Photosensitizer probe TFDB as well as preparation method and application thereof

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

Active Publication Date: 2020-09-01
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 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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  • Photosensitizer probe TFDB as well as preparation method and application thereof
  • Photosensitizer probe TFDB as well as preparation method and application thereof
  • Photosensitizer probe TFDB as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
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 a preparation method and application thereof. The preparation method comprises the following steps: dissolving pentafluorobenzonitrile in a solvent, stirring for reaction, dropwise adding ammonia water in an ice bath, and treating a reaction product to obtain an intermediate 1; dissolving the intermediate 1 in ultra-dry dichloromethane in a nitrogen atmosphere, slowly adding diisobutyl aluminum hydride at-78 DEG C, stirring for reaction at-78 DEG C, and treating a reaction product to obtain an intermediate 2; dissolving the intermediate 2, 2, 4-dimethylpyrrole and trifluoroacetic acid in a solvent, stirring for reaction, adding 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone, quickly adding triethylamine and a boron trifluoride diethyl ether complex in an ice bath, and treating areaction product to obtain an intermediate 3; and dissolving the intermediate 3 and N-iodosuccinimide in dichloromethane, and treating areaction product to obtain the photosensitizer probe TFDB. The photosensitive probe TFDB 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, 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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IPC IPC(8): C07F5/02A61K41/00A61P35/00C09K11/06
CPCC07F5/022A61K41/0057A61P35/00C09K11/06C09K2211/1055C09K2211/1007
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 UNIV OF TECH
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