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Mitochondrion-targeting BODIPY compound and preparation method and application of liposome-coated nanoparticles of BODIPY compound

A fluoroboron dipyrrole and nanoparticle technology, which is applied in the field of fluoroboron dipyrrole compounds, can solve problems such as limiting the enrichment of nanoparticles, uneven particle size distribution of nanoparticles, and inconspicuous photodynamic effects

Active Publication Date: 2020-10-30
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the experimental results show that the particle size distribution of the nanoparticles formed after the combination of HA and the photosensitizer is not uniform, which limits the enrichment of the nanoparticles in the tumor site, and the resulting photodynamic effect is not obvious.

Method used

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  • Mitochondrion-targeting BODIPY compound and preparation method and application of liposome-coated nanoparticles of BODIPY compound
  • Mitochondrion-targeting BODIPY compound and preparation method and application of liposome-coated nanoparticles of BODIPY compound
  • Mitochondrion-targeting BODIPY compound and preparation method and application of liposome-coated nanoparticles of BODIPY compound

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Experimental program
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Effect test

Embodiment 1

[0041] Synthetic R 1 for-OCH 3 The specific preparation process of the modified mitochondria-targeted fluoroborate dipyrrole compound includes:

[0042] (1) Dissolve 4-methoxybenzaldehyde (409 mg, 3 mmol) in 90 mL of anhydrous tetrahydrofuran. Under stirring, 2,4-dimethylpyrrole (0.63 g, 6.6 mmol) and 0.25 mL of trifluoroacetic acid were added, and the reaction solution was reacted under nitrogen protection for 14 hours. After that, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.68g, 3mmol) was dissolved in 120mL of anhydrous tetrahydrofuran, and added dropwise to the above reaction solution, and the reaction was continued for 4 hours . After the above reaction solution was placed in a mixture of ice and water, 18 mL of triethylamine was added dropwise. After the reaction solution was reacted in an ice-water mixture for 30 minutes, 18 mL of boron trifluoride diethyl ether was added dropwise, and the reaction solution was continued to react at 25° C. for 14 hours. After the ...

Embodiment 2

[0056] Synthetic R 1 for -N(C 2 h 5 ) 2 The specific preparation process of the modified mitochondria-targeted fluoroborate dipyrrole compound includes:

[0057] (1) Dissolve 4-(N,N-diethyl)aminobenzaldehyde (532 mg, 3 mmol) in 90 mL of anhydrous tetrahydrofuran. Under stirring, 2,4-dimethylpyrrole (0.63 g, 6.6 mmol) and 0.25 mL of trifluoroacetic acid were added, and the reaction solution was reacted under nitrogen protection for 14 hours. After that, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.68g, 3mmol) was dissolved in 120mL of anhydrous tetrahydrofuran, and added dropwise to the above reaction solution, and the reaction was continued for 4 hours . After the above reaction solution was placed in a mixture of ice and water, 18 mL of triethylamine was added dropwise. After the reaction solution was reacted in an ice-water mixture for 30 minutes, 18 mL of boron trifluoride diethyl ether was added dropwise, and the reaction solution was continued to react at 25° C. for...

Embodiment 3

[0071] Synthetic R 1 for The specific preparation process of the modified mitochondria-targeted fluoroborate dipyrrole compound includes:

[0072] (1) Dissolve 4-(4-morpholine)benzaldehyde (574 mg, 3 mmol) in 90 mL of anhydrous tetrahydrofuran. Under stirring, 2,4-dimethylpyrrole (0.63 g, 6.6 mmol) and 0.25 mL of trifluoroacetic acid were added, and the reaction solution was reacted under nitrogen protection for 14 hours. After that, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.68g, 3mmol) was dissolved in 120mL of anhydrous tetrahydrofuran, and added dropwise to the above reaction solution, and the reaction was continued for 4 hours . After the above reaction solution was placed in a mixture of ice and water, 18 mL of triethylamine was added dropwise. After the reaction solution was reacted in an ice-water mixture for 30 minutes, 18 mL of boron trifluoride diethyl ether was added dropwise, and the reaction solution was continued to react at 25° C. for 14 hours. After th...

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Abstract

The invention relates to a mitochondria-targeting BODIPY compound and a preparation method and application of liposome-coated nanoparticles of the BODIPY compound. The BODIPY compound contains a cationic group which is easily combined with a mitochondrial membrane with negative electricity in cells, so that the BODIPY compound is targeted to mitochondrial organelles of the cells. The BODIPY compound is wrapped by liposome, and liposome nanoparticles with uniform particle size are prepared in an aqueous solution. The nanoparticles have high stability and good biocompatibility in an aqueous solution. After the nanoparticles are taken by tumor cells, the liposome structure is destroyed, and the released BODIPY compound is targeted to cell mitochondria. Besides, under the 665nm illumination condition, active oxygen generated by the BODIPY compound causes oxidative damage to active molecules in mitochondria, so that tumor cells are killed. The liposome nanoparticles can be applied to tumorphotodynamic therapy as a drug for delivering various photosensitizers.

Description

technical field [0001] The invention belongs to the field of medicine and pharmaceutics, and in particular relates to a mitochondria-targeted fluoroborate dipyrrole compound, and a preparation method and application thereof for liposome-encapsulated nanoparticles. Background technique [0002] Photodynamic therapy (PDT) is a non-invasive technique for treating tumors. To exert PDT, three basic conditions need to be met, namely photosensitizer, light of specific wavelength and ground state oxygen. Its therapeutic mechanism is that after the photosensitizer is intravenously injected into the human body, the photosensitizer is enriched in the tumor area. When the region is irradiated with light of a specific wavelength, the photosensitizer absorbs the light energy and transitions to an excited state, and the photosensitizer in the excited state transfers energy to the ground state oxygen around the tumor tissue and cells, thereby generating highly oxidative reactive oxygen spe...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06C09B57/00A61K41/00A61K9/127A61K47/24A61K47/10A61P35/00B82Y5/00B82Y20/00
CPCC07F5/022C09K11/06C09B57/00A61K41/0057A61K9/127A61K47/24A61K47/10A61P35/00B82Y5/00B82Y20/00C09K2211/1055
Inventor 张权张永和孔祥东赵瑞波祖柏尔卢嘉驹
Owner ZHEJIANG SCI-TECH UNIV
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