CN110787316B - AIE composite electrostatic spinning fibrous membrane and preparation method and application thereof - Google Patents
AIE composite electrostatic spinning fibrous membrane and preparation method and application thereof Download PDFInfo
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- CN110787316B CN110787316B CN201911105977.9A CN201911105977A CN110787316B CN 110787316 B CN110787316 B CN 110787316B CN 201911105977 A CN201911105977 A CN 201911105977A CN 110787316 B CN110787316 B CN 110787316B
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- aie
- electrostatic spinning
- fiber membrane
- composite
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
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Abstract
The AIE composite electrostatic spinning fibrous membrane is a nano fibrous membrane formed by a biocompatible polymer and AIE molecules, can slowly release the AIE molecules serving as antibacterial active ingredients in the using process, effectively inhibits and kills bacteria, does not generate any side effect on normal cells, can promote the adhesion, growth and proliferation of the cells, has good antibacterial and air permeability, can be completely attached to the surface of a wound to maintain a stable physiological environment, and accelerates the healing speed of the wound. The AIE composite electrostatic spinning fibrous membrane is prepared by an electrostatic spinning technology, has simple preparation method and low cost, is suitable for large-scale industrial production, and has important application value in the treatment aspect of chronic wounds such as wounds or burns.
Description
Technical Field
The invention belongs to the technical field of biomedical materials, and particularly relates to an AIE composite electrostatic spinning fibrous membrane as well as a preparation method and application thereof.
Background
Chronic wounds such as burns and wounds are easy to suffer from bacterial infection, further cause septicemia, acute renal failure and other infection-related complications, and particularly after methicillin-resistant staphylococcus aureus (MRSA) and other super-drug-resistant bacteria appear, wound infection becomes an almost unavoidable clinical problem. According to the statistics of the world health organization, over 2500 million people worldwide each year suffer from wound infections, which have become a significant challenge to future human health because the cost of treatment for wound infections is more than billions of dollars. Moreover, with the abuse of antibiotics, the mutation frequency of bacteria is remarkably accelerated, more and more variant strains with drug resistance exist, and the continuous evolution of super-drug-resistant bacteria makes the research and development requirements of human on novel antibacterial drugs and antibacterial materials particularly urgent.
In the treatment of chronic wounds such as burns and wounds, the treatment of systemic antibiotics often causes that the local drug concentration of the wounds cannot reach the effective range for preventing and treating infection, and the increase of the drug dosage brings certain side effects to patients, so that the treatment aims of reducing wound infection and promoting wound healing are achieved by using the appropriate local antibacterial dressing, and the dressing is a consensus of the clinical community at present.
In recent years, various dressings with antibacterial performance are developed, and are mainly classified into types of fibers, films, hydrogels, sponges and the like according to the forms of carriers, and antibacterial active substances loaded on the dressings comprise natural antibacterial molecules, traditional antibiotics and derivatives thereof, antibacterial polymers, antibacterial nanoparticles and the like. For example, CN104740676A discloses a procyanidine crosslinked gelatin antibacterial dressing and a preparation method thereof, wherein the preparation method comprises the following steps: and (2) casting a gelatin solution with a certain concentration into a mold, freeze-drying to obtain a gelatin sponge scaffold, soaking the gelatin sponge scaffold into a procyanidine solution for crosslinking, adding an antibiotic solution at the same time to allow antibiotic small molecules to enter the gelatin, and freeze-drying again to obtain the antibacterial dressing. The material has better physical and chemical properties and biocompatibility, and can be used for repairing and replacing wound surfaces in the medical field. CN105709262A discloses a silver-carrying antibacterial dressing and a preparation method thereof, wherein the preparation method comprises the following steps: respectively dissolving silver salt components and stabilizing agent components in water to obtain silver salt antibacterial solution, then soaking or padding the antibacterial dressing base materials such as fibers in the silver salt antibacterial solution, and drying to obtain the silver-loaded antibacterial dressing. The silver-loaded antibacterial dressing has excellent antibacterial performance, silver ions are stably released, and the silver shedding pigment deposition of wounds is not easy to cause. CN103920180A discloses a chitosan hydrogel for antibacterial dressing and a preparation method thereof, wherein the preparation method comprises the following steps: introducing carboxyl on chitosan by using a free radical polymerization mode, carrying out amidation reaction on the carboxyl on the chitosan and the antibacterial agent poly-guanidine hexamethylene hydrochloride, grafting the poly-guanidine hexamethylene hydrochloride on the chitosan to obtain chitosan for the antibacterial dressing, and further carrying out crosslinking to obtain the chitosan hydrogel for the antibacterial dressing. The chitosan hydrogel for the antibacterial dressing has the characteristics of good drug resistance, good antibacterial property, lasting antibacterial property, high water absorption rate and good mechanical property.
However, in the existing antibacterial dressing, the antibiotics and the derivatives thereof have quick effect, but cross drug resistance is easy to occur; the antibacterial polymer has strong toxic and side effects and poor solubility, and cannot be directly used for treating infectious diseases; the stability, toxicity and in vivo drug metabolism mechanism of the antibacterial particles such as nano silver are not completely clear and need to be further researched.
Therefore, the development of a novel high-efficiency antibacterial material for inhibiting wound bacteria and promoting wound healing is the research focus in the field.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an AIE composite electrostatic spinning fiber membrane, a preparation method and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an AIE composite electrospun fiber membrane, which is an electrospun fiber membrane formed of a biocompatible polymer and AIE molecules.
The AIE composite electrostatic spinning fiber membrane provided by the invention is loaded with AIE molecules, the AIE is Aggregation-induced emission material (Aggregation-induced emission), can enhance fluorescence in an Aggregation state, has the characteristics of good biocompatibility, low background fluorescence, good light stability and the like, and has a great application prospect in the fields of biological detection, biological imaging, diagnosis and treatment integration and the like. According to the invention, through research, the AIE molecule with a plurality of conjugated rigid arm structures can insert the conjugated rigid arm structures into bacterial cell walls, and excellent antibacterial performance is realized by inhibiting the synthesis of the bacterial cell walls.
On one hand, the AIE composite electrostatic spinning fiber membrane has an excellent antibacterial function based on the introduction of AIE molecules; on the other hand, the electrostatic spinning nanofiber membrane has large specific surface area and high porosity, is a three-dimensional reticular structure similar to the structure of human extracellular matrix, and is beneficial to promoting the adhesion, growth and proliferation of cells and accelerating the wound healing; meanwhile, the biocompatible polymer in the AIE composite electrostatic spinning fibrous membrane has good biocompatibility and blood compatibility, and is an ideal biomedical raw material. Therefore, the AIE composite electrostatic spinning fiber membrane provided by the invention has good antibacterial performance and wound healing promotion performance through the mutual synergistic cooperation of the biocompatible polymer, the antibacterial AIE molecules and the spatial three-dimensional structure of the electrostatic spinning fiber membrane, so that the AIE composite electrostatic spinning fiber membrane has important clinical significance and application value in the aspect of chronic wound treatment.
Preferably, the AIE molecule is selected from any one of, or a combination of at least two of, tetraphenylethylene, 1,2, 2-tetrakis- [ 4-carboxy- (1, 1-biphenyl) ] ethylene, or tetrakis- (4-hydroxyphenyl) ethylene.
Preferably, the biocompatible polymer is selected from any one of or a combination of at least two of polylactic acid, polylactic acid-glycolic acid copolymer, polycaprolactone, lactide-caprolactone copolymer, sodium alginate, chitosan or hyaluronic acid.
Preferably, the mass ratio of the biocompatible polymer to the AIE molecule is 1 (0.001 to 0.1), for example, 1:0.002, 1:0.004, 1:0.005, 1:0.007, 1:0.009, 1:0.01, 1:0.02, 1:0.03, 1:0.04, 1:0.05, 1:0.06, 1:0.07, 1:0.08, 1:0.09, or 1:0.095, and more preferably 1 (0.01 to 0.08).
According to the invention, when the mass ratio of the biocompatible polymer to the AIE molecules is 1 (0.001-0.1), the obtained AIE composite electrostatic spinning fiber membrane has excellent antibacterial performance, and if the content of the AIE molecules is too low, the antibacterial effect of the AIE composite electrostatic spinning fiber membrane is weakened, and the effects of inhibiting bacteria and promoting wound healing cannot be realized; if the content of the AIE molecules is too high, it may cause waste of the antibacterial active ingredient.
Preferably, the AIE composite electrospun fiber membrane has a fiber diameter of 100 to 800nm, for example, 120nm, 150nm, 170nm, 200nm, 230nm, 250nm, 280nm, 300nm, 330nm, 350nm, 380nm, 400nm, 420nm, 450nm, 480nm, 500nm, 520nm, 550nm, 570nm, 600nm, 630nm, 650nm, 680nm, 700nm, 720nm, 750nm, 770nm, 790nm, or the like.
According to the invention, when the fiber diameter of the AIE composite electrostatic spinning fiber membrane is 100-800 nm, the electrostatic spinning fiber membrane with high porosity and large specific surface area can be obtained, so that the spatial three-dimensional structure of the AIE composite electrostatic spinning fiber membrane is similar to the structure of human extracellular matrix, and the AIE composite electrostatic spinning fiber membrane is beneficial to promoting cell adhesion and growth and accelerating wound healing. If the diameter of the fiber exceeds the range, the obtained electrostatic spinning fiber membrane cannot simulate the extracellular matrix of the human body, and the aim of promoting cell growth cannot be fulfilled.
In another aspect, the present invention provides a method for preparing the AIE composite electrospun fiber membrane as described above, comprising the steps of:
(1) mixing AIE molecules with an organic solvent to obtain an AIE solution;
(2) mixing a biocompatible polymer with an organic solvent to obtain an electrostatic spinning precursor solution;
(3) mixing and dispersing the AIE solution obtained in the step (1) and the electrostatic spinning precursor solution obtained in the step (2) to obtain an electrostatic spinning solution;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3) to obtain the AIE composite electrostatic spinning fiber membrane.
Preferably, the organic solvent in step (1) is selected from any one of or a combination of at least two of dimethyl sulfoxide, N-dimethylformamide or acetone.
Preferably, the concentration of the AIE molecule in the AIE solution of step (1) is 0.5-100 mg/mL, such as 0.6mg/mL, 0.8mg/mL, 1mg/mL, 3mg/mL, 5mg/mL, 8mg/mL, 10mg/mL, 15mg/mL, 20mg/mL, 25mg/mL, 30mg/mL, 35mg/mL, 40mg/mL, 45mg/mL, 50mg/mL, 55mg/mL, 60mg/mL, 65mg/mL, 70mg/mL, 75mg/mL, 80mg/mL, 85mg/mL, 90mg/mL, 95mg/mL, or 99mg/mL, etc.
Preferably, the mixing of step (1) is carried out under ultrasonic conditions.
Preferably, the frequency of the ultrasound is 20 to 50kHz, such as 22kHz, 25kHz, 27kHz, 30kHz, 33kHz, 35kHz, 38kHz, 40kHz, 42kHz, 45kHz, 47kHz or 49kHz and the like.
Preferably, the power of the ultrasound is 100-200W, such as 105W, 110W, 115W, 120W, 125W, 130W, 135W, 140W, 145W, 150W, 155W, 160W, 165W, 170W, 175W, 180W, 185W, 190W or 195W, and the like.
Preferably, the time of the ultrasound is 5-60 min, such as 8min, 10min, 15min, 20min, 25min, 30min, 35min, 40min, 45min, 50min, 55min or 58 min.
Preferably, the AIE solution of step (1) is stored under protection from light.
Preferably, the organic solvent in step (2) is selected from any one of acetone, N-dimethylformamide, dimethyl sulfoxide, dichloromethane, chloroform, absolute ethanol, tetrahydrofuran or hexafluoroisopropanol or a combination of at least two of the same.
Preferably, the dispersion of step (3) is carried out under exclusion of light.
Preferably, the dispersing time in the step (3) is 2 to 12 hours, such as 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours, 5 hours, 5.5 hours, 6 hours, 6.5 hours, 7 hours, 7.5 hours, 8 hours, 8.5 hours, 9 hours, 9.5 hours, 10 hours, 10.5 hours, 11 hours or 11.5 hours, etc.
Preferably, the mass percentage of the biocompatible polymer in the electrospinning solution in the step (3) is 10-30%, for example, 12%, 14%, 15%, 17%, 19%, 20%, 22%, 24%, 25%, 27%, or 29%.
Preferably, the mass ratio of AIE molecules to biocompatible polymer in the electrospinning solution of step (3) is (0.001-0.1): 1, such as 0.002:1, 0.004:1, 0.005:1, 0.007:1, 0.009:1, 0.01:1, 0.015:1, 0.02:1, 0.03:1, 0.04:1, 0.05:1, 0.06:1, 0.07:1, 0.08:1, 0.09:1, or 0.095: 1.
Preferably, the parameters of the electrostatic spinning in the step (4) are set as follows: the electrospinning solution is injected at a rate of 0.2 to 2mL/h (e.g., 0.3mL/h, 0.5mL/h, 0.7mL/h, 0.9mL/h, 1mL/h, 1.2mL/h, 1.4mL/h, 1.6mL/h, 1.8mL/h, or 1.9 mL/h), a load voltage of 10 to 20kV (e.g., 11kV, 12kV, 13kV, 14kV, 15kV, 16kV, 17kV, 18kV, or 19 kV), a receiving distance of 10 to 25cm (e.g., 11cm, 13cm, 15cm, 17cm, 19cm, 20cm, 22cm, or 24 cm), and a diameter of the spinning nozzle of 0.3 to 1mm (e.g., 0.4mm, 0.5mm, 0.6mm, 0.7mm, 0.8mm, or 0.9 mm).
Preferably, the preparation method specifically comprises the following steps:
(1) dissolving AIE molecules in an organic solvent under the assistance of ultrasonic waves to obtain an AIE solution with the AIE molecular concentration of 0.5-100 mg/mL, and storing the AIE solution in a dark place;
(2) dissolving a biocompatible polymer in an organic solvent to obtain an electrospinning precursor solution with the static mass percentage of the biocompatible polymer of 10-30%;
(3) mixing the AIE solution obtained in the step (1) with the electrostatic spinning precursor solution obtained in the step (2), and uniformly dispersing in a dark place to obtain an electrostatic spinning solution with the mass ratio of AIE molecules to biocompatible polymers being (0.001-0.1): 1;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: and the injection speed of the electrostatic spinning solution is 0.2-2 mL/h, the loading voltage is 10-20 kV, the receiving distance is 10-25 cm, and the diameter of a spinning nozzle is 0.3-1 mm, so that the AIE composite electrostatic spinning fiber membrane is obtained.
In another aspect, the invention provides an application of the AIE composite electrospun fiber membrane in preparation of biomedical materials.
In another aspect, the present invention provides an antimicrobial dressing comprising the AIE composite electrospun fiber membrane described above.
Compared with the prior art, the invention has the following beneficial effects:
the AIE composite electrostatic spinning fibrous membrane provided by the invention is an electrostatic spinning fibrous membrane which takes a biocompatible polymer as a base material and is loaded with antibacterial AIE molecules and has a three-dimensional network structure, the AIE composite electrostatic spinning fibrous membrane can slowly release antibacterial active ingredient AIE molecules in the using process, pathogenic bacteria including staphylococcus aureus and methicillin-resistant staphylococcus aureus can be effectively inhibited and killed, no side effect is generated on normal cells, the adhesion, growth and proliferation of the cells can be promoted, the AIE composite electrostatic spinning fibrous membrane has good antibacterial and air permeability, the AIE composite electrostatic spinning fibrous membrane can be completely attached to the surface of a wound to maintain a stable physiological environment, and the healing speed of the wound is accelerated. The AIE composite electrostatic spinning fibrous membrane is prepared by an electrostatic spinning technology, has simple preparation method and low cost, is suitable for large-scale industrial production, and has important application value in the treatment aspect of chronic wounds such as wounds or burns.
Drawings
FIG. 1 is a scanning electron micrograph of an AIE composite electrospun fiber membrane provided in example 1;
FIG. 2 is a scanning electron micrograph of the AIE composite electrospun fiber membrane provided in example 2;
FIG. 3 is a graph of the cell viability test of the AIE composite electrospun fiber membrane provided in example 1;
FIG. 4 is a graph of the cell viability test of the AIE composite electrospun fiber membrane provided in example 2;
FIG. 5 is a test chart of cell morphology on the AIE composite electrospun fiber membrane provided in example 1;
FIG. 6 is a test chart of cell morphology on the AIE composite electrospun fiber membrane provided in example 2;
FIG. 7 is a comparison graph of the bacteriostatic performance of the AIE composite electrospun fiber membranes provided in example 1, example 5 and comparative example 1;
FIG. 8 is a comparison graph of the bacteriostatic performance of the AIE composite electrospun fiber membranes provided in example 1, example 5 and comparative example 1;
FIG. 9 is a graphical representation of Staphylococcus aureus morphology on the AIE composite electrospun fiber membrane provided in example 1.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The experimental materials used in the following examples of the present invention include:
(1) biocompatible polymer: polycaprolactone (PCL) with molecular weight of 80000 g/mol; polylactic-co-glycolic acid (PLGA) having a molecular weight of 120000 g/mol; polylactic acid (PLA), molecular weight 100000g/mol, lactide-caprolactone copolymer (PLCL), molecular weight 110000 g/mol.
(2) AIE molecule: tetraphenylethylene, 1,2, 2-tetrakis- [ 4-carboxy- (1, 1-biphenyl) ] ethylene, and tetrakis- (4-hydroxyphenyl) ethylene were purchased from Xuzhou Dayang Biochemical technology, Inc.
Example 1
The embodiment provides an AIE composite electrostatic spinning fibrous membrane, which is prepared by the following specific steps:
(1) adding 20mg of 1,1,2, 2-tetra- [ 4-carboxyl- (1, 1-biphenyl) ] ethylene particles into 7mL of N, N-dimethylformamide, and carrying out ultrasonic treatment for 10min to completely dissolve the AIE particles to obtain an AIE solution with the AIE molecular concentration of 2.86mg/mL, wherein the AIE solution is stored in a dark place;
(2) dissolving 2g of PCL in 7mL of tetrahydrofuran, and magnetically stirring for 3h at room temperature until the PCL is completely dissolved to obtain electrostatic spinning precursor solution;
(3) adding the AIE solution obtained in the step (1) into the electrostatic spinning precursor solution obtained in the step (2), stirring for 2 hours in a dark place to completely dissolve the AIE solution, standing for 0.5 hour to obtain a uniform and stable electrostatic spinning solution, wherein the mass percentage of PCL in the electrostatic spinning solution is 13%;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: the injection speed of the electrostatic spinning solution is 1mL/h, the loading voltage is 15kV, the receiving distance is 10cm, the diameter of a spinning nozzle is 0.7mm, and the AIE composite electrostatic spinning fiber membrane is obtained, wherein the average fiber diameter of the AIE composite electrostatic spinning fiber membrane is 300 nm.
Example 2
The embodiment provides an AIE composite electrostatic spinning fibrous membrane, which is prepared by the following specific steps:
(1) adding 50mg of 1,1,2, 2-tetra- [ 4-carboxyl- (1, 1-biphenyl) ] ethylene particles into 2g N, N-dimethylformamide, and carrying out ultrasonic treatment for 10min to completely dissolve the AIE particles to obtain an AIE solution with the AIE molecular concentration of 23.8mg/mL, wherein the AIE solution is stored in a dark place;
(2) mixing 1g of PLGA, 1g N, N-dimethylformamide and 1g of acetone, and magnetically stirring for 3 hours at room temperature until the mixture is completely dissolved to obtain an electrostatic spinning precursor solution;
(3) adding the AIE solution obtained in the step (1) into the electrostatic spinning precursor solution obtained in the step (2), stirring for 2 hours in a dark place to completely dissolve the AIE solution, standing for 0.5 hour to obtain uniform and stable electrostatic spinning solution, wherein the mass percentage of PLGA in the electrostatic spinning solution is 20%;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: and the injection speed of the electrostatic spinning solution is 0.8mL/h, the loading voltage is 20kV, the receiving distance is 15cm, and the diameter of the spinning nozzle is 0.7mm, so that the AIE composite electrostatic spinning fiber membrane is obtained, wherein the average fiber diameter of the AIE composite electrostatic spinning fiber membrane is 500 nm.
Example 3
The embodiment provides an AIE composite electrostatic spinning fibrous membrane, which is prepared by the following specific steps:
(1) adding 5mg of tetraphenylethylene particles into 10mL of dimethyl sulfoxide solvent, and carrying out ultrasonic treatment for 10min to completely dissolve the tetraphenylethylene to obtain an AIE solution with the AIE molecular concentration of 0.5mg/mL, wherein the AIE solution is stored in a dark place;
(2) dissolving 2g of PLA in 5mL of dimethyl sulfoxide, and magnetically stirring for 3h at room temperature until the PLA is completely dissolved to obtain an electrostatic spinning precursor solution;
(3) adding the AIE solution obtained in the step (1) into the electrostatic spinning precursor solution obtained in the step (2), stirring overnight in a dark place to completely dissolve the AIE solution, standing for 0.5h to obtain uniform and stable electrostatic spinning solution, wherein the mass percentage of PLA in the electrostatic spinning solution is 11%;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: and the injection speed of the electrostatic spinning solution is 0.2mL/h, the loading voltage is 10kV, the receiving distance is 10cm, and the diameter of the spinning nozzle is 0.3mm, so that the AIE composite electrostatic spinning fiber membrane is obtained, wherein the average fiber diameter of the AIE composite electrostatic spinning fiber membrane is 100 nm.
Example 4
The embodiment provides an AIE composite electrostatic spinning fibrous membrane, which is prepared by the following specific steps:
(1) mixing 360mg of tetra- (4-hydroxyphenyl) ethylene particles with 2mL of N, N-dimethylformamide and 1.5mL of acetone, and carrying out ultrasonic treatment for 10min to completely dissolve tetraphenylethylene to obtain an AIE solution with the AIE molecular concentration of 0.5mg/mL, wherein the AIE solution is stored in a dark place;
(2) dissolving 4.5g of PLCL in 7mL of N, N-dimethylformamide, and magnetically stirring for 3h at room temperature until the PLCL is completely dissolved to obtain an electrostatic spinning precursor solution;
(3) adding the AIE solution obtained in the step (1) into the electrostatic spinning precursor solution obtained in the step (2), stirring overnight in a dark place to completely dissolve the AIE solution, standing for 1h to obtain uniform and stable electrostatic spinning solution, wherein the mass percentage of chitosan in the electrostatic spinning solution is 30%;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: and the injection speed of the electrostatic spinning solution is 2mL/h, the loading voltage is 15kV, the receiving distance is 25cm, the diameter of a spinning nozzle is 1mm, and the AIE composite electrostatic spinning fiber membrane is obtained, wherein the average fiber diameter of the AIE composite electrostatic spinning fiber membrane is 800 nm.
Example 5
This example differs from example 1 in that the amount of AIE particles added in step (1) was 100 mg.
Comparative example 1
The comparative example provides an electrospun fiber membrane, and the specific preparation method comprises the following steps:
(1) dissolving 2g of PCL in 7mL of tetrahydrofuran, and magnetically stirring for 3h at room temperature until the PCL is completely dissolved to obtain electrostatic spinning precursor solution;
(3) adding 7mL of N, N-dimethylformamide into the electrostatic spinning precursor solution obtained in the step (1), and uniformly stirring to obtain a uniform and stable electrostatic spinning solution, wherein the mass percentage of PCL in the electrostatic spinning solution is 13%;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: the injection speed of the electrostatic spinning solution is 0.2-2 mL/h, the loading voltage is 15kV, the receiving distance is 10cm, the diameter of a spinning nozzle is 0.7mm, and the electrostatic spinning fiber membrane is obtained, wherein the average fiber diameter of the electrostatic spinning fiber membrane is 300 nm.
Comparative example 2
This comparative example differs from example 1 only in that the 1,1,2, 2-tetrakis- [ 4-carboxy- (1, 1-biphenyl) ] ethylene particles in step (1) are replaced by equal mass of tetrakis- (4-bromobenzene) ethylene particles.
Comparative example 3
This comparative example differs from example 1 only in that the amount of 1,1,2, 2-tetrakis- [ 4-carboxy- (1, 1-biphenylyl) ] ethylene particles added in step (1) was 300 mg.
Test example 1
The test example is a morphology test experiment of the AIE composite electrostatic spinning fibrous membrane, and the specific method is as follows:
the morphology of the AIE composite electrospun fiber membranes provided in examples 1-5 and comparative examples 1-3 of the invention was tested by a scanning electron microscope (SEM, SU8200 type). Illustratively, the scanning electron micrograph of the AIE composite electrospun fiber membrane of example 1 is shown in fig. 1, the AIE composite electrospun fiber membrane has a uniform three-dimensional network structure with an average fiber diameter of 300 nm; the scanning electron micrograph of the AIE composite electrospun fiber film of example 2, which had a uniform three-dimensional network structure and an average fiber diameter of 500nm, is shown in fig. 2.
Test example 2
The test example is a cell survival test experiment on an AIE composite electrostatic spinning fibrous membrane, and the specific method is as follows:
(1) cutting the AIE composite electrostatic spinning fibrous membrane provided in the embodiment 1 into rectangles of 4cm multiplied by 5cm, soaking in 75% ethanol for 30min for sterilization, drying in the air, and cleaning twice with PBS to remove residues; then at 2X 104/cm23T3 cells were seeded on AIE composite electrospun fiber membranes at 37 ℃ with 5% CO2After 3 days of incubation in the environment, 3T3 cells on the AIE composite electrospun fiber membranes were slowly washed with PBSAnd staining with LIVE/DEAD LIVE-DEAD staining kit, and observing and photographing under a single-photon laser confocal microscope to obtain a cell survival test chart as shown in FIG. 3. As can be seen from FIG. 3, 3T3 cells have good growth morphology on the surface of the AIE composite electrospun fiber membrane provided in example 1, and the AIE composite electrospun fiber membrane is beneficial to proliferation and spreading of cells.
(2) Cutting the AIE composite electrostatic spinning fibrous membrane provided in the embodiment 2 into rectangles of 4cm multiplied by 5cm, soaking in 75% ethanol for 30min for sterilization, drying in the air, and cleaning twice with PBS to remove residues; then at 2X 104/cm2The HUVEC cells were seeded on AIE composite electrospun fiber membranes at 37 ℃ with 5% CO2After culturing for 3 days in the environment, the HUVEC cells on the AIE composite electrospun fiber membrane were slowly washed with PBS, stained with LIVE-DEAD staining kit LIVE/DEAD, and then observed and photographed under a single-photon laser confocal microscope, and the obtained cell survival test chart is shown in fig. 4, as can be seen from fig. 4, the growth morphology of the HUVEC cells on the surface of the AIE composite electrospun fiber membrane was good, and the AIE composite electrospun fiber membrane in example 2 was favorable for proliferation and spreading of the HUVEC cells.
Test example 3
The test example is a cell morphology test experiment on an AIE composite electrostatic spinning fibrous membrane, and the specific method is as follows:
(1) 3T3 cells were seeded on the AIE composite electrospun fiber membrane provided in example 1 according to the method of step (1) in test example 2 at 37 ℃ with 5% CO2After culturing for 3 days in the environment, gently cleaning the cells for 3 times by PBS (phosphate buffer solution), fixing the cells by prepared 4% paraformaldehyde, and placing the cells in a refrigerator at 4 ℃ overnight; then washing with distilled water for 3 times to remove paraformaldehyde residues; and (3) performing gradient dehydration and replacement by using alcohol, wherein the alcohol concentration is respectively 30%, 50%, 70%, 80% and 90%, and the water in the cells is fully replaced by performing dehydration three times at 100% for 10min each time. Drying the sample in a vacuum freeze dryer for 1h, fixing the sample on a sample table, and performing secondary electron imaging by using a gold jet for 60s before SEM observation to obtain the cell morphology on the AIE composite electrostatic spinning fiber membrane in the example 1As shown in fig. 5, it can be seen from fig. 5 that 3T3 cells had good cell morphology and growth state on the AIE composite electrospun fiber membrane provided by the present invention.
(2) HUVEC cells were seeded on the AIE composite electrospun fiber membrane provided in example 2 according to the method of step (2) in test example 2 at 37 ℃ with 5% CO2After culturing for 3 days in the environment, gently cleaning the cells for 3 times by PBS (phosphate buffer solution), fixing the cells by prepared 4% paraformaldehyde, and placing the cells in a refrigerator at 4 ℃ overnight; then washing with distilled water for 3 times to remove paraformaldehyde residues; and (3) performing gradient dehydration and replacement by using alcohol, wherein the alcohol concentration is respectively 30%, 50%, 70%, 80% and 90%, and the water in the cells is fully replaced by performing dehydration three times at 100% for 10min each time. The sample is dried for 1h in a vacuum freeze dryer, then the sample is fixed on a sample table, and secondary electron imaging is carried out by spraying gold for 60s before SEM observation, so that a cell morphology test chart on the AIE composite electrostatic spinning fiber membrane in example 2 is obtained as shown in FIG. 6, and as can be seen from FIG. 6, HUVEC cells have good cell morphology and growth state on the AIE composite electrostatic spinning fiber membrane provided by the invention.
Test example 4
The test example is a cell proliferation activity test experiment on an AIE composite electrostatic spinning fibrous membrane, and the specific method is as follows:
the cytotoxicity of the AIE composite electrostatic spinning fibrous membranes provided in examples 1 to 5 and comparative examples 1 to 3 of the present invention was evaluated by using cell count Kit-8(CCK-8), and the AIE composite electrostatic spinning fibrous membranes were sterilized and washed, and then subjected to 1X 10 washing4/cm2The density of (A) was seeded on AIE composite electrospun fibrous membranes with Human Umbilical Vein Endothelial Cells (HUVEC) at 37 ℃ with 5% CO2After 24 hours of culture in an incubator, the cells were stained with CCK-8, and after 2 hours of incubation, the optical density of the cells at 450nm was measured with a multifunctional microplate reader, thereby obtaining the cell viability (%) of HUVEC cells on the AIE composite electrospun fiber membrane.
The cell viability of the AIE composite electrospun fiber membranes provided in examples 1 to 5 and comparative examples 1 to 3 was tested according to the above experimental methods, and the obtained test data is shown in table 1.
TABLE 1
As can be seen from the data in Table 1, the AIE composite electrospun fiber membranes provided in the embodiments 1-5 of the invention have good biosafety and do not affect the growth and proliferation of cells; comparative example 3 provides an AIE composite electrospun fibrous membrane in which the mass ratio of AIE molecules to biocompatible polymer is 0.15:1, exceeding the preferred mass range of the present invention, resulting in an excess of AIE molecules that affects the cell viability of normal fibroblasts.
Test example 5
The test example is an antibacterial performance test experiment of the AIE composite electrostatic spinning fiber membrane, and the specific method is as follows:
(1) sucking 100 mu L of staphylococcus aureus (S.aureus) bacterial liquid, adding the bacterial liquid into a 96-well plate, and testing an OD value by using an enzyme-labeling instrument; the bacterial liquid concentration is diluted to 10 by LB culture medium5The culture medium was inoculated to the AIE composite electrospun fiber membranes provided in examples 1, 5 and 1, respectively, by sucking 10. mu.L of the bacterial suspension, cultured at 37 ℃ for 24 hours in an incubator, and then placed in a 24-well plate, and prepared 10 with LB medium4Taking 100 mu L of bacterial liquid with concentration of/mL, sucking the bacterial liquid onto a solid culture plate, and uniformly coating the bacterial liquid by using a coating rod; the membrane was placed upside down in an incubator at 37 ℃ for 24 hours, colonies were taken out and photographed, and a comparison graph of the antibacterial performance of the AIE composite electrospun fiber membranes in examples 1, 5 and comparative example 1 was obtained as shown in fig. 7, and it can be seen from fig. 7 that the PCL electrospun fiber membrane (comparative example 1) containing no AIE molecule as an antibacterial active ingredient had almost no antibacterial performance, the AIE composite electrospun fiber membranes containing AIE molecules in examples 1 and 5 of the present invention had remarkable antibacterial performance, and the antibacterial performance in example 5 was superior to that of example 1, demonstrating that as the antibacterial performance of the electrospun fiber membranes was improvedThe antibacterial performance of the AIE is further obviously improved by increasing the concentration of the AIE.
(2) Sucking 100 mu L of methicillin-resistant staphylococcus aureus (MRSA) bacterial liquid, adding the bacterial liquid into a 96-well plate, and testing an OD value by using an enzyme-labeling instrument; the bacterial liquid concentration is diluted to 10 by LB culture medium5The culture medium was inoculated to the AIE composite electrospun fiber membranes provided in examples 1, 5 and 1, respectively, by sucking 10. mu.L of the bacterial suspension, cultured at 37 ℃ for 24 hours in an incubator, and then placed in a 24-well plate, and prepared 10 with LB medium4Taking 100 mu L of bacterial liquid with concentration of/mL, sucking the bacterial liquid onto a solid culture plate, and uniformly coating the bacterial liquid by using a coating rod; the obtained AIE composite electrospun fiber membranes in examples 1, 5 and comparative example 1 have almost no antibacterial performance, as can be seen from FIG. 8, the AIE composite electrospun fiber membranes containing AIE molecules in examples 1 and 5 of the invention have obvious antibacterial performance to MRSA, which is a super drug-resistant bacterium, and the AIE composite electrospun fiber membranes in example 5 are superior to example 1, and the prepared AIE composite electrospun fiber membranes have further obviously improved antibacterial performance to the super drug-resistant bacterium along with the increase of AIE concentration in the electrospun fiber membranes, as shown in FIG. 8.
The inhibition rates of the AIE composite electrospun fiber membranes provided in examples 1 to 5 and comparative examples 1 to 3 to staphylococcus aureus (s.aureus) and methicillin-resistant staphylococcus aureus (MRSA) were respectively tested by a plate colony counting method according to the above experimental steps, and the obtained test data are shown in table 2.
TABLE 2
As can be seen from the data in table 2, compared with the common PCL electrospun fiber membrane (comparative example 1) which does not contain the AIE molecule as an antibacterial active ingredient, the AIE composite electrospun fiber membranes provided in the embodiments 1 to 5 of the present invention have excellent inhibitory effects on staphylococcus aureus and methicillin-resistant staphylococcus aureus, which is a super-resistant bacterium, and the bacteriostatic rate is more than 97%. Comparative example 2 provides an AIE composite electrospun fiber membrane in which the AIE molecule is tetra- (4-bromobenzene) ethylene, not tetraphenylethylene, 1,2, 2-tetra- [ 4-carboxy- (1, 1-biphenyl) ] ethylene or tetra- (4-hydroxyphenyl) ethylene, which is preferred in the present invention, and thus it has almost no bacteriostatic effect. Therefore, the selection of the specific AIE molecules of the invention endows the AIE composite electrostatic spinning fiber membrane with high-efficiency antibacterial performance, and if the selection exceeds the preferable range of the invention, an antibacterial material with good performance cannot be obtained.
Test example 6
The test example is a bacterial morphology test experiment on an AIE composite electrostatic spinning fibrous membrane, and the specific method is as follows:
staphylococcus aureus was inoculated onto the AIE composite electrospun fiber membrane provided in example 1 according to the method of step (1) in test example 5, after culturing for 24 hours in an incubator at 37 ℃, dehydrated with 2.5% glutaraldehyde and 30%, 50%, 70%, 80%, 90%, 95% and 100% ethanol, and observed on the surface of the AIE composite electrospun fiber membrane by using a scanning electron microscope, to obtain a pattern for testing the morphology of Staphylococcus aureus on the AIE composite electrospun fiber membrane in example 1, as shown in FIG. 9, it can be seen from FIG. 9 that AIE molecules in the AIE composite electrospun fiber membrane are released and wrap on the surface of Staphylococcus aureus, thereby destroying the cell wall of bacteria and killing bacteria to inhibit proliferation.
The applicant states that the present invention is illustrated by the above examples to show an AIE composite electrospun fiber membrane of the present invention, and the preparation method and application thereof, but the present invention is not limited to the above process steps, i.e. it does not mean that the present invention must rely on the above process steps to be implemented. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.
Claims (21)
1. An AIE composite electrostatic spinning fiber membrane with antibacterial performance is characterized in that the AIE composite electrostatic spinning fiber membrane is an electrostatic spinning fiber membrane formed by a biocompatible polymer and AIE molecules;
the AIE molecule is tetra- (4-hydroxyphenyl) ethylene;
the mass ratio of the biocompatible polymer to the AIE molecules is 1 (0.001-0.1).
2. The AIE composite electrospun fiber membrane of claim 1, wherein the biocompatible polymer is selected from any one of polylactic acid, polylactic acid-glycolic acid copolymer, polycaprolactone, lactide-caprolactone copolymer, sodium alginate, chitosan or hyaluronic acid or a combination of at least two thereof.
3. The AIE composite electrospun fiber membrane of claim 1, wherein the mass ratio of the biocompatible polymer to the AIE molecule is 1 (0.01-0.08).
4. The AIE composite electrospun fiber membrane of claim 1, wherein the fiber diameter of the AIE composite electrospun fiber membrane is 100-800 nm.
5. A method of preparing the AIE composite electrospun fiber membrane of any one of claims 1 to 4, comprising the steps of:
(1) mixing AIE molecules with an organic solvent to obtain an AIE solution;
(2) mixing a biocompatible polymer with an organic solvent to obtain an electrostatic spinning precursor solution;
(3) mixing and dispersing the AIE solution obtained in the step (1) and the electrostatic spinning precursor solution obtained in the step (2) to obtain an electrostatic spinning solution;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3) to obtain the AIE composite electrostatic spinning fiber membrane.
6. The method according to claim 5, wherein the organic solvent in step (1) is selected from any one of or a combination of at least two of dimethyl sulfoxide, N-dimethylformamide and acetone.
7. The method according to claim 5, wherein the concentration of AIE molecules in the AIE solution of step (1) is 0.5-100 mg/mL.
8. The method of claim 5, wherein the mixing of step (1) is performed under ultrasonic conditions.
9. The method according to claim 8, wherein the ultrasonic wave has a frequency of 20 to 50 kHz.
10. The preparation method according to claim 8, wherein the power of the ultrasound is 100 to 200W.
11. The preparation method according to claim 8, wherein the time of the ultrasonic treatment is 5 to 60 min.
12. The method according to claim 5, wherein the AIE solution of step (1) is stored under protection from light.
13. The method according to claim 5, wherein the organic solvent in step (2) is selected from any one or a combination of at least two of acetone, N-dimethylformamide, dimethyl sulfoxide, dichloromethane, chloroform, absolute ethanol, tetrahydrofuran and hexafluoroisopropanol.
14. The method according to claim 5, wherein the dispersion in step (3) is carried out under light-shielding conditions.
15. The preparation method according to claim 5, wherein the dispersing time in the step (3) is 2-12 h.
16. The preparation method according to claim 5, wherein the mass percentage of the biocompatible polymer in the electrospinning solution in the step (3) is 10-30%.
17. The preparation method according to claim 5, wherein the mass ratio of AIE molecules to the biocompatible polymer in the electrospinning solution in the step (3) is (0.001-0.1): 1.
18. The method according to claim 5, wherein the parameters of the electrostatic spinning in the step (4) are set as follows: the injection speed of the electrostatic spinning solution is 0.2-2 mL/h, the loading voltage is 10-20 kV, the receiving distance is 10-25 cm, and the diameter of the spinning nozzle is 0.3-1 mm.
19. The preparation method according to claim 5, comprising the following steps:
(1) dissolving AIE molecules in an organic solvent under the assistance of ultrasonic waves to obtain an AIE solution with the AIE molecular concentration of 0.5-100 mg/mL, and storing the AIE solution in a dark place;
(2) dissolving a biocompatible polymer in an organic solvent to obtain an electrospinning precursor solution with the static mass percentage of the biocompatible polymer of 10-30%;
(3) mixing the AIE solution obtained in the step (1) with the electrostatic spinning precursor solution obtained in the step (2), and uniformly dispersing in a dark place to obtain an electrostatic spinning solution with the mass ratio of AIE molecules to biocompatible polymers being (0.001-0.1): 1;
(4) and (4) carrying out electrostatic spinning on the electrostatic spinning solution obtained in the step (3), wherein the parameters of the electrostatic spinning are as follows: and the injection speed of the electrostatic spinning solution is 0.2-2 mL/h, the loading voltage is 10-20 kV, the receiving distance is 10-25 cm, and the diameter of a spinning nozzle is 0.3-1 mm, so that the AIE composite electrostatic spinning fiber membrane is obtained.
20. Use of the AIE composite electrospun fiber membrane of any one of claims 1 to 4 in the preparation of biomedical materials.
21. An antimicrobial dressing comprising the AIE composite electrospun fiber membrane of any one of claims 1-4.
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| CN113117185B (en) * | 2021-04-20 | 2022-10-04 | 南方科技大学 | Venous indwelling needle based on liquid metal and electrostatic spinning modification and preparation method thereof |
| CN113122947B (en) * | 2021-04-25 | 2022-11-01 | 江苏新视界先进功能纤维创新中心有限公司 | Multi-base color-changing luminescent fiber with antibacterial property and preparation method thereof |
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