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β-cyclodextrin-based 21-arm star polymer, preparation method thereof, and unimolecular micelle/gold nanoparticle hybrid material

A star-shaped polymer and cyclodextrin technology, which is applied in the preparation of X-ray contrast agents, can solve the problems of restricting biomedical use, producing small molecular by-products, etc., and achieves high efficiency reduction and stability, small particle size, and easy availability of raw materials. Effect

Inactive Publication Date: 2019-08-27
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are some shortcomings in this method, such as the production of small molecular by-products during the reaction, which restricts the subsequent biomedical and medical applications.
At the same time, scientific issues such as how micelles and polymer structures affect the distribution of AuNPs, and the regulation mechanism of particle size and morphology remain to be further studied.

Method used

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  • β-cyclodextrin-based 21-arm star polymer, preparation method thereof, and unimolecular micelle/gold nanoparticle hybrid material
  • β-cyclodextrin-based 21-arm star polymer, preparation method thereof, and unimolecular micelle/gold nanoparticle hybrid material
  • β-cyclodextrin-based 21-arm star polymer, preparation method thereof, and unimolecular micelle/gold nanoparticle hybrid material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1: Amphiphilic 21-arm star polymer β-CD-(PDMA-b-PHEMA-b-PPEGMA) 21 (structural formula is as shown in formula (1), wherein x:y:z=8:10:8) preparation

[0069] (1) Preparation of macromolecular initiator β-CD-(Br) 21 : Take a 250mL three-neck flask, add a stirrer, weigh β-CD (4.54g, 4mmol) and add it to the reaction flask, add the solvent anhydrous THF (120mL) and then pass argon gas for 10 minutes. After sealing the flask, add TEA (25mL, 180mmol ) into the flask, cooled to 0° C. with an ice-water bath, and then 2-bromoisobutyryl bromide (BIBB) (22.5 mL, 180 mmol) was added dropwise into the flask with a syringe. React at 0°C for 5 hours and then at room temperature for 24 hours. Remove the solvent by rotary evaporation, add 100mL dichloromethane to dissolve, transfer the reaction solution into a separatory funnel, and successively add 200mL water, 200mL 0.5M NaHCO 3 solution and 200mL water extraction, organic phase with anhydrous MgSO 4 After drying and filt...

Embodiment 2

[0080] Example 2: Amphiphilic 21-arm star polymer β-CD-(PDMA-b-PHEMA-b-PPEGMA) 21 (structural formula is shown in formula (1), wherein x:y:z=4:15:25) preparation

[0081] (1) Preparation of macromolecular initiator β-CD-(Br) 21 : Take a 250mL three-necked flask, add a stirrer, weigh β-CD (4.54g, 4mmol) and add it to the reaction flask, add the solvent anhydrous THF (120mL) and then flow argon gas for 10 minutes, seal the flask and mix TEA (11.6mL, 84mmol) into the flask, cooled to 0°C with an ice-water bath, and then 2-bromoisobutyryl bromide (10.5mL, 84mmol) was added dropwise into the flask with a syringe. React at 0°C for 4 hours and then at room temperature for 48 hours. Remove the solvent by rotary evaporation, add 100mL dichloromethane to dissolve, transfer the reaction solution into a separatory funnel, and successively add 200mL water, 200mL 0.5M NaHCO 3 solution and 200mL water extraction, organic phase with anhydrous MgSO 4 After drying and filtering, the solvent...

Embodiment 3

[0088] Example 3: Amphiphilic 21-arm star polymer β-CD-(PDMA-b-PHEMA-b-PPEGMA) 21 (structural formula is shown in formula (1), wherein x:y:z=20:4:5) preparation

[0089] (1) Preparation of macromolecular initiator β-CD-(Br) 21 : Get a 250mL three-neck flask, add a stirring bar, weigh β-CD (4.54g, 4mmol) and add in the reaction flask, add solvent anhydrous dichloromethane (120mL) and lead to argon for 10 minutes, seal the flask and mix TEA (46.4 mL, 336mmol) into the flask, cooled to 0°C with an ice-water bath, and then 2-bromoisobutyryl bromide (42mL, 336mmol) was added dropwise into the flask with a syringe. React at 0°C for 2 hours and then at room temperature for 48 hours. Remove the solvent by rotary evaporation, add 100mL dichloromethane to dissolve, transfer the reaction solution into a separatory funnel, and successively add 200mL water, 200mL 0.5M NaHCO 3 solution and 200mL water extraction, organic phase with anhydrous MgSO 4 After drying and filtering, the solven...

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Abstract

The invention belongs to the technical field of biomedical polymer materials, and discloses a β-cyclodextrin-based 21-arm star polymer and a preparation method thereof, and a monomolecular micelle / gold nanoparticle hybrid material system based on the same and imaging applications. The polymer has a structure shown in the following formula (1), wherein, x=4-20, y=4-15, z=5-25. The polymer is easy to adjust the ratio of each block, and can prepare unimolecular micelles with stable structure and small particle size. The present invention also provides the in-situ preparation of gold nanoparticles with small particle size and good stability based on the above-mentioned polymer unimolecular micelle system to realize in vitro CT imaging and provide a valuable preparation technology for future integrated diagnosis and treatment systems.

Description

technical field [0001] The invention belongs to the technical field of biomedical polymer materials, in particular to an amphiphilic β-cyclodextrin-based 21-arm star polymer and a preparation method thereof, and a monomolecular micelle / gold nanoparticle hybrid based on the same. Chemical material systems and imaging applications. Background technique [0002] With the rapid development of nanomedicine, polymer carriers have made remarkable progress in addressing the defects of small molecule anticancer drugs (poor water solubility, poor pharmacokinetics, serious side effects, etc.). Among them, there are many studies on linear polymers and their self-assembled micelle carriers, but since self-assembled micelles exist in thermodynamic equilibrium with individual block copolymer molecular chains in aqueous media, they are a "dynamic" aggregation-stable structure. It is easily destroyed by shear force, dilution, temperature, pH and salt effect, resulting in sudden drug release...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/34C08F220/28C08J3/07A61K49/04
CPCA61K49/04C08F293/005C08J3/07C08F2438/01C08J2353/00C08F220/286C08F220/34C08F220/281
Inventor 林文静易国斌俎喜红薛兆麟
Owner GUANGDONG UNIV OF TECH
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