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Fluorinated covalent organic polymer loaded with perfluorocarbon and preparation method and application thereof

A covalent organic and polymer technology, applied in the field of medicine, can solve problems such as hypoxia at the tumor site and limit the effect of photodynamic therapy substance therapy, so as to improve the effect, improve the hypoxic microenvironment of the tumor, and improve the effect of photodynamic therapy Effect

Active Publication Date: 2018-11-30
SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Since the 21st century, with the increasing number of new cancer cases, traditional tumor treatment methods such as surgery, chemotherapy and radiotherapy are difficult to meet the needs of clinical tumor treatment due to their own shortcomings.
[0003] However, due to the irregular vascular structure and the rapid metabolism of tumor cells, a hypoxic microenvironment will be formed in the tumor site, which greatly limits the therapeutic effect of photodynamic therapy substances.

Method used

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  • Fluorinated covalent organic polymer loaded with perfluorocarbon and preparation method and application thereof
  • Fluorinated covalent organic polymer loaded with perfluorocarbon and preparation method and application thereof
  • Fluorinated covalent organic polymer loaded with perfluorocarbon and preparation method and application thereof

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preparation example Construction

[0033] The present invention also provides a method for preparing a perfluorocarbon-loaded fluorinated covalent organic polymer, comprising:

[0034] 1) Mixing and reacting carboxy-terminated polyethylene glycol, perfluorosebacic acid and meso-5-10-15-20-tetrakis(4-hydroxyphenyl)porphyrin to obtain a fluorinated covalent organic polymer;

[0035] 2) Mixing the fluorinated covalent organic polymer obtained in step 1) with perfluorocarbon to obtain a fluorinated covalent organic polymer loaded with perfluorocarbon.

[0036] According to the present invention, the present invention mixes and reacts carboxy-terminated polyethylene glycol, perfluorosebacic acid and meso-5-10-15-20-tetrakis (4-hydroxyphenyl) porphyrin to obtain fluorinated covalent organic polymer wherein, the molar ratio of the meso-5-10-15-20-tetrakis (4-hydroxyphenyl) porphyrin to perfluorosebacic acid is preferably 1: (1 ~ 2), more preferably 1: 1.5; the mol ratio of the meso-5-10-15-20-tetra(4-hydroxyphenyl) p...

Embodiment 1

[0041] Example 1. Preparation of fluorinated covalent organic polymer loaded with perfluorocarbon (PFC@THPP-PFSEA)

[0042] Dissolve meso-5-10-15-20-tetrakis(4-hydroxyphenyl)porphyrin (0.04mmol) (THPP) and perfluorosebacic acid (0.06mmol) in 50mL ultra-dry THF solution, then add di Cyclohexylcarbodiimide (0.8mmol) and 4-dimethylaminopyridine (0.8mmol) were heated in an oil bath to 45°C and reacted in the dark for 24 hours. Add carboxy-terminated polyethylene glycol (0.16 mmol) into the reaction system, react at 45° C. for 24 hours, and terminate the reaction. In order to purify the free meso-5-10-15-20-tetrakis(4-hydroxyphenyl)porphyrin and PFSEA small molecules in the product, the reaction solvent tetrahydrofuran was removed by a rotary evaporator, a small amount of methanol was added to dissolve the reaction product and washed with a large amount of ice Precipitate with diethyl ether, centrifuge at 5000rpm for 5 minutes and discard the supernatant, repeat this step until th...

Embodiment 2

[0046] The fluorinated covalent organic polymer obtained in Example 1 was characterized (including: UV-Vis absorption spectrum, dynamic light scattering, transmission electron microscopy, singlet oxygen generation ability), the results are shown in Figure 1 to Figure 5 ;

[0047] figure 1 It is the dynamic laser particle size distribution diagram of THPP-PFSEA nanoparticles described in Example 1 before and after hydration. It can be seen from the figure that the particle size of the material does not change greatly before and after hydration, indicating that the compound can be prepared into a powder product after lyophilization, which is convenient for long-term storage and transportation.

[0048] figure 2 It is the dynamic laser particle size distribution diagram of THPP-PFSEA nanoparticles described in Example 1 before and after loading perfluorocarbon. It can be seen from the figure that the diameter of nanoparticles formed by THPP-PFSEA is about 80nm, and the parti...

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Abstract

The invention provides a fluorinated covalent organic polymer loaded with perfluorocarbon. The fluorinated covalent organic polymer is obtained by a mixed reaction of carboxyl terminated polyethyleneglycol, perfluorosebacic acid, and meso-5-10-15-20-four (four-hydroxy phenyl) porphyrin, the obtained fluorinated covalent organic polymer are mixed with the perfluorocarbon, and the fluorinated covalent organic polymer loaded with the perfluorocarbon is obtained. Through the experiment, the fluorinated covalent organic polymer loaded with the perfluorocarbon can not only be used as nano-materialsfor photodynamic therapy, but also improve the tumor anaerobic microenvironment, the photodynamic therapy effect is further improved, so that efficient tumor photodynamic therapy is achieved.

Description

technical field [0001] The invention relates to the field of medicines, in particular to a perfluorocarbon-loaded fluorinated covalent organic polymer and a preparation method and application thereof. Background technique [0002] Since the 21st century, with the increasing number of new cancer cases, traditional tumor treatment methods such as surgery, chemotherapy and radiotherapy are difficult to meet the needs of current clinical tumor treatment due to their own shortcomings. Therefore, the development of new safe and efficient tumor treatment methods has been extensively and deeply studied. In recent years, tumor photodynamics has attracted much attention due to its advantages of less invasiveness, low toxicity and side effects, and high targeting. The basic principle of tumor photodynamic therapy is: under the irradiation of laser light of specific wavelength, photosensitive molecules convert oxygen into singlet oxygen. Singlet oxygen causes damage to cells and induce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61P35/00C08G63/685C08G63/682C08G63/668
CPCA61K41/0071A61P35/00C08G63/668C08G63/6824C08G63/6854
Inventor 刘庄陶丹蕾冯良珠
Owner SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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