A redox-responsive hyperbranched polyprodrug nanomicelle and its preparation method and application

A hyperbranched polymer and nanomicelle technology, which is applied in the field of biomedical materials, can solve problems such as increased blood circulation time, and achieve the effects of low cytotoxicity, good stability, and long blood circulation time.

Active Publication Date: 2021-04-27
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, hyperbranched polymers lead to a dramatic increase in blood circulation time compared to their linear counterparts due to their increased chain flexibility and deformability

Method used

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  • A redox-responsive hyperbranched polyprodrug nanomicelle and its preparation method and application
  • A redox-responsive hyperbranched polyprodrug nanomicelle and its preparation method and application
  • A redox-responsive hyperbranched polyprodrug nanomicelle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the synthesis of curcumin-SS-methacrylate

[0061] Take 444 mg of compound 1 (2 mmol) and 0.7 mL of N,N-diisopropylethylamine (DIPEA, 4 mmol) and dissolve in 50 mL of anhydrous tetrahydrofuran (THF). Dissolve 297 mg of triphosgene in 5 mL of anhydrous THF and add it dropwise to the above solution in an ice bath. After reacting for 3 hours, remove the insoluble matter by suction filtration. Take 736 mg of curcumin (2 mmol) and 0.7 mL of DIPEA and dissolve it in 10 mL of anhydrous THF, add the above-mentioned suction-filtered solution to the solution dropwise in an ice bath, and react overnight. After the reaction, first spin dry THF, add ethyl acetate to dissolve, wash with 0.1M dilute hydrochloric acid two to three times, then wash with water two to three times, take the upper organic phase, add anhydrous magnesium sulfate to remove water , filtered, and then the ethyl acetate was spin-dried to obtain a crude product. The crude product was passed through...

Embodiment 2

[0066] Example 2: Synthesis of Poly(ACPP-SS-CUR)

[0067] Take 259mg curcumin-SS-methacrylate (0.42 mmol), 19.64mg ACPP (2-((2-(acryloyloxy)-ethyl)-disulfanyl)ethyl 4-cyano-4 -(((Propylthiocarbonylthiocarbonyl)-thio)pentanoate)) (0.042mmol) and 1.37mg AIBN (azobisisobutyronitrile, 0.0084 mmol) to a round bottom flask, add 1mL DMSO solution Dissolve, then freeze and pump in liquid nitrogen for 30 minutes, thaw again, pass argon gas for 2-3 minutes, and then freeze and pump in liquid nitrogen for 30 minutes; repeat the above freezing and pumping process for 3 times; react the solution in an oil bath at 90°C After 30h, cool. The above solution was added dropwise to ether to precipitate, centrifuged, and the precipitate was collected. Add 2-3 mL of tetrahydrofuran to make it dissolve, and then make it precipitate in ether, repeat the precipitation three times, and take the precipitate. The purified precipitate was vacuum-dried for 24 h to obtain a redox-responsive hyperbranched...

Embodiment 3

[0070] Example 3: Synthesis of Poly(ACPP-SS-CUR-OEGMA)

[0071] 50 mg of ACPP-SS-CUR prepared in Example 2, 250 mg of OEGMA and 1.95 mg of AIBN were dissolved in 1.5 mL of DMSO. Then freeze and pump in liquid nitrogen for 30 minutes, thaw again, pass argon gas (2-3 minutes), and freeze and pump in liquid nitrogen for 30 minutes, repeat the above freezing and pumping process for a total of 3 times; After reacting for 30h, it was cooled. The above solution was added dropwise to ether to precipitate, centrifuged, and the precipitate was collected. Add a small amount of dichloromethane to dissolve it, and then make it precipitate in ether, repeat the precipitation three times, and take the precipitate. The purified precipitate was vacuum-dried for 24 h to obtain a redox-responsive hyperbranched polyprodrug Poly (ACPP-SS-CUR-OEGMA).

[0072] Schematic diagram of the redox-responsive hyperbranched polyprodrug Poly (ACPP-SS-CUR-OEGMA) is shown in Figure 5 ; H NMR spectrum, see ...

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Abstract

The invention provides a redox-responsive hyperbranched polyprodrug nano-micelle and its preparation method and application. In the invention, the hydrophobic drug is connected with the disulfide bond that can be cut by high GSH, and then the redox-responsive amphiphilic hyperbranched polyprodrug nano-micelle is synthesized through two-step RAFT polymerization. The redox-responsive hyperbranched polyprodrug nano-micelle of the present invention has the advantages of simple preparation process, good stability, prolonged blood circulation time, improved bioavailability of drugs, and the like. Moreover, the nano-micelle can break under the reducing environment of high GSH concentration in tumor cells, release hydrophobic drugs rapidly, and inhibit the proliferation of tumor cells. The redox-responsive hyperbranched polyprodrug nanomicelles of the present invention provide a new option for tumor therapy.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and mainly relates to a redox-responsive hyperbranched polyprodrug unimolecular micelle and a preparation method and application thereof. [0002] technical background [0003] Chemotherapy is still the most commonly used method in clinical treatment of cancer. Chemotherapy is a treatment method that uses chemical drugs to prevent the proliferation, invasion, and metastasis of cancer cells, and finally kill cancer cells. However, commonly used chemotherapeutic drugs such as paclitaxel and camptothecin are mostly hydrophobic small-molecule drugs, and their poor water solubility makes it difficult to prepare clinically. Moreover, small-molecule drugs have no targeting and extremely low bioavailability. The effective concentration has to be increased in dosage, which will inevitably damage the normal cells of the human body while killing cancer cells, resulting in serious toxic and side effects. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/69A61K47/60A61K31/12A61K31/4745A61K31/337A61P35/00A61P29/00B82Y5/00
CPCA61K31/12A61K31/337A61K31/4745A61K47/60A61K47/6907A61P29/00A61P35/00B82Y5/00
Inventor 翁祖铨汤强黄达
Owner FUZHOU UNIV
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