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Platinum-based bodipy compound, preparation method and application

A technology for fluorinated boron dipyrrole and compound, which is applied to platinum-based fluorinated boron dipyrrole compounds and the fields of preparation and application, and can solve the problem of limited application of antitumor drugs, insignificant solubilization effect, easy quenching of singlet oxygen, etc. problem, to achieve the effect of improving photodynamic therapy activity, enhancing non-radiative transition, and good water solubility

Active Publication Date: 2017-03-22
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Although linear polymer micelles have shown great advantages and potentials in the drug delivery process as the carrier of insoluble water-soluble drugs, there are problems of micellar depolymerization, ineffective solubilization, easy quenching of singlet oxygen, and targeting Insufficient sex and other problems obviously limit its application in the targeted delivery of antitumor drugs such as photosensitizers. Therefore, a new molecular structure that can overcome the efficient targeted delivery of photosensitizers has been designed.

Method used

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  • Platinum-based bodipy compound, preparation method and application
  • Platinum-based bodipy compound, preparation method and application
  • Platinum-based bodipy compound, preparation method and application

Examples

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Effect test

Embodiment 1

[0045] Prepare R 1 Be the platinum-based fluoroboron dipyrrole compound of polyethylene glycol group (molecular weight is 5000), concrete steps are as follows:

[0046] (1) Preparation of fluorobodipyrrole derivatives: 2,4-dimethylpyrrole, p-formylpyridine, 2,3-dichloro Add -5,6-dicyano-p-benzoquinone, diisopropylethylamine, boron trifluoride ethyl ether, and trifluoroacetic acid into 50mL of dichloromethane, and react at 25°C (room temperature) for 16h to obtain fluoroboron dipyrrole derivatives thing;

[0047] (2) Preparation of fluorobodipyrrole conjugates: Dissolve 130 mg of fluorobodipyrrole derivatives obtained in step (1) and 147 mg p-hydroxybenzaldehyde in 50 ml of toluene, and add 1 mL of glacial acetic acid and 1 mL of piperidine , heated to reflux at 112°C for 20 hours under a nitrogen atmosphere, and ice-bathed for 30 minutes. The resulting solid product was washed several times with toluene, and then spin-dried by a rotary evaporator to obtain the primary produc...

Embodiment 2

[0054] The steps of this example are basically the same as those of Example 1, the difference being that in step (3), 80 mg of fluoroborate dipyrrole conjugates and 207 mg of 3-bromopropyne are added to 50 mL of acetonitrile, and potassium carbonate is used as a catalyst, heated and condensed to reflux After 24 hours of reaction, the product yield was 30%.

Embodiment 3

[0056] The steps of this example are basically the same as those of Example 1, the difference being that in step (5), under light-shielding conditions, 10 mg of platinum-based fluoroborate dipyrrole derivatives containing alkynyl groups at the terminal, 20 mg of alkynyl dipyrrole derivatives with a molecular weight of 1000, and Nitrogen polyethylene glycol polymer (molar ratio 1:2) is added to 10% of anhydrous and oxygen-free dimethyl sulfoxide solvent, and an appropriate amount of copper sulfate pentahydrate and sodium ascorbate are added as catalysts, operated in a glove box, 50 ° C After 24 hours of reaction, the final product yield was 30%.

[0057] The platinum-based fluoroboron dipyrrole compound prepared in this example is prepared for the preparation of nanomicelles. The specific steps are: weigh 1 mg of the sample, dissolve it in 5 mL of dichloromethane, and remove the dichloromethane by rotary evaporation with a rotary evaporator, so that The substance forms a thin f...

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Abstract

The invention provides synthesis of a platinum-based bodipy compound and a new application thereof in pharmacy, and particularly relates to the synthesis of platinum-based bodipy molecules and derivatives thereof, preparation of a nano-scale medicament, and an application to anti-tumor photosensitive medicament in photodynamics and photothermal therapy. Self-assembling nano-particles with photodynamic and photothermal dual activities are constructed by taking bodipy dye molecules as parent nuclei, introducing divalent platinum ions in a covalent coordination mode, and performing modifying through a polymer hydrophilic chain. Under light conditions, a self-assembling nano-scale medicament shows good photodynamic and photothermal therapeutic effects. The platinum-based bodipy compound confirms dual effects of the photodynamics and photothermal therapy at cell and animal levels, and the light induction of tumor ablation is realized.

Description

technical field [0001] The invention relates to a platinum-based fluoroboron dipyrrole compound and its preparation method and application. Background technique [0002] Tumors are gradually threatening the quality of life of people all over the world. It is the most difficult medical problem to be overcome in this century. In medicine, we must improve the detection technology and treatment methods of tumors to fight against the disasters brought by tumors to human beings. In clinical practice, the commonly used methods for tumor detection are mainly imaging technology and pathological technology, and the treatment methods are mainly surgery, chemotherapy, radiation therapy, and emerging photodynamic therapy and photothermal therapy. However, a single diagnosis and treatment method is difficult to achieve the desired effect. Effective combination of multiple diagnosis and treatment methods is an important means and method to solve the limitations of current tumor diagnosis a...

Claims

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Application Information

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IPC IPC(8): C08G65/337A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057C08G65/337
Inventor 陈华兵郭正清邹烨璘何慧邓益斌柯亨特杨红饶佳明
Owner SUZHOU UNIV
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