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A kind of intelligent photosensitizer and its preparation method and application

A photosensitizer and intelligent technology, applied in the field of biochemistry, can solve the problems of the persistent photosensitivity of the residual photosensitizer, and achieve the effects of good singlet oxygen generation ability, good application prospect and simple preparation process

Active Publication Date: 2021-05-11
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The primary purpose of the present invention is to provide an intelligent photosensitizer with the advantages of high targeting, low residual phototoxicity, high fluorescence quantum yield, high absorption coefficient, relatively clear emission spectrum, easy functionalization, and excellent photostability. Aim to solve the defect of persistent photosensitivity of residual photosensitizer in existing photodynamic therapy

Method used

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  • A kind of intelligent photosensitizer and its preparation method and application
  • A kind of intelligent photosensitizer and its preparation method and application
  • A kind of intelligent photosensitizer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (1) Under nitrogen atmosphere, dissolve 7-diethylamino-4-methylcoumarin (2.3g, 10mmol) in 12mL of N,N-dimethylformamide, then add N,N-di Methylformamide dimethyl acetal (2.6 mL); the reaction was refluxed overnight and cooled to room temperature;

[0032] Dichloromethane (50mL) and saturated sodium bicarbonate (50mL) were added to the reaction mixture, and the layers were shaken, the aqueous phase was extracted with dichloromethane (10mL×3), and the combined organic phases were dried over anhydrous sodium sulfate. Concentrated to remove organic solvents;

[0033] The residue was dissolved in a mixed solvent (60mL, THF:H 2 O=1:1), sodium periodate (6.2g, 29mmol) was added at room temperature to react for 2 hours, the filtered solid was washed with ethyl acetate until the washings were colorless, and the organic solvent in the filtrate was removed under reduced pressure , the residue was layered with dichloromethane (50mL) and saturated sodium bicarbonate (50mL), the aq...

Embodiment 2

[0049] (1) Under nitrogen atmosphere, dissolve 7-diethylamino-4-methylcoumarin (2.3g, 10mmol) in 12mL of N,N-dimethylformamide, then add N,N-di Methylformamide dimethyl acetal (2.6 mL); the reaction was refluxed overnight and cooled to room temperature;

[0050] Dichloromethane (50mL) and saturated sodium bicarbonate (50mL) were added to the reaction mixture, and the layers were shaken, the aqueous phase was extracted with dichloromethane (10mL×3), and the combined organic phases were dried over anhydrous sodium sulfate. Concentrated to remove organic solvents;

[0051] The residue was dissolved in a mixed solvent (60mL, THF:H 2 O=1:1), sodium periodate (6.2g, 29mmol) was added at room temperature to react for 2 hours, the filtered solid was washed with ethyl acetate until the washings were colorless, and the organic solvent in the filtrate was removed under reduced pressure , the residue was layered with dichloromethane (50mL) and saturated sodium bicarbonate (50mL), the aq...

Embodiment 3

[0067] Embodiment 3 of the present invention is basically the same as above-mentioned Embodiment 2, and difference points out to be:

[0068] (3) Under a nitrogen atmosphere, Intermediate 2 (738.2 mg, 2 mmol) and N-iodosuccinimide (9 mmol) were dissolved in ultra-dry dichloromethane (220 mL), and the mixture was stirred at room temperature for 24 h;

[0069] Pour into water (100mL) to separate the layers, the aqueous phase was extracted with dichloromethane (20mL×3), the combined organic phase was dried over anhydrous sodium sulfate, and concentrated to remove the organic solvent; the residue was purified by column chromatography to obtain a deep red Intermediate 3 (coordination complex 1: boron, difluoro[3-iodo-5-[(4-iodo-3,5-5-dimethyl-2H-pyrrole--2-alkylene-κN) (4-nitrophenyl))[methyl]-2,4-dimethyl-1H-pyrrolo-κN]-, (T-4)-coordination compound);

[0070] (4) Under a nitrogen atmosphere, add palladium carbon (0.6mmol), intermediate 3 (622.7mg, 1mmol), and hydrazine hydrate (...

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Abstract

The invention discloses an intelligent photosensitizer, a preparation method and application thereof. The present invention synthesizes intermediate 1 by reacting 7-diethylamino-4-methylcoumarin with N,N-dimethylformamide dimethyl acetal, and through 2,4-dimethylpyrrole and p-nitrogen Base benzaldehyde synthesized intermediate 2 through condensation reaction, and then carried out iodination on the 2 and 6 positions of intermediate 2 to obtain intermediate 3 (coordination complex 1), and reduced the nitro group of coordination complex 1 to amino group to obtain Intermediate 4 (coordination complex 2), and finally the coordination complex 2 is covalently combined with the above-mentioned intermediate 1 to obtain a new type of intelligent photosensitive probe CMDB. The photosensitizer CMDB of the present invention has good singlet oxygen generation ability, controllable photosensitivity characteristics and observable fluorescence turn-on characteristics after degradation, so it can be applied to the photodynamic therapy of tumors and has a good application prospect.

Description

technical field [0001] The invention belongs to the field of biochemistry, in particular to an intelligent photosensitizer 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, there are still multiple limitations of PDT, including low targeting and high residual phototoxicity, which severely limit the further application of PDT. [0003] The BODIPY class of dyes ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06A61K41/00A61P35/00
CPCA61K41/0057A61P35/00C07F5/022
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 TECH UNIV
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