CN112336685A - Antibacterial micro-emulsion gel and preparation method thereof - Google Patents
Antibacterial micro-emulsion gel and preparation method thereof Download PDFInfo
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- CN112336685A CN112336685A CN202011177785.1A CN202011177785A CN112336685A CN 112336685 A CN112336685 A CN 112336685A CN 202011177785 A CN202011177785 A CN 202011177785A CN 112336685 A CN112336685 A CN 112336685A
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Abstract
The invention relates to an antibacterial micro-emulsion gel and a preparation method thereof. The preparation method of the microemulsion gel takes Pickering emulsion as a template and comprises the following steps: (1) preparing a continuous phase consisting of distilled water, gelatin nanoparticles, aminoglycoside antibiotics and oxidized polysaccharide; (2) adding a dispersion phase containing antibacterial essential oil into the continuous phase, emulsifying to obtain a Pickering emulsion, and reacting and crosslinking for a certain time to obtain the antibacterial micro-emulsion gel. The micro-emulsion gel constructed by the invention is an intelligent micro-emulsion gel for drug delivery according to needs, can regulate and control the release of antibiotics and antibacterial essential oil according to in vitro environmental conditions, has higher antibacterial activity, and can be applied to the biomedical fields of drug controlled release systems, medical dressings and the like.
Description
Technical Field
The invention belongs to the field of biomedical engineering, and particularly relates to an antibacterial micro-emulsion gel and a preparation method thereof.
Background
Bacterial infections are one of the most challenging problems in the medical field, and until today, bacterial infections remain a serious threat to human life. Aminoglycoside antibiotics are a broad-spectrum antibacterial drug for treating gram-negative bacilli infection, and are listed as important antibacterial drugs for treating tuberculosis, endocardial and meningeal infections by the world health organization. Although they have good clinical efficacy, aminoglycoside antibiotics are often plagued by adverse side effects, and with the widespread clinical use of antibacterial drugs, bacterial resistance is becoming more severe, making drug-resistant and multi-drug resistant infections one of the most urgent public health problems today.
The natural plant essential oil is a novel antibacterial agent which is valued in recent years, and has the characteristics of low toxicity, easy decomposition, difficult generation of drug resistance, rich production raw materials, environmental friendliness and the like. The essential oil has unique aromatic odor and good antibacterial property, oxidation resistance, insecticidal property and the like. The plant essential oil and the antibiotics are used together, so that a large amount of pathogenic bacteria can be resisted, the using amount of the antibiotics can be reduced, and the same antibacterial effect can be achieved. However, the plant essential oil is volatile at normal temperature, and the effective components of the plant essential oil are unstable in light, heat and oxygen environments, so that the application of the natural plant essential oil as an antibacterial drug is greatly limited. Therefore, a new controlled release carrier for drugs is needed to achieve synergistic antibacterial effect of antibiotics and plant essential oils.
The microemulsion gel is a novel drug carrier which combines emulsion and gel matrix, wherein the emulsion two-phase system can load easily volatile and water-insoluble drugs. The microemulsion gel has the advantages of both microemulsion and gel, can increase the solubility of insoluble drugs, improve the bioavailability, and reduce the toxicity, irritation and adverse reaction of the drugs; meanwhile, the viscosity of the microemulsion can be improved, the adhesiveness and the spreadability of the medicine and the skin can be improved, and the medicine retention time can be prolonged. The reported antibacterial microemulsion gel is prepared by taking cinnamon oil as a disperse phase to prepare O/W type concentrated emulsion, and the microemulsion gel carrying the cinnamon oil is constructed by acrylamide free radical polymerization in an emulsion continuous phase (Polym.chem.2014, 5 (14): 4227-4234). Antibacterial research shows that the composite hydrogel has a good slow-release function on the loaded cinnamon oil, and the microemulsion hydrogel has good antibacterial property on staphylococcus aureus and escherichia coli. Chinese patent literature discloses 'a chitin thyme essential oil gel and a preparation method thereof', and application publication number is CN111053942A, the invention adopts chitin suspension and/or chitin compound suspension and thyme essential oil to prepare Pickering emulsion, and the product is frozen and dried to form the thyme essential oil gel. Although these gels achieve loading of natural plant essential oils, the release of essential oils results from free diffusion, lack of fine control of the concentration, and may result in too low a concentration of the antimicrobial agent to achieve therapeutic purposes, making it difficult to truly apply to complex clinical situations.
Disclosure of Invention
The invention aims to overcome the adverse side effect of single aminoglycoside antibiotic, reduce the drug resistance of bacteria, widen the antibacterial spectrum, combine the aminoglycoside antibiotic and a natural antibacterial agent (plant essential oil) for use and provide the microemulsion gel with intelligent controlled release, good antibacterial action and biocompatibility.
The invention also provides a preparation method of the antibacterial microemulsion gel by a Pickering emulsion template method, which comprises the steps of mixing the gelatin particles used as a stabilizer and an aqueous solution containing oxidized polysaccharide and aminoglycoside antibiotics used as a continuous phase with a dispersion phase containing plant essential oil, and carrying out emulsion polymerization and gelation to obtain the antibacterial microemulsion gel. The raw materials of gelatin and biological polysaccharide have wide sources and low cost. The Pickering emulsion template has high stability, and can increase the load rate of plant essential oil and improve the stability of the plant essential oil.
In order to achieve the purpose, the invention adopts the following technical scheme:
(1) dissolving B type gelatin in distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding acetone to form a precipitate, redissolving the precipitate in distilled water and adjusting the pH value to 12.0, dropwise adding acetone again until the precipitate is generated, then adding a cross-linking agent into the solution, continuing to react at the constant temperature of 50 ℃ for 3-10 hours, and centrifuging the reacted solution for 20-30 minutes under the condition of 10000g to obtain gelatin nanoparticles; (2) dissolving natural polysaccharide in water, dropwise adding a sodium periodate solution, reacting at room temperature in a dark place for 3-8 hours, centrifuging to obtain a clear solution, precipitating a product by using ethylene glycol, dialyzing by using deionized water, and freeze-drying to obtain oxidized polysaccharide; (3) mixing distilled water, a continuous phase consisting of gelatin nanoparticles, oxidized polysaccharide and aminoglycoside antibiotics and a dispersed phase containing plant essential oil at 10000-15000 rpm according to a volume ratio of 1: 1.5-1: 5 to form O/W type Pickering emulsion; (4) and standing at normal temperature in the dark for 3-5h to obtain the antibacterial micro-emulsion gel prepared by the Pickering emulsion method. In the invention, the cross-linking agent for preparing the gelatin nano-particles can be selected from glutaraldehyde or genipin; the natural polysaccharide can be any one of sodium carboxymethylcellulose, dextran, sodium alginate, sodium hyaluronate, chondroitin sulfate, starch or agarose; the aminoglycoside antibiotic is any one of amikacin, tobramycin, neomycin and netilmicin; the plant essential oil can be one or more of tea tree essential oil, thyme essential oil, cortex Cinnamomi essential oil, Lavender essential oil and Rosmarinus officinalis essential oil; the medicinal oil is one of isopropyl myristate, corn oil, sunflower seed oil, MCT and soybean oil.
The invention takes natural high molecular gelatin as raw material to prepare nano particles, and takes gelatin nano particles with extremely small dosage as emulsifier to prepare the Pickering emulsion template with excellent stability. Adding oxidized polysaccharide in the continuous phase, and performing Schiff base reaction on aldehyde group on the oxidized polysaccharide and amino glycoside antibiotic rich in amino to form gel through continuous cross-linking reaction. The gelatin nano-particle adsorption layer on the interface of the emulsion template can effectively isolate oxygen and improve the stability of essential oil. The microemulsion gel provided by the invention has an inward volume fraction of 60-83%, and can be loaded with a large amount of antibacterial essential oil; and the gel network structure of the continuous phase is formed by crosslinking Schiff base. The Schiff base is a dynamic reversible covalent bond with pH sensitivity, and can be continuously degraded according to the change of the pH value of an infected area. At the same time, the essential oil in the dispersed phase is gradually released along with the degradation of the continuous phase gel. The aminoglycoside antibiotic produced by degradation and essential oil act synergistically to inhibit the growth of bacteria in the infected area. Therefore, the microemulsion gel provided by the invention has an intelligent controlled release effect and good antibacterial activity, and has good application prospects in biomedical fields such as drug controlled release systems and medical dressings.
Therefore, the microemulsion gel prepared by the invention has the following advantages:
(1) the gelatin nano-particles prepared by the invention have good wettability and stability, and only a small amount of gelatin nano-particles are needed for forming the Pickering emulsion.
(2) The oxidized polysaccharide adopted by the invention has good biocompatibility, high water solubility and biodegradability, and can be widely used for preparing hydrogel; adjusting the degree of hydroformylation of the polysaccharide can control the time of formation of the hydrogel.
(3) The aminoglycoside antibiotics adopted by the invention are rich in amino and can realize rapid gelation by crosslinking reaction with oxidized polysaccharide; by varying the dose or type of aminoglycoside in the gel, the gel strength, erosion rate and drug release kinetics can be precisely adjusted.
(4) The Pickering emulsion template adopted by the invention has a large volume fraction of the internal phase, can load a large amount of antibacterial essential oil, improves the antibacterial activity of the essential oil, and has great significance for improving the resource utilization of natural products, reducing the use of antibiotics and resisting drug-resistant bacterial infection.
(5) The microemulsion gel prepared by the invention has the advantages that the antibacterial effect and the gel strength can be flexibly changed by adjusting the content of aminoglycoside antibiotics and the concentration of gelatin nanoparticles, and the requirement of various applications can be conveniently met.
(6) The microemulsion gel prepared by the invention can regulate and control the degradation of the gel and the release of essential oil according to the change of the pH value of a bacterial infection area, realizes the synergistic bacteriostasis of antibiotics and essential oil, and is an intelligent drug controlled release system.
(7) The antibacterial microemulsion gel prepared by the invention has the advantages of wide raw material source, low material toxicity risk, good biocompatibility, extremely strong antibacterial effect, effective control of the release effect of the medicament, short preparation time and great production and application values.
Drawings
FIG. 1 gel diagram of the antibacterial microemulsion prepared in example 1;
FIG. 2 is a confocal laser microscopy image of the antibacterial microemulsion gel prepared in comparative example 1;
Detailed Description
The present invention will be further described with reference to specific embodiments, and the advantages and features of the present invention will become more apparent from the description of the embodiments, but the embodiments are only exemplary and do not limit the scope of the present invention in any way.
Example 1
Dissolving 1.25g B type gelatin in 25mL of distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding 25mL of acetone, removing the supernatant, redissolving the precipitate in 15mL of distilled water and adjusting the pH value to 12.0, dropwise adding acetone again until a precipitate is generated, then adding 250 μ L of glutaraldehyde solution (25% aqueous solution) into the solution, continuing to react at the constant temperature of 50 ℃ for 3 hours, and carrying out refrigerated centrifugation on the reacted solution for 30 minutes under the condition of 10000g to obtain the gelatin nanoparticles.
8mL of sodium periodate (0.5M) solution was added to 10mL of aqueous dextran solution (1g, 10% w/v, M)w60000), stirred at room temperature for 4 hours in the dark, and 10mL of ethylene glycol solution was added to terminate the reaction. And then, fully dialyzing the solution by using deionized water, and freeze-drying to obtain the oxidized polysaccharide.
Preparing 2mL of aqueous solution of a continuous phase, wherein the concentration of the gelatin nanoparticles is 5mg/mL, the concentration of the amikacin is 0.105mg/mL, and the concentration of the oxidized polysaccharide is 8 mg/mL; preparing 3mL of dispersed phase, wherein the tea tree essential oil is 0.5mL, and the isopropyl myristate is 2.5 mL; and stirring the two phases at 12000rpm for 30s, and reacting for 3 hours at normal temperature in the dark to obtain the antibacterial micro-emulsion gel.
Example 2
Dissolving 1.25g B type gelatin in 25mL of distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding 25mL of acetone, removing the supernatant, redissolving a white precipitate in 15mL of distilled water, adjusting the pH value to 12.0, dropwise adding acetone again until a white precipitate is generated, adding 1.25mL of genipin aqueous solution (10%) into the solution, continuing the constant temperature reaction at 50 ℃ for 5 hours, and freezing and centrifuging the reacted solution for 30 minutes under the condition of 10000g to obtain the gelatin nanoparticles.
8mL of sodium periodate (0.5M) solution was added to 10mL of an aqueous solution of sodium hyaluronate (1g, 10% w/v), stirred at room temperature for 4 hours in the dark, and 10mL of ethylene glycol solution was added to terminate the reaction. And then, fully dialyzing the solution by using deionized water, and freeze-drying to obtain the oxidized polysaccharide.
Preparing 1mL of aqueous solution of a continuous phase, wherein the concentration of the gelatin nanoparticles is 5mg/mL, the concentration of the neomycin is 0.07mg/mL, and the concentration of the oxidized polysaccharide is 10 mg/mL; preparing 4mL of dispersed phase, wherein 1mL of thyme essential oil and 3mL of corn oil are contained; and stirring the two phases at 12000rpm for 30s, and reacting the obtained product for 3 hours at normal temperature in a dark place to obtain the antibacterial micro-emulsion gel.
Example 3
Dissolving 1.25g B type gelatin in 25mL of distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding 25mL of acetone, removing the supernatant, redissolving the precipitate in 15mL of distilled water and adjusting the pH value to 12.0, dropwise adding acetone again until a precipitate is generated, then adding 625 mu L of genipin aqueous solution (5%) into the solution, continuing to react at the constant temperature of 50 ℃ for 10 hours, and carrying out refrigerated centrifugation on the reacted solution for 30 minutes under the condition of 10000g to obtain the gelatin nanoparticles.
8mL of sodium periodate (0.5M) solution was added to 10mL of sodium carboxymethylcellulose aqueous solution (1g, 10% w/v, M)w90000), stirred at room temperature for 4 hours in the dark, and 10mL of ethylene glycol solution was added to terminate the reaction. And then, fully dialyzing the solution by using deionized water, and freeze-drying to obtain the oxidized polysaccharide.
Preparing 1.5mL of aqueous solution of a continuous phase, wherein the concentration of gelatin nanoparticles is 10mg/mL, the concentration of amikacin is 0.105mg/mL, and the concentration of oxidized polysaccharide is 8 mg/mL; preparing 3.5mL of dispersed phase, wherein the cinnamon essential oil is 0.7mL, and the MCT is 2.8 mL; the two phases are stirred at 15000rpm for 30s and reacted for 3 hours at normal temperature in the dark to obtain the antibacterial micro-emulsion gel.
Example 4
Dissolving 1.25g B type gelatin in 25mL of distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding 25mL of acetone, removing the supernatant, redissolving the precipitate in 15mL of distilled water and adjusting the pH value to 12.0, dropwise adding acetone again until a precipitate is generated, then adding 125 mu L of glutaraldehyde aqueous solution (25%) into the solution, continuing the constant temperature reaction at 50 ℃ for 10 hours, and carrying out refrigerated centrifugation on the reacted solution for 30 minutes under the condition of 10000g to obtain the gelatin nanoparticles.
8mL of sodium periodate (0.5M) solution was added to 10mL of chondroitin sulfate aqueous solution (1g, 15% w/v), stirred at room temperature for 4 hours in the dark, and 10mL of ethylene glycol solution was added to terminate the reaction. And then, fully dialyzing the solution by using deionized water, and freeze-drying to obtain the oxidized polysaccharide.
Preparing 2mL of aqueous solution of a continuous phase, wherein the concentration of the gelatin nanoparticles is 8mg/mL, the concentration of the netilmicin is 0.08mg/mL, and the concentration of the oxidized polysaccharide is 10 mg/mL; preparing 3mL of dispersed phase, wherein the rosemary oil is 0.5mL, and the corn oil is 2.5 mL; and stirring the two phases at 12000rpm for 30s, and reacting the obtained product for 3 hours at normal temperature in a dark place to obtain the antibacterial micro-emulsion gel.
Example 5
Dissolving 1.25g B type gelatin in 25mL of distilled water, stirring at a constant temperature of 50 ℃ to form a gelatin solution, adding 25mL of acetone, removing the supernatant, redissolving the precipitate in 15mL of distilled water and adjusting the pH value to 12.0, dropwise adding acetone again until a precipitate is generated, adding 250 mu L of glutaraldehyde aqueous solution (25%) into the solution, continuing to react at the constant temperature of 50 ℃ for 3 hours, and carrying out refrigerated centrifugation on the reacted solution for 30 minutes under the condition of 10000g to obtain the gelatin nanoparticles.
10mL of starch (1g, 8% w/v) was added to 8mL of sodium periodate (0.5M) solution, stirred at room temperature for 4 hours in the dark, and 10mL of ethylene glycol solution was added to terminate the reaction. And then, fully dialyzing the solution by using deionized water, and freeze-drying to obtain the oxidized polysaccharide.
Preparing 2mL of aqueous solution of a continuous phase, wherein the concentration of the gelatin nanoparticles is 5mg/mL, the concentration of the neomycin is 0.065mg/mL, and the concentration of the oxidized polysaccharide is 5 mg/mL; preparing 3mL of dispersed phase, wherein 0.45mL of lavender essential oil and 2.55mL of soybean oil are contained; the two phases are stirred at 15000rpm for 30s, and the obtained product is reacted for 3 hours at normal temperature in the dark to obtain the antibacterial microemulsion gel.
Claims (10)
1. An antibacterial micro-emulsion gel and a preparation method thereof, the preparation method comprises the following steps:
(1) preparing a continuous phase consisting of distilled water, gelatin nanoparticles, aminoglycoside antibiotics and oxidized polysaccharide, wherein the concentration ranges of the gelatin nanoparticles, the aminoglycoside antibiotics and the oxidized polysaccharide are respectively 4-10 mg/mL, 0.035-0.105 mg/mL and 6-10 mg/mL;
(2) mixing the continuous phase and the dispersed phase according to the volume ratio of 1: 1.5-1: 5 under the condition of 10000-15000 rpm to form an O/W type Pickering emulsion;
(3) and reacting for 3-5 hours at normal temperature in a dark place to obtain the intelligent antibacterial micro-emulsion gel.
2. The antibacterial microemulsion gel according to claim 1, wherein the gelatin nanoparticles are emulsion stabilizers and the preparation method comprises: fully dissolving B type gelatin in distilled water, adding acetone to obtain a precipitate, re-dissolving the precipitate in distilled water, adjusting the pH value to 12.0, dropwise adding acetone again until the precipitate is generated, then adding a cross-linking agent into the solution, continuing to perform constant temperature reaction at 50 ℃ for 3-10 hours, and centrifuging the reacted solution for 20-30 minutes under the condition of 10000g to obtain the gelatin nano-particles.
3. The antibacterial microemulsion gel according to claim 2, wherein the cross-linking agent is any one of genipin and glutaraldehyde, wherein the genipin accounts for 5-10% of the mass of the gelatin, and the glutaraldehyde accounts for 2.5-5% of the mass of the gelatin.
4. The antibacterial microemulsion gel according to claim 1, wherein the oxidized polysaccharide is prepared by the following method: dissolving natural polysaccharide in water, dropwise adding a sodium periodate solution, reacting at room temperature in a dark place for 3-8 hours, centrifuging to obtain a clear solution, precipitating a product by using ethylene glycol, dialyzing by using deionized water, and freeze-drying to obtain oxidized polysaccharide.
5. The antibacterial microemulsion gel according to claim 4, wherein the natural polysaccharide is any one of sodium carboxymethylcellulose, dextran, sodium alginate, sodium hyaluronate, chondroitin sulfate, starch or agarose.
6. The antibacterial microemulsion gel according to claim 1, wherein the aminoglycoside antibiotic is any one of amikacin, tobramycin, neomycin, and netilmicin.
7. The antibacterial microemulsion gel according to claim 1, wherein the dispersed phase is formed by mixing plant essential oil and medicinal oil according to a ratio of 1: 3-1: 5.
8. The antibacterial microemulsion gel according to claim 7, wherein the plant essential oil is one or more of tea tree essential oil, thyme essential oil, cinnamon essential oil, lavender essential oil and rosemary oil.
9. The antibacterial microemulsion gel according to claim 7, wherein the medicinal oil is any one of isopropyl myristate, corn oil, sunflower seed oil, MCT and soybean oil.
10. The antibacterial microemulsion gel according to any one of claims 1 to 9, which is an intelligent microemulsion gel for drug delivery on demand, has good bacteriostatic action and biocompatibility, and can be applied to biomedical fields such as drug controlled release systems, medical dressings and the like.
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| CN113730596A (en) * | 2021-09-15 | 2021-12-03 | 北京化工大学 | Microenvironment adaptive nano-drug delivery system for severe lower respiratory tract infection and preparation method thereof |
| CN113952292A (en) * | 2021-10-28 | 2022-01-21 | 河南中医药大学 | Rosemary essential oil nanoemulsion gel, preparation method and application thereof |
| CN115322421A (en) * | 2022-09-16 | 2022-11-11 | 广西大学 | Preparation method of pH-responsive intelligent antibacterial biomass-based packaging film |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113952292A (en) * | 2021-10-28 | 2022-01-21 | 河南中医药大学 | Rosemary essential oil nanoemulsion gel, preparation method and application thereof |
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| CN115322421A (en) * | 2022-09-16 | 2022-11-11 | 广西大学 | Preparation method of pH-responsive intelligent antibacterial biomass-based packaging film |
| CN115322421B (en) * | 2022-09-16 | 2023-06-27 | 广西大学 | Preparation method of pH response intelligent antibacterial biomass-based packaging film |
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