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Reduction responding covalent organic polymer and preparation method and application thereof

A covalent organic and polymer technology, applied in the field of medicine, can solve the problems of covalent organic polymers that have not been reported before, achieve good resolubility, avoid toxic and side effects, and improve the effect of hypoxia

Active Publication Date: 2017-01-25
SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the use of COP materials as a carrier-free nano-drug delivery system is still rare, and the use of covalent organic polymers as drug delivery carriers in the combined treatment of cancer with photodynamics and chemotherapy has never been reported.

Method used

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  • Reduction responding covalent organic polymer and preparation method and application thereof
  • Reduction responding covalent organic polymer and preparation method and application thereof
  • Reduction responding covalent organic polymer and preparation method and application thereof

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preparation example Construction

[0043]The present invention also provides a method for preparing a reduction-responsive covalent organic polymer, comprising: mixing and reacting carboxy-terminated polyethylene glycol, a compound of formula (I) and a carboxylated cisplatin prodrug to obtain a reduction-responsive Covalent organic polymers;

[0044]

[0045] Among them, R 1 , R 2 , R 3 and R 4 are independently selected from amino or hydroxy.

[0046] According to the present invention, the present invention mixes carboxyl-terminated polyethylene glycol, a compound of formula (I) and carboxylated cisplatin prodrug to obtain a reduction-responsive covalent organic polymer; wherein, the carboxyl-terminated polyethylene glycol The diol is monocarboxyl-terminated polyethylene glycol, i.e. The molecular weight of the carboxy-terminated polyethylene glycol is preferably 1KDa~10KDa, more preferably 3KDa~8Kda; the carboxylated cisplatin prodrug preferably has formula (Pt-1) or formula (Pt-2)

[0047]

[0...

Embodiment 1

[0054] Preparation of reduction-responsive covalent organic polymer (THPP-Pt-PEG)

[0055] Using 5, 10, 15, 20-tetrakis(4-hydroxyphenyl) porphyrin, carboxylated cisplatin prodrug and polyethylene glycol as reaction raw materials, a reduction-responsive covalent organic polymer THPP was prepared by esterification -Pt-PEG. Specifically include the following steps:

[0056] 27.2mg of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin, 32.1mg of carboxylated cisplatin prodrug, 49.4mg of N,N'-dicyclohexylcarbodiimide and 29.3mg The 4-dimethylaminopyridine was dissolved in dried tetrahydrofuran, and stirred and reacted for 24 hours at 35°C under a nitrogen atmosphere;

[0057] Then, 100 mg of polyethylene glycol with a carboxyl group at the single end, 12.4 mg of N, N'-dicyclohexylcarbodiimide and 7.3 mg of 4-dimethylaminopyridine were added to the system. The reaction was stirred for 24 hours. The resulting solution was concentrated and added dropwise to glacial ether to obtain the ...

Embodiment 3

[0065] Embodiment 3: THPP-Pt-PEG prepared in Example 1 is tested for the killing ability of tumor cells

[0066] The original drug of cisplatin and the covalent organic polymer THPP-PEG without cisplatin were selected as the control group, and the additional condition was 660nm laser irradiation, and 4T1 cells were selected to verify the killing ability of THPP-Pt-PEG on tumor cells.

[0067] The cumulative survival rate of 4T1 cells co-cultured with THPP-Pt-PEG and cisplatin with or without 660nm laser irradiation for 48 hours was tested by MTT test, the results are shown in Figure 6 , Figure 6 Prepare the cell viability figure of THPP-Pt-PEG and cisplatin and mouse breast cancer cell (4T1 cell) co-culture for embodiment 1, as can be seen from the figure, THPP-Pt-PEG compares with cisplatin and has more Strong lethality, and after laser irradiation, the lethality is greatly enhanced, which proves that compared with single chemotherapy, the combination of chemotherapy and p...

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Abstract

The invention provides a reduction responding covalent organic polymer and a preparation method and application thereof. The polymer provided by the invention is obtained by mixing and reacting carboxyl terminated polyethylene glycol, a compound with a structure shown in formula (I) and carboxylic cis-platinum prodrug, wherein the compound is obtained by respectively connecting 5,10,15,20-tetra(4-hydroxyphenyl) porphyrin with cis-platinum prodrug and polyethylene glycol, thus having good water solubility and biocompatibility; the obtained nano particles not only can produce singlet oxygen under laser radiation, but also can generate dissociation under the condition with high reducibility of cancer cells to release cis-platinum drugs, and has certain application in combined treatment of tumor; furthermore, the compound can also be directly used as a drug delivery system without a carrier, thus effectively avoiding use of additional carriers.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a reduction-responsive covalent organic polymer and its preparation method and application. Background technique [0002] Cancer is one of the major diseases that endanger human health. With the development of science and technology, nano-drug delivery system has gradually emerged in the treatment of tumors. Common drug delivery systems including liposomes, polymer micelles, and albumin nanoparticles have entered clinical research in nanotransition medicine. However, due to the limitation of drug loading, most traditional nano-drug delivery systems are often accompanied by a large number of carrier materials, which inevitably increases metabolic pressure and causes toxic side effects on physiological tissues, such as the commonly used polyester drug delivery system. The acidic degradation products produced by the metabolism of the system in the body can cause local inflammatory reactions...

Claims

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Application Information

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IPC IPC(8): A61K47/59A61K33/24A61K41/00A61K45/06A61P35/00C08G65/337C08G65/333
Inventor 刘庄王海蓉
Owner SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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