CN108310392B - Preparation method of medical graphene oxide antibacterial agent - Google Patents
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Abstract
The invention discloses a preparation method of a medical graphene oxide antibacterial agent, which comprises the following steps: adding a carboxyl ethyl silanetriol sodium salt aqueous solution into a 2-morpholine ethanesulfonic acid buffer solution; adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution; adding tetrapeptide into the solution for reaction; dissolving the kanamycin in a 2-morpholine ethanesulfonic acid buffer solution, adding the reaction solution, and continuing to react; preparing graphene oxide dispersion, mixing with the reaction solution, reacting at 50-80 ℃, dialyzing for 7-10 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent. The preparation method is simple and easy to implement, mild in reaction conditions, green, environment-friendly and efficient, and the prepared medical graphene oxide antibacterial agent has good biocompatibility, can achieve the antibacterial rate of 100% to escherichia coli, has an obvious antibacterial effect, does not release kanamycin when in use, and effectively avoids abuse of antibiotics.
Description
Technical Field
The invention relates to the field of biomedical antibacterial materials, and particularly relates to a preparation method of a medical graphene oxide antibacterial agent.
Background
Along with the improvement of the living standard of people, the consciousness of people to health is continuously strengthened. However, various pathogenic microorganisms are widely distributed in nature, and their growth and reproduction seriously threaten human health. Thus, there is an increasing interest in the research and development of safe, highly effective and low cost antimicrobial agents. Most of the existing antibacterial agents are release type, are usually loaded in a carrier, and enter the bacterial body through continuous release to further exert the antibacterial action. This leads to the decrease in antibacterial performance until the disappearance, and therefore, it is important to develop a non-releasing type antibacterial agent. The non-releasing antibacterial agent does not need to release the drug, but only needs to directly contact with the bacteria to achieve the purpose of killing the bacteria. The service time is prolonged as much as possible while the antibacterial requirement is met; in addition, the problem of drug toxicity residue can be avoided. Therefore, the antibacterial agent has lasting and stable antibacterial performance, low toxicity or no toxicity, and obviously improves the safety and health of human beings.
The graphene oxide is a graphene derivative, rich oxygen-containing groups are connected on a basal plane of the graphene oxide, hydroxyl groups and epoxy groups are contained on a plane, and carboxyl groups are contained on the edge of the graphene oxide. Through a large number of researches, the antibacterial performance of the graphene oxide is not obvious. Therefore, the graphene oxide is modified by the small peptide and the antibiotic, so that the performance of the graphene oxide is obviously improved, such as the toxicity of the graphene oxide is reduced, the biological activity is improved, and the abuse of the antibiotic is avoided. Meanwhile, the research and development requires less investment, the preparation method is simple, green and pollution-free, and the antibacterial material has higher application value in biomedical antibacterial materials.
Disclosure of Invention
The purpose of the invention is as follows: in order to solve the problems, the invention provides a preparation method of a medical graphene oxide antibacterial agent, which is simple and feasible, mild in reaction conditions, green, environment-friendly and efficient, and has a high application value in the field of biomedical antibacterial materials.
The technical scheme is as follows: in order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding the water solution of the carboxyl ethyl silane triol sodium salt into the 2-morpholine ethanesulfonic acid buffer solution to ensure that the concentration range of the carboxyl ethyl silane triol sodium salt is between 1 and 8 percent, and stirring for 10 to 30 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution obtained in the step 1), wherein the concentration of the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide is 1-4mM, and the concentration of the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide is 4-10mM, and stirring for 30-120 minutes;
3) adding tetrapeptide into the solution to make the concentration range between 0.05 and 0.6mg/mL, and reacting for 1 to 4 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration range between 0.05 and 0.6 mg/mL;
5) adding the reaction solution obtained in the step 3) into the solution, and reacting for 2-6 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and performing ultrasonic treatment to obtain graphene oxide dispersion liquid with the concentration of 0.25-1.5 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 12-24 hours at 50-80 ℃, dialyzing for 7-10 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
In the step 1), the pH range of the 2-morpholine ethanesulfonic acid buffer solution is between 5.5 and 6.5.
In the step 1), the concentration of the water concentration of the carboxyethyl silanetriol sodium salt is 25%.
In step 3), the tetrapeptide is arginine-glycine-aspartic acid-lysine (commercially available).
The kanamycin is kanamycin sulfate.
In the step 6), the ultrasonic treatment is ultrasonic treatment with 300-1000W for 5-30 minutes.
The medical graphene oxide antibacterial agent is prepared by the preparation method of the medical graphene oxide antibacterial agent.
The medical graphene oxide antibacterial agent has the following structural formula:
the medical graphene oxide antibacterial agent is applied to bacteriostasis.
Has the advantages that: compared with the prior art, the preparation method of the medical graphene oxide antibacterial agent has the advantages that the solvent is the 2-morpholine ethanesulfonic acid buffer solution, and the preparation method does not need to be protected from light, so that the preparation method is green, environment-friendly, convenient and efficient. According to the method, the kanamycin and the tetrapeptide can be grafted to the graphene oxide, and the kanamycin, the tetrapeptide and the graphene oxide can be effectively and reasonably combined to be applied. The prepared medical graphene oxide antibacterial agent has good biocompatibility, the antibacterial rate of the antibacterial agent on escherichia coli can reach 100%, the antibacterial effect is obvious, and the using amount of kanamycin is effectively reduced under the condition of the same antibacterial rate. In use, the medical graphene oxide antibacterial agent cannot release kanamycin, so that the problems of drug resistance, generation of super bacteria and the like caused by abuse of antibiotics are effectively solved, and the medical graphene oxide antibacterial agent has good practicability.
Drawings
Fig. 1 is an atomic force microscope image of a medical graphene oxide antibacterial agent;
FIG. 2 is a transmission electron micrograph of a medical graphene oxide antimicrobial;
fig. 3 is a photograph of the inhibition zone of the medical graphene oxide antibacterial agent on escherichia coli.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 5.5) to enable the concentration of the carboxyethyl silanetriol sodium salt to be 2%, and stirring for 10 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to a concentration of 1.5mM and 5mM, respectively, and stirring for 60 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.2mg/mL, and reacting for 1 hour;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.2 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 4 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic 1000W treatment for 5 minutes to obtain graphene oxide dispersion liquid with the concentration of 0.5 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 12 hours at 70 ℃, dialyzing for 7 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent. The structural formula of the obtained medical graphene oxide antibacterial agent is as follows:
the prepared medical graphene oxide antibacterial agent is subjected to performance test, and the specific steps are as follows:
1) atomic force microscopy testing
An atomic force microscope image of the medical graphene oxide antibacterial agent is shown in fig. 1. The thickness of the single-layer graphene oxide is about 1 nanometer, and the thickness of the medical graphene oxide antibacterial agent is obviously thickened and increased to 3.5 nanometers from the figure.
2) Transmission electron microscopy testing
A transmission electron micrograph of the medical graphene oxide antibacterial agent is shown in fig. 2. The single-layer graphene oxide is of a semitransparent sheet structure, and as can be seen from fig. 2, the translucency of the medical graphene oxide antibacterial agent is obviously reduced, and the medical graphene oxide antibacterial agent is converted into an opaque sheet, which is consistent with the atomic force microscope result, and indicates that the medical graphene oxide antibacterial agent is successfully prepared.
3) Zone of inhibition test
And dripping the medical graphene oxide antibacterial agent dispersion liquid on round filter paper, and carrying out drying and ultraviolet sterilization treatment. The bacterial liquid containing a certain amount of escherichia coli is evenly coated on a solid culture medium, and then a sterile sample is placed on the culture medium and cultured in a constant temperature incubator at 37 ℃ overnight.
The photograph of the inhibition zone of the medical graphene oxide antibacterial agent on escherichia coli is shown in fig. 3. The figure clearly shows that no inhibition zone is generated around the medical graphene oxide antibacterial agent, which indicates that the medical graphene oxide antibacterial agent prepared by the method cannot release kanamycin, and effectively avoids the problems of drug resistance, generation of super bacteria and the like caused by abuse of antibiotics.
Example 2
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 6.5) to ensure that the concentration of the carboxyethyl silanetriol sodium salt is 6%, and stirring for 20 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to give concentrations of 4mM and 8mM, respectively, and stirring for 100 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.3mg/mL, and reacting for 3 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.3 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 2 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic 600W treatment for 15 minutes to obtain graphene oxide dispersion liquid with the concentration of 1 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 24 hours at the temperature of 60 ℃, dialyzing for 10 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
Example 3
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 6) to enable the concentration of the carboxyethyl silanetriol sodium salt to be 10%, and stirring for 15 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to give concentrations of 3mM and 10mM, respectively, and stirring for 40 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.25mg/mL, and reacting for 4 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.25 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 2 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic treatment for 15 minutes at 500W to obtain graphene oxide dispersion liquid with the concentration of 0.75 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 18 hours at 80 ℃, dialyzing for 10 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
Example 4
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 5.5) to ensure that the concentration of the carboxyethyl silanetriol sodium salt is 5%, and stirring for 20 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to give concentrations of 5mM and 9mM, respectively, and stirring for 50 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.35mg/mL, and reacting for 4 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.35 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 4 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic treatment for 20 minutes at 300W to obtain graphene oxide dispersion liquid with the concentration of 1.2 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 20 hours at 75 ℃, dialyzing for 8 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
Example 5
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 6.2) to ensure that the concentration of the carboxyethyl silanetriol sodium salt is 5%, and stirring for 30 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to give concentrations of 2.5mM and 6mM, respectively, and stirring for 80 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.5mg/mL, and reacting for 3.5 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.5 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 3.5 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic 400W treatment for 30 minutes to obtain graphene oxide dispersion liquid with the concentration of 1.5 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 16 hours at 65 ℃, dialyzing for 7 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
Example 6
A preparation method of a medical graphene oxide antibacterial agent comprises the following steps:
1) adding a 25% aqueous solution of carboxyethyl silanetriol sodium salt into a 2-morpholine ethanesulfonic acid buffer solution (pH 5.8) to enable the concentration of the carboxyethyl silanetriol sodium salt to be 8%, and stirring for 25 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution of 1) to give concentrations of 4.5mM and 9mM, respectively, and stirring for 120 minutes;
3) adding tetrapeptide into the solution to make the concentration of the tetrapeptide to be 0.45mg/mL, and reacting for 3.5 hours;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration of kanamycin be 0.45 mg/mL;
5) adding the solution into the reaction solution obtained in the step 3), and reacting for 3.5 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and carrying out ultrasonic treatment for 700W for 25 minutes to obtain graphene oxide dispersion liquid with the concentration of 1.25 mg/mL;
7) and (3) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 14 hours at 70 ℃, dialyzing for 10 days, and freeze-drying to obtain the medical graphene oxide antibacterial agent.
Example 7 bacteriostatic Property test
Adding pre-cultured Escherichia coli liquid into 10mL tryptone soybean broth culture medium by liquid culture system to make its concentration 1 × 108CFU/mL, with no sample as a blank control group, respectively adding 10mg of medical graphene oxide antibacterial agent, 10mg of graphene oxide, 10mg of kanamycin and 10mg of tetrapeptide, culturing for 5 hours in a shaker at 37 ℃, and counting the surviving bacteria by adopting a dilution plating method, wherein the bacteriostasis rate is calculated by the following formula:
R(％)＝(Nblank space-NTest specimen)/NTest specimen×100％
Wherein N isBlank spaceAnd NTest specimenThe number of colonies in the blank control conical flask and the conical flask added with the medical graphene oxide antibacterial agent are respectively. The results of the bacteriostatic rate are shown in table 1.
Table 1 shows the bacteriostatic rate of the prepared medical graphene oxide antibacterial agent
As can be seen from table 1, the antibacterial rate of the medical graphene oxide antibacterial agent prepared in the examples to escherichia coli can reach 100%. Under the condition of the same bacteriostasis rate, the using amount of the kanamycin is effectively reduced.
Claims (8)
1. A preparation method of a medical graphene oxide antibacterial agent is characterized by comprising the following steps:
1) adding the water solution of the carboxyl ethyl silane triol sodium salt into the 2-morpholine ethanesulfonic acid buffer solution to ensure that the concentration range of the carboxyl ethyl silane triol sodium salt is between 1 and 8 percent, and stirring for 10 to 30 minutes;
2) adding 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide to the solution obtained in the step 1), wherein the concentration of the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide is 1-4mM, and the concentration of the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide is 4-10mM, and stirring for 30-120 minutes;
3) adding tetrapeptide into the solution to make the concentration range between 0.05 and 0.6mg/mL, and reacting for 1 to 4 hours; the tetrapeptide is arginine-glycine-aspartic acid-lysine;
4) dissolving kanamycin in 2-morpholine ethanesulfonic acid buffer solution to make the concentration range between 0.05-0.6 mg/mL;
5) adding the reaction solution obtained in the step 3) into the solution, and reacting for 2-6 hours;
6) dispersing graphene oxide into absolute ethyl alcohol, and performing ultrasonic treatment to obtain graphene oxide dispersion liquid with the concentration of 0.25-1.5 mg/mL;
7) mixing the reaction liquid obtained in the step 5) with the graphene oxide dispersion liquid, stirring for 12-24 hours at 50-80 ℃, dialyzing for 7-10 days, and freeze-drying to obtain a medical graphene oxide antibacterial agent;
the structural formula of the obtained medical graphene oxide antibacterial agent is as follows:
2. the method for preparing the medical graphene oxide antibacterial agent according to claim 1, wherein the method comprises the following steps: in the step 1), the pH range of the 2-morpholine ethanesulfonic acid buffer solution is between 5.5 and 6.5.
3. The method for preparing the medical graphene oxide antibacterial agent according to claim 1, wherein the method comprises the following steps: in the step 1), the concentration of the water concentration of the carboxyethyl silanetriol sodium salt is 25%.
4. The method for preparing the medical graphene oxide antibacterial agent according to claim 1, wherein the method comprises the following steps: the kanamycin is kanamycin sulfate.
5. The method for preparing the medical graphene oxide antibacterial agent according to claim 1, wherein the method comprises the following steps: in the step 6), the ultrasonic treatment is ultrasonic treatment with 300-1000W for 5-30 minutes.
6. A medical graphene oxide antibacterial agent obtained by the preparation method of the medical graphene oxide antibacterial agent according to any one of claims 1 to 4.
7. The medical graphene oxide antibacterial agent according to claim 6, wherein the structural formula is as follows:
8. the medical graphene oxide antibacterial agent of claim 6, wherein the medical graphene oxide antibacterial agent is used for preparing a bacteriostatic agent.
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| CN112023058B (en) * | 2019-06-04 | 2022-10-18 | 成都中医药大学 | Graphene oxide-based beta-lactam antibiotic and preparation method thereof |
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