Multi-iodine modified fluoroboron dipyrrole derivatives and its preparation method and application

A technology of pyrroles and derivatives, applied in the field of photosensitizers, can solve the problems of single photodynamic therapy effect of photosensitizers, limited application of low intersystem crossing efficiency, poor water solubility, etc., so as to improve photodynamic therapy activity and improve singlet state. Oxygen yield, water solubility improvement effect

Active Publication Date: 2021-08-24
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many fluorescent dye molecules have suitable absorption wavelengths, good biocompatibility, and unique cell, subcellular organelle, and biomolecular binding capabilities, but low crossing efficiency limits their application in the field of phototherapy
(2) Since the emission wavelength of fluoroborate dipyrrole derivatives is generally between 400 and 580 nanometers, and their water solubility is poor, the application of such compounds in imaging of living cells and whole tissues and organs is limited; (3) Clinical application Many photosensitizers often only have a single photodynamic therapy effect, and many patients tend to relapse after receiving treatment. Combining photothermal therapy and photodynamic therapy can achieve better therapeutic effects

Method used

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  • Multi-iodine modified fluoroboron dipyrrole derivatives and its preparation method and application
  • Multi-iodine modified fluoroboron dipyrrole derivatives and its preparation method and application
  • Multi-iodine modified fluoroboron dipyrrole derivatives and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0042] 1. Synthesis of Compound 1

[0043]Add 3,5-diiodo-p-hydroxybenzaldehyde and 2,4-dimethylpyrrole into the reaction vessel at a molar ratio of 1:2, and then add tetrahydrofuran 100 times the weight of 2,4-dimethylpyrrole as Solvent and 3-5 drops of trifluoroacetic acid as catalyst. Stir at 25°C for 12 hours. Subsequently, 2,3-dichloro-5,6-dicyano-p-benzoquinone dissolved in 2,4-bis In tetrahydrofuran with 10 times the weight of methylpyrrole, the reaction was stirred at room temperature for 12 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, filter with a sandboard Buchner funnel, concentrate under reduced pressure and rotate, add a small amount of dilute hydrochloric acid and stir for 3 hours. After concentrating again, it was extracted with dichloromethane. The extract was sub...

Embodiment 2

[0053] 1. Synthesis of Compound 1

[0054] Add 3,5-diiodo-p-hydroxybenzaldehyde and 2,4-dimethylpyrrole to the reaction vessel at a molar ratio of 1:3, and then add 50 times the weight of 2,4-dimethylpyrrole. Methane was used as solvent and 3-5 drops of trifluoroacetic acid as catalyst. Stir at 25°C for 24 hours. Subsequently, 2,3-dichloro-5,6-dicyano-p-benzoquinone dissolved in 2,4-bis 20 times the weight of methylpyrrole in tetrahydrofuran, stirred at room temperature for 12 hours. Finally, triethylamine 25 times the weight of 2,4-dimethylpyrrole was added, and boron trifluoride·ethyl ether 25 times the weight of 2,4-dimethylpyrrole was added dropwise in an ice-water bath to react overnight. After the reaction, filter with a sandboard Buchner funnel, concentrate under reduced pressure and rotate, add a small amount of dilute hydrochloric acid and stir for 1.5 hours. After concentrating again, it was extracted with dichloromethane. The extract was subjected to column chr...

Embodiment 3

[0064] 1. Synthesis of Compound 1

[0065] Add 3,5-diiodo-p-hydroxybenzaldehyde and 2,4-dimethylpyrrole to the reaction vessel at a molar ratio of 1:2, and then add 50 times the weight of 2,4-dimethylpyrrole Methane was used as solvent and 3-5 drops of trifluoroacetic acid as catalyst. Stir at 25°C for 24 hours. Subsequently, 2,3-dichloro-5,6-dicyano-p-benzoquinone dissolved in 2,4-bis 20 times the weight of methylpyrrole in tetrahydrofuran, stirred at room temperature for 12 hours. Finally, diisopropylamine 25 times the weight of 2,4-dimethylpyrrole was added, and boron trifluoride·ethyl ether 30 times the weight of 2,4-dimethylpyrrole was added dropwise in an ice-water bath to react overnight. After the reaction, filter with a sandboard Buchner funnel, concentrate under reduced pressure and rotate, add a small amount of dilute hydrochloric acid and stir for 6 hours. After concentrating again, it was extracted with dichloromethane. The extract was subjected to column chr...

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Abstract

The invention discloses a polyiodine-modified fluoroboridipyrrole derivative. The fluoroboridipyrrole derivative uses fluoroboridipyrrole as a mother nucleus, prolongs the conjugated system of fluoroboridipyrrole through condensation reaction, and It is obtained by introducing a hydrophilic ethylene glycol chain at the end, and then introducing different numbers of iodine atoms through an electrophilic substitution reaction. The invention also discloses the preparation method and application of the fluoroboron dipyrrole derivatives. The polyiodine-modified fluoroborate dipyrrole derivatives of the present invention have both photodynamic and photothermal therapeutic effects, and correspondingly avoid the shortcomings of single therapeutic effect and poor targeting of clinical photosensitizers.

Description

technical field [0001] The invention relates to the technical field of photosensitizers, in particular to a polyiodine-modified fluoroboron dipyrrole derivative and a preparation method and application thereof. Background technique [0002] As we all know, malignant tumors pose a major threat to human health. How to improve the quality of life of cancer patients has become a hot spot in the field of medical research. At present, cancer treatment methods are mainly divided into three categories: surgery, chemotherapy and radiotherapy, but they often have certain defects, such as low selectivity, high toxicity and side effects, etc. The patient's treatment is painful, resulting in a sharp decline in the quality of life of the patient. Therefore, it is particularly important to find a multimodal method in the current diagnosis and treatment of tumors. As a new cancer treatment method, phototherapy has the advantages of strong selectivity and low side effects, which has become...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/337C08G65/333A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057A61P35/00C08G65/33396C08G65/337A61K2300/00
Inventor 郭正清何慧陈华兵杨红饶佳明史梦柯王孟雅应宇辰张韶
Owner SUZHOU UNIV
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