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Near-infrared nano photosensitizer as well as preparation method and application thereof

A near-infrared, photosensitizer technology, applied in the field of photosensitizers, can solve the problems of poor photostability, shallow treatment depth, etc., and achieve the effects of small polarizability, improved water solubility, and increased singlet oxygen yield

Active Publication Date: 2022-04-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] For this reason, the technical problem to be solved by the present invention is to overcome the problems of poor photostability and shallow treatment depth in the prior art

Method used

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  • Near-infrared nano photosensitizer as well as preparation method and application thereof
  • Near-infrared nano photosensitizer as well as preparation method and application thereof
  • Near-infrared nano photosensitizer as well as preparation method and application thereof

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Embodiment 1

[0049] Such as figure 1 Shown, a kind of near-infrared nano photosensitizer and preparation method thereof, specifically comprise the following steps:

[0050] (1) Synthesis of Compound 1: Put alkyne-containing p-hydroxybenzaldehyde and 2,4-dimethylpyrrole in a molar ratio of 1:1 into the reaction vessel, and then add 100% of the weight of 2,4-dimethylpyrrole times THF as solvent and 6-10 drops of trifluoroacetic acid as catalyst. Stir at 25 °C for 24 h. Then, 2,3-dichloro-5,6-dicyano-p-benzoquinone with a molar ratio of 1:1.5 to 2,4-dimethylpyrrole was added to the above reaction solution, and stirred at room temperature for 24 hours. Finally, triethylamine 50 times the weight of 2,4-dimethylpyrrole was added, and boron trifluoride·ethyl ether 50 times the weight of 2,4-dimethylpyrrole was added dropwise in an ice-water bath to react overnight. After the reaction was finished, it was extracted with ethyl acetate and water, concentrated by a rotary evaporator, and the crude...

Embodiment 2

[0055] A near-infrared nano photosensitizer and a preparation method thereof, specifically comprising the following steps:

[0056] (1) Synthesis of compound 1: Add alkyne-containing p-hydroxybenzaldehyde and 2,4-dimethylpyrrole into the reaction vessel at a molar ratio of 1:3, and then add 50% of the weight of 2,4-dimethylpyrrole times THF as solvent and 3-5 drops of trifluoroacetic acid as catalyst. Stir at 40 °C for 24 h. Then, 2,3-dichloro-5,6-dicyano-p-benzoquinone with a molar ratio of 1:3 to 2,4-dimethylpyrrole was added to the above reaction liquid, and stirred at room temperature for 24 hours. Finally, triethylamine 100 times the weight of 2,4-dimethylpyrrole was added, and boron trifluoride·ethyl ether 100 times the weight of 2,4-dimethylpyrrole was added dropwise in an ice-water bath to react overnight. After the reaction was finished, it was extracted with ethyl acetate and water, concentrated by a rotary evaporator, and the crude product was obtained by flash co...

Embodiment 3

[0061] A near-infrared nano photosensitizer and a preparation method thereof, specifically comprising the following steps:

[0062] (1) Synthesis of Compound 1: Put alkyne-containing p-hydroxybenzaldehyde and 2,4-dimethylpyrrole in a molar ratio of 1:5 into the reaction vessel, and then add 30% of the weight of 2,4-dimethylpyrrole times dichloromethane as solvent and 6-10 drops of trifluoroacetic acid as catalyst. Stir at 60 °C for 48 h. Then, 2,3-dichloro-5,6-dicyano-p-benzoquinone with a molar ratio of 1:2 to 2,4-dimethylpyrrole was added to the above reaction liquid, and stirred at room temperature for 24 hours. Finally, triethylamine 50 times the weight of 2,4-dimethylpyrrole was added, and boron trifluoride·ethyl ether 50 times the weight of 2,4-dimethylpyrrole was added dropwise in an ice-water bath to react overnight. After the reaction was finished, it was extracted with ethyl acetate and water, concentrated by a rotary evaporator, and the crude product was obtained ...

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Abstract

The invention relates to a near-infrared nano photosensitizer as well as a preparation method and application thereof, and relates to the technical field of photosensitizers. According to the near-infrared nano photosensitizer disclosed by the invention, the absorption and emission spectrum of the near-infrared nano photosensitizer is close to a near-infrared light region by performing conjugate extension modification on a BODIPY parent nucleus; introducing a polyfluoroalkane group and a polyethylene glycol group into the BODIPY structure to obtain the amphiphilic photosensitizer; the nano photosensitive micelle with an ultralow CMC (Carboxymethyl Cellulose) value is finally constructed by utilizing the strong fluorine-fluorine action between the polyfluoroalkane groups and the hydrophilic action of the polyethylene glycol groups; j-aggregation of the BODIPY is induced by utilizing a fluorine-fluorine effect, so that the maximum absorption peak of the BODIPY is red-shifted to a near-infrared region, and deep phototherapy of tumors is facilitated.

Description

technical field [0001] The invention relates to the technical field of photosensitizers, in particular to a near-infrared nano photosensitizer and its preparation method and application. Background technique [0002] Tumor is a chelate formed by the proliferation of local tissue cells under the action of various tumorigenic factors. The development of new tumor treatment methods is an important direction in the field of medicine. In recent years, with the development and application of laser technology, photodynamic therapy has gradually become a new tumor treatment method. As the core element of photodynamic therapy, photosensitizers can transfer the energy of excitation light to oxygen in tissues, converting them into reactive oxygen species (such as singlet oxygen), and then oxidizing endogenous molecules such as lipids, proteins and nucleic acids. , leading to irreversible tissue damage. However, most photosensitizers generally have defects such as poor photostability,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/337A61K9/107A61K41/00A61P35/00
CPCA61P35/00C08G65/337A61K41/0057A61K47/6907A61K47/60A61K47/543A61K9/5146A61K9/1075
Inventor 郭正清何慧史梦柯徐晗纪丹丹黄阳阳何秋瑾
Owner SUZHOU UNIV
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