Porphyrin-containing acid-responsive photodynamic therapy polymer nano-drug

A technology of nano-medicine and acetal polymer, which is applied in the field of biomedicine, can solve problems such as the reduction of the effect of photodynamic therapy, and achieve the effects of weakening the stacking quenching effect, improving efficiency, and improving utilization.

Pending Publication Date: 2020-07-17
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has a big limitation, that is, because it contains a large π-bonded conjugated ring, there is a π-π conjugation between different porphyrin molecules, which makes it easy to accumulate and aggregate, and eventually quenched (i.e. the ACQ effect), which leads to the failure of photodynamic therapy. Reduced effect

Method used

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  • Porphyrin-containing acid-responsive photodynamic therapy polymer nano-drug
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  • Porphyrin-containing acid-responsive photodynamic therapy polymer nano-drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of amphiphilic block copolymer POEGMA-b-[PTPPC6MA-co-PTTMA](PM):

[0050] Block copolymers were prepared by subsequent raft polymerization of TPPC6MA and TTMA using POEGMA as the macromolecular RAFT agent. Add POEGMA (200 mg) TPPC6MA (150 mg), TTMA (95 mg), AIBN (1.82 mg) and 3ml THF to a dry polymerization tube equipped with a magnetic stir bar as follows. The polymerization tube was then sealed under vacuum by going through at least three freeze-thaw cycles while evacuating nitrogen. The degassed solution was immersed in an oil bath at 70° C. and stirred at a constant temperature for 48 hours, and then the polymerization tube was treated with liquid nitrogen to freeze the solution. The mixture was then precipitated three times in excess diethyl ether and dried in a vacuum oven at room temperature. Final product (181 mg, 35%).

Embodiment 2

[0059]Self-Assembly of Amphiphilic Block Copolymers:

[0060] Dissolve 10 mg of the copolymer in 10 ml of tetrahydrofuran to prepare an organic concentrated solution of 1 mg / ml. Then, the copolymer solution (1 mg) was slowly dropped into 4.0 ml phosphate buffered saline (PBS, 10 mm, pH=7.4) under stirring with a magnetic stirrer, and this process lasted for 1 h. After further stirring for 1 h, micelles formed. The resulting solution was stirred overnight and THF was removed by dialysis (MWCO 3.5 kDa) against PBS buffer (pH=7.4) for 3 days.

[0061] The invention obtains three kinds of porphyrin-containing polymer nano drug micelles, two of which have innovative acetal structures. The ultraviolet absorption test was carried out, and it was found that the position of the ultraviolet absorption peak of the substance changed only slightly before and after assembly, indicating that the structure of the chemical substance did not change significantly before and after assembly, and...

Embodiment 3

[0063] Cell uptake test:

[0064] Cellular drug uptake was detected by confocal laser scanning microscopy (CLSM). Firstly, cells were plated in culture dishes, 10,000 cells per dish, and 2 ml medium was added for culture. After 24 hours, the culture solution was taken out, and 2 ml of the prepared medium containing the drug (porphyrin) concentrate at a concentration of 25ug / ml was added to a six-well plate, and cultured for 4 hours and 24 hours, respectively. Afterwards, remove the medium, wash the cells with PBS 3 times, then add 4% paraformaldehyde solution to the culture dish, and wait for 20 minutes. Cells were then rinsed again with PBS to remove excess paraformaldehyde, DAPI was added to the dish for nuclear staining, and waited 3 min. Finally, the cells were washed with PBS to remove excess DAPI, and the cells were imaged with a laser confocal microscope. The results showed that the three polymer drug micelles could be well absorbed by the cells, and the drug concent...

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Abstract

The invention designs a porphyrin-containing acid-responsive acetal polymer nano-drug for improving the photodynamic therapy effect. The preparation method comprises the following steps: (1) synthesizing a hydrophobic tetraphenylporphyrin acrylate monomer and a hydrophobic acetal acrylate monomer, (2) firstly synthesizing a hydrophilic poly(oligo(ethylene glycol)methyl ether methacrylate) (POEGMA)chain segment as a macromolecular RAFT reagent through RAFT polymerization, (3) further copolymerizing a hydrophobic tetraphenylporphyrin acrylate monomer and a hydrophobic acetal acrylate monomer bytaking POEGMA as a hydrophilic chain segment through an RAFT polymerization method to construct an amphiphilic polymer, and (4) carrying out self-assembly on the amphiphilic polymer through a dialysis method to construct a nano-micelle, wherein hydrophobic porphyrin and acetal monomers form an inner core of the nano-micelle, and hydrophilic POEGMA forms a shell of the nano-micelle. In a weakly acidic environment of cancer cells, an acetal structure of the drug is hydrolyzed to form a hydrophilic structure, and micelles absorb water to expand, so that the distance between porphyrins is increased, the problem that the porphyrins are easy to gather and quench is effectively solved, and the photodynamic therapy effect is improved.

Description

technical field [0001] The invention belongs to the field of biomedicine, in particular to the development of a porphyrin-containing acid-responsive acetal polymer nano-medicine, which is used to improve the effect of photodynamic therapy. Background technique [0002] Cancer is the leading cause of death in the world today. The traditional cancer treatment method is a combination of chemotherapy, surgery, radiotherapy and immunotherapy, which has great side effects. In recent years, cancer photodynamic therapy has entered people's field of vision. The basic principle of photodynamic therapy for tumors is to use photosensitizers to generate singlet oxygen and other reactive oxygen species (ROS) under the irradiation of light to kill tumor cells. Due to the use of non-surgical intervention methods, and the ROS produced are limited to radiation Therefore, it has less side effects and better tumor cell killing effect, especially for the elderly, weak or immune system deficien...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00A61K41/00A61K47/58A61P35/00
CPCA61K41/0071A61K47/58A61P35/00C08F293/005C08F2438/03
Inventor 曹红亮许倍坚罗耀钦许雨诗许煊钟晟
Owner EAST CHINA UNIV OF SCI & TECH
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