CN112569402B - Water-soluble silicon-based gel antibacterial wound dressing and preparation method and application thereof - Google Patents

Water-soluble silicon-based gel antibacterial wound dressing and preparation method and application thereof Download PDF

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CN112569402B
CN112569402B CN202011387402.3A CN202011387402A CN112569402B CN 112569402 B CN112569402 B CN 112569402B CN 202011387402 A CN202011387402 A CN 202011387402A CN 112569402 B CN112569402 B CN 112569402B
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雷波
程威
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Xian Jiaotong University
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    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0061—Use of materials characterised by their function or physical properties
    • A61L26/008—Hydrogels or hydrocolloids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0203—Adhesive plasters or dressings having a fluid handling member
    • A61F13/0213—Adhesive plasters or dressings having a fluid handling member the fluid handling member being a layer of hydrocoloid, gel forming material
    • A—HUMAN NECESSITIES
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    • A61F13/00—Bandages or dressings; Absorbent pads
    • A61F13/02—Adhesive plasters or dressings
    • A61F13/0276—Apparatus or processes for manufacturing adhesive dressings or bandages
    • A61F13/0289—Apparatus or processes for manufacturing adhesive dressings or bandages manufacturing of adhesive dressings
    • A—HUMAN NECESSITIES
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    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
    • A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
    • A61L26/0052—Mixtures of macromolecular compounds
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    • A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
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    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
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    • A—HUMAN NECESSITIES
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    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents

Abstract

The invention provides a water-soluble silicon-based gel antibacterial wound dressing as well as a preparation method and application thereof, wherein the preparation method comprises the following steps: melting citric acid, and then adding polyethylene glycol and aminopropyltriethoxysilane to perform one-pot thermal polycondensation to prepare a PCGS polymer; reacting polyoxyethylene polyoxypropylene (F127) with p-toluenesulfonyl chloride to obtain an F127-TsCl intermediate, and reacting the F127-TsCl intermediate with epsilon-polylysine to obtain an FE polymer; dissolving FE, F127 and PCGS polymers according to different proportions and crosslinking to form a stable and homogeneous hydrogel dressing, namely obtaining the water-soluble silicon-based gel antibacterial wound dressing FEPCGS. The water-soluble silicon-based gel antibacterial wound dressing also shows good biocompatibility in vivo and in vitro and has good antibacterial property, so the hydrogel dressing has good application prospect in wound healing tissue regeneration and antibiosis.

Description

Water-soluble silicon-based gel antibacterial wound dressing and preparation method and application thereof
Technical Field
The invention belongs to the technical field of degradable biomedical materials, and particularly relates to a water-soluble silicon-based gel antibacterial wound dressing as well as a preparation method and application thereof.
Background
The development of high-bioactivity wound dressing capable of accelerating wound healing and skin regeneration and multifunctional antibacterial is the key of clinical wound reconstruction, and serious multidrug resistant bacteria (MDRB) infected chronic wound repair and skin regeneration become medical problems to be solved urgently in the world. Traditional antimicrobial materials, including inorganic silver, copper, zinc nanoparticles and organic molecules such as quaternary ammonium compounds, guanidines, may combat MDRB, but poor biocompatibility limits their further medical applications. Therefore, it is necessary and urgent to develop new therapeutic techniques to promote MDRB-induced wound healing.
In recent years, silicon-based biomaterials for tissue repair and regeneration, including silicate bioactive glasses and ceramics and polysiloxanes, have received much attention due to their low cost, high biocompatibility and bioactivity. Silicate bioactive glasses and ceramics have good biocompatibility, tissue repair activity and angiogenesis, but their fragile and rigid nature limits their wide application in wound repair and skin regeneration. Polysiloxane polymers have excellent elasticity and biocompatibility, but their use in wound repair dressings is also limited by their bioinert and non-degradable properties.
The development of novel silicon-based bioactive materials, combining the advantages of inorganic silicates and organopolysiloxane materials, is an effective way to prepare satisfactory wound-healing bioactive materials. To date, studies on the use of water-soluble hybrid polymers based on citric acid-ethylene glycol-siloxane (PCGS) and hydrogel dressings combining PCGS and FE polymers for wound healing tissue regeneration and multi-drug resistant bacteria (MDRB) infected wound repair and skin regeneration have not been reported.
Disclosure of Invention
The first purpose of the invention is to provide a preparation method of the water-soluble silicon-based gel antibacterial wound dressing, the method has simple process, and the prepared hydrogel dressing has good biocompatibility, broad-spectrum antibacterial activity and excellent tissue repair performance.
The second aim of the invention is to provide a water-soluble silicon-based gel antibacterial wound dressing.
The third purpose of the invention is that the water-soluble silicon-based gel antibacterial wound dressing has important application in promoting the regeneration of wound healing tissues and the repair of wounds infected by multidrug resistant bacteria (MDRB).
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
a preparation method of water-soluble silicon-based gel antibacterial wound dressing comprises the following steps:
melting citric acid, adding polyethylene glycol and aminopropyltriethoxysilane, and performing one-pot thermal polycondensation to obtain a PCGS polymer;
f127 and p-toluenesulfonyl chloride are reacted to obtain an F127-TsCl intermediate, and the F127-TsCl intermediate and epsilon-polylysine are reacted to obtain an FE polymer;
and adding the FE polymer into the PBS buffer solution of F127, adding the PCGS polymer after the FE polymer is completely dissolved, and performing crosslinking reaction at 60-70 ℃ to form the homogeneous water-soluble silicon-based gel antibacterial wound dressing.
As a further improvement of the invention, the molar ratio of the citric acid to the polyethylene glycol to the aminopropyltriethoxysilane is 1: 1: (0.01-0.4).
As a further improvement of the invention, the melting temperature of the citric acid is 150-170 ℃, the one-pot thermal reaction temperature is 130-150 ℃, and the reaction time is 2-4 hours.
As a further improvement of the invention, the post-treatment method for obtaining the PCGS polymer comprises the following steps:
after one-pot thermal polycondensation is finished, the product is dissolved by deionized water and dialyzed in a dialysis bag, and the prepared polymer is frozen and dried to obtain the PCGS polymer.
As a further improvement of the present invention, the molar ratio of F127 to p-toluenesulfonyl chloride is 1: 10 was reacted in anhydrous dichloromethane at room temperature to give the F127-TsCl intermediate.
As a further improvement of the invention, the F127-TsCl intermediate is mixed with epsilon-polylysine in a molar ratio of 1: 2 in dimethyl formamide at 55-65 ℃.
As a further improvement of the invention, the mass concentration of the FE in the PBS solution is 3%, the mass concentration of the PBS solution of F127 is 22%, the mass concentration of the PCGS is 1-5%, and the dissolving condition is ice bath.
As a further improvement of the present invention, the PCGS polymer has the structural formula:
Figure BDA0002811383700000031
the structural formula of the FE polymer is as follows:
Figure BDA0002811383700000032
a water-soluble silicon-based gel antibacterial wound dressing is prepared by the preparation method.
The water-soluble silicon-based gel antibacterial wound dressing prepared by the preparation method is applied to preparation of wound healing tissue regeneration promotion and wound dressing infected by multidrug resistant bacteria.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a preparation method of a novel dressing for wound healing and tissue regeneration. The method takes citric acid, polyethylene glycol and aminopropyltriethoxysilane as raw materials, and obtains the PCGS polymer through one-pot thermal polycondensation; f127 and p-toluenesulfonyl chloride are reacted to obtain an F127-TsCl intermediate, and the F127-TsCl intermediate and epsilon-polylysine are reacted to obtain an FE polymer; and finally, dissolving FE, F127 and PCGS polymers according to different proportions and crosslinking to form a stable and homogeneous hydrogel dressing, thus obtaining the water-soluble silicon-based gel antibacterial wound dressing FEPCGS. The preparation method is simple, no organic solvent is left, the used raw materials are green and environment-friendly, the operation is convenient and fast, and the cost is low. Experimental results prove that the water-soluble silicon-based gel antibacterial wound dressing prepared by the method has good biocompatibility and biological effect both inside and outside a body.
The water-soluble silicon-based gel antibacterial wound dressing prepared by the invention has the advantages of simple preparation method process, environment-friendly raw materials and low cost, can show good antibacterial performance, can accelerate wound healing and can promote tissue regeneration, so the hydrogel wound dressing has good application prospect in wound healing.
Drawings
FIG. 1 is the structural formula of each monomer and polymer in the water-soluble silicon-based gel antibacterial wound dressing synthesized by the invention;
FIG. 2 is a 1H-NMR spectrum of the resulting PCGS;
FIG. 3 shows the antibacterial performance of the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the present invention;
FIG. 4 shows cytotoxicity assays for fibroblasts (L929, FIG. 4A) and human umbilical vein endothelial cells (HUVECs, FIG. 4B) of the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared according to the present invention;
FIG. 5 shows the in vivo healing of normal wounds with the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared according to the present invention;
FIG. 6 shows the result of wound healing after infection of multidrug resistant bacteria (MDRB) in the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the invention.
Detailed Description
The invention is described in further detail below with reference to the accompanying drawings:
the invention relates to a preparation method of a water-soluble silicon-based gel antibacterial wound dressing, which comprises the following steps:
1) firstly, preparing a PCGS polymer by one-pot thermal polycondensation, completely melting citric acid in a flowing nitrogen flow at 150-170 ℃ for 5-10 minutes at a stirring speed of 200 revolutions per minute in a 50 ml three-neck flask under the protection of nitrogen until the polymer is clear, wherein the molar ratio of polyethylene glycol to citric acid is 1: 1) the addition was rapid with increasing stirring rate of the magnetons. Then, APTES (in a molar ratio of 1: 0.01-0.4 to citric acid) is added dropwise into the mixed and melted system at a certain molar ratio. Then the temperature is reduced to 130-150 ℃, and the whole system is reacted for 2-3 hours under the vacuum condition (2Pa) at the rotating speed of 650 revolutions per minute. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored at 4 ℃ for use.
2) 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Then, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 55-65 ℃ for 3 days. The F127-EPL polymer was obtained by freeze-drying after dialysis for three days through a dialysis bag with a molecular weight cut-off of 3500 Da.
3) Adding the FE polymer into 22% of PBS (phosphate buffer solution) of F127, stirring in an ice bath for dissolving, adding a PCGS polymer (0.5% -5%) in a certain proportion after the FE polymer is completely dissolved, continuing stirring in the ice bath, and carrying out a crosslinking reaction at 60-70 ℃ to form a homogeneous hydrogel dressing, so as to form a stable and homogeneous compound, thereby obtaining the oxygen water-soluble silicon-based gel antibacterial wound dressing.
Wherein the citric acid-ethylene glycol-siloxane (PCGS) polymer has the structural formula:
Figure BDA0002811383700000061
the structural formula of the FE polymer is as follows:
Figure BDA0002811383700000062
the invention aims to prepare the wound dressing which has good biocompatibility and can accelerate wound healing and promote tissue repair.
The principle is as follows: the development of novel silicon-based bioactive materials, combining the advantages of inorganic silicates and organopolysiloxane materials, is an effective way to prepare satisfactory wound-healing bioactive materials. The F127 (polyoxyethylene polyoxypropylene ether block copolymer) has the body temperature response gel behavior, has good biocompatibility, is environment-friendly, cheap and easy to obtain. Epsilon-polylysine (EPL) is a natural product of biological metabolism and has good bactericidal activity and heat stability. The function of the F127-EPL is further enriched by grafting the epsilon-polylysine (EPL) to the F127, and the amino group on the EPL can also participate in the formation of a dynamic chemical bond hydrogen bond.
And then compounding the PCGS and the FE to obtain the water-soluble silicon-based gel antibacterial wound dressing, wherein the wound dressing shows good biocompatibility and good antibacterial performance, and is a hydrogel wound dressing for accelerating wound healing and promoting tissue repair.
For better understanding of the present invention, the present invention will be described in detail with reference to the following embodiments, but the present invention is not limited to the following examples.
Example 1
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.1) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (1%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
The water-soluble silicon-based gel antibacterial wound dressing prepared by the method shows good biocompatibility and good antibacterial performance, is a hydrogel wound dressing for accelerating wound healing and promoting tissue repair, and is analyzed in detail by combining experimental data.
FIG. 1 is the structural formula of each monomer and polymer in the water-soluble silicon-based gel antibacterial wound dressing synthesized by the invention, wherein A is the structural formula of Citric Acid (CA), B is the structural formula of polyethylene glycol (PEG), C is the structural formula of Aminopropyltriethoxysilane (APTES), D is the structural formula of PCGS polymer, and E is the structural formula of FE polymer.
FIG. 2 is a 1H-NMR spectrum of the prepared PCGS, and peaks at 2.74ppm to 3.04ppm and 3.69ppm are considered to be generated from methylene (-CH 2-) of citric acid and polyethylene glycol. The peaks at 1.65ppm and 0.66ppm were attributed to the methylene group of APTES, indicating successful preparation of PCGS polymer.
Fig. 3 shows the antibacterial performance of the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the invention, and the FEPCGS hydrogel dressing shows quite strong antibacterial capability, and the sterilization rate of three typical bacteria, namely staphylococcus aureus, escherichia coli and methicillin-resistant staphylococcus aureus, reaches more than 99.99 percent.
Fig. 4 shows cytotoxicity tests of the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the invention on fibroblasts (L929, fig. 4A) and human umbilical vein endothelial cells (HUVECs, fig. 4B), and it can be seen from the graphs that the FEPCGS hydrogel shows good biocompatibility on the fibroblasts and the human umbilical vein endothelial cells.
Fig. 5 shows the healing results of the water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the present invention on normal wound in vivo, and it can be seen from the figure that the relative wound area ratios of the 3M, FE, FEPCGS and FEPCGS hydrogels on day 4 are 81.8%, 67.1%, 67.6% and 43.7%, respectively. The FEPCGS hydrogel significantly promoted wound healing within 15 days compared to the other groups. Wounds treated with FEPCGS hydrogels can be closed within about 10 days, and the 3M, FE, FEPCG groups required more than 15 days to completely close the wound.
Fig. 6 shows the healing results of the wounds infected with multidrug resistant bacteria (MDRB) in the water-soluble silica-based gel antibacterial wound dressing (FEPCGS) prepared according to the present invention, and it can be seen that after methicillin resistant staphylococcus aureus infection, the 3M group showed more inflammatory exudate, while the FE, FEPCG, FEPCGS groups showed some scabs and no significant inflammatory fluid exudation. Infected wounds treated with water-soluble silicon-based gel antimicrobial wound dressing (FEPCGS) showed significantly higher repair rates after 7 days compared to the other groups.
Example 2
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.1) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (5%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 3
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.2) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (1%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 4
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.2) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (5%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 5
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.4) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (1%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 6
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 160 ℃ under a flowing nitrogen stream with a stirring rate of 200 rpm for 5-10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.4) was added dropwise to the mixed and melted system. The temperature was then lowered to 140 ℃ and the whole system was reacted under vacuum (2Pa) at a rotation rate of 650 revolutions per minute for 2-3 hours. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 60 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (5%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 65 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 7
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 150 ℃ under a flowing nitrogen stream for 5 minutes with 200 rpm stirring until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Subsequently, APTES (molar ratio to citric acid: 1: 0.01) was added dropwise to the mixed and melted system. The temperature was then lowered to 130 ℃ and the whole system was reacted under vacuum (2Pa) for 3 hours at a rotation rate of 650 revolutions per minute. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 55 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (5%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 60 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
Example 8
1) Method for the preparation of citric acid-ethylene glycol-siloxane (PCGS) polymer: PCGS polymer was first prepared using a one-pot thermal polycondensation, citric acid was completely melted in a 50 ml three-neck flask under nitrogen at 170 ℃ under flowing nitrogen stream with 200 rpm stirring rate for 10 minutes until clear, and polyethylene glycol (1: 1 molar ratio to citric acid) was added rapidly with increasing magneton stirring rate. Thereafter, APTES (molar ratio to citric acid: 1: 0.3) was added dropwise to the mixed molten system. The temperature was then lowered to 150 ℃ and the whole system was reacted under vacuum (2Pa) for 2 hours at a rotation rate of 650 revolutions per minute. Then cooled to room temperature naturally, the product was dissolved in 50 ml of deionized water and dialyzed in a dialysis bag having a molecular weight cut-off of 1000Da for 3 days. Finally, the prepared polymer was freeze-dried and stored for use at 4 ℃;
2) preparation method of FE polymer: 6.3g (0.5mmol) of F127 are dissolved in 100 ml of dry dichloromethane, and then 0.695 ml of triethylamine (5mmol) are added. Then, 0.9535g of p-toluenesulfonyl chloride dissolved in anhydrous dichloromethane was slowly added dropwise to the above system under a nitrogen atmosphere. The mixture was reacted at room temperature for 2 days, and then an amount of hydrochloric acid and a saturated aqueous sodium bicarbonate solution were added, respectively, to conduct extraction to remove impurities. Finally, the precipitate was precipitated with ether, filtered off with suction and dried in vacuo to give the F127-TsCl intermediate, which was stored at 4 ℃ in preparation for further synthesis of F127-EPL. Thereafter, 3.5g of ε -polylysine (1mmol) and 6.4475g (0.5mmol) of F127-TsCl were dissolved in DMF and reacted at 65 ℃ for 3 days. F127-EPL polymer is obtained by freeze drying after dialysis for three days by a dialysis bag with the molecular weight cutoff of 3500 Da;
3) the preparation method of the water-soluble silicon-based gel antibacterial wound dressing comprises the following steps: adding the FE polymer into 22% of PBS buffer solution of F127, stirring and dissolving in ice bath, adding PCGS polymer (5%) according to a certain proportion after the FE polymer is completely dissolved, continuing stirring in ice bath to form a stable and homogeneous compound, and crosslinking for 12 hours at 70 ℃ to obtain the water-soluble silicon-based gel antibacterial wound dressing.
The water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the invention has the advantages of simple preparation method process, environment-friendly raw materials and low cost, can show good antibacterial performance, can accelerate wound healing and can promote tissue regeneration, so the hydrogel wound dressing has good application prospect in wound healing.
The invention also has the following advantages:
(1) the F127 used in the invention has the body temperature response gel behavior, and simultaneously has good biocompatibility, is environment-friendly, cheap and easy to obtain.
(2) The epsilon-polylysine (EPL) used in the present invention is a natural biological metabolite and has excellent bactericidal activity and heat stability. The function of the F127-EPL is further enriched by grafting the epsilon-polylysine (EPL) to the F127, and the amino group on the EPL can also participate in the formation of a dynamic chemical bond hydrogen bond.
(4) The water-soluble silicon-based gel antibacterial wound dressing (FEPCGS) prepared by the invention has antibacterial capability.
(5) The synthesis of the PCGS polymer in the present invention is a one-pot thermal polycondensation process without any organic solvent.
In conclusion, the preparation method of the dilute water-soluble silicon-based gel antibacterial wound dressing provided by the invention comprises the steps of melting citric acid, adding polyethylene glycol and aminopropyltriethoxysilane, and carrying out one-pot thermal polycondensation to prepare a PCGS polymer; reacting polyoxyethylene polyoxypropylene (F127) with p-toluenesulfonyl chloride to obtain an F127-TsCl intermediate, and reacting the F127-TsCl intermediate with epsilon-polylysine to obtain an FE polymer; dissolving FE, F127 and PCGS polymers according to different proportions and crosslinking to form a stable and homogeneous hydrogel dressing, namely obtaining the water-soluble silicon-based gel antibacterial wound dressing FEPCGS.
The FEPCGS also shows good biocompatibility in vivo and in vitro, and simultaneously has good antibacterial property, so the hydrogel dressing has good application prospect in wound healing and tissue regeneration.
The above-mentioned contents are only for illustrating the technical idea of the present invention, and the protection scope of the present invention is not limited thereby, and any modification made on the basis of the technical idea of the present invention falls within the protection scope of the claims of the present invention.

Claims (8)

1. A preparation method of water-soluble silicon-based gel antibacterial wound dressing is characterized by comprising the following steps:
melting citric acid, adding polyethylene glycol and aminopropyltriethoxysilane, and performing one-pot thermal polycondensation to obtain a PCGS polymer;
f127 and p-toluenesulfonyl chloride are reacted to obtain an F127-TsCl intermediate, and the F127-TsCl intermediate and epsilon-polylysine are reacted to obtain an FE polymer;
adding the FE polymer into a PBS (phosphate buffer solution) of F127, adding the PCGS (Poly-phenol-sulfonate) polymer after the FE polymer is completely dissolved, and performing crosslinking reaction to form a homogeneous water-soluble silicon-based gel antibacterial wound dressing;
the molar ratio of the F127 to the p-toluenesulfonyl chloride is 1: 10 in anhydrous dichloromethane to obtain an F127-TsCl intermediate at room temperature;
the F127-TsCl intermediate and epsilon-polylysine are mixed in a molar ratio of 1: 2 reacting in dimethylformamide at 55-65 ℃ to obtain the FE polymer.
2. The method for preparing the water-soluble silicon-based gel antibacterial wound dressing according to claim 1, wherein the molar ratio of the citric acid to the polyethylene glycol to the aminopropyltriethoxysilane is 1: 1: (0.01-0.4).
3. The preparation method of the water-soluble silicon-based gel antibacterial wound dressing according to claim 1, wherein the melting temperature of the citric acid is 150-170 ℃, the one-pot thermal reaction temperature is 130-150 ℃, and the reaction time is 2-4 hours.
4. The method for preparing the water-soluble silicon-based gel antibacterial wound dressing according to claim 1, wherein the post-treatment method for obtaining the PCGS polymer comprises the following steps:
after one-pot thermal polycondensation is finished, the product is dissolved by deionized water and dialyzed in a dialysis bag, and the prepared polymer is frozen and dried to obtain the PCGS polymer.
5. The preparation method of the water-soluble silicon-based gel antibacterial wound dressing according to claim 1, wherein the mass concentration of the FE polymer in the PBS buffer solution is 3%, the mass concentration of the F127 in the PBS buffer solution is 22%, and the mass concentration of the PCGS polymer is 0.5-5%;
the dissolving condition is ice bath;
the crosslinking reaction temperature is 60-70 ℃.
6. The method for preparing a water-soluble silicon-based gel antibacterial wound dressing according to claim 1, wherein the structural formula of the PCGS polymer is:
Figure FDA0003174915720000021
the structural formula of the FE polymer is as follows:
Figure FDA0003174915720000022
7. a water-soluble silicon-based gel antibacterial wound dressing prepared by the preparation method of any one of claims 1 to 6.
8. The use of the water-soluble silicon-based gel antibacterial wound dressing prepared by the preparation method of any one of claims 1 to 6 in the preparation of wound dressings for promoting wound healing tissue regeneration and multi-drug resistant bacteria infection.
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