CN107376019B - Polydopamine polyethyleneimine modifier, preparation method thereof and application thereof in esophageal cancer resistance - Google Patents

Polydopamine polyethyleneimine modifier, preparation method thereof and application thereof in esophageal cancer resistance Download PDF

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CN107376019B
CN107376019B CN201710563646.4A CN201710563646A CN107376019B CN 107376019 B CN107376019 B CN 107376019B CN 201710563646 A CN201710563646 A CN 201710563646A CN 107376019 B CN107376019 B CN 107376019B
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张琨
李敬安
马珊珊
白雨鑫
开昆仑
邢衢
李檀
关方霞
李庆华
张彦婷
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    • A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
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Abstract

The invention provides a polydopamine polyethyleneimine modifier, a preparation method thereof and application thereof in esophageal cancer resistance. The preparation method of the polydopamine polyethyleneimine modifier comprises the following steps: the polyethyleneimine is grafted onto the polydopamine by a michael addition and schiff base reaction. The preparation method is simple and easy to operate, does not need expensive and complicated equipment, and has low process cost and obvious effect. The polydopamine polyethyleneimine modifier can promote apoptosis or necrosis of esophageal cancer cells, has good effect of resisting esophageal cancer, can obviously make up the defects of limited drug-loading amount, insufficient anti-cancer function of a drug-loading coating and the like of a drug-loading esophageal cancer stent, and endows the stent with continuous anti-cancer curative effect.

Description

Polydopamine polyethyleneimine modifier, preparation method thereof and application thereof in esophageal cancer resistance
Technical Field
The invention relates to a polydopamine polyethyleneimine modifier, a preparation method thereof and application thereof in esophageal cancer resistance.
Background
Since frimbeger successfully adopts a self-expandable metal stent to treat malignant esophageal stenosis for the first time in 1983, the stent types for treating esophageal cancer mainly comprise a bare metal stent, a covered stent, a drug-loaded stent, a particle stent and the like through clinical adaptation and improvement. The naked metal stent can not inhibit the growth of tumor cells and the generation of inflammation, and the tectorial membrane stent is selected to effectively prevent the tumor from growing to the cavity, but can not control the tumor growth, the displacement of the stent is easy to occur, and the end part of the stent is easy to cause restenosis. The high surgical level requirements of particle scaffolds and the need for radioactive particle recovery are currently questioned. The problems of the drug-loaded stent are mainly represented in the following two aspects: (1) the drug loading on the surface of the stent is limited, the loading is gradually reduced along with the release of the drug, the effective concentration of the drug is gradually reduced to zero, and finally the function of killing tumor cells is lost; (2) the gradually exposed material substrate can not effectively resist cells, but can promote the growth of tumor cells, myofibroblasts, epithelial cells and the like due to the good cell compatibility of the stent material, which is also an important factor influencing the long-term curative effect of the stent.
Therefore, introducing a functional bottom layer of impedance cells (such as tumor cells, myofibroblasts, epithelial cells) with good stability on the surface of the esophageal stent material and endowing the stent with the functions of continuously inhibiting tumor growth, tissue proliferation and inflammation process are bottleneck problems to be solved urgently in the current esophageal stent development.
Polyethyleneimine (also referred to herein as PEI) is a cytotoxic substance, but it has been reported in the literature that its toxicity is significantly reduced after copolymerization. At present, no patent or other literature is available for reporting that PEI and polydopamine (also referred to as PDA) can be copolymerized to have remarkable esophageal cancer resistance.
Disclosure of Invention
The invention develops a new method, overcomes the prejudice of the prior art, insists on exploring the polyethyleneimine modifier, and finds that the polyethyleneimine modifier of polydopamine has better effect of resisting esophageal cancer.
In one aspect, the invention relates to the use of a polyethyleneimine modifier of polydopamine for the preparation of a promoter for promoting apoptosis or necrosis of esophageal cancer cells, wherein the promoter can be an anti-esophageal cancer drug, such as a pharmaceutical stent.
In another aspect, the present invention relates to a method for preparing a polyethyleneimine modification product of said polydopamine, comprising: the polyethyleneimine is grafted onto the polydopamine by a michael addition and schiff base reaction.
Optionally, the polyethyleneimine for grafting has a molecular weight of 1.8 × 103-7×104E.g. 1.8 × 103、104、2.5×104Or 7 × 104。
Optionally, the polydopamine for grafting is provided in a form deposited on the surface of a stent material, which may be a commonly used tissue engineering material such as stainless steel, nitinol, or magnesium alloy for medical use.
Optionally, the grafting reaction comprises: preparing 0.5-2mg/ml of aqueous solution of polyethyleneimine, and soaking polydopamine in the aqueous solution of polyethyleneimine to perform the grafting reaction.
Optionally, the temperature of the grafting reaction is 20-40 ℃, such as 37 ℃.
Optionally, the grafting reaction time is 0.5 to 3 days, such as 24 hours.
Optionally, the polydopamine is obtained by polymerizing dopamine under the condition of oxygen and pH8-9, the reaction can be directly carried out in the presence of oxygen, and the pH can be 8.5, for example, Tris (Tris hydroxymethyl aminomethane) buffer is used.
Optionally, the mass ratio of dopamine to polyethyleneimine used is 1: 1.
Optionally, the concentration of dopamine is 0.5-2 mg/ml.
Optionally, the polydopamine is prepared by soaking the scaffold material in a dopamine solution at a temperature of 20-30 deg.C, e.g. 250 deg.C, for a period of 0.5-3 days, e.g. 48 hours.
In yet another aspect, the invention relates to a modification made by the foregoing method.
The invention has the following beneficial effects:
under the condition that PEI copolymerization is taught to obviously reduce the effect of PEI in the prior art, the invention is based on the prejudice that a polyethyleneimine modifier is continuously explored, and the unexpected discovery shows that the polyethyleneimine modifier of polydopamine has good roughness and wettability and better anti-esophageal cancer effect, can obviously make up the defects of limited drug-loading amount, insufficient anti-cancer function of a drug-loading coating and the like of a drug-loading esophageal cancer stent, and endows the stent with continuous anti-cancer curative effect. In addition, the preparation method is simple and easy to operate, does not need expensive and complicated equipment, and has low process cost and obvious effect.
Drawings
Fig. 1 is a comparison of the surface atomic force diagram roughness values of the respective samples.
Fig. 2 shows the quantitative results of the amine groups on the surface of each sample (. p. <0.05, mean ± SD, n ═ 3).
FIG. 3 shows the results of the measurement of the surface water contact angle of each sample, which are shown in FIGS. 3-1 to 3-6, respectively.
Detailed Description
The present invention will be described in detail below, and materials or methods used therefor are all conventional ones unless otherwise specified.
The first embodiment is as follows:
the preparation method of the polyethyleneimine modifier of the polydopamine comprises the following steps:
a dopamine polymer film was deposited on the polished stainless steel 317LSS (1cm × 1 cm): dissolving dopamine in a Tris buffer solution with the pH value of 8.5, wherein the concentration of the dopamine is 2mg/ml, immersing the material, performing polymerization deposition for 48 hours at the temperature of 25 ℃, absorbing residual reaction liquid after the reaction is finished, washing unpolymerized molecules with deionized water, and drying to obtain a material (named as a PDA bracket) with a PDA film deposited on the surface for later use;
PEI is grafted on the surface of the dopamine polymer film through Michael addition and Schiff base reaction, wherein the molecular weight is 1.8 × 103DA、1×104DA、2.5×104DA、7×104PEI of DA is dissolved in deionized water, PEI aqueous solution PEI-1, PEI-2, PEI-3 and PEI-4 (named from small to large according to the molecular weight of PEI as a solute) with the concentration of 2mg/ml are prepared in sequence; respectively immersing the PDA support deposited with the dopamine polymer film in the step A into the PEI solution, reacting for 24h at 37 ℃, absorbing residual reaction liquid after the reaction is finished, washing unfixed PEI molecules with deionized water,respectively preparing polydopamine polyethyleneimine modifier scaffolds PDA/PEI-1, PDA/PEI-2, PDA/PEI-3 and PDA/PEI-4 (the PDA/PEI-1 refers to the scaffold obtained by the reaction of the PDA scaffold and a PEI-1 solution, and the rest is analogized).
Second, performance testing
And (3) respectively detecting the performances of the PDA/PEI-1, PDA/PEI-2, PDA/PEI-3 and PDA/PEI-4 of the supports by taking the stainless steel 317LSS used as the raw material in the step A and the PDA support obtained in the step A as a comparison, wherein the atomic force picture and the roughness value of each sample are shown in a graph 1, the amino density data pair of the material surface is shown in a graph 2, and the water contact angle of the support material surface is shown in a graph 3.
Test example of esophageal cancer:
placing 1cm × 1cm 317LSS, PDA and different PDA/PEI samples in 24-well plate after ultraviolet sterilization respectively, adding a certain amount of esophageal cancer Eca109 tumor cell suspension, and performing 5% CO treatment at 37 deg.C2And after statically culturing for 4h, 1d and 3d under the condition, carrying out fluorescent staining by using an AO/PI double-staining apoptosis detection kit, and observing the growth condition of Eca109 tumor cells on the surface of the sample under an inverted fluorescent microscope. The complete green fluorescence of the cell nucleus is a live cell, the condensed green fluorescence of the chromatin of the cell nucleus is early apoptosis, the condensed orange fluorescence of the chromatin of the cell nucleus is late apoptosis, the red fluorescence is a necrotic cell, the apoptosis rate and the necrosis rate of the cell are calculated through cell counting, the growth condition of the anti-tumor cell of the modified layer is quantitatively evaluated, the statistics is shown in tables 1 and 2, and the test result of the esophageal cancer is described in detail below.
TABLE 1317 apoptosis rates of Eca109 tumor cells on LSS, PDA and different PDA/PEI samples
317L SS PDA PDA/PEI-1 PDA/PEI-2 PDA/PEI-3 PDA/PEI-4
4h 0.0％±0.0％ 0.0％±0.0％ 73.4％±6.9％ 94.6±12.7％ 98.0±2.9％ 100.0％±0.0％
1d 0.0％±0.0％ 0.0％±0.0％ 95.4％±10.8％ 99.5±20.3％ 100.0％±1.3％ 100.0％±0.6％
3d 0.0％±0.0％ 0.0％±0.0％ 95.4％±19.1％ 97.6±24.7％ 100.0％±0.0％ 100.0％±0.0％
TABLE 2317 necrosis rates of Eca109 tumor cells on the surface of LSS, PDA and different PDA/PEI samples
317L SS PDA PDA/PEI-1 PDA/PEI-2 PDA/PEI-3 PDA/PEI-4
4h 0.0％±0.0％ 0.0％±0.0％ 5.5％±2.0％ 9.7±4.2％ 79.1±2.9％ 98.4％±0.0％
1d 0.0％±0.0％ 0.0％±0.0％ 10.7％±3.8％ 66.2±22.5％ 96.7％±1.3％ 100.0％±0.0％
3d 0.0％±0.0％ 0.0％±0.0％ 52.7％±10.4％ 70.2±13.1％ 100.0％±0.0％ 100.0％±0.0％

Claims (6)

1. The application of the polyethyleneimine modifier of polydopamine in preparing the accelerant for promoting esophageal cancer cell apoptosis or necrosis is characterized in that the modifier is prepared by grafting polyethyleneimine on the polydopamine through Michael addition and Schiff base reaction, wherein the molecular weight of the polyethyleneimine for grafting is 7 × 104(ii) a The polydopamine for grafting is provided in a form deposited on the surface of a scaffold material; the polydopamine is obtained by polymerizing dopamine for 0.5-3 days under the conditions of oxygen and pH 8-9; the time of the grafting reaction is 0.5 to 3 days.
2. Use according to claim 1, characterized in that the grafting reaction comprises: preparing 0.5-2mg/ml of aqueous solution of polyethyleneimine, and soaking polydopamine in the aqueous solution of polyethyleneimine to perform the grafting reaction.
3. The use according to claim 1, wherein the mass ratio of dopamine to polyethyleneimine is 1: 1.
4. Use according to claim 1 or 3, wherein the dopamine is present in a concentration of 0.5-2 mg/ml.
5. A process for preparing the polyethyleneimine modifier of polydopamine by Michael addition and mattingGrafting polyethyleneimine onto polydopamine by virtue of Schiff base reaction, wherein the molecular weight of the polyethyleneimine for grafting is 7 × 104(ii) a The polydopamine for grafting is provided in a form deposited on the surface of a scaffold material; the polydopamine is obtained by polymerizing dopamine for 0.5-3 days under the conditions of oxygen and pH 8-9; the time of the grafting reaction is 0.5 to 3 days.
6. The polyethyleneimine modification of polydopamine produced according to the method of claim 5.
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