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A kind of vasoblocking agent bonded flubororpyrrole derivative and its preparation method and application

A vascular blocker and fluoroboropyrin technology, applied in the field of near-infrared dyes and nano-medicine, can solve the problems of decreased photodynamic effect, hinder clinical application, etc., and achieve the effects of simple synthesis method, precise tumor treatment and clear structure.

Active Publication Date: 2022-03-08
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the generation of singlet oxygen is closely related to the oxygen concentration, and when the oxygen concentration inside the tumor decreases during treatment, the photodynamic effect drops sharply, hindering its clinical application.

Method used

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  • A kind of vasoblocking agent bonded flubororpyrrole derivative and its preparation method and application
  • A kind of vasoblocking agent bonded flubororpyrrole derivative and its preparation method and application
  • A kind of vasoblocking agent bonded flubororpyrrole derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Vasoblocker-linked BDPVDA synthesis

[0056] (1) In a 500mL flask, dissolve 4-methoxybenzaldehyde (0.37g, 3.0mmol) and 2,4-dimethylpyrrole (0.63g, 6.6mmol) in 90mL tetrahydrofuran, add 0.1mL three Fluoroacetic acid, stirring at room temperature for 12 hours; adding 12 ml of 2,3-dichloro-dicyano-p-benzoquinone (0.68 g, 3.0 mmol) tetrahydrofuran solution to the reaction solution, and continuing the reaction at room temperature for 4 hours; , add 18mL triethylamine and 18mL boron trifluoride diethyl ether dropwise to the reaction liquid, and continue to react for 12 hours; V / V) to obtain an orange solid product (compound 1, 0.459g, about 45% yield), the structural formula is as follows:

[0057]

[0058] The chemical name of compound 1 is: 4-(5,5-difluoro-1,3,7,9-tetramethyl-5H-4λ 4 , 5λ 4 -dipyrrole[1,2-c:2',1'-f][1,3,2]diazaboron)-phenol.

[0059] (2), in a 50mL round bottom flask, dissolve compound 1 (0.34g, 1.0mmol) and 4-dimethylaminobenzaldehyde (0.33g, 2.4mmo...

Embodiment 2

[0067] Preparation of mPEG-PPDA-coated BDPVDA nanoparticles (PBV NPs)

[0068] Dissolve 100mg of mPEG-PPDA (the molecular weight of mPEG is 2000, and the degree of polymerization of PPDA is 80) and 4mg of BDPVDA in 5mL of tetrahydrofuran, stir for 5 minutes, drop it into 80mL of deionized water under ultrasonic conditions (200W), and continue to sonicate for 30 minute. The tetrahydrofuran was removed by vacuum rotary evaporation, and PBV NPs were obtained by filtration with a 220 nm filter head.

[0069] Such as Figure 4 As shown, in the ultraviolet-visible absorption spectrum of PBV NPs, there are strong absorption peaks in the wavelength range of 570nm-850nm, and the highest absorption peak is at 733nm, indicating that PBV NPs have excellent near-infrared absorption properties. At the same time, if Figure 5 As shown, the particle size distribution test showed that the particle size distribution of PBV NPs was 60.7±5.1 nm.

Embodiment 3

[0071] Acid Stimulus-Responsive Release Properties of Vasoblocker DMXAA

[0072] 20 mL of phosphate buffer solution containing PBV NPs (50 μg / mL) was placed in a dialysis bag (molecular weight cut-off: 1000), and placed in phosphate buffer with different pH values ​​(5.0, 6.5, 7.4) for slow release. Record the absorption value of DMXAA at different time points to detect the release amount. Such as Image 6 As shown, the cumulative release rate of DMXAA increased with the decrease of pH value, indicating that PBVNPs have good acid stimulation responsiveness, which will be beneficial to realize the drug release stimulated by tumor micro acid.

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Abstract

The invention discloses a vasoborpyrrole derivative bonded with a blood vessel blocking agent, which is formed by covalently bonding a near-infrared photosensitizer fenpyrrole and a blood vessel blocking agent 2,5-pentoxifylline. Simultaneously, the present invention also discloses a nano-diagnosis reagent obtained by self-assembly of the derivative and the electron-rich amphiphilic polymer methoxy-poly(ethylene glycol)-poly(2-diisopropylamino)methyl methacrylate And its application in type I photodynamic synergistic angioblocking therapy in tumor treatment. The structure of the target product of the present invention is clear, the synthesis process is simple, and the diagnostic and therapeutic reagent based on the target product has both type I photodynamic and pH-responsive vascular blocker release properties. Accurately reach the tumor site, block tumor blood vessels and kill tumor cells, effectively preventing tumor recurrence and metastasis.

Description

technical field [0001] The invention belongs to the field of near-infrared dyes and nanomedicine, and specifically relates to a blood vessel blocking agent-bonded flubororpyrrole derivative and a preparation method thereof, and the preparation of the blood vessel blocking agent-bonded flubororpyrrole derivative in the preparation of fluorescence imaging mediation Application of type I photodynamic / vascular blockade synergistic drugs in tumor therapy. Background technique [0002] In the process of cancer development, when the tumor diameter reaches 2-3 mm, the oxygen and nutrients in the tumor are not enough to support the further growth of the tumor, which induces the upregulation of vascular endothelial growth factor (VEGF) in the tumor microenvironment, and generates new blood vessels to provide tumor support. oxygen and nutrients. When the tumor develops to a certain extent, the surrounding immune system is attacked, and a large number of free cancer cells and exosomes ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/55A61K41/00A61K9/51A61P35/00C07F5/02A61K31/352
CPCA61K41/0057C07F5/022A61P35/00A61K31/352A61K47/55A61K9/5146A61K9/0019
Inventor 董晓臣陈大鹏邵进军司伟丽张琪黄维
Owner NANJING TECH UNIV
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