A kind of polymer fluorescent probe and its application

A fluorescent probe and polymer technology, applied in the field of fluorescent probes, can solve the problems of easy shedding, application limitations, and difficulty in achieving long-term tracking of organisms.

Active Publication Date: 2021-12-14
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are still many problems with small-molecule fluorescent probes. For example, most small-molecule fluorescent probes are insoluble in water, and are prone to fall off when directly compounded with polymers. It is difficult to achieve long-term tracking and targeted tracking in vivo. Therefore, in biomedicine The field of application is greatly limited

Method used

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  • A kind of polymer fluorescent probe and its application
  • A kind of polymer fluorescent probe and its application
  • A kind of polymer fluorescent probe and its application

Examples

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preparation example Construction

[0059] The present invention also provides a preparation method for the above-mentioned polymer-based fluorescent probe, comprising: carrying out a copolymerization reaction of a hydrophobic monomer and a hydrophilic monomer to obtain an amphiphilic block copolymer; Reacting with the thiol-responsive monomer represented by formula (I) and / or the dichlorofluorescein monomer represented by formula (II) to obtain a polymer-based fluorescent probe;

[0060]

[0061] Wherein, R is the alkyl group of C1~C10; R 1 with R 2 Each independently is an alkyl group of C1~C5; said R, R 1 with R 2 All are the same as above, and will not be repeated here;

[0062] The hydrophobic monomer is preferably one or more of alkoxy acrylate, alkoxy methacrylate, hydroxyalkyl acrylate and hydroxyalkyl methacrylate; the alkoxy acrylate, The number of carbon atoms in the alkyl group in the alkoxy methacrylate, hydroxyalkyl acrylate and hydroxyalkyl methacrylate is independently preferably 1-10, mor...

preparation example 1

[0072] Preparation Example 1: Preparation method of dichlorofluorescein molecule (DSF-COOH) protected with (ethylthio)acetic acid

[0073]

[0074] Weigh mercaptoacetic acid (5g, 54.4mmol), then add bromoethane (6.45g, 59.8mmol) in batches to sodium hydroxide (3mol / L) in methanol solution (100mL), reflux the mixture for 8h, after cooling Spin to dry to obtain ethylthioacetic acid (5.9g, yield: 90%); Oxalyl chloride (6.8g, 53.9mmol) was added to ethylthioacetic acid (5.9g, 49.2mmol) at 0°C under stirring In dichloromethane solution (100 mL), the reaction mixture was heated to 40° C. until no more hydrogen chloride was evolved (approximately two hours). After the reaction was finished, dichloromethane was removed by rotary evaporation under vacuum conditions to obtain ethylthioacetyl chloride (6.5g, 46.7mmol, yield: 95%); then ethylthioacetyl chloride (6.5g, 46.7mmol) and 5-carboxy-2',7'-dichlorofluorescein (9.4g, 21.2mmol) were dissolved in anhydrous N,N-dimethylformamide (...

preparation example 2

[0075] Preparation Example 2: Preparation of NAM-COOH by Amidation Reaction of Aminonaphthalene Diimide and Maleic Anhydride

[0076]

[0077] 4-Amino-N-butylnaphthalene diimide (5g, 18.6mmol) and maleic anhydride (2.8g, 28.0mmol) were dissolved in chloroform (80mL), refluxed for 12h, cooled to room temperature after the reaction, and After the solvent was removed by rotary evaporation under vacuum conditions, column chromatography separation was carried out with pure ethyl acetate as eluent to obtain the fluorescent moiety 4-maleimido-1,8-naphthoimide NAM- COOH (6.7 g, yield: 80%).

[0078] The 4-maleimido-1,8-naphthalimide NAM-COOH obtained in Preparation Example 2 is analyzed by nuclear magnetic resonance, and its hydrogen nuclear magnetic resonance spectrum is obtained as figure 1 shown.

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Abstract

The invention provides a polymer-based fluorescent probe, which comprises an amphiphilic block copolymer and a thiol-responsive group and / or a dichlorofluorescein group grafted on the amphiphilic block copolymer. Compared with the prior art, the present invention uses naphthalimides as sulfhydryl-responsive fluorescent molecules, which have a relatively large rigid coplanar structure and a conjugated system. There is a photoinduced electron transfer mechanism in this structure. When naphthalimides After Michael addition with sulfhydryl groups, fluorescence is produced due to the obstruction of PET; thioether-esterified dichlorofluorescein molecules are used as acid-responsive fluorescent molecules, which can be induced by H + The ester bond in its structure is hydrolyzed to make it have a conjugated structure, thereby generating fluorescence; and the present invention grafts the above-mentioned fluorescent molecules on the amphiphilic block copolymer as a polymer-based fluorescent probe with a highly sensitive mercapto group And / or the detection function of acidity, so as to realize the fluorescent tracking of the path of micelles entering the living body.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, in particular to a polymer-based fluorescent probe and its application. Background technique [0002] Mercapto compound is a very important compound among organisms, and its important functional group is mercapto. A large number of biochemical reactions in living organisms require the participation of sulfhydryl compounds, and the main sulfhydryl compounds in living organisms are glutathione, cysteine ​​and homocysteine. Among them, glutathione is the most widely distributed in the cells of organisms and its concentration is higher than other sulfhydryl compounds. It plays an important role in the redox biochemical reactions in organisms and can maintain the cysteine ​​in proteins. In a non-oxidized state, it ensures that the protein in the organism is not oxidized and maintains the normal biological activity of the protein in the organism. Therefore, glutathione has become an importa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C09K11/06C08F220/54C08F220/20C08F8/30C08F8/34C08F293/00A61K49/00
CPCC08F220/54C08F8/30C08F8/34A61K49/0021A61K49/0043A61K49/0054G01N21/6428C09K2211/145C09K2211/1466G01N2021/6417C08F220/20C08F293/00
Inventor 张国颖郭文豪刘固寰江国顺
Owner UNIV OF SCI & TECH OF CHINA
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