CN112316136A - Preparation method and application of antibacterial nano dressing AuNS-AMP-PEG - Google Patents
Preparation method and application of antibacterial nano dressing AuNS-AMP-PEG Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0052—Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/60—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes the organic macromolecular compound being a polyoxyalkylene oligomer, polymer or dendrimer, e.g. PEG, PPG, PEO or polyglycerol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/143—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with inorganic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Abstract
The invention belongs to the technical field of metal nano materials, and particularly discloses preparation and application of an antibacterial nano dressing AuNS-AMP-PEG. The antimicrobial peptide of sequence GKRWWKWWRRC was linked to gold nanostar (AuNS) via an Au-S bond. The photo-thermal material AuNS is introduced to carry out photo-thermal antibacterial (PTT), and is utilized to generate heat under the irradiation of laser, so that microorganisms are heated, cell damage and cell death are caused, and the photo-thermal material AuNS and antibacterial peptide (AMP) generate a synergistic antibacterial effect, and PEG is added to increase the stability of the material. An animal wound model shows that the antibacterial nano material dressing AuNS-AMP-PEG prepared by the invention can kill bacteria infecting the surface of a mouse wound, thereby promoting wound healing.
Description
Technical Field
The invention belongs to the technical field of antibacterial materials, and particularly relates to a preparation method and application of a novel nano dressing AuNS-AMP-PEG with a photothermal antibacterial property.
Background
With the continuous improvement of living standard of people, the requirements on sanitation and health are also improved. However, there are a large number of bacteria in our surroundings, which pose a great threat to people's life. The wound patient loses the natural barrier protection function due to the damage of the skin integrity, a shortcut is provided for the invasion of various bacteria, wound healing of the patient is delayed due to wound infection, and even infectious shock is caused by serious patients, so that the life of the patient is threatened. How to effectively reduce or avoid the harm of bacteria to trauma patients so as to reduce the occurrence of bacterial infectious diseases has become the focus of social attention. In 2000, there were 4000 million hospitalizations and 3100 million outpatient surgeries requiring wound care in the united states alone, and in addition, about 650 million patients are currently affected by chronic wound infection annually, with healthcare costs of $ 250 million. This number is also continuing to rise due to expansion of currency, aging of the population, increased incidence of diabetes and obesity. In addition, wound therapy has a tremendous commercial potential, and statistically, there is a market demand for approximately $ 150 million wound care products and $ 120 million wound scar therapy products per year.
Photothermal therapy (PTT) is an effective method against drug-resistant bacteria, and has received much attention due to its non-invasiveness and fewer side effects. Photothermal therapy utilizes a material with high photothermal conversion efficiency to convert light energy into heat energy under the irradiation of an external light source, so that the surface of bacteria is heated, the protein of the bacteria is denatured, the death of the bacteria is further caused, and the generation of drug resistance can be avoided.
Antimicrobial peptide (AMP) is a polypeptide with antibacterial activity, and is a novel antibacterial drug with good handiness due to its advantages of wide antibacterial range, high activity, and multiple species. When AMPs bind to the target membrane, membrane permeation occurs, resulting in leakage of cellular components and ultimately cell death. Bacterial infections represent one of the greatest clinical challenges, and antimicrobial peptides are an effective method of combating bacterial infections and have attracted considerable attention in the past decade. Ma et al (ACS infectious diseases, 2017, 3(11): 820-. Among these peptides, WRL3 (WLRAFRRLVRRLARGLRRNH 2) was more cell selective for bacterial cells than erythrocytes and macrophages. In addition, WRL3 shows effective antibacterial activity on MRSA with the minimum inhibitory concentration of 2 mug/mL, and in vivo studies show that WRL3 can control the proliferation of MRSA in wound tissues and provide a more favorable environment for wound healing. WRL3 has great potential as a novel antibacterial agent, and can be used for treating clinical MRSA infection on skin burn wound.
In the invention, a photo-thermal material AuNS is coupled with antibacterial peptide (AMP), PEG is added to increase the stability of the AuNS, and thus a novel multifunctional antibacterial nano dressing AuNS-AMP-PEG is developed. The photo-thermal material AuNS is introduced for PTT antibacterial, and is utilized to generate heat under the irradiation of laser, so that microorganisms are heated, cell damage and cell death are caused, and the photo-thermal material AuNS and antibacterial peptide (AMP) generate synergistic antibacterial effect.
Disclosure of Invention
The invention couples the antibacterial peptide (AMP) with the photothermal material AuNS, provides an AuNS-AMP-PEG composite nano antibacterial material, combines the antibacterial peptide with the photothermal material, plays a synergistic antibacterial role, and has excellent antibacterial performance, good biocompatibility and high safety. Has great potential of chronic wound dressing and wide application prospect in treating clinical chronic wounds.
The specific technical scheme of the invention is as follows:
1. the AuNS-AMP-PEG nano dressing prepared by the invention is composed of two parts of gold nanostars (AuNS) and antibacterial peptides (AMP).
2. The gold nanostars (AuNS) in the AuNS-AMP-PEG nano dressing prepared by the invention are irregular stars (triangles, four-corner stars and the like), are uniformly dispersed, have the grain size of 30-50 nm, and have strong penetrating power due to the polygonal shape of the gold nanostars, so that nano materials can easily enter bacterial membranes.
3. The sequence of the antibacterial peptide (AMP) in the AuNS-AMP-PEG nano dressing is GKRWWKWWRRC, and the antibacterial peptide (AMP) is synthesized by a conventional solid phase Fmoc method, namely, the solid phase resin is deprotected by Fmoc-protected monomer amino acid to expose amino, and a peptide bond is formed with carboxyl of the amino acid in a solution through a condensation reaction, so that the amino acid is connected to the resin, and the peptide chain is extended from the C end to the N end until the required peptide chain is synthesized.
4. The photo-thermal material AuNS in the AuNS-AMP-PEG nano dressing prepared by the invention can generate heat under the irradiation of near-infrared laser (808 nm), thereby triggering the damage and death of bacteria and having obvious photo-thermal antibacterial effect (PTT).
5. The synthesis method of the AuNS-AMP-PEG nano dressing prepared by the invention comprises the following steps: adding 400 μ L AMP (250 μ M) into 400 μ L gold nanostars, placing in a shaker at 250 r/min for 20 min, adding 20 μ L PEG, and placing in a shaker at 250 r/min for 20 h. After the reaction was completed, the mixed solution was collected in a 2 mL high-speed centrifuge tube, and the solution was centrifuged at 13000 rpm for 15 min with a high-speed centrifuge. After the centrifugation, the supernatant was removed and deionized water was added to the pellet to resuspend the pellet and the centrifugation was repeated 3 times. And obtaining the final AuNS-AMP-PEG antibacterial nano dressing.
Compared with the prior art, the invention has the following beneficial effects:
the AuNS-AMP-PEG antibacterial nano dressing prepared by the method disclosed by the invention combines the traditional antibacterial peptide (AMP) and the photothermal therapy (PTT) to play a synergistic antibacterial role, has higher antibacterial activity, and takes the nano material as a carrier, so that the stability of the material can be improved, and the biocompatibility can be improved. An animal wound model shows that the antibacterial nano material dressing AuNS-AMP-PEG prepared by the invention can kill bacteria infecting the surface of a mouse wound, thereby promoting wound healing. The preparation process disclosed by the invention is simple, wide in raw material source, mild in reaction condition, easy to synthesize and suitable for popularization and use.
Drawings
FIG. 1 Transmission Electron microscopy of gold nanostars (AuNS).
Fig. 2 photo-thermal killing effect of AuNS-AMP-PEG nano-dressing on s.
Fig. 3 photo-thermal killing effect of AuNS-AMP-PEG nano dressing on e.
Fig. 4 photo-thermal killing effect of AuNS-AMP-PEG nano-dressing on s.
Figure 5 wound changes of s. aureus bacteria infected mice for 10 days for three different treatment regimes.
Detailed Description
The present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.
Example 1
1. Synthesis and characterization of materials
(1) Synthesis and characterization of photo-thermal material AuNS
Weighing 2g of NaOH solid in a beaker, and adding 50 mL of deionized water into the beaker to prepare 1M NaOH solution for later use; chloroauric acid tetrahydrate (HAuCl) was accurately weighed using an analytical balance4.4H2O) 0.412g into a 50 mL centrifuge tube, 25 mL deionized water was added to the centrifuge tube, and the mixture was vortexed uniformly to obtain an aqueous chloroauric acid solution with a concentration of 40mM for use. Accurately weighing 1 g of Hepes in a 50 mL centrifuge tube, adding 26.4 mL of deionized water and 3.6 mL of 1M NaOH solution into the centrifuge tube, and uniformly vortex and oscillate to obtain the product with the concentration of 140 × 10-3M, Hepes solution with pH 7.4. The above operation was repeated 3 times to obtain a final volume of 90 mL of Hepes solution. mu.L of 40mM chloroauric acid aqueous solution was added to the Hepes solution to obtain a pale yellow mixed solution, and the mixed solution was quickly stirred with a gun and allowed to stand for reaction for 1 hour in the dark. And observing the color of the mixed solution after the reaction is finished, wherein if the color of the solution is changed from light yellow to dark blue, the reaction is successful. The mixed solution was dispersed in 350 mL high-speed centrifuge tubes, and the solution was centrifuged at 13000 rpm for 15 min using a high-speed centrifuge. After completion of centrifugation, the supernatant was removed and 10 mL of deionized water was added to the pellet to resuspend it, and centrifugation was repeated 3 times. The resulting precipitate was finally distributed into 10 mL of deionized water for use.
Sucking 20 mu L of the prepared AuNS into a 1.5 mL centrifuge tube, adding 980 mu L of deionized water, diluting by 50 times, and then carrying out ultrasonic treatment on the diluted AuNS in an ultrasonic cleaning machine for 5min to uniformly disperse the AuNS. After the completion of the ultrasonic treatment, 10. mu.L of the diluted nanomaterial was dropped onto a carbon-supported copper mesh, and the copper mesh was dried overnight in an electronic dry box.
(2) Synthesis of antimicrobial peptides (AMPs)
Firstly, GKRWWKWWRRC polypeptide is synthesized, which is based on 2-Chlorotrityl Chloride resin with Fmoc protective group and is obtained by solid phase peptide synthesis method. The method specifically comprises the following steps: amino acid (chemically modified alpha-amino acid), HBTU and HOBT were weighed out in amounts of 5 times the molar weight of the resin, respectively, dissolved in DMF and coupled with DIEA for 30 min. Then 20% piperidine is added to react for 30 min to remove the Fmoc protecting group, and the step is repeated until the required peptide chain is synthesized.
(3) Synthesis of AuNS-AMP-PEG (AuNS-AMP-polyethylene glycol) antibacterial nano dressing
Adding 400 μ L AMP (250 μ M) into 400 μ L gold nanostars, placing in a shaker at 250 r/min for 20 min, adding 20 μ L PEG, and placing in a shaker at 250 r/min for 20 h. After the reaction was completed, the mixed solution was collected in a 2 mL high-speed centrifuge tube, and the solution was centrifuged at 13000 rpm for 15 min with a high-speed centrifuge. After the centrifugation, the supernatant was removed and deionized water was added to the pellet to resuspend the pellet and the centrifugation was repeated 3 times. And obtaining the final AuNS-AMP-PEG antibacterial nano dressing.
2. In vitro antibacterial experiment of AuNS-AMP-PEG antibacterial nano dressing
1) Preparing 70 μ M AuNS-AMP-PEG with sterile water, and collecting 108Mixing 1mL of CFU/mL S.aureus bacterial solution with 250 μ L of sample, incubating at 37 deg.C for 1 hr, irradiating with 808nm laser for 5min or not, and diluting 103After 100. mu.L of the coated plate was put into a biochemical incubator and incubated at 37 ℃ for 15 hours, the number of colonies on the plate was observed.
As shown in fig. 2, the colony of s.aureus is significantly reduced after the AuNS-AMP-PEG nano dressing is added, which may be caused by the action of AMP, and the effect is better after the AuNS-AMP-PEG nano dressing is added and irradiated with light, because after laser irradiation, the AuNS-AMP-PEG nano dressing generates a large amount of heat, the microorganism is heated and causes cell damage and death, and the Auns-AMP-PEG nano dressing has a synergistic effect with AMP, so that the antibacterial effect is better.
2) Preparing 100 μ M AuNS-AMP-PEG with sterile water, and collecting 108Mixing 1mL of CFU/mL E.coli liquid with 250 μ L of sample, incubating at 37 deg.C for 1 hr, irradiating with 808nm laser for 5min, and diluting 103100 μ L of the coated plate was taken out and put into a biochemical incubator to be incubated at 37 ℃ for 15 hours.
As shown in fig. 3, the e.coli colonies were significantly reduced after the AuNS-AMP-PEG nanocoating was added and irradiated.
3) Take 1mL108CFU/mL S.aureus bacterial liquid and 1mL108Mixing CFU/mL E.coli bacteria solution, incubating 1mL mixed bacteria solution with 250 μ L AuNS-AMP-PEG nanometer dressing (70 μ M) for 1 hr, irradiating with 660nm laser for 5min or not, diluting 103100 μ L of the coated plate was taken out and put into a biochemical incubator to be incubated at 37 ℃ for 15 hours. (red circles are colonies of S.aureus, blue circles are colonies of E.coli)
As shown in fig. 4, after the AuNS-AMP-PEG nano dressing was added, colonies of s.aureus were significantly reduced, colonies of e.coli were not significantly changed, which may be caused by the action of AMP, and after the AuNS-AMP-PEG nano dressing was added and irradiated with light, only colonies of e.coli were left on the plate, and the number of colonies of e.coli was also significantly reduced compared to the Control group.
3. In vivo antibacterial experiment of AuNS-AMP-PEG nano dressing
In order to study the antibacterial effect of the AuNS-AMP-PEG nano dressing on S.aureus bacterial infection parts of mice, an S.aureus bacterial infection model is firstly established for each group of mice, surgical scissors and surgical forceps are disinfected by 75% of ethanol, during experiments, 75 muL of 4% chloral hydrate is injected into the abdominal cavity of BALB/c female mice, after the mice are completely anesthetized, the backs of the mice are upwards, an oval full-thickness wound with a long axis of about 8 mm and a short axis of about 6 mm is made on the backs of the mice by a puncher, and the wounds are treated by the disinfected surgical scissors and surgical forceps. 50 mu.L of the suspensionS. aureus（109CFU/mL) was dropped on the wound on the back to infect, and the wound was air-dried with the bacterial solution overnight, and the infection was observed the next day.
After completion of wound infection, the infected mice were divided into 3 groups (1, 2, 3). Each group of mice had 5 mice, and all mice were housed in cages to prevent mutual scratching and licking. Dripping 50 mu L of PBS on the infected wound of the group 1, and marking as a control group; dripping 50 mu L of AuNS-AMP-PEG nano dressing into the group 2, and recording as an AuNS-AMP-PEG group; add 50. mu.L of AuNS-AMP-PEG nanocoating to group 3 drop-wise and use laser (808 nm)，0.8 W/cm2) Irradiated for 10 min, and recorded as AuNS-AMP-PEG light group. Wound healing was observed at the same time each day and digital photographs of the back wound were taken.
Fig. 5 is a graph showing the change of wounds of three groups of mice, and it can be seen from the graph that the area of the S. aureus infected part of the mice in the Control group is gradually increased from day 0 to day 4, and slightly decreased from day 4 to day 10, and the wounds are in a ulcerated state all the time. Although the bacterial infection site of mice in the AuNS-AMP-PEG light group also had ulceration, the wounds of the mice in this group rapidly scabbed and gradually healed until the infection site healed completely on day 10, compared to the first two groups.
Claims (5)
1. An antibacterial nano dressing AuNS-AMP-PEG is characterized by consisting of two parts of a gold nano star (AuNS) and an antibacterial peptide (AMP).
2. The nano-dressing of claim 1, wherein the photo-thermal molecular gold nano-star (AuNS) has an irregular star shape (triangle, quadrangle star, etc.), is uniformly dispersed, and has a particle size of 30-50 nm.
3. The nanocdressing of claim 1, wherein the antimicrobial peptide (AMP) has the sequence GKRWWKWWRRC and is synthesized using conventional solid phase Fmoc method.
4. The nanomaterial of claim 1, wherein AMP and PEG are attached to the gold nanostars by Au-S bonds and centrifuged to remove unreacted materials.
5. The nanomaterial according to claim 1, characterized in that the synthesis method thereof is as follows: adding 400 mu L AMP (250 mu M) into 400 mu L gold nanostar, putting into a shaking table for 250 r/min and 20 min, then adding 20 mu L PEG, putting into a shaking table for 250 r/min and 20 h, collecting the mixed solution into a 2 mL high-speed centrifuge tube after the reaction is finished, centrifuging the solution for 15 min at 13000 rpm by using a high-speed centrifuge, removing supernatant, adding deionized water into the precipitate for heavy suspension, and repeatedly centrifuging for 3 times to obtain the final AuNS-AMP-PEG antibacterial nano dressing.
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| CN116212084A (en) * | 2023-02-01 | 2023-06-06 | 中国科学院深圳先进技术研究院 | Degradable wound dressing with double antibacterial effects and preparation method and application thereof |
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| CN107441489A (en) * | 2017-07-31 | 2017-12-08 | 江苏大学 | The Preparation method and use of the composite optothermal antiseptic of antibacterial peptide modification gold nanorods |
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| CN116212084A (en) * | 2023-02-01 | 2023-06-06 | 中国科学院深圳先进技术研究院 | Degradable wound dressing with double antibacterial effects and preparation method and application thereof |
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