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Preparation and application of a photosensitizer composite nano-functional material

A multifunctional, photosensitizer technology, applied in the fields of biomedicine and photodynamic therapy, can solve the problems of poor water solubility of cercosporin, undeveloped photodynamic therapy function, lack of targeting, etc., to reduce the leakage of photosensitizer, Facilitating real-time imaging and increasing the effect of release

Active Publication Date: 2019-04-23
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, similar to other photosensitizers, cercosporin is poorly soluble in water and lacks targeting, and its photodynamic therapy function has not yet been developed. At present, there are no reports about using it as a photosensitizer for photodynamic therapy.

Method used

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  • Preparation and application of a photosensitizer composite nano-functional material
  • Preparation and application of a photosensitizer composite nano-functional material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: the preparation of bromorhodamine B initiator

[0040] Weigh 15.52g (25.00mmol) of ethylene glycol and 1.01g (10.00mmol) of triethylamine in a 100mL conical flask, stir, ice-water bath to 0 ℃, add dropwise under nitrogen atmosphere dissolved 1.20mL (10.00mmol) of 2 -bromoisobutyryl bromide, then slowly warmed to room temperature and magnetically stirred for 3 hours. The reacted solution was quenched by adding 100 mL of deionized water, and then extracted with dichloromethane (100 mL×3). The collected organic phases were extracted with deionized water (100 mL×3). An appropriate amount of anhydrous magnesium sulfate was added to the organic phase obtained by extraction and dried for 12 hours. After filtration, rotary evaporation was performed to obtain an oily crude product, which was distilled under reduced pressure (85° C., 30 mTorr) to obtain a colorless viscous product, hydroxyethyl isobromobutyrate.

[0041] Take 4.81g (10.00mmol) rhodamine B, 2.90g ...

Embodiment 2

[0042] Example 2: 3-azido-2-hydroxypropyl methacrylate GMA-N 3 preparation

[0043] Dissolve 3.71 g (57.00 mmol) sodium azide, 3.81 g (45.20 mmol) sodium bicarbonate in 60 mL tetrahydrofuran / water (5:1 v v -1 ), slowly added 5.42 g (37.80 mmol) of glycidyl methacrylate, and reacted at room temperature for 48 hours. After the insoluble salts were removed by filtration, the solvent was removed by rotary evaporation, the obtained concentrate was extracted twice with dichloromethane, the organic phase obtained was dried and filtered with anhydrous magnesium sulfate, and the solvent was removed by rotary evaporation. Ethyl acetate=9:1) was isolated to obtain 3-azido-2-hydroxypropyl methacrylate. For specific methods, please refer to the literature (Polymer Chemistry, 2015, 6, 3875-3884; Soft Matter, 2009, 5, 4788-4796).

Embodiment 3

[0044] Example 3: Rhodamine B covalently linked poly(N,N-dimethylaminoethyl methacrylate) and poly(3-azido-2-hydroxypropyl methacrylate) copolymer (RhB-PDMAEMA42- c-PGMA62-N 3 ) preparation

[0045] Accurately weigh 70.0mg (0.10mmol) of bromorhodamine B initiator, 484.0mg (2.75mmol) of monomer DMAEMA and 1.01g (5.50mmol) of compound 3-azido-2-hydroxypropyl methacrylate and added to 25mL In a round-bottomed flask, dissolve with 2 mL of tetrahydrofuran, and pass argon for 30 minutes to remove oxygen in the flask. The monomer DMAEMA needs to remove the stabilizer in advance, that is, the crude DMAEMA is quickly passed through the basic alumina column. Under nitrogen protection, 18.9 mg (0.10 mmol) of CuBr and PMDETA (28 μL, 0.10 mmol) were added successively, the flask was sealed, and the reaction was carried out at room temperature for 8 hours under nitrogen protection. After the reaction was completed, tetrahydrofuran (10 mL) was added to the reaction solution, and the react...

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Abstract

The invention discloses preparation and application of a photosensitizer composite nanometer multifunctional material, and belongs to the technical field of photodynamic therapy and the field of biomedicine. The photosensitizer composite nano-functional material provided by the present invention is prepared by self-assembly of cercosporin and an acid-sensitive copolymer multi-functional material with liver tumor cell targeting and traceability, wherein the acid-sensitive copolymer multi-functional material It may be galactose-modified rhodamine B covalently bonded poly-N,N-dimethylaminoethyl methacrylate and poly-3-azido-2-hydroxypropyl methacrylate copolymer. The photosensitizer composite nano-multifunctional material of the present invention can specifically recognize liver tumor cells and be endocytosed into cells through the interaction of galactose-asialoglycoprotein receptors, and can trigger the release of photosensitizer Cercospora under acidic pH conditions factors to exert the efficiency of photodynamic therapy. The invention has a good application prospect in the targeted photodynamic therapy of tumor cells.

Description

technical field [0001] The invention relates to the preparation and application of a novel photosensitizer composite nano-multifunctional material, in particular to a cercosporin, which is further encapsulated into an acid-sensitive copolymer with liver tumor cell targeting and traceability The invention relates to the preparation of a novel photosensitizer composite nano-multifunctional material, a preparation method and an application thereof, belonging to the technical field of photodynamic therapy and the field of biomedicine. Background technique [0002] Photodynamic therapy is a non-invasive new technology for the treatment of tumor diseases. By incubating photosensitizers and cooperating with specific light irradiation, singlet oxygen with strong oxidizing ability can be generated, so as to achieve the purpose of killing tumor tissues and cells. After years of development, photodynamic therapy has become more and more widely used, and its mechanism of action has beco...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/69A61K47/58A61K47/54A61K41/00A61K49/00A61P35/00
CPCA61K41/0057A61K49/0041A61K49/0054A61K49/0082C08F220/36C08F220/34A61P35/00A61K31/357C08F2/50A61K47/58A61K49/0078A61K9/1075A61K47/32
Inventor 尹健胡静叶舟饶义剑
Owner JIANGNAN UNIV
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