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A kind of ultrasonic responsive polymer and its nanoparticle, preparation method and application

A nanoparticle and polymer technology, applied in microcapsules, nanocapsules, pharmaceutical formulations, etc., can solve the problems of the body's inflammatory response, large particle size, liposome instability, etc., and achieve sensitive ultrasonic response and small dispersion coefficient , little cytotoxic effect

Active Publication Date: 2022-05-10
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the existing ultrasound-responsive drug carriers include liposomes with ultrasound-responsive microbubbles. The liposomes need to contain an inert gas inside, and then form ultrasound-responsive microbubbles with a first shell on the outside. Ultrasound-responsive microbubbles are formed with the help of an extruder, and the drug forms liposomes with a second shell on the outside, but the prepared liposomes with ultrasonic-responsive microbubbles are unstable and easily degraded by the body, which is more likely to cause Side effects such as the body's inflammatory response; the other is to use short peptides composed of 9 amino acid molecules to assemble ultrasound-responsive nano-microbubbles, and use polyethylene glycol to modify the amino groups of the polypeptides, and the surface of the drug-loaded nanoparticles is carboxylated polyethylene The end of the diol is connected to a new type of short peptide, the connection force is weak, and the process of screening the peptide is complicated, the cost of preparing ultrasonic responsive nano-microbubbles is high, unstable, and the particle size of the nano-carrier is above 500nm, the particle size is large, And it only acts on vascular growth-promoting factors, the scope of action is relatively limited, and ultrasound response verification has not yet been carried out

Method used

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  • A kind of ultrasonic responsive polymer and its nanoparticle, preparation method and application
  • A kind of ultrasonic responsive polymer and its nanoparticle, preparation method and application
  • A kind of ultrasonic responsive polymer and its nanoparticle, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1 synthetic tetrahydropyranyl methacrylate monomer:

[0074] Firstly, 2-tetrahydropyranyl methacrylate monomer (Tetrahydropyranyl methacrylate, THPMA) was synthesized. 2-tetrahydropyran was synthesized from methacrylic acid (MAA) and 3,4-dihydro-2H-pyran (3,4-Dihydro-2H-pyran, DHP) by addition reaction p-Toluenesulfonic acid monohydrate (p-Toluenesulfonic acid monohydrate, TsOH) is added in the reaction system as the catalyst of reaction; Pyridine (Pyridine, Py) is added in the reaction system to make MAA and DHP An addition reaction occurs to produce the THPMA product.

[0075] TsOH, MAA, and Py were weighed and put into a 500mL round bottom flask according to the amount and ratio of each reactant designed in advance, as shown in Table 1, and 160mL of dichloromethane was added as a solvent, and then The measured DHP was slowly and gradually added dropwise to the reaction system at room temperature, and finally the stirring was turned on at a speed of 300 r...

Embodiment 2

[0081] Example 2 Synthesis and kinetics of PDMA-RAFT (poly N, N'-dimethylacrylamide-RAFT macromolecular chain transfer agent):

[0082] RAFT polymerization can obtain a linear polymer with a small dispersion coefficient of the polymer. In the present invention, all polymers are synthesized by RAFT polymerization.

[0083] First, adopt the method for RAFT polymerization, RAFT chain transfer agent (Chain Transfer Agent, CTA) 4-cyano-4-[(dodecylsulfanylthiocarbonyl) sulfanyl] pentanoic acid ([(dodecylsulfanylthiocarbonyl) )sulfanyl]pentanoic acid, CDSPA) and N,N'-dimethylacrylamide monomer (N,N'-Dimethylacrylamide, DMA) are prepared by copolymerizing the two into PDMA-RAFT (polyN, N'-dimethylacrylamide-RAFT macromolecular chain transfer agent), the synthetic route is as follows, that is, CDSPA and DMA are dispersed in 1,4-dioxane, and then the initiator AIBN is added, at 80°C A copolymerization reaction was carried out to obtain PDMA-RAFT. The proportions of each reaction are s...

Embodiment 3

[0092] The synthesis of embodiment 3 PDMA-co-PTHPMA:

[0093] On the basis of the high-purity ultrasonic response compound THPMA monomer obtained in Example 1, THPMA monomer and N,N',-dimethylacrylamide monomer (N,N'- Dimethylacrylamide, DMA) adopts the method of RAFT polymerization, uses CDSPA chain transfer agent, and AIBN is used as initiator, and the two are prepared by copolymerization into PDMA-co-PTHPMA (poly(N,N'-dimethylacrylamide-co-tetrafluoroethylene Hydropyranyl methacrylate)), the specific reaction equation is shown in the following synthetic route. Subsequent ultrasonic response tests of THPMA and PDMA-co-PTHPMA polymers were carried out separately.

[0094] The synthetic route is as follows:

[0095]

[0096] In the process of synthesizing PDMA-co-PTHPMA using the RAFT polymerization method, according to the proportion of each component calculated in advance, as shown in Table 3, since the purchased DMA contains the polymerization inhibitor p-methoxyphenol...

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Abstract

The invention relates to an ultrasonic responsive polymer and its nanoparticle, preparation method and application, and specifically discloses an ultrasonic responsive polymer, the polymer is selected from poly(N,N'-dimethylacrylamide- b‑tetrahydropyranyl methacrylate) diblock copolymer, or poly(N,N'‑dimethylacrylamide‑co‑tetrahydropyranyl methacrylate) random copolymer. Also disclosed is an ultrasound-responsive nanoparticle prepared by the above-mentioned ultrasound-responsive polymer. The ultrasonic response of the nanoparticles of the invention is sensitive, the process for preparing the nanoparticles is simple, the cost is low, the cytotoxicity is small, and the universality is great.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and specifically discloses an ultrasonic responsive polymer and its nanoparticle, a preparation method and an application. Background technique [0002] At present, in the field of biological and new medical technology, the polymer nanoparticles that have been applied cannot achieve fast and fully effective controllable drug delivery and release, because most endogenous stimuli (glutathione, pH gradient, active oxygen gradient , enzyme concentration, etc., and combinations thereof) will be largely depleted during drug release. Therefore, stimuli-responsive polymer nanoparticles to select exogenous stimuli to achieve controllable drug delivery and release have better practical controllability and greater advantages in tumor chemotherapy. At present, researchers have found that the feasible exogenous stimuli sources that can be used for stimuli-responsive polymer nanoparticles include te...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F220/28C08F220/54A61K9/51A61K47/32
CPCC08F293/005C08F220/281A61K47/32A61K9/5138C08F2438/03C08F220/54
Inventor 耿晋连前进张一川林善梦
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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