification of cyanine dyes, poor stability, and influence on promotion, and achieve good photostability, reduce photodamage, and enhance penetration. effect of ability

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

AI Technical Summary

Problems solved by technology

However, the current cyanine dyes have the disadvantages of poor stability, and are easily attacked by various biological species to cause dye decomposition, and cyanine dyes are difficult to modify, which affects their application.

Method used

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  • A kind of aminobenzopyranocyanine fluorescent dye and probe and its synthesis method and application
  • A kind of aminobenzopyranocyanine fluorescent dye and probe and its synthesis method and application
  • A kind of aminobenzopyranocyanine fluorescent dye and probe and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of embodiment 1 intermediate 5

[0060] The synthetic route of intermediate 5 is as follows, specifically comprises the following steps:

[0061]

[0062] Put 46mmol of compound 1 and 4.4mL of acetic anhydride in a round-bottomed flask, add 200mL of tetrahydrofuran to dissolve, then stir the reaction at room temperature for 2h, remove the tetrahydrofuran in the reaction solution after the reaction is complete, and obtain compound 2 after recrystallization;

[0063] Take 4mmol of compound 2, 4mmol of phthalic anhydride and 10mmol of aluminum trichloride in a round-bottomed flask, add 13mL of 1,1,2,2-tetrachloroethane under ice cooling until the reactants are completely dissolved, and react at room temperature for 2h. Then the reaction was heated to 100°C and stirred for 12 hours; after the reaction was completed, it was cooled to room temperature, poured into ice water to precipitate a solid, and compound 3 was obtained;

[0064] Take 1 mmol of compou...

Embodiment 2

[0066] Embodiment 2 Aminobenzopyranocyanine fluorescent dye NIR-NH of type I structural formula 2 Synthesis

[0067] 0.2mmol of intermediate 5 (prepared in Example 1) and 0.2mmol of X are C(CH 3 ) 2 , R 1 is methyl, L is hydrogen, and m is 0, compound 6-1 (structural formula is as follows) is placed in a round-bottomed flask, mixed in 4 mL of acetic anhydride solution, and stirred at room temperature for 1.5 h; The instrument was spin-dried under reduced pressure, and purified with a silica gel column to obtain intermediate 8-1 (structural formula is as follows).

[0068]

[0069] Intermediate 8-1 (0.11g, 0.2mmol) was dissolved in 6mL of acetic acid / concentrated hydrochloric acid (1:2, v / v) solution, stirred at 110°C for 2h, then cooled to room temperature, and the mixture was poured into ice water , basified with sodium hydroxide solution, stirred at room temperature for 0.5h, then extracted with dichloromethane, dried the organic phase with anhydrous sodium sulfate, t...

Embodiment 3

[0073] Example 3 Aminobenzopyranocyanine Fluorescent Dye Ben-NIR-NH of Type II Structural Formula 2 Synthesis

[0074] 0.2mmol of intermediate 5 (prepared in Example 1) and 0.2mmol of X are C(CH 3 ) 2 , R 1 is methyl, L is hydrogen, and m is 0, compound 7-1 (structural formula is as follows) is placed in a round-bottomed flask, mixed in 4 mL of acetic anhydride solution, and stirred at room temperature for 2 hours; after the reaction is complete, the reaction solution is It was spin-dried under reduced pressure and purified by a silica gel column to obtain intermediate 9-1 (structural formula is as follows).

[0075]

[0076] Intermediate 9-1 (0.138g, 0.2mmol) was dissolved in 6mL of acetic acid / concentrated hydrochloric acid (1:2, v / v) solution, stirred at 110°C for 2h. Then it was cooled to room temperature, the mixture was poured into ice water, basified with sodium hydroxide solution, stirred at room temperature for 0.5h, then extracted with dichloromethane, the org...

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Abstract

The invention discloses an aminobenzopyranocyanine-based fluorescent dye and a probe as well as its synthesis method and application. The fluorescent dye is any one of structural formulas I to II: the aminobenzopyranocyanine of the present invention The near-infrared fluorescent dyes I and II of the structure have high fluorescence quantum yield and good photostability. Tissue sample tissue penetrating ability, reducing light damage, and biomolecular autofluorescence is weak, which can avoid the interference of autofluorescence in biological systems and obtain a higher signal-to-noise ratio, thereby improving sensitivity.

Description

technical field [0001] The invention belongs to the field of chemistry and biotechnology, and in particular relates to an aminobenzopyranocyanine fluorescent dye and a probe as well as a synthesis method and application thereof. Background technique [0002] In recent years, with the development of fluorescence analysis and detection technology, fluorescent dyes have been widely used in various fields such as biomolecular labeling, enzyme analysis, environmental monitoring, cell staining, and clinical examination and diagnosis. The development of various functional fluorescent dye molecules with practical value has become a research hotspot that has attracted much attention. Molecular fluorescent probes based on organic fluorescent dyes have many advantages such as high sensitivity, easy operation, good reproducibility, good membrane permeability, and in situ detection. In addition, combined with fluorescence imaging technology, molecular fluorescent probes can be convenien...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/80C09K11/06C09B23/10G01N21/64
CPCC09B23/105C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/643G01N21/6486
Inventor 袁林程丹张晓兵吕芸柳东杰魏艳芬
Owner HUNAN UNIV
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