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Ph/reduction double-sensitive carrier material formed by cys and its derivatives and polyester polymer and its preparation method and application

A polymer and sensitive technology, which is applied in the field of functional polymer materials and biomedicine, can solve the problems of poor biological safety, poor circulation stability, poor targeting, etc., and achieve short reaction cycle, excellent biological safety and few reaction steps Effect

Active Publication Date: 2021-06-29
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is to overcome the defects and deficiencies of the above-mentioned prior art, and provide a pH / reduction dual-sensitive carrier material formed by Cys and its derivatives and polyester polymers, so that the positioning of drugs in tumor cells can be achieved. Controlled release, the whole system has good biological safety, biodegradability and long-term circulation stability, and has the characteristics of efficient tumor targeting and efficient inhibition of tumor cell growth, which can effectively solve the problem of poor systemic circulation stability of nano-drug carriers, Many problems such as poor targeting and poor biological safety

Method used

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  • Ph/reduction double-sensitive carrier material formed by cys and its derivatives and polyester polymer and its preparation method and application
  • Ph/reduction double-sensitive carrier material formed by cys and its derivatives and polyester polymer and its preparation method and application
  • Ph/reduction double-sensitive carrier material formed by cys and its derivatives and polyester polymer and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0112] Synthesis of the polyester polymer PCL-CHO of embodiment 1 formylation

[0113] 1, the synthetic of the polyester polymer PCL-CHO of aldehydization, comprises the following steps:

[0114] (1) Polycaprolactone (PCL 2K ) (4.03g, 2.01mmol), 4-chlorobenzoic acid (p-CBA) (0.82g, 5.46mmol) and 4-dimethylaminopyridine (DMAP) (0.33g, 0.27mmol) were blended in a 50mL round bottom In the flask, after adding 30mL of anhydrous dichloromethane, place it in a cold trap, control the temperature at 0°C, add dicyclohexylcarbodiimide (DCC) (1.34g, 6.51mmol) under nitrogen protection environment, and set the temperature at 0°C Stir for 24h to obtain an aldylated polyester product;

[0115] (2) after the obtained product is rotary evaporated, pass through silica gel column chromatography, first use the dichloromethane / acetone of volume ratio 5:1 as eluent elution, remove by-product DCU; / methanol was used as the eluent for purification, and the product was further purified to finally o...

Embodiment 2

[0121] Embodiment 2 has the synthesis of pH / reduction double sensitive polymer Cys-PCL

[0122] 1. The synthesis of the polymer Cys-PCL with pH / reduction double sensitivity comprises the following steps:

[0123] (1) Put L-cystine dimethyl ester dihydrochloride (Cys) (0.34g, 1.01mmol) and aldylated polyester polymer PCL-CHO (2.05g, 1.02mmol) in a 50mL circle In the bottom flask, add 30mL ethanol, reflux overnight, and after rotary evaporation, the resulting product is purified by Sephadex LH-20 gel chromatography with methanol as the eluent, and finally a yellow waxy solid is obtained, which is pH / reduction The double-sensitive polymer Cys-PCL has a reaction yield of 86.7%.

[0124] The structural formula of gained polymer Cys-PCL is as shown in formula (I):

[0125]

[0126] 2. Results

[0127] The H NMR spectrum of the polymer Cys-PCL is as image 3 shown. Depend on image 3 It can be seen that the signal at ~10.12ppm corresponds to the disappearance of the proton a...

Embodiment 3

[0129] Example 3 Preparation, Characterization, In Vitro Drug Release and Cell-to-Pair Experiment of Cys-PCL@PTX Drug-loaded Nanoparticles

[0130] 1. Prepare Cys-PCL@PTX drug-loaded nanoparticles by the following nanoprecipitation method, including the following steps:

[0131] (1) 10mg Cys-PCL, 2.5mg DSPE-PEG 2K , 2mg of PTX were dissolved in 1.0mL DMSO together as the oil phase, and under stirring, the oil phase was added dropwise to 20mL of PBS solution at a rate of 0.05mL / sec to obtain a drug-loaded nanoparticle solution with uniform and stable particle size;

[0132] (2) Concentrate the obtained nanoparticle solution by ultrafiltration at 2500 rpm, dilute to 2 mL, and freeze-dry to obtain Cys-PCL@PTX drug-loaded nanoparticles.

[0133] 2. Characterize the obtained Cys-PCL@PTX drug-loaded nanoparticles, and the results of in vitro drug release and cytotoxicity are as follows:

[0134] (1) As detected by DLS, the particle size of the drug-loaded nanoparticles of the pres...

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Abstract

The invention discloses a pH / reduction double-sensitive carrier material formed of Cys and its derivatives and polyester polymer, as well as its preparation method and application. The present invention uses the aldylated polyester polymer and Cys containing disulfide bonds or its derivatives as raw materials to successfully prepare a pH / reduction dual-sensitive new polymer with imino bonds and disulfide bonds, and successfully constructs Nano-carriers for targeted delivery of anti-tumor drugs; through hydrophilic-hydrophobic interactions, drugs with different hydrophilicity and hydrophobicity can be physically encapsulated to form a uniform particle size and stable environmental dual-responsive nano-drug loading system. In the environment of tumor cells, the dual-sensitive polymer nanoparticles can be quickly disintegrated and the drug-loaded drugs can be released rapidly. The whole system has good biological safety, biodegradability and long-term circulation stability, and has high-efficiency tumor targeting and It has the characteristics of effectively inhibiting the growth of tumor cells; in addition, its preparation method is simple, and it has good application prospects in the field of biomedicine.

Description

technical field [0001] The invention belongs to the technical fields of functional polymer materials and biomedicine. More specifically, it relates to a pH / reduction dual-sensitive carrier material formed of Cys and its derivatives and polyester polymer, as well as its preparation method and application. Background technique [0002] Cancer is one of the major diseases that endanger human health and cause human death. Clinically, advanced cancer patients are mainly treated with chemical drugs, but small-molecule anti-cancer drugs are easily destroyed in the body due to their poor selectivity, short half-life, and large toxic and side effects. It is inevitable to cause damage to normal cells, and the safe and effective delivery of small molecule anticancer drugs into the body is an urgent problem to be solved. With the interdisciplinary development of nanotechnology and various disciplines, the combination of traditional small molecule anti-tumor drugs and nanotechnology to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/91A61K9/51A61K45/00A61K31/519A61K47/34A61P35/00
CPCA61K9/5153A61K31/519A61K45/00A61K47/34A61P35/00C08G63/912
Inventor 吴钧康洋张鑫宇
Owner SUN YAT SEN UNIV
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