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Fluorine-boron complex-based micromolecular photo-thermal reagent and preparation method and application thereof

A photothermal reagent and small molecule technology, which is applied in the synthesis and application of medical materials, can solve the problems of difficult to achieve NIR-II absorption and low photothermal conversion efficiency, and achieve ideal therapeutic effect, simple structure and low raw material cost.

Active Publication Date: 2021-02-12
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the defects of low photothermal conversion efficiency of small molecule photothermal reagents in the prior art and it is difficult to realize efficient NIR-II absorption, and to provide a small molecule photothermal reagent based on fluoroboron complexes and its preparation method and application, a photothermal reagent with high photothermal conversion efficiency (80%) and absorption in the second near-infrared region was synthesized through a simple preparation method and low-cost raw materials

Method used

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  • Fluorine-boron complex-based micromolecular photo-thermal reagent and preparation method and application thereof
  • Fluorine-boron complex-based micromolecular photo-thermal reagent and preparation method and application thereof
  • Fluorine-boron complex-based micromolecular photo-thermal reagent and preparation method and application thereof

Examples

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Embodiment 1

[0059] 1-(4-bromophenyl)-1,2,2-triphenylene / 1-(4-bromophenyl)-2,2-bis(4-methoxyphenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis(4-N,N-dimethylaminophenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis( The preparation of 4-N,N-dioctylaminophenyl)-1-styrene: add zinc powder (1.2g, 18.2mmol) in the reactor, dissolve in 50mL tetrahydrofuran, and drop titanium tetrachloride ( 1.0mL, 9.2mmol), stirred for 1 hour to rise to room temperature and continued to stir for 3 hours. Then add piperidine (1.6mL, 4.6mmol), continue to stir at room temperature for 20 minutes, add 4-bromobenzoylbenzene (1.2g, 4.7mmol) and benzophenone (0.7g, 3.6mmol) / 4,4 '-Dimethoxybenzophenone (0.9g,3.6mmol) / 4,4'-bis(N,N-dimethylamino)benzophenone (1.0g,3.6mmol) / 4,4'- Any one of bis(N,N-dioctylamino)benzophenones (2.4g, 3.6mmol), the reaction was heated under reflux for 10 hours. After the reaction was completed, it was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered with suction, and spin...

Embodiment 2

[0070] 1-(4-bromophenyl)-1,2,2-triphenylene / 1-(4-bromophenyl)-2,2-bis(4-methoxyphenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis(4-N,N-dimethylaminophenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis( The preparation of 4-N,N-dioctylaminophenyl)-1-styrene: add zinc powder (1.2g, 18.2mmol) in the reactor, dissolve in 50mL tetrahydrofuran, and drop titanium tetrachloride ( 1.2mL, 11.1mmol), stirred for 2 hours, raised to room temperature and continued to stir for 5 hours. Then add piperidine (1.6mL, 4.6mmol), after stirring at room temperature for 30 minutes, add 4-bromobenzoylbenzene (0.92g, 3.6mmol) and benzophenone (0.7g, 3.6mmol) / 4,4 '-Dimethoxybenzophenone (0.9g,3.6mmol) / 4,4'-bis(N,N-dimethylamino)benzophenone (1.0g,3.6mmol) / 4,4'- Any one of bis(N,N-dioctylamino)benzophenones (2.4g, 3.6mmol), the reaction was heated under reflux for 16 hours. After the reaction was completed, it was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered with suction, and spi...

Embodiment 3

[0076] 1-(4-bromophenyl)-1,2,2-triphenylene / 1-(4-bromophenyl)-2,2-bis(4-methoxyphenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis(4-N,N-dimethylaminophenyl)-1-styrene / 1-(4-bromophenyl)-2,2-bis( The preparation of 4-N,N-dioctylaminophenyl)-1-styrene: add zinc powder (1.2g, 18.2mmol) in the reactor, dissolve in 50mL tetrahydrofuran, and drop titanium tetrachloride ( 1.0mL, 9.2mmol), stirred for 2 hours, raised to room temperature and continued to stir for 5 hours. Then add piperidine (1.6mL, 4.6mmol), continue to stir at room temperature for 30 minutes, add 4-bromobenzoyl benzene (1.1g, 4.3mmol) and benzophenone (0.7g, 3.6mmol) / 4,4 '-Dimethoxybenzophenone (0.9g,3.6mmol) / 4,4'-bis(N,N-dimethylamino)benzophenone (1.0g,3.6mmol) / 4,4'- Any one of bis(N,N-dioctylamino)benzophenones (2.4g, 3.6mmol), the reaction was heated under reflux for 12 hours. After the reaction was completed, it was extracted with dichloromethane, dried over anhydrous magnesium sulfate, filtered with suction, and sp...

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Abstract

The invention discloses a small-molecule photo-thermal reagent based on a fluorine-boron complex and a preparation method and application thereof. The structural formula of the small-molecule photo-thermal reagent is shown in the specification. The photo-thermal reagent with high photo-thermal conversion efficiency and near-infrared two-region absorption is synthesized by virtue of a simple and convenient preparation method and low-cost raw materials; meanwhile, an ideal treatment effect is achieved in anti-tumor application.

Description

technical field [0001] The invention relates to a small molecule photothermal reagent based on a fluoroboron complex and a preparation method and application thereof, belonging to the technical field of synthesis and application of medical materials. Background technique [0002] Photothermal therapy (PTT) based on laser irradiation has been favored by researchers due to its potential application in the field of cancer treatment. Compared with traditional cancer treatment methods (such as surgery, radiotherapy, and chemotherapy), PTT has attracted attention because of its advantages such as less trauma, controllable treatment time and space, and non-toxic photothermal materials in the absence of light. . Although photothermal reagents such as gold nanostructures, 2D carbon materials, and conjugated polymers exhibit high photothermal conversion efficiency (PCE), their poor biodegradability limits their further applications in the biological field. Photothermal materials bas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61K41/00A61P35/00
CPCC07F5/022A61K41/0052A61P35/00
Inventor 刘志鹏姜志勇王小青严鸣
Owner NANJING FORESTRY UNIV