CN112142998A - Preparation method of antibacterial sodium polymaleate/PHMG composite micron particles - Google Patents
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- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
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Abstract
The invention discloses a preparation method of antibacterial sodium polymalic acid/PHMG composite micro particles, and relates to the field of composite micro particle antibacterial materials. After PMLA is obtained by a polycondensation method, the pH value of the solution is adjusted by a pH meter to obtain a sodium polymalate aqueous solution. The sodium polymalate/PHMG microsphere particles with different antibacterial properties are prepared by an ion crosslinking method by taking sodium polymalate aqueous solutions with different concentrations as anionic solutions and a PHMG aqueous solution as a cationic solution, and the antibacterial activity, cytotoxicity, particle size distribution and the like of the sodium polymalate/PHMG microsphere particles are further researched. The product not only reduces the toxicity of PHMG to cells, but also provides good water solubility, and is expected to be used for treating traumatic wounds in the future.
Description
Technical Field
The invention relates to the field of composite micron-sized particle antibacterial materials, in particular to a poly-sodium malate/PHMG composite micron-sized particle and a preparation method thereof.
Background
Bacterial infections have become one of the major threats to human health. Antibiotics are widely used in the treatment of various bacterial infections, but the excessive use of antibiotics causes the generation of drug-resistant bacteria and causes environmental pollution. Therefore, the development of efficient and safe antibacterial materials can inhibit the growth of bacteria outside human bodies and reduce the harm to the human bodies, and the antibacterial material has very important practical significance and wide application prospect.
The novel biodegradable polymer materials commonly used at present comprise polylactic acid, polyglycolic acid and the like, and compared with the polylactic acid, the polymalic acid (PMLA) has unique advantages. PMLA has the excellent characteristics of high molecular weight polymers due to its special functional group structure. The side carboxyl group of PMLA has easy substitution, so that the product after being substituted is various, and the product after self-degradation has non-antigenic and non-toxic characteristics, and it is usually used as carrier and is very effective in medicine.
Polylactic acid, polyglycolic acid, and the like are insoluble in water, and the release of the embedded drug molecules in vivo is slow, which affects the drug efficacy. The side group of PMLA contains a lot of carboxyl, which is easy to dissolve in water, and the carboxyl can be used as polyanion to crosslink with polycation antibacterial agent to form microsphere particles after forming sodium salt, thus reducing the cytotoxicity of the polycation antibacterial agent. Because of the existence of a plurality of carboxyl groups on the side group, the cross-linked drug molecule not only has good water solubility, but also can be specifically combined with toxic groups, thereby reducing the toxicity. These advantages make it very promising in many application-level and location areas.
Polyhexamethylene guanidine (PHMG) is a cationic polymer, has broad-spectrum antibacterial properties, and is low in price, non-toxic and harmless. Guanidine salt groups with positive electricity in the structure of the PHMG have strong adsorption and killing effects on bacteria with negative electricity. Has good long-acting antibacterial performance on staphylococcus aureus and escherichia coli, belongs to a new generation of bactericide, and has the following advantages: 1. high efficiency: the excellent antibacterial, mildew-proof and algae-killing effects can be shown only by a small amount of addition, and the average killing rate reaches 99.9%; 2. safety: the compound preparation has no toxic or side effect, no stimulation to skin, mucous membrane and eyes, and no allergy to skin, and toxicological tests show that half of female and male mice with lethal dose (LD50) of polyhexamethylene guanidine hydrochloride mice are greater than 10000mg/kg in acute oral toxicity tests, and belong to nontoxic grade; 3. and (3) stabilizing: stable to light and heat, and stable in a wide pH range (pH 1-10); 4. long-acting: the drug resistance of bacteria can not be generated, and the long-term effect is achieved; 5. the method is environment-friendly: colorless, tasteless, non-volatile, free of heavy metal and phenolic substances, and non-corrosive to various treatment surfaces. Polyhexamethylene guanidine has excellent performance and is widely applied to the fields of medical treatment and health, daily chemistry, textile, paper making, aquatic products, agriculture, animal husbandry and the like.
Therefore, the PHMG can be used as a polycation antibacterial agent to be crosslinked with the sodium polymalicate to form antibacterial microspheres, so that the toxicity of the PHMG to cells is reduced, and good water solubility is provided. The method is simple and scalable, which is very important for future commercialization.
Disclosure of Invention
The inventive concept consists of two parts. Firstly, synthesizing a novel biodegradable polymer material PMLA; and secondly, after the PMLA is prepared into a sodium polymalate solution, the sodium polymalate solution is used as an anion solution, the PHMG solution is used as a cation solution, and the two are subjected to ion crosslinking to form the microsphere particles. Designs a composite micron particle spray which can resist bacterial infection and promote wound healing, can be used for treating trauma wounds in the future and has good biocompatibility and biodegradability.
The technical scheme of the invention is as follows:
the preparation method of the sodium polymalate/PHMG ion crosslinked microsphere particles comprises the following steps:
Step 3, preparing the sodium polymalate/PHMG composite micron particles: and (3) under the ultrasonic oscillation state, dropwise adding the sodium polymalate solution into PHMG solutions with different concentrations to synthesize the ion-crosslinked microsphere particles. By controlling the concentrations of the sodium polymalate solution and the PHMG solution, a plurality of microsphere suspensions are finally synthesized.
Technical analysis of the invention:
the polymer PMLA, the repeating unit malic acid, structurally contains various side groups and is dicarboxylic acid containing hydroxyl. In the polymerization process, hydroxyl and hydrogen bond are combined and esterified to obtain the polymer PMLA. The higher the reaction temperature is, the higher the rate of the side reaction of intramolecular glycidyl to fumaric acid is, and therefore, the reaction temperature and time should be controlled well to avoid temperature overshoot, which causes the reaction to be severe and the yield to be low. When the reaction temperature is 140 ℃ and the polymerization reaction time is 12 hours, the molecular weight of the obtained polymer is higher. The PHMG can be used as a polycation antibacterial agent and crosslinked with sodium polymalate to form antibacterial microspheres, and the guanidino has high activity, so that the polymer is electropositive and is easy to be adsorbed by various bacteria and viruses; the PHMG diffuses through the cell membrane and binds to the cytoplasmic membrane, forms a complex with the phospholipid bilayer, disrupts the osmotic balance and the cytoplasmic membrane, resulting in cell leakage, and reacts strongly with nucleic acids, thereby inhibiting division of bacterial viruses, rendering bacteria and viruses incapable of reproduction.
In conclusion, the guanidyl antibacterial microsphere is a promising antibacterial material. The microsphere structure can be characterized by Scanning Electron Microscopy (SEM). The material has good chemical stability, strong water resistance and antibacterial property, and good antibacterial property to Escherichia coli and Staphylococcus aureus.
The invention has the advantages and beneficial effects that:
1) the preparation process of the crosslinking microspheres does not need to use an organic solvent and an aldehyde crosslinking curing agent, and the preparation method is simple and easy to implement and is very important for future commercialization.
2) The guanidine polymer basically does not produce target-target specific combination with bacteria, but achieves the final sterilization purpose through an electrostatic attraction mode with cell membranes, so that the guanidine polymer is not easy to generate drug resistance.
3) Because the outer layer of the mammalian cell membrane is neutral in electricity, the outer layer of the bacterial/fungal cell membrane is negatively charged, so that the positively charged guanidine polymer has strong selectivity on the bacterial or fungal cell membrane, and the toxicity of the guanidine polymer on the mammalian cell is further reduced.
4) By adjusting the concentration of the sodium polymalate and the PHMG solution in different proportions, the ion crosslinked microsphere particle suspension with different antibacterial properties can be obtained.
Drawings
FIG. 1 is a schematic diagram of the PMLA synthesis scheme;
FIG. 2 is a comparison graph of the anti-Escherichia coli of ion-crosslinked microspheres with different concentrations;
FIG. 3 is a graph showing the relationship between the bactericidal rate and concentration of the ion-crosslinked microspheres with different sodium salt concentrations;
FIG. 4 is a graph showing cytotoxicity of ion-crosslinked microspheres tested by the MTT method.
FIG. 5 is an SEM representation of cross-linked sodium polymalate/PHMG ion microspheres;
FIG. 6 is a graph of particle size for different concentrations of ionomer microspheres;
Detailed Description
The present invention will be further described with reference to the following examples.
And (3) preparing ion crosslinking microsphere solutions with different concentrations.
Example 1:
10g of L-malic acid is added,SnCl20.1g, poured into a 100ml single-neck flask. Oil bath at 150 deg.c, and vacuum reaction for 12 hr while stirring vigorously. Dissolving with tetrahydrofuran, centrifuging, precipitating with diethyl ether and petroleum ether mixed solvent to obtain crude product, and vacuum drying at 90 deg.C for 24 hr to obtain final product PMLA. The specific synthetic route is shown in figure 1.
And (3) dropwise adding a NaOH solution into the PMLA solution until the pH jump point, thus obtaining the sodium polymalate solution. Under the ultrasonic oscillation state, 5ml of 0.1mg/ml sodium polymalate solution is dripped into 5ml of PHMG solution with the concentration of 0.5mg/ml to synthesize the ion-crosslinked microsphere particles. It was designated as PMLA 0.1/PHMG.
Example 2:
mixing L-malic acid 10g, SnCl20.1g, poured into a 100ml single-neck flask. Oil bath at 150 deg.c, and vacuum reaction for 12 hr while stirring vigorously. Dissolving with tetrahydrofuran, centrifuging, precipitating with diethyl ether and petroleum ether mixed solvent to obtain crude product, and vacuum drying at 90 deg.C for 24 hr to obtain final product PMLA. And (3) dropwise adding a NaOH solution into the PMLA solution until the pH jump point, thus obtaining the sodium polymalate solution. Under the ultrasonic oscillation state, 5ml of 1.05mg/ml sodium polymalate solution is dripped into 5ml of PHMG solution with the concentration of 0.5mg/ml to synthesize the ion-crosslinked microsphere particles. It is recorded as PMLA 1.05/PHMG.
Example 3:
mixing L-malic acid 10g, SnCl20.1g, poured into a 100ml single-neck flask. Oil bath at 150 deg.c, and vacuum reaction for 12 hr while stirring vigorously. Dissolving with tetrahydrofuran, centrifuging, precipitating with diethyl ether and petroleum ether mixed solvent to obtain crude product, and vacuum drying at 90 deg.C for 24 hr to obtain final product PMLA.
And (3) dropwise adding a NaOH solution into the PMLA solution until the pH jump point, thus obtaining the sodium polymalate solution. Under the ultrasonic oscillation state, 5ml of 2.0mg/ml sodium polymalate solution is dripped into 5ml of PHMG solution with the concentration of 0.5mg/ml to synthesize the ion-crosslinked microsphere particles. It is designated as PMLA 2.0/PHMG.
And (3) carrying out comparative test on the antibacterial activity of the ionic crosslinking microsphere solutions with different concentrations.
The three suspensions with different sodium salt concentrations are prepared into aqueous solutions of 12.5 mu g/ml and 25 mu g/ml, and then the aqueous solutions and the Escherichia coli suspension are shaken in a shaker at 37 ℃ for 10min, coated on a plate and placed in an incubator at 37 ℃ for culturing for 16 h. The magnitude of the antibacterial activity was compared by the colony counting method, as shown in FIG. 2 (FIG. 2a shows guanidine salt concentration of 12.5. mu.g/ml, wherein sodium salt concentration is sequentially increased; FIG. 2b shows guanidine salt concentration of 25. mu.g/ml, wherein sodium salt concentration is sequentially increased). And the relationship between the concentration and the sterilization rate is obtained, and is shown in figure 3.
The antibacterial result shows that the higher the concentration of PHMG in the ion-crosslinked nano microsphere solution is, the better the bactericidal effect is; the higher the concentration of the sodium polymalate in the ion-crosslinked nano microsphere solution is, the weaker the sterilization effect is.
And (3) testing the cytotoxicity of the ionic crosslinking microsphere solution with different concentrations.
The cytotoxicity of the sodium polymalate/PHMG composite microparticles is researched by an MTT method. PMLA0.1/PHMG, PMLA1.05/PHMG and PMLA2.0/PHMG are prepared into aqueous solutions with the concentrations of 12.5 mu g/mL and 25 mu g/mL for research, and the cytotoxicity of a plurality of ion-crosslinked microspheres on L929 cells is realized. The result shows that the higher the PHMG content in the poly-sodium malate/PHMG ion crosslinked microsphere suspension is, the higher the cytotoxicity is; the higher the sodium polymalate content, the lower the cytotoxicity. See figure 4.
And observing the form and the particle size of the sodium polymalic acid/PHMG ion crosslinked microspheres.
From antibacterial experiments and cytotoxicity, it is known that PMLA1.05/PHMG has both good antibacterial property and low cytotoxicity. Thus, we performed SEM characterization using PMLA1.05/PHMG as a template. This was centrifuged to obtain a supernatant and a precipitate. Adding small amount of water, ultrasonic dispersing for 40min, and freeze drying for 48 hr. The morphology of the particles was observed by scanning transmission electron microscopy. See figure 5 (pellet from centrifugation in the first row and supernatant from centrifugation in the second row). The particle size distribution of the synthesized three microsphere suspensions of PMLA0.1/PHMG, PMLA1.05/PHMG and PMLA2.0/PHMG is measured by a dynamic light scattering instrument DLS, and the measured particle sizes are 265nm, 447.5nm and 605.2nm in sequence. The results show that as the concentration of sodium salt increases, the particle size of the microspheres also increases. The results are shown in FIG. 6 (FIGS. 6 a-c, increasing sodium salt concentrations).
Claims (4)
1. The preparation method of the antibacterial sodium polymalate/PHMG composite microparticles is characterized in that the method takes the sodium polymalate as a polyanion cross-linking agent and the PHMG as a polycation antibacterial agent, and the two are ionically cross-linked to form antibacterial microspheres; wherein the sodium polymalate is obtained by dripping NaOH solution into PMLA solution to a pH jump point.
2. The method for preparing antibacterial sodium polymalate/PHMG composite microparticles as claimed in claim 1, wherein: the ion crosslinking is completed under the ultrasonic oscillation state, and the concentration ratio of the poly-sodium malate to the PHMG is 0.1 mg/mL-2.0 mg/mL: 0.5 mg/mL.
3. The method for preparing antibacterial sodium polymalate/PHMG composite microparticles according to claim 1 or 2, wherein: finally synthesizing different ion crosslinked microsphere particle suspensions by controlling the concentration of the sodium polymalate solution and the concentration of the PHMG solution.
4. The method for preparing antibacterial sodium polymalate/PHMG composite microparticles as claimed in claim 3, wherein: the different ion crosslinked microsphere particle suspension comprises: dripping 5ml of 0.1mg/ml sodium polymalate solution into 5ml of PHMG solution with the concentration of 0.5mg/ml to obtain ion-crosslinked microsphere particles, and recording as PMLA 0.1/PHMG;
dripping 5ml of 1.05mg/ml sodium polymalate solution into 5ml of PHMG solution with the concentration of 0.5mg/ml to obtain ion-crosslinked microsphere particles, and recording as PMLA 1.05/PHMG;
5ml of 2.0mg/ml sodium polymalate solution is dripped into 5ml of PHMG solution with the concentration of 0.5mg/ml to obtain the ion-crosslinked microsphere particles, which are marked as PMLA 2.0/PHMG.
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