Preparation method and application A-D-A type organic molecule/amphiphilic polymer composite nanoparticles

A composite nanoparticle, A-D-A technology, applied in non-active ingredients medical preparations, active ingredients-containing medical preparations, general/multifunctional contrast agents, etc., to achieve good photochemical properties, good application prospects, good tumor selectivity Effect

Active Publication Date: 2020-03-24
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Use amphiphilic polymers to coat bifunctional photosensitizers to form water-soluble composite nanoparticles, which overcomes the shortcomings of poor water solubility of organic small molecules and cannot be directly applied in the field of biomedicine, improves its water solubility and tissue distribution, and improves tumor phototherapy. curative effect

Method used

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  • Preparation method and application A-D-A type organic molecule/amphiphilic polymer composite nanoparticles
  • Preparation method and application A-D-A type organic molecule/amphiphilic polymer composite nanoparticles
  • Preparation method and application A-D-A type organic molecule/amphiphilic polymer composite nanoparticles

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 1) Synthesis of SM-1

[0045] The schematic diagram of the synthesis of SM-1 is shown in Figure 12 As shown, first add (1)(6-bromo-4,4-bis(2-ethylhexyl)-4H-cyclopentane[2,1-b:3,4-b ']dithiobenzene-2-carbal) (0.2g, 0.392mmol), bis(pinacolate)diboron (0.12g, 0.47mmol), potassium acetate (1.154g, 11.759mmol) and DMSO (4mL) , after purging with nitrogen for 0.5 hours and adding 1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (9.6mg, 1.2×10 - 2 mmol). The mixture was heated to 80° C. and stirred for 8 h. After the reaction, it was naturally cooled to room temperature and washed with water. The aqueous layer was extracted with chloroform, treated with anhydrous sodium sulfate, and then concentrated. The obtained primary product was purified by column chromatography (eluent PE:DCM=6:1, v / v) to obtain 0.17 g (85%) of product (2) as a dark red solid.

[0046] Intermediate (2) (0.3 g, 0.349 mmol) and indenophenone dicyano (3) (0.407 g, 2.1 mmol) were dissolved in ...

Embodiment 2

[0054] 1) Synthesis of SM-1

[0055] The synthesis of SM-1 is shown in Example 1.

[0056] 2) Synthesis of amphiphilic high son AP-2

[0057] Add 150mg BLA-NCA and 0.3mL DMF to a round bottom flask, add 3mL CH 3 -PEG-NH 2 Chloroform solution (303mg), the reaction was carried out at 40°C for 48 hours. After the reaction, the product was precipitated with excess glacial ether and centrifuged.

[0058] 3) Preparation of NPs-2 nanoparticles

[0059] The present invention prepares NPs-2 by nanoprecipitation method, first dissolves 5mgSM-1 in 1mLCHCl 3 , and then the SM-1 solution was slowly and uniformly added dropwise to 50mLAP-2 in DMSO solution (0.5mg / mL). CHCl was then removed under nitrogen flow 3 , to be CHCl 3 After complete removal, the solution was transferred to a dialysis bag (molecular weight cut-off: M W 3.5 kDa) to remove DMSO followed by lyophilization.

Embodiment 3

[0061] 1) Synthesis of SM-1

[0062] The synthesis of SM-1 is shown in Example 1.

[0063] 2) Preparation of NPs-3 nanoparticles

[0064] The present invention adopts the method of nanoprecipitation to prepare NPs-3, at first 5mgSM-1 is dissolved in 1mLCHCl 3 Then, the SM-1 solution was slowly and evenly added dropwise to 50 mL of a DMSO solution of distearoylphosphatidylethanolamine-polyethylene glycol (AP-3) (0.5 mg / mL). CHCl was then removed under nitrogen flow 3 , to CHCl 3 After complete removal, the solution was transferred to a dialysis bag (molecular weight cut-off: M W 3.5 kDa) to remove DMSO followed by lyophilization.

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Abstract

The invention discloses a preparation method and an application of A-D-A type organic molecule/amphiphilic polymer composite nanoparticles, and relates to an application of organic molecules in the field of biological medicines. A non-fullerene receptor with an A-D-A structure, widely used in the organic photovoltaic field, has the unique advantages of easiness in structure adjustment, strong near-infrared light absorption capacity and low fluorescence quantum efficiency, and has the huge potential of being used as a photosensitizer for photo-thermal/photodynamic combined treatment. The organic molecule with the A-D-A structure is coated with an amphiphilic macromolecule to form the water-soluble composite nanoparticles, the composite nanoparticles show a high photothermal conversion efficiency and a high reactive oxygen generation capacity under irradiation of near-infrared laser with a certain wavelength, and mouse in-vivo experiments show that the water-soluble composite nanoparticles have an obvious inhibition effect on tumors. Therefore, the composite nanoparticles have great practical prospects and social values in the field of novel tumor treatment.

Description

technical field [0001] The invention belongs to the technical field of nanomedical materials, and specifically relates to the preparation of an organic molecule / polymer composite nanoparticle with an acceptor-donor-acceptor (A-D-A) structure and its application in tumor photodynamic / photothermal combined therapy. Background technique [0002] At present, malignant tumors have become one of the most serious diseases that threaten human health and cause human death. Compared with traditional tumor treatment methods such as surgery, radiotherapy, and chemotherapy, optical therapy has attracted widespread attention due to its characteristics of convenient operation, non-invasiveness, local selectivity, low drug resistance, and small side effects. Among them, photodynamic therapy (PDT) and photothermal therapy (PTT) are two typical phototherapy methods, and their treatment principles are based on the photochemical reaction of photosensitizers and photothermal agents. After intra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K9/51A61K47/34A61K47/24A61P35/00A61K49/00A61K49/22
CPCA61K41/0052A61K41/0057A61K9/5146A61P35/00A61K49/0002A61K49/0054A61K49/225
Inventor 陆燕贺诤赵琳琳
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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