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A kind of photosensitizer probe tfdb and its preparation method and application

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

Active Publication Date: 2021-07-16
NANJING TECH UNIV
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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 preparation method of the above-mentioned photosensitizer probe TFDB, aiming to solve the problems of poor photostability and low singlet oxygen quantum yield in the existing photosensitizer preparation methods;

Method used

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  • A kind of photosensitizer probe tfdb and its preparation method and application
  • A kind of photosensitizer probe tfdb and its preparation method and application
  • A kind of photosensitizer probe tfdb and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0032] (1) Dissolve pentafluorobenzonitrile (0.3861g, 2mmol) in acetonitrile (10mL), stir at room temperature for 8min to obtain the first reaction solution, add ammonia (0.6mL) to the first reaction solution under ice-bath conditions , stirred at room temperature for 4 h, and after removing the solvent in the reaction solution, the obtained crude product was purified by column chromatography to obtain white intermediate 1;

[0033] (2) Under a nitrogen atmosphere, Dissolve Intermediate 1 (0.3509g, 1.85mmol) in ultra-dry dichloromethane (10mL) to obtain a second reaction solution, diisobutylaluminum hydride (2.2mL) in - Add dropwise to the second reaction solution at 78°C, and stir the mixture at -78°C for 4h to obtain the reaction product;

[0034] The reaction product was poured into water (30 mL) for layering, the aqueous phase was extracted with dichloromethane (10 mL×3), the combined organic phase was dried over anhydrous sodium sulfate, and concentrated to remove the org...

Embodiment 2

[0042] (1) Dissolve pentafluorobenzonitrile (0.3861g, 2mmol) in acetonitrile (9mL), stir at room temperature for 5min to obtain the first reaction solution, add ammonia (0.5mL) to the first reaction solution under ice-bath conditions , stirred at room temperature for 3.5h, and after removing the solvent in the reaction solution, the obtained crude product was purified by column chromatography to obtain white intermediate 1;

[0043](2) Under a nitrogen atmosphere, Dissolve Intermediate 1 (0.3509g, 1.85mmol) in ultra-dry dichloromethane (9mL) to obtain a second reaction solution, diisobutylaluminum hydride (2.1mL) in - Add dropwise to the second reaction solution at 75°C, and stir the mixture at -75°C for 4h to obtain the reaction product;

[0044] The reaction product was poured into water (30 mL) for layering, the aqueous phase was extracted with dichloromethane (10 mL×3), the combined organic phase was dried over anhydrous sodium sulfate, and concentrated to remove the organ...

Embodiment 3

[0054] (1) Dissolve pentafluorobenzonitrile (0.3861g, 2mmol) in acetonitrile (11mL), stir at room temperature for 10min to obtain the first reaction solution, add ammonia (0.7mL) to the first reaction solution under ice-bath conditions , stirred at room temperature for 5 h, and after removing the solvent in the reaction solution, the obtained crude product was purified by column chromatography to obtain white intermediate 1;

[0055] (2) Under a nitrogen atmosphere, Dissolve Intermediate 1 (0.3509g, 1.85mmol) in ultra-dry dichloromethane (11mL) to obtain a second reaction solution, diisobutylaluminum hydride (2.3mL) in - Add dropwise to the second reaction solution at 80°C, and stir the mixture at -80°C for 4h to obtain the reaction product;

[0056] The reaction product was poured into water (30 mL) for layering, the aqueous phase was extracted with dichloromethane (10 mL×3), the combined organic phase was dried over anhydrous sodium sulfate, and concentrated to remove the or...

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Abstract

The invention discloses a photosensitizer probe TFDB as well as its preparation method and application. In the present invention, pentafluorobenzonitrile is dissolved in a solvent and stirred for reaction, ammonia water is added dropwise in an ice bath, and the reaction product is processed to obtain intermediate 1; under nitrogen atmosphere, intermediate 1 is dissolved in ultra-dry dichloromethane , slowly add diisobutylaluminum hydride at -78°C, stir the reaction at -78°C, process the reaction product to obtain intermediate 2; dissolve intermediate 2, 2,4-dimethylpyrrole and trifluoroacetic acid in Stir the reaction in a solvent, add 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, quickly add triethylamine and boron trifluoride etherate complex in an ice bath, and process the reaction product Intermediate 3 was obtained; Intermediate 3 and N-iodosuccinimide were dissolved in dichloromethane, and the reaction product was processed to obtain the photosensitizer probe TFDB. The photosensitive probe TFDB of the present invention exhibits high-efficiency singlet oxygen generation ability and fluorescence emission ability, 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, in particular to a photosensitizer probe TFDB and its preparation method and application. 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 dyes have the advantages of large molar absorptivity, high fluores...

Claims

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Application Information

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