CN113956503A - Polycation nano antibacterial agent, preparation method and application thereof - Google Patents
Polycation nano antibacterial agent, preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of disinfectants, in particular to a polycation nano antibacterial agent, a preparation method and application thereof, wherein a quaternary ammonium salt monomer and a hydrophobic monomer are copolymerized to obtain an amphiphilic polymer nano micelle, the particle size of the amphiphilic polymer nano micelle is 10-800nm, and the polycation nano antibacterial agent disclosed by the invention has good water solubility and antibacterial effect and can realize effective sterilization at a lower concentration; the polycation nano micelle disclosed by the invention can be combined with the bacterial cell membrane with negative charges to generate static electricity, so that bacteria die, and the polycation nano micelle is a safe and efficient antibacterial preparation.
Description
Technical Field
The invention relates to the technical field of disinfectants, in particular to a polycation nano antibacterial agent, a preparation method and application thereof.
Background
Bacterial infections have become a significant health and safety issue for humans. The development and use of a large number of antibiotics has greatly limited the development of bacterial infections, but has also brought about the development of bacterial resistance. Therefore, in order to reduce the use of antibiotics, a large number of cationic antibacterial agents, metal ions, metal nanoparticle antibacterial agents are widely developed, making it more difficult for bacteria to develop resistance. Due to the double-layer phospholipid structure of the cell membrane, most of bacterial cell membranes are negatively charged, and the cationic antibacterial polymer carrying positive charges can be combined with the cell membrane through electrostatic adsorption, so that the integrity of the cell membrane is damaged, and the effect of killing bacteria is achieved. The bacteria are killed by the electrostatic adsorption, so that the bacteria are difficult to generate drug resistance.
The quaternary ammonium salt type cationic antibacterial agent is a broad-spectrum antibacterial agent, and is rich in structural variety. Cationic polymers are less toxic to the environment than small molecule cationic compounds. However, the antibacterial activity of the quaternary ammonium salt type cationic polymer is related to molecular weight, anion type, charge density, and the like. Generally, too low a molecular weight results in insufficient destruction of the bacterial cell membrane, and too high a molecular weight results in failure to penetrate the cell wall and thus reduced killing capacity. Meanwhile, the quaternary ammonium salt cationic polymer can be promoted to form micelles by certain hydrophobicity, so that positive charges on the surface are enriched, and the hydrophobic chain segment can also damage the cell membrane structure through interaction with the bacterial cell membrane, so that the antibacterial activity is improved.
In view of the above-mentioned drawbacks, the inventors of the present invention have finally obtained the present invention through a long period of research and practice.
Disclosure of Invention
The invention aims to solve the problems of improving antibacterial activity and reducing the using amount, and provides a polycation nano antibacterial agent, a preparation method and application thereof.
In order to achieve the purpose, the invention discloses a polycation nano antibacterial agent which comprises a polymer nano micelle consisting of a hydrophilic polycation section and a hydrophobic section, wherein the hydrated particle size of the nano micelle is 10-800 nm.
The polymer structure is shown below:
wherein R is1Is H or CH3，R2Is a hydrophobic segment.
The polymerization degree of the cationic monomer is 5-100, the hydrophobic chain segment is PCL, PLA, polymethyl methacrylate, polymethyl acrylate, polybutyl acrylate or polybutyl methacrylate, and the molecular weight of the hydrophobic chain segment is 300-30000.
The invention also discloses a preparation method of the polycation nano antibacterial agent, which comprises the following steps:
s1: preparation of polycationic amphiphilic polymers: connecting a polycation monomer with a hydrophobic chain segment through controllable free radical polymerization to obtain a polycation amphiphilic polymer;
s2: preparing a polycation nano antibacterial agent: and (4) dispersing the polycation amphiphilic polymer obtained in the step (S1) in a water phase, fully dissolving, and bottling to obtain the polycation nano antibacterial agent.
In the step S2, the aqueous phase is any one of PBS, water and NaCl aqueous solution.
The invention also discloses application of the polycation nano antibacterial agent in antibiosis and mildew prevention.
Compared with the prior art, the invention has the beneficial effects that:
(1) according to the invention, the cheap and easily-obtained cationic monomer and the hydrophobic monomer are copolymerized to obtain the amphiphilic polymer chain segment, and the polycation is used as the hydrophilic segment to ensure that the charge is more uniformly distributed on the surface of the polymer nano micelle, so that the binding capacity of the nano antibacterial agent and the bacterial cell membrane can be effectively promoted, thereby increasing the killing power to bacteria, reducing the dosage and being beneficial to environmental protection.
(2) The minimum sterilization concentration of the nano antibacterial agent can reach 30mg/mL, the nano antibacterial agent has good stability in an aqueous solution, long sterilization duration time and higher safety to non-target organisms, and is an efficient, safe and stable antibacterial agent.
(3) The nano antibacterial agent has simple preparation process, can reduce the use of organic solvents compared with the conventional antibacterial agent, and is an environment-friendly antibacterial preparation.
Drawings
FIG. 1 is a drawing showing methacryloyloxyethyl trimethyl ammonium chloride1H-NMR spectrum;
FIG. 2 is a dynamic light scattering diagram of polycationic amphiphilic polymer nano-micelles;
FIG. 3 is a minimum inhibitory concentration curve for a polycationic nano-antibacterial agent;
FIG. 4 is a co-culture diagram of polycation nano antibacterial agent and staphylococcus aureus with different concentrations.
Detailed Description
The above and further features and advantages of the present invention are described in more detail below with reference to the accompanying drawings.
Example 1
The preparation method of the polycation nano antibacterial agent comprises the following steps:
s1: preparation of polycationic amphiphilic polymers:
(1) synthesis of Polymethacryloyloxyethyltrimethyl ammonium chloride (P-DMC): 21mg of S-thiobenzoylmercaptoacetic acid, 1g of methacryloyloxyethyl trimethylammonium chloride (A)1The H-NMR spectrum is shown in FIG. 1), 3mg of AIBN is dissolved in 10mL of DMF, and then polymerized for 12H at 70 ℃ after nitrogen charging and oxygen removing. After the reaction is finished, the mixture is settled in ethanol and dried to obtain 0.8g P-DMC.
(2) Synthesis of P-DMC-b-MMA: the P-DMC obtained above was dissolved in 10mL of DMF, 0.2g of methyl methacrylate and 6mg of AIBN were added, oxygen was removed by nitrogen injection, and polymerization was carried out at 70 ℃ for 12 hours. After the reaction, the product was precipitated in ethanol and dried to obtain 0.9g of polycationic amphiphilic polymer P-DMC-b-MMA.
S2: 0.1g P-DMC-b-MMA was weighed and dissolved in 10mL of deionized water to obtain the polycation nano antibacterial agent. The hydrated particle size was 68nm as shown in figure 2, as evidenced by the uniform nano-size of the polycation, as detected by dynamic light scattering.
Example 2
The preparation method of the polycation nano antibacterial agent comprises the following steps:
s1: preparation of polycationic amphiphilic polymers:
(1) synthesis of Polymethacryloyloxyethyltrimethyl ammonium chloride (P-DMC): 42mg of S-thiobenzoylmercaptoacetic acid, 3g of methacryloyloxyethyl trimethylammonium chloride (A)1The H-NMR spectrum is shown in FIG. 1), 10mg of AIBN is dissolved in 20mL of DMF, and then polymerized for 12H at 70 ℃ after nitrogen charging and oxygen removing. After the reaction is finished, the mixture is settled in ethanol and dried to obtain 2.8g P-DMC.
(2) Synthesis of P-DMC-b-MMA: the P-DMC obtained above was dissolved in 20mL of DMF, 0.6g of methyl methacrylate and 9mg of AIBN were added, oxygen was removed by nitrogen filling, and polymerization was carried out at 70 ℃ for 12 hours. After the reaction, the product was precipitated in ethanol and dried to obtain 3.1g of polycationic amphiphilic polymer P-DMC-b-MMA.
S2: 0.1g P-DMC-b-MMA was weighed and dissolved in 5mL of deionized water to obtain the polycation nano antibacterial agent.
Example 3
The polycation nano antibacterial agent prepared in example 1 was subjected to antibacterial test: placing the staphylococcus aureus strain in a liquid culture medium, and culturing until the number of bacteria is 108CFU/mL, followed by dilution 1000-fold to 10-fold5CFU/mL. 1mL of the polycation nano-antibacterial agent prepared in example 1 and 0.1mL of the bacterial solution at concentrations of 0.1mg/mL, 0.5mg/mL, 1mg/mL, 4mg/mL and 8mg/mL are respectively placed in a test tube, co-cultured in an incubator for 24h, sampled every 4h to test the ultraviolet-visible absorption spectrum, and the absorption value at 600nm is calculated. As shown in FIG. 3, the minimum inhibitory concentration was 4mg/mL, at which bacterial proliferation was effectively inhibited.
Taking 0.1mL of bacteria with the number of 105The CFU/mL bacterial solution was mixed with 0.1mL polycation nano antibacterial agent prepared in example 1 at concentrations of 0.1mg/mL, 0.5mg/mL, 1mg/mL, 4mg/mL and 8mg/mL, respectively, and the mixture was cultured for 2 hours, then plated, and after the plate was hardened, the plate was placed in an incubator at 37 ℃Culturing for 24 h. The number of colonies was then visualized by photography, as shown in FIG. 4, with a minimum bactericidal concentration of 8mg/mL, at which no colonies had been present on the medium.
The foregoing is merely a preferred embodiment of the invention, which is intended to be illustrative and not limiting. It will be understood by those skilled in the art that various changes, modifications and equivalents may be made therein without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (6)
1. The polycation nano antibacterial agent is characterized by comprising a polymer nano micelle consisting of hydrophilic polycation segments and hydrophobic segments, wherein the hydration particle size of the nano micelle is 10-800 nm.
2. The polycation nanoantimicrobial of claim 1, wherein the polymer structure is as follows:
wherein R is1Is H or CH3，R2Is a hydrophobic segment.
3. The polycation nano antibacterial agent according to claim 1, wherein the degree of polymerization of the cationic monomer is 5-100, the hydrophobic segment is PCL, PLA, polymethyl methacrylate, polymethyl acrylate, polybutyl acrylate or polybutyl methacrylate, and the molecular weight of the hydrophobic segment is 300-30000.
4. A method for preparing the polycation nano antibacterial agent according to any one of claims 1 to 3, which comprises the following steps:
s1: preparation of polycationic amphiphilic polymers: connecting a polycation monomer with a hydrophobic chain segment through controllable free radical polymerization to obtain a polycation amphiphilic polymer;
s2: preparing a polycation nano antibacterial agent: and (4) dispersing the polycation amphiphilic polymer obtained in the step (S1) in a water phase, fully dissolving, and bottling to obtain the polycation nano antibacterial agent.
5. The method of claim 4, wherein the aqueous phase in step S2 is any one of PBS, water and aqueous NaCl solution.
6. The application of the polycation nano antibacterial agent as defined in any one of claims 1 to 3 in antibiosis and mildew prevention.
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