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A stimuli-responsive multifunctional nanovesicle drug delivery system for targeting and fluorescent tracking

A stimuli-responsive, fluorescent tracking technology, applied in the field of nano-biomedical materials, to solve the inefficiency, achieve rapid release, and avoid the modification process.

Active Publication Date: 2022-07-22
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research on activatable stimuli-responsive supramolecular nano-drug delivery systems constructed using dicyanomethylene-4H-pyran chromophores is still focused on loading fluorescent drugs, for the visual delivery of weakly fluorescent or non-fluorescent drugs There is still a gap in the research, so it is of great significance to construct a multifunctional nanovesicle drug delivery system with targeted delivery, controlled release and fluorescent tracking

Method used

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  • A stimuli-responsive multifunctional nanovesicle drug delivery system for targeting and fluorescent tracking
  • A stimuli-responsive multifunctional nanovesicle drug delivery system for targeting and fluorescent tracking
  • A stimuli-responsive multifunctional nanovesicle drug delivery system for targeting and fluorescent tracking

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of Compound 1

[0039] The synthetic route of compound 1 is as follows:

[0040]

[0041] Accurately weigh hydroquinone (5.5g, 50mmol) and 1,4-dibromobutane (41.4g, 300mmol) in a round-bottomed flask, add potassium carbonate (43.2g, 200mmol), under nitrogen protection, use Acetone (300 mL) was stirred to dissolve, and then heated to reflux for 48 h. After the reaction was completed, it was poured into ice water to quench, the residue was dissolved in dichloromethane after filtration, and washed with deionized water, the organic phases were combined, and anhydrous MgSO 4 After drying and filtration, the filtrate was distilled under reduced pressure to obtain the crude product, and finally column chromatography separation (eluent: petroleum ether / dichloromethane=1:1, v / v) gave compound 1 as a white solid.

Embodiment 2

[0042] Example 2: Synthesis of Compound 2

[0043] The synthetic route of compound 2 is as follows:

[0044]

[0045] Accurately weigh compound 1 (641.7 mg, 1.69 mmol) and add it to a 100 mL round-bottomed flask, then add paraformaldehyde (65.8 mg, 0.73 mmol) and 1,2-dichloroethane (20 mL), stir for 10 min, and add Boron trifluoride ether (0.271 g, 0.2 mmol) was added to quench with ice water after the reaction for 2 h. After separation and washing with water, the organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The filtrate was distilled under reduced pressure to remove the solvent. Finally, column chromatography separation (eluent: petroleum ether / dichloromethane=1:1, v / v) gave compound 2 as a white solid.

Embodiment 3

[0046] Example 3: Synthesis of Compound 3

[0047] The synthetic route of compound 3 is as follows:

[0048]

[0049] Compound 2 (101 mg, 0.05 mmol) was weighed and dissolved in N,N-dimethylformamide (14 mL), and NaN was added. 3 (36 mg, 0.55 mmol), stirred and heated to 80 °C for 12 h. After the reaction was completed, it was cooled to room temperature, 30 mL of dichloromethane was added, washed with water (3×15 mL), then washed with saturated brine (3×15 mL), and finally dried with anhydrous sodium sulfate, filtered, and then distilled under reduced pressure to remove the solvent, Finally, column chromatography was used to obtain compound 3 as a white solid.

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PUM

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Abstract

The invention relates to a stimuli-responsive multi-functional nanovesicle drug-loading system with targeting and fluorescent tracer, using sugar-functionalized pillar[5]arene with targeting selectivity as the main molecule, and having GSH response-fluorescence display A traced disulfide bridged trimethylamine derivative of dicyanomethylene-4H-pyran was used as a guest molecule, and a GSH-responsive column with targeting and fluorescent tracer was prepared through host-guest interaction [5] Aromatic amphiphilic molecules, form nanovesicles through hydrophilic-hydrophobic interactions in solution, and encapsulate anticancer drugs in the vesicle cavity. Due to the specific binding of mannose to the overexpressed mannose receptor on the surface of breast cancer cells, targeted and selective entry into cancer cells is achieved; at the same time, under the action of a higher concentration of GSH in cancer cells, disulfide bonds are rapidly broken, which promotes vesicles The rupture enables rapid release of anticancer drugs; in addition, dicyanomethylene-4H-pyran acts as a fluorescent chromophore for fluorescent tracking. It can be used for the application of anticancer drug delivery and tracer.

Description

technical field [0001] The invention belongs to the field of nanometer biomedical materials, in particular to a stimuli-responsive multifunctional nanovesicle drug-carrying system with targeting and fluorescent tracing. Background technique [0002] Chemotherapy, as the main means of cancer treatment, still faces the problems of low bioavailability of anticancer drugs (drug water solubility, poor targeting, etc.) and large side effects. By constructing a targeted and stimuli-responsive drug delivery system, the water solubility of anticancer drugs can be improved, the stability of the drug can be improved, the circulation time of the drug in the blood can be effectively prolonged, and the bioavailability of the drug can be improved. Compared with crown ethers, cyclodextrins, calixarenes, and cucurbituril, the fifth-generation supramolecular host compounds, macrocyclic molecular pillararenes, are the most promising candidates for supramolecular vesicles due to their structura...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K9/127A61K49/00A61K45/00A61K47/22A61P35/00A61K47/69
CPCA61K9/1271A61K9/1277A61K49/0021A61K47/22A61K49/0084A61K45/00A61P35/00A61K47/6949
Inventor 裴志超晁爽黄佩裴玉新沈紫嫣
Owner NORTHWEST A & F UNIV
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