Photosensitizer probe as well as preparation method and application thereof

A photosensitizer and probe technology, applied in the field of biochemistry, can solve the problems of low singlet oxygen quantum yield and poor photostability, and achieve the effects of high-efficiency singlet oxygen production capacity, simple and safe preparation method, and good application prospects

Active Publication Date: 2020-08-28
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Another object of the present invention is to provide a method for preparing the above-mentioned photosensitizer probe, which aims to solve the problems of poor photostability and low quantum yield of singlet oxygen existing in the existing photosensitizer preparation method;

Method used

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  • Photosensitizer probe as well as preparation method and application thereof
  • Photosensitizer probe as well as preparation method and application thereof
  • Photosensitizer probe as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] (1) Under nitrogen atmosphere, dissolve p-nitrobenzaldehyde (1.5g, 10mmol), 2,4-dimethylpyrrole (2.1g, 22mmol) and trifluoroacetic acid (0.2mL) in tetrahydrofuran (30mL) , stirring overnight to obtain the first reaction solution;

[0033] Add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (2.3g, 10mmol, DDQ) into tetrahydrofuran (20mL) to obtain a tetrahydrofuran solution, and add the tetrahydrofuran solution to the first reaction solution Dissolved and reacted for 2 to 4 hours, quickly added triethylamine (20mL) and boron trifluoride diethyl ether complex (BF 3 : 46.5%, 30mL), then transferred to room temperature and reacted for 4 to 12 hours to obtain the reaction solution;

[0034] The solvent of the reaction solution was removed: the solvent was concentrated, the residue was layered with dichloromethane (100mL) and saturated sodium bicarbonate (100mL), the aqueous phase was extracted with dichloromethane (20mL×3), and the combined organic phases were separated in After...

Embodiment 2

[0044] (1) Under nitrogen atmosphere, dissolve p-nitrobenzaldehyde (1.5g, 10mmol), 2,4-dimethylpyrrole (21mmol) and trifluoroacetic acid (0.1mL) in tetrahydrofuran (28mL), and stir for 2h Obtain the first reaction solution;

[0045] Add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 9mmol) into tetrahydrofuran (10mL) to obtain a tetrahydrofuran solution, add the tetrahydrofuran solution to the first reaction solution to dissolve and After reacting for 2 hours, triethylamine (10 mL) and boron trifluoride etherate (BF 3 : 40%, 20mL), then transferred to room temperature and reacted overnight to obtain a reaction solution;

[0046] The solvent of the reaction solution was removed: the solvent was concentrated, the residue was layered with dichloromethane (100mL) and saturated sodium bicarbonate (100mL), the aqueous phase was extracted with dichloromethane (20mL×3), and the combined organic phases were separated in After the drying of sodium sulfate in water, concentrate and re...

Embodiment 3

[0056] (1) Under nitrogen atmosphere, p-nitrobenzaldehyde (1.5g, 10mmol), 2,4-dimethylpyrrole (23mmol) and trifluoroacetic acid (0.3mL) were dissolved in tetrahydrofuran (32mL), stirred for 24 Obtain the first reaction solution;

[0057] Add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (11mmol, DDQ) into tetrahydrofuran (22mL) to obtain a tetrahydrofuran solution, add the tetrahydrofuran solution to the first reaction solution to dissolve and After reacting for 6 hours, triethylamine (30mL) and boron trifluoride etherate (BF 3 : 50%, 40mL), then transferred to room temperature and reacted for 24h to obtain the reaction solution;

[0058] The solvent of the reaction solution was removed: the solvent was concentrated, the residue was layered with dichloromethane (100mL) and saturated sodium bicarbonate (100mL), the aqueous phase was extracted with dichloromethane (20mL×3), and the combined organic phases were separated in After the drying of sodium sulfate in water, concentrate a...

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Abstract

The invention discloses a photosensitizer probe as well as a preparation method and application thereof. The preparation method comprises the following steps: in a nitrogen atmosphere, dissolving p-nitrobenzaldehyde, 2,4-dimethylpyrrole and trifluoroacetic acid into a solvent, reacting under stirring, adding 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, quickly adding triethylamine and a boron trifluoride diethyl ether complex under an ice bath condition, stirring at room temperature, and treating a reaction product to obtain an intermediate 1; dissolving the intermediate 1 and N-iodosuccinimideinto dichloromethane, stirring at room temperature, and treating a reaction product to obtain an intermediate 2; adding palladium on carbon, the intermediate 2, hydrazine hydrate and ethanol, performing a reflux stirring reaction, cooling to room temperature, and treating a reaction product to obtain an intermediate 3; dissolving the intermediate 3 and an alkali in a solvent, dropwise adding an acetyl chloride solvent, reacting under stirring and treating a reaction product to obtain the photosensitizer probe ACDB. The photosensitizer probe shows efficient singlet oxygen generation capacity and fluorescence emission capacity, and has the potential of being used for real-time monitoring of tumor photodynamic therapy and fluorescence imaging.

Description

technical field [0001] The invention belongs to the field of biochemistry, and in particular relates to a photosensitizer probe and a preparation method and application thereof. Background technique [0002] Photodynamic therapy (PDT) has emerged as an effective therapy for tumors and various non-malignant diseases, including infections. During the PDT process, the photosensitizer (PS) is initially excited to form a singlet state by absorbing light, and then transforms into a long-lived excited triplet state. This triplet state undergoes a photochemical reaction in the presence of oxygen to form reactive oxygen species (ROS, including singlet oxygen) that can destroy tumor cells and pathogenic microorganisms. Although many photosensitizers have been developed and even obtained clinical approval, the poor photostability and low quantum yield of singlet oxygen severely limit the further application of PDT. [0003] BODIPY-based dyes have multiple uses and outstanding propert...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06A61K41/00A61P35/00
CPCA61K41/0057A61P35/00C07F5/022C09K11/06C09K2211/1007C09K2211/1055
Inventor 程夏民高靖崔德志李晓曼位前程范佳丽朱二树鹿永娜
Owner NANJING UNIV OF TECH
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