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PH/reducing double-sensitive carrier material formed by Cys, derivative of Cys and polyester polymer as well as preparation method and application of pH/reducing double-sensitive carrier material

A polymer and sensitive technology, applied in the field of functional polymer materials and biomedicine, can solve the problems of poor targeting, poor biological safety, poor stability of systemic circulation, etc., to reduce adverse reactions, improve bioavailability, and excellent anti-tumor effect Effect

Active Publication Date: 2019-01-18
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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/reducing double-sensitive carrier material formed by Cys, derivative of Cys and polyester polymer as well as preparation method and application of pH/reducing double-sensitive carrier material
  • PH/reducing double-sensitive carrier material formed by Cys, derivative of Cys and polyester polymer as well as preparation method and application of pH/reducing double-sensitive carrier material
  • PH/reducing double-sensitive carrier material formed by Cys, derivative of Cys and polyester polymer as well as preparation method and application of pH/reducing double-sensitive carrier material

Examples

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 / reducing double-sensitive carrier material formed by Cys, a derivative of Cys and a polyester polymer as well as a preparation method and application of the pH / reducing double-sensitive carrier material. According to the preparation method, a novel pH / reducing double-sensitive polymer containing imine bonds and disulfide bonds is successfully prepared from an aldehydepolyester polymer and Cys containing disulfide bonds or a derivative of Cys, and a nanp-carrier capable of delivering anti-tumor drugs in a targeted manner is successfully prepared; and different hydrophilic and hydrophobic drugs can be physically packaged by virtue of the interaction of hydrophilic and hydrophobic effects, and a uniform-particle and stable environmental double-response nano-medicine carrying system is formed. In a tumor cell environment, a double-sensitive polymer nano-particle can be rapidly disintegrated, and a carried drug can be rapidly released, the whole system has verygood biosecurity, biodegradability and long-cycle stability and has the characteristics of being capable of efficiently targeting tumors and inhibiting the growth of tumor cells; and besides, the preparation method is simple and has relatively good application prospects in the field of biological medicine.

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 Applications(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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