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Acid-responsive hyperbranched poly-prodrug nano-micelle as well as preparation method and application thereof

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, improved bioavailability and stability, and good stability.

Active Publication Date: 2022-04-05
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • Acid-responsive hyperbranched poly-prodrug nano-micelle as well as preparation method and application thereof
  • Acid-responsive hyperbranched poly-prodrug nano-micelle as well as preparation method and application thereof
  • Acid-responsive hyperbranched poly-prodrug nano-micelle as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of an acid-responsive hyperbranched polyprodrug nanomicelle

[0055] The hydrophobic drug is prednisone (PNS), the compound 1 is VEA, the RAFT chain transfer agent is MTDDA (4-methyl-9-thioxo-3,5-dioxa-8,10-dithiatridecy acrylate), the water-soluble monomer D is OEGMA and the catalyst is azobisisobutyronitrile (AIBN).

[0056] 1. Synthesis of PNS-acetal-methacrylate

[0057] Prednisone PNS (1mmol) was dissolved in 20mL of anhydrous tetrahydrofuran to prepare solution 1, PPTS (pyridine p-toluenesulfonate 1.3g mmol) was dissolved in 1mLDMSO, and then added to solution 1, in ice bath, N 2 Under protection, 5 mL of anhydrous tetrahydrofuran containing compound 1 (VEA, ethylene-vinyl acetate copolymer) (2 mmol) was added dropwise, and then allowed to rise naturally to room temperature to react overnight. Add 0.5g K 2 CO 3 Terminate the reaction, stir for 30 minutes and filter with a G5 sand core funnel and filter paper. The filtrate was collected,...

Embodiment 2

[0070] Example 2: Preparation of an acid-responsive hyperbranched polyprodrug nanomicelle

[0071] The hydrophobic drug is simvastatin (SIM), the compound 1 is VEA, the RAFT chain transfer agent is MTDDA, the water-soluble monomer D is OEGA and the catalyst is azobisisobutyronitrile (AIBN). Specific steps are as follows:

[0072] 1. Synthesis of SIM-acetal-methacrylate:

[0073] Simvastatin (SIM) (1mmol) was dissolved in 20mL of anhydrous tetrahydrofuran to prepare solution 1, PPTS (pyridine p-toluenesulfonate 1.3g mmol) was dissolved in 1mLDMSO, and then added to solution 1, under ice bath and N2 protection 5 mL of anhydrous tetrahydrofuran containing compound 1 (VEA, ethylene-vinyl acetate copolymer) (2 mmol) was added dropwise, and then allowed to rise to room temperature to react overnight. Add 0.5g K 2 CO 3 Terminate the reaction, stir for 30 minutes and filter with a G5 sand core funnel and filter paper. The filtrate was collected, and the solvent and volatile matte...

Embodiment 3

[0079] Example 3: Preparation of an acid-responsive hyperbranched polyprodrug nanomicelle

[0080] The hydrophobic drug is coupled with epicatechin (EC), compound 1 as VEA, RAFT chain transfer agent as MTDDA, water-soluble monomer D as poly(ethylene glycol) methyl ether methacrylate (PEGMA) and catalyst. Azobisisobutyronitrile (AIBN).

[0081] 1. Synthesis of EC-acetal-methacrylate: Dissolve epicatechin EC (1mmol) in 20mL anhydrous tetrahydrofuran to make solution 1, PPTS (pyridine p-toluenesulfonate 1.3g mmol) is dissolved in 1mLDMSO, After adding solution 1, 5 mL of anhydrous tetrahydrofuran containing compound 1 (VEA, ethylene-vinyl acetate copolymer) (2 mmol) was added dropwise in an ice bath under N2 protection, and then allowed to rise to room temperature to react overnight. Add 0.5g K 2 CO 3 Terminate the reaction, stir for 30 minutes and filter with a G5 sand core funnel and filter paper. The filtrate was collected, and the solvent and volatile matter were removed ...

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Abstract

The invention provides an acid-responsive hyperbranched poly-prodrug nano-micelle as well as a preparation method and application thereof. The preparation method comprises the following steps: firstly linking a hydrophobic drug with an organic compound through an acid-sensitive acetal bond, and then synthesizing the amphiphilic hyperbranched poly-prodrug nano-micelle with acid responsiveness through a two-step reversible addition fragmentation transfer (RAFT) polymerization reaction. The acid-responsive hyperbranched poly-prodrug nano-micelle disclosed by the invention is simple in preparation process and has the advantages of being good in stability, prolonging the blood circulation time and improving the bioavailability of the drug. In addition, the nano-micelle can be broken in a low-pH environment in an inflammation or tumor microenvironment, a hydrophobic drug is rapidly released, and disease development is inhibited. The acid-responsive hyperbranched poly-prodrug nano-micelle disclosed by the invention provides a new choice for treating inflammatory diseases and tumors.

Description

technical field [0001] The invention belongs to the field of biomedical materials, and mainly relates to an acid-responsive hyperbranched polyprodrug unimolecular micelle and its preparation method and application. [0002] technical background [0003] Nowadays, the clinical drug delivery method for the treatment of inflammatory diseases or cancer is still oral or injection of free small molecule drugs. For example, the commonly used anticancer drugs paclitaxel, camptothecin, etc., and the anti-inflammatory drugs dexamethasone, prednisone, ibuprofen, etc. are mostly hydrophobic small molecule drugs, and their poor water solubility makes it difficult to prepare clinically, and the small molecule drugs have no target tropism and extremely low bioavailability, clinically in order to achieve the effective concentration at the lesion site, the dose has to be increased, which will inevitably damage the normal cells of the human body while treating the disease, resulting in serious...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00A61K47/69A61K45/00A61K47/58A61K31/573A61K31/366A61K31/353A61P29/00A61P35/00
Inventor 翁祖铨牟金艺黄达
Owner FUZHOU UNIV
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