CN111675649B - Dinaphthalene pyridinium antibacterial material and preparation method and application thereof - Google Patents
Dinaphthalene pyridinium antibacterial material and preparation method and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of micromolecular antibacterial agents, and particularly relates to a naphthyridine salt antibacterial material, and a preparation method and application thereof. Reaction of S-1,1 '-bi-2-naphthol with 1, 4-bis (bromomethyl) benzene produces 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1 '-binaphthyl, 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1 '-binaphthyl is reacted with pyridine in DMF to produce 1,1' - (((((((((([ 1,1 '-binaphthyl ] -2,2' -diylbis (oxy)) bis (methylene)) bis (4, 1-phenylene)) bis (methylene)) bis (pyridine-1) bromide. The dinaphthalene pyridinium antibacterial material can effectively kill gram-negative bacteria. The method determines the killing effect of gram-negative bacteria by a plate coating method, has low damage to cells under the antibacterial concentration and has low cytotoxicity.
Description
Technical Field
The invention relates to the technical field of micromolecular antibacterial agents, and particularly relates to a naphthyridine salt antibacterial material, and a preparation method and application thereof.
Background
Bacteria are widely present in nature and are closely related to human activities. Some bacteria are beneficial bacteria, such as lactic acid bacteria, bifidobacteria, etc. However, some bacteria often cause diseases, such as Salmonella typhimurium which can cause gastrointestinal discomfort and even septicemia, Pseudomonas aeruginosa which can cause wound suppuration, and Klebsiella pneumoniae which is the cause of pneumonia. Since the discovery of penicillin, many antibiotics have been reported in succession to exert excellent bactericidal effects for some time. However, some antibiotics have not been effective against bacteria due to the wide use and abuse of antibiotics, and new effective antibacterial agents are urgently needed to solve the situation.
From the structure of bacteria, the bacteria have cell walls and cell membranes, a plurality of proteins are contained in the cell walls and the cell membranes, the isoelectric points of the proteins are generally between 3 and 5, the external pH is generally neutral and is higher than the isoelectric points, so the proteins are negatively charged, and the bacteria are negatively charged under the general external conditions. Positively charged compounds such as those with groups such as quaternary ammonium salts, quaternary phosphonium salts, guanidinium salts, and pyridinium salts have been shown to electrostatically attract bacteria and thereby interfere with normal physiological activities of the bacteria to kill them. Since many antibacterial agents tend to damage normal cells during use, it is of great importance to develop efficient and low-toxic antibacterial agents.
Disclosure of Invention
Aiming at the problems, the invention provides a dinaphthyl pyridinium antibacterial material, a preparation method and application.
In order to achieve the purpose, the invention adopts the following technical scheme:
the antibacterial material of the dinaphthyl pyridinium has the structural formula as follows:
a preparation method of a dinaphthyl pyridinium antibacterial material comprises the following steps:
step 1, heating and vigorously stirring S-1,1' -bi-2-naphthol and acetone to obtain a uniform mixed solution, then adding 1, 4-di (bromomethyl) benzene and potassium carbonate into the mixed solution under the protection of inert gas, heating, refluxing and stirring, filtering a solid while the reaction is finished, extracting with dichloromethane and water, collecting an organic phase, drying with anhydrous sodium sulfate, removing the solvent in a vacuum rotary manner, and performing column chromatography on the obtained crude product by using dichloromethane/petroleum ether (1/3 (v/v) as an eluent to obtain 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl;
and 2, adding 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl and pyridine into DMF (dimethyl formamide), heating and reacting under stirring, cooling to room temperature, adding into an acetone solution, filtering out a white solid after the white solid is separated out, washing with DMF, acetone and diethyl ether in sequence, and drying in vacuum to obtain 1,1' - (((((((([ 1,1' -binaphthyl ] -2,2' -diylbis (oxy)) bis (methylene)) bis (4, 1-phenylene)) bis (methylene)) bis (pyridine-1) bromide, namely the binaphthyl pyridinium antibacterial material.
Further, the mass ratio of the S-1,1' -bi-2-naphthol to the acetone in the step 1 is 1: 18-1: 22;
in the step 1, the molar ratio of 1, 4-bis (bromomethyl) benzene to potassium carbonate is 3.5: 1-5: 1;
the volume ratio of the mixed solution, 1, 4-bis (bromomethyl) benzene and potassium carbonate in the step 1 is 6: 1-8: 1.
Further, the heating time of heating, refluxing and stirring in the step 1 is 6 hours;
the heating temperature for heating and violently stirring in the step 1 is 65 ℃, and the stirring time is 4-8 hours;
the heating temperature of the heating reaction in the step 2 is 70-80 ℃, and the reaction time is 48 h.
Further, the molar ratio of pyridine and 2,2 '-bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl to DMF in step 2 was 2:1: 86.5.
Further, the amount of DMF, acetone and ether washing is as follows: 150 mL-200 mL;
the temperature of the vacuum drying is 25 ℃, and the time is 48 h.
An application of the antibacterial material of dinaphthyl pyridinium in killing gram-negative bacteria.
Further, the gram-negative bacteria include escherichia coli, enterobacter cloacae, salmonella typhimurium, klebsiella pneumoniae, and pseudomonas aeruginosa.
An application method of a binaphthyl pyridinium antibacterial material determines the killing effect of gram-negative bacteria by a coating plate method, and has low damage to cells and low cytotoxicity under antibacterial concentration.
Compared with the prior art, the invention has the following advantages:
the invention discloses a preparation method and application of an antibacterial material containing a binaphthyl skeleton and a pyridinium functional group. The dinaphthalene pyridinium antibacterial material obtained by the invention is a low-toxicity and high-efficiency antibacterial material, has good antibacterial performance on various gram-negative bacteria, and has lower cytotoxicity. The material can be used as an antibacterial agent for treating bacterial infection. The preparation method is simple and has mild conditions.
Drawings
FIG. 1 shows an ultraviolet absorption spectrum and a fluorescence emission spectrum of the antibacterial material of the present invention in dimethyl sulfoxide;
FIG. 2 shows the results of the bactericidal test of the antibacterial material of the present invention against five gram-negative bacteria;
FIG. 3 shows the toxicity test results of the antibacterial material of the present invention against human cervical cancer cells;
FIG. 4 is a scanning electron micrograph of the antibacterial material of the present invention killing Escherichia coli.
Detailed Description
Example 1
Step 1, adding 0.57g (2.00mmol) of S-1,1' -bi-2-naphthol and 15mL of acetone into a three-necked flask with a magnetic stirrer, heating at 65 ℃ and carrying out vigorous stirring to obtain a uniform mixed solution, then adding 2.11g (8.00mmol) of 1, 4-bis (bromomethyl) benzene and 0.30g (2.20mmol) of potassium carbonate under the protection of nitrogen, heating, refluxing and stirring for 6 hours, filtering the solid while hot after the reaction is finished, and extracting with dichloromethane and water. The organic phase was collected, dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to give a crude product, which was subjected to column chromatography using dichloromethane/petroleum ether-1/3 (v/v) as an eluent to give 0.45g of 2,2 '-bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl, yield: 34.5 percent.
1H NMR(DMSO-d6,600MHz)δ9.12(d,2H),8.60(t,1H),8.14(t,2H),8.04(d,1H),7.95(d,1H),7.61(d,1H),7.35(t,1H),7.30(d,2H),7.24～7.25(m,1H),7.02(d,2H),6.97(d,1H),5.75(s,2H),5.15(m,2H)；HRMS-ESI for C46H38N2O2 2+(m/z)325.1461。
Example 2
1)2,2 '-bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl was prepared as in example 1;
2) adding 0.33g (0.50mmol) of 2,2 '-bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl) and 0.12mL of pyridine (1.5mmol) into a 25mL three-neck round-bottom flask containing 10mL of DMF under the protection of nitrogen, stirring at 60 ℃ for reaction for 72h, cooling to room temperature after the reaction is finished, stirring to reduce the reaction, pouring into 200mL of acetone to precipitate white solid, filtering the white solid, washing with DMF and diethyl ether in sequence, and drying in vacuum to obtain 0.13g of 1,1'- (((((([ 1,1' -binaphthyl)]2,2' -diylbis (oxy)) bis (methylene)) bis (4, 1-phenylene)) bis (methylene)) bis (pyridine-1) bromide in 32.1% yield.1H NMR(DMSO-d6,600MHz)δ9.12(d,2H),8.60(t,1H),8.14(t,2H),8.04(d,1H),7.95(d,1H),7.61(d,1H),7.35(t,1H),7.30(d,2H),7.24～7.25(m,1H),7.02(d,2H),6.97(d,1H),5.75(s,2H),5.15(m,2H)；HRMS-ESI for C46H38N2O2 2+(m/z)325.1461。
Example 3
And (3) measuring the fluorescence emission spectrum and the ultraviolet absorption spectrum of the antibacterial material:
dissolving antibacterial material in DMSO to obtain a solution with a concentration of 1.0 × 10-5mol/L solution. Accurately transferring 2.0mL of the solution into a quartz cuvette, and measuring the solution on a HITACHI UH5300 ultraviolet absorption instrument by taking a pure DMSO solution as a reference, wherein the absorption peaks are positioned at 265nm and 335 nm. Likewise, 2mL of the sample was accurately transferred at a concentration of 1.0X 10-5mol/L DMSO solution was added to a quartz cuvette and then measured on a HITACHI F-4600 fluorometer with an excitation slit width of 10nm and an emission slit width of 10 nm. The excitation wavelength was 346nm and the maximum emission wavelength was 422nm, and all tests were performed at room temperature and ambient atmospheric pressure.The test normalization results are shown in FIG. 1.
Example 4
Cytotoxicity test of antibacterial materials:
the cytotoxicity of the antibacterial material is tested by taking a human cervical carcinoma cell HeLa cell as a research object and using an MTT (methyl thiazolyl tetrazolium) experiment. HeLa cells cultured to logarithmic growth phase were cultured at 10%7Uniformly spreading the cells/mL in a 96-well plate, culturing for 24h, removing the culture medium, adding a new culture medium containing 0 mu M, 2.5 mu M, 5 mu M,10 mu M and 20 mu M of antibacterial materials, continuously culturing for 12h, removing the culture medium, adding a culture medium containing 5mg/mL MTT, culturing for 4-6 h, removing the culture medium, washing with sterile 1 XPBS, adding DMSO, shaking on a microplate reader for 2min, and reading data. The test results are shown in FIG. 3. As can be seen from FIG. 3, the survival rate of the cells is still around 80% at 20. mu.M, indicating that the antibacterial material has low damage to the cells and low cytotoxicity.
Example 5
And (3) testing the sterilization performance of the antibacterial material on bacteria:
the bactericidal performance of the antibacterial material on escherichia coli (Top 10) is tested as follows:
sterilizing a super clean bench and instruments, transferring 10mL of culture medium into a 50mL centrifuge tube, adding 10 mu L of 50mg/mL ampicillin sodium water solution and 20 mu L of Escherichia coli strains, performing shake culture at 37 ℃ and 180rpm for 6-8 h, sucking 2mL of bacterial solution, centrifuging (7100rpm and 2min), precipitating Escherichia coli, washing the precipitated Escherichia coli with 1 XPBS, centrifuging and precipitating again, repeating twice, discarding supernatant, resuspending the bacterial solution in 1 XPBS, adjusting OD (optical density) to adjust600Is 1.0.
100. mu.L of a bacterial solution (OD) was added to a 1.5mL centrifuge tube6001.0) and a quantity of antibacterial material (final concentrations of 5 μ M,10 μ M,15 μ M,20 μ M, respectively), the volume was supplemented to 500 μ L with sterile 1 × PBS, and incubated for 20min at 37 ℃ in the dark, diluted 4000 times, 100 μ L of the bacterial solution was aspirated and spread evenly on 90mm LB solid medium (containing 50mg/mL ampicillin sodium), and cultured at 37 ℃ for 18h to 20h to count colony forming units.
(II) the antibacterial performance test of the antibacterial material on Enterobacter cloacae (CICC 10017):
sterilizing a super clean bench and instruments, transferring 10mL of culture medium into a 50mL centrifuge tube, culturing 20 mu L of enterobacter cloacae strain by shaking at 180rpm at 37 ℃ for about 10h, sucking 2mL of bacterial liquid, centrifuging (7100rpm,2min), precipitating the enterobacter cloacae, washing the precipitated enterobacter cloacae with 1 XPBS, centrifuging again, precipitating, repeating twice, discarding supernatant, resuspending the bacterial liquid in 1 XPBS, and adjusting OD600Is 1.0.
100. mu.L of a bacterial solution (OD) was added to a 1.5mL centrifuge tube6001.0) and a quantity of antimicrobial material (final concentrations of 5 μ M,10 μ M,15 μ M,20 μ M, respectively), the volume was supplemented to 500 μ L with sterile 1 × PBS and incubated in the dark at 37 ℃ for 20min, diluted 4000 times, 100 μ L of the bacterial suspension was aspirated and spread evenly on 90mm solid medium, incubated at 37 ℃ for 18-20 h and the colony forming units were counted.
And (III) the antibacterial performance test steps of the antibacterial material on salmonella typhimurium (CICC 21484), pseudomonas aeruginosa (CICC21100) and klebsiella pneumoniae (CICC 10781) are the same as the steps in the second step.
The survival rate of the bacteria is (bacterial colony number of the drug adding group/bacterial colony number of the control group) × 100%
The result of the sterilization performance test of the antibacterial material against bacteria (see fig. 2): when the concentration of the antibacterial material is 10 mu M, the killing rate to Klebsiella pneumoniae can reach more than 99.5 percent; the sterilization rate of the antibacterial material to escherichia coli, enterobacter cloacae, salmonella typhimurium and pseudomonas aeruginosa can reach more than 96% at 20 mu M, and the data show that the antibacterial material has excellent antibacterial performance and shows good killing capability to various gram-negative bacteria.
Example 6
Scanning Electron Microscope (SEM) experiments on killing of escherichia coli by antibacterial materials:
after the E.coli was subjected to the drug action according to the procedure of the antibacterial test in example 5, the unreacted drug was removed by centrifugation (7100rmp, 5min), the precipitated E.coli was resuspended in 100. mu.L of sterile 1 XPBS, 10. mu.L of the suspension was dropped onto a clean silicon wafer, air-dried in a clean bench, and then 1 XPBS solution containing 1% glutaraldehyde was added. After overnight fixation at 4 ℃, excess glutaraldehyde was washed off with ultrapure water, and the samples were subjected to gradient dehydration with 40%, 70%, 90% and 100% ethanol in that order for 6 min/time. And after the sample is completely dried, carrying out experiment after vacuum freeze drying for 1-2 h.
From the scanning electron micrograph of fig. 4, it can be observed that the escherichia coli of the control group maintains good cell morphology, and most of the surfaces of the escherichia coli of the drug-adding group have collapse deformation, which shows that the antibacterial material has good killing effect on the escherichia coli.
Those skilled in the art will appreciate that the invention may be practiced without these specific details. Although illustrative embodiments of the present invention have been described above to facilitate the understanding of the present invention by those skilled in the art, it should be understood that the present invention is not limited to the scope of the embodiments, and various changes may be made apparent to those skilled in the art as long as they are within the spirit and scope of the present invention as defined and defined by the appended claims, and all matters of the invention which utilize the inventive concepts are protected.
Claims (9)
1. The antibacterial material of the dinaphthyl pyridinium is characterized in that: the structural formula is as follows:
2. a preparation method of a dinaphthyl pyridinium antibacterial material is characterized by comprising the following steps: the method comprises the following steps:
step 1, heating and vigorously stirring S-1,1' -bi-2-naphthol and acetone to obtain a uniform mixed solution, then adding 1, 4-di (bromomethyl) benzene and potassium carbonate into the mixed solution under the protection of inert gas, heating, refluxing and stirring, filtering a solid while the reaction is finished, extracting with dichloromethane and water, collecting an organic phase, drying with anhydrous sodium sulfate, removing the solvent in a vacuum rotary manner, and performing column chromatography on the obtained crude product by using dichloromethane/petroleum ether (1/3 (v/v) as an eluent to obtain 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl;
and 2, adding 2,2' -bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl and pyridine into DMF (dimethyl formamide), heating and reacting under stirring, cooling to room temperature, adding into an acetone solution, filtering out a white solid after the white solid is separated out, washing with DMF, acetone and diethyl ether in sequence, and drying in vacuum to obtain 1,1' - (((((((([ 1,1' -binaphthyl ] -2,2' -diylbis (oxy)) bis (methylene)) bis (4, 1-phenylene)) bis (methylene)) bis (pyridine-1) bromide, namely the binaphthyl pyridinium antibacterial material.
3. The method for preparing the naphthyridine salt antibacterial material according to claim 2, characterized in that: the mass ratio of the S-1,1' -bi-2-naphthol to the acetone in the step 1 is 1: 18-1: 22;
in the step 1, the molar ratio of 1, 4-bis (bromomethyl) benzene to potassium carbonate is 3.5: 1-5: 1;
the volume ratio of the mixed solution, 1, 4-bis (bromomethyl) benzene and potassium carbonate in the step 1 is 6: 1-8: 1.
4. The method for preparing the naphthyridine salt antibacterial material according to claim 2, characterized in that: the heating time of heating reflux stirring in the step 1 is 6 hours;
the heating temperature for heating and violently stirring in the step 1 is 65 ℃, and the stirring time is 4-8 hours;
the heating temperature of the heating reaction in the step 2 is 70-80 ℃, and the reaction time is 48 h.
5. The method for preparing the naphthyridine salt antibacterial material according to claim 2, characterized in that: the molar ratio of pyridine and 2,2 '-bis ((4- (bromomethyl) benzyl) oxy) -1,1' -binaphthyl to DMF in step 2 was 2:1: 86.5.
6. The method for preparing the naphthyridine salt antibacterial material according to claim 2, characterized in that: the washing amount of DMF, acetone and diethyl ether is as follows: 150 mL-200 mL;
the temperature of the vacuum drying is 25 ℃, and the time is 48 h.
7. Use of the dinaphthalene pyridinium antimicrobial material of claim 1 for the preparation of a medicament, wherein: the medicine is used for killing gram-negative bacteria.
8. The use of the bipyridylium salt antibacterial material of claim 7 for preparing a medicament, wherein: the gram-negative bacteria are escherichia coli, enterobacter cloacae, salmonella typhimurium, klebsiella pneumoniae and pseudomonas aeruginosa.
9. A method of using the dinaphthalene pyridinium antimicrobial material of claim 1, wherein: the killing effect of gram-negative bacteria is determined by a plate coating method, the damage to cells is low under the antibacterial concentration, and the cytotoxicity is low.
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| WO2015123130A1 (en) * | 2014-02-11 | 2015-08-20 | Trustees Of Dartmouth College | Type 4 prepilin peptidase inhibitors and methods of use |
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| WO2015123130A1 (en) * | 2014-02-11 | 2015-08-20 | Trustees Of Dartmouth College | Type 4 prepilin peptidase inhibitors and methods of use |
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| Self-assembling films of chiral bipyridinium bisthiols;Massimiliano Lamberto等;《Journal of Materials Chemistry》;20091214;第20卷(第5期);第981-989页 * |
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