CN113563261A - Water-soluble polyurea antibacterial molecule and preparation method and application thereof - Google Patents
Water-soluble polyurea antibacterial molecule and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a water-soluble polyurea antibacterial molecule, a preparation method and application thereof. The application of the polyurea molecule in the biological field is expanded, and a new thought is provided for solving the problem of the development of the drug resistance of bacteria.
Description
Technical Field
The invention belongs to the technical field of compound synthesis, and particularly relates to a water-soluble polyurea antibacterial molecule, and a preparation method and application thereof.
Background
The discovery of antibiotics lays a key role for human beings to overcome pathogenic microorganisms. However, over the last century, the abuse of antibiotics has led to the development and enhancement of bacterial resistance to antibiotics, even with the emergence of multi-resistant superbacteria, which has severely threatened the life health of all humans, and the problem of bacterial resistance has become a major challenge in the global public health sector. However, the speed of development of new antibiotics has not kept pace with the development of bacterial resistance. Therefore, developing new strategies and means to compensate for the deficiencies of traditional antibiotics and to slow down the rate of development of bacterial resistance has become one of the major tasks for researchers.
Anions are ubiquitous in biological and environmental systems and play an important role in maintaining the normal operation of organisms and maintaining ecological balance. "anion coordination chemistry" has evolved over decades from simple molecular recognition model systems to complex and highly ordered molecular self-assembly, becoming an important branch of supramolecular chemistry. The great development has also led researchers to recognize that anion coordination chemistry can well mimic the structure and processes in living organisms, for example, studying the binding properties of phosphate binding proteins, sulfate binding proteins, and the like. The team of the applicant has designed and constructed various structures based on the polyurea molecules in earlier work, and finds that the molecules can recognize anions such as phosphate radical in the water phase. However, the water solubility of the molecules has been a bottleneck to prevent further application in the fields of biology and the like.
It is known that bacteria, especially gram-negative bacteria, contain abundant phospholipid molecules in their negatively charged cell wall outer membrane, and can effectively bind urea molecules through non-covalent interactions. At the same time, urea-like structures have been reported to interact non-covalently with DNA molecules. Therefore, DNA in bacterial cell membranes and the polyurea molecules can construct a compound structure of the urea molecules and the DNA through molecular recognition.
Disclosure of Invention
The invention can provide rich recognition sites for the polyurea molecules based on the bacterial cell walls and DNA in the film, designs and develops a novel antibacterial material combining film targeting and non-film targeting based on water-soluble polyurea molecules, and realizes excellent antibacterial performance by improving the bonding strength of the molecules and bacteria. The preparation of the novel polyurea molecules can not only expand the application of the polyurea molecules in the biological field, but also provide a new idea for solving the problem of the development of the drug resistance of bacteria.
In order to achieve the technical purpose, the invention specifically adopts the following technical scheme:
a water-soluble polyurea antibacterial molecule, wherein the structural formula of the water-soluble polyurea antibacterial molecule is as follows:
the introduction of the terminal quaternary ammonium salt in the water-soluble polyurea antibacterial molecule has the function of increasing the water solubility of the polyurea molecule.
In another aspect of the present invention, there is provided a method for preparing the water-soluble polyurea antibacterial molecule, comprising the steps of:
1) dropwise adding an amine compound and a tetrahydrofuran solution of o-nitroisocyanate together, and heating for reaction to obtain a yellow solid compound;
2) dissolving the compound obtained in the step 1) and palladium carbon in tetrahydrofuran, then dripping hydrazine hydrate into the tetrahydrofuran for heating, dissolving the mixture by using N, N-dimethylformamide after the reaction is finished, removing the palladium carbon, and adding anhydrous ether to obtain a white solid compound;
3) dripping the N, N-dimethylformamide solution of the compound obtained in the step 2) into the tetrahydrofuran solution of 4,4' -methylene bis (phenyl isocyanate), and heating for reaction to obtain a white compound;
4) mixing the N, N-dimethylformamide solution of the white compound in the step 3) with the acetonitrile solution of 3-bromine-N, N, N-trimethylpropane-1-ammonium bromide, and heating for reaction to obtain a gray target product.
Further, in the step 1), the amine compound is selected from 4,4' -diaminodiphenylmethane.
Further, the heating conditions in steps 1) to 3) were 80 ℃.
Further, the heating condition in the step 4) is 120 ℃.
In another aspect of the present invention, there is also provided the use of the above water-soluble polyurea antibacterial molecule as an antibacterial agent. The water-soluble polyurea antibacterial molecule has excellent antibacterial effect on gram-negative bacteria and gram-positive bacteria.
Preferably, the gram-negative bacterium is escherichia coli, and the gram-positive bacterium is staphylococcus aureus.
The important function of the carbamido skeleton and the terminal quaternary ammonium salt in the water-soluble polyurea antibacterial molecular structure in antibiosis is obviously improved along with the increase of the carbamido quantity in the polyurea molecule. The introduction of the quaternary ammonium salt can well increase the water solubility of the polyurea molecule, so the quaternary ammonium salt also has a certain effect in the exertion of the antibacterial effect.
The invention has the beneficial effects that:
the invention provides a water-soluble polyurea antibacterial molecule with antibacterial effect, which can be effectively contacted with a bacterial cell wall through non-covalent interaction, so that the outer membrane and the inner membrane of the bacterial cell wall are damaged, and the micromolecular content in the cell leaks to cause bacterial death; on the other hand, the DNA can also be diffused into cells through damaged cell membranes, and effectively combined with DNA in the membranes through non-covalent interaction, so that the conformation of the DNA is changed, and the cells are killed. Provides a new idea for solving the problem of the development of the drug resistance of bacteria.
Drawings
FIG. 1 shows fluorescence molecule uptake assays after disruption of the outer membrane (a) and the inner membrane (b) of the E.coli cell wall of the present invention;
FIG. 2 shows galactoside hydrolysis assay (a) and DNA/RNA molecule leakage assay (b) of the present invention;
FIG. 3 is a graph of the in vitro pDNA of the invention before (a) and after (b) binding to 6U;
FIG. 4 shows the results of agarose gel after the in vitro pDNA of the present invention was bound to 6U;
FIG. 5 shows the result of DNA agarose gel after co-culturing Escherichia coli of the present invention with 6U;
FIG. 6 is the strength of the binding of the polyurea molecules of the invention to DOPE and DOPG;
FIG. 7 is the strength of the binding of the polyurea molecules of the invention to DA.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to specific embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Synthetic route of water-soluble polyurea antibacterial molecule (6U):
1) synthesis of fragment Compound 3
The amine compound (0.8g,3.5mmol) was dissolved in 20ml THF, the o-nitroisocyanate (0.437g,1.75mmol) was dissolved in 20ml THF, the two different reaction solutions were added dropwise and the temperature was raised to 80 ℃. Reflux was carried out with vigorous stirring for 2.5 hours to give a large amount of yellow solid, and the liquid was discarded by suction filtration. The resulting yellow solid was washed with anhydrous tetrahydrofuran and diethyl ether, respectively, under sonication, and dried in a vacuum oven to give pure compound 3(0.98g,1.4mmol) as a yellow solid in 85% yield.
2) Synthesis of fragment Compound 4
Compound 3(0.9g,1.4mmol) and Pd/C10% (0.09g, cat.) were suspended in 200mL of THF at room temperature, and hydrazine hydrate (1.0mL) was added dropwise and the temperature was raised to 80 ℃. Reflux was carried out with vigorous stirring for 5 h, the solid was filtered off with suction, dissolved in DMF (50mL) and the Pd/C was removed by filtration through tight celite. The DMF solution of the dissolved product is evaporated to about 3ml, after standing at normal temperature, 200ml of anhydrous ether is slowly added, white precipitate is collected, the white solid is washed for 3 times by anhydrous tetrahydrofuran and anhydrous ether under the ultrasonic condition respectively, and vacuum drying is carried out to obtain pure white solid compound 4(0.6g,0.8mmol), wherein the yield is 75%.
3) Synthesis of fragment Compound 5
Compound 4(0.6g,0.8mmol) was dissolved in 2mL of DMF at room temperature, and a hot solution of 4,4' -methylenebis (phenylisocyanate) (0.263g,1.6mmol) in THF (20.0mL) was added dropwise to the solution, and the temperature was raised to 80 ℃. Reflux was carried out with vigorous stirring for 2.5 hours, and the precipitate was collected by filtration, washed 3 times with THF, dry ether and then dried in vacuo to give pure white compound 5(0.6g,0.58mmol) in about 80% yield.
4) Synthesis of Compound 6U
Compound 5(0.6g,0.58mmol) was weighed into 2.5mL DMF and dissolved completely under heat sonication. 3-bromo-N, N, N-trimethylpropane-1-ammonium bromide (0.756g,2.9mmol) is dissolved in 40ml of acetonitrile solution, the two reaction solutions are mixed uniformly, the temperature is raised to 120 ℃, the reaction solution flows back for 8 hours, and a large amount of gray solid is generated and attached to the wall of the bottle. The solid was collected and washed 3 times with acetonitrile, dry ether, respectively, and then dried under vacuum to give 6U of crude product.
The crude product was dissolved in 6ml of DMF under heating and a solution of 3-bromo-N, N, N-trimethylpropane-1-ammonium bromide (0.35g,1.4mmol) in acetonitrile was added again, the temperature was raised to 120 ℃ and after 5 hours the grey solid in the flask was collected and washed three times with acetonitrile and dry ether to give pure 6U (0.54g,0.348mmol) as a grey solid in 60% yield.
Example 2 experiment of bacteriostatic Effect
Continuously diluting the compound to be detected with 100 μ L liquid culture medium in 96-well plate, and adding 100 μ L test bacteria liquid (10 μ L) into each tube6CFU/mL), and observing the growth of the bacteria after culture, and comparing with a blank control, and judging the Minimum Inhibitory Concentration (MIC) of the medicine according to the lowest concentration of the clear culture medium without bacteria growth observed by naked eyes. Each strain was repeated 3 times, and the average was calculated. The drug and the strain without bacterial growth were streaked onto new agar plates for culture and the Minimum Bactericidal Concentration (MBC) of the drug was further determined.
As a result, it was found that the minimal inhibitory concentration of compound 6U of example 1 against E.coli growth was 3.75. mu.M, and that the minimal inhibitory concentration against E.coli was 7.5. mu.M as the concentration continued to increase. The antibacterial result can be compared with the antibacterial effect of the antibacterial peptide polymyxin B on the bacteria, the minimum inhibitory concentration of the polymyxin B on escherichia coli is 3.75 mu M, and the minimum bactericidal concentration is 7.5 mu M.
Example 3
In order to explore the damage of the bacterial cell wall caused by the compound 6U, a fluorescence molecule uptake experiment is carried out.
1) Preparation of bacterial solution (OD)6000.34), 150. mu.L of the above-mentioned cell suspension was put in a 96-well plate, and N-phenyl-2-naphthylamine (NPN) (40. mu.M, 50. mu.L) was further added thereto, followed by co-incubation for 5 minutes. Subsequently, 20. mu.L of Compound 6U (60. mu.M) was added, and fluorescence emission at 420nm was observed at various times.
Preparation of bacterial solution (OD)6000.34), 150. mu.L of the above-mentioned bacterial suspension was put in a 96-well plate, and Propidium Iodide (PI) (40. mu.M, 50. mu.L) was further added thereto, followed by co-culture for 5 minutes. Subsequently, 20. mu.L of Compound 6U (60. mu.M) was added, and the fluorescence emission intensity at 617nm was observed at various times.
Through NPN and PI uptake experiments, it was confirmed that the addition of compound 6U can cause the breakage of the outer and inner membranes of the E.coli cell wall (FIG. 1).
2) Preparation of bacterial solution (OD)6000.34), 180 μ L of the above-mentioned bacterial suspension was put in a 96-well plate, and 20 μ L of compound 6U (60 μ M) was added. After 1 hour of co-incubation, the cells were centrifuged at 1000rpm for 5 minutes, and the supernatant was taken to measure the absorption intensity at 260 nm.
Preparing 15mM PBS solution of nitrophenylgalactoside; preparation of bacterial solution (OD)6000.34), the resulting suspension was diluted to a concentration of 10 using a PBS solution of nitrophenylgalactoside6CFU/mL solution. mu.L of the above-mentioned bacterial suspension was put in a 96-well plate, and 20. mu.L of compound 6U (60. mu.M) was added thereto. The absorption intensity at 410nm was observed at different times.
Galactoside hydrolysis experiments and DNA absorbance experiments confirmed that disruption of the cell wall inner membrane can result in leakage of small molecules, such as intramembrane proteins, but cannot promote leakage of large molecules, such as DNA and RNA molecules, from the disrupted cell membrane (FIG. 2).
Example 4
1) AFM experiments the experimental procedure for exploring the binding of compounds to DNA was as follows: taking an aqueous solution of pDNA, adding a solution of 6U with a certain concentration, standing for 30 minutes, and observing the morphological change of the pDNA before and after adding the compound by AFM.
AFM experiments showed that the supercoiled structure of pDNA undergoes a significant conformational change upon addition of 7.5. mu.M Compound 6U, turning into granular aggregates (FIG. 3). This result indicates that the compound 6U molecule has non-covalent interactions with pDNA.
2) The agarose gel electrophoresis experimental procedure was as follows: 1% (w/V) agarose gel is prepared, pDNA and 6U compound solution with different concentrations are added into an electrophoresis tank, the mixture is run for 30 minutes under the voltage of 60V, and the corresponding DNA electrophoresis result is shot by a gel imager.
Agarose gel electrophoresis experiments revealed that compound 6U forms a complex with pDNA, resulting in a retardation phenomenon of DNA electrophoresis (fig. 4).
3) In order to investigate the interaction between the DNA in the bacterial cells and the molecules of the compound 6U, after the compound 6U is co-cultured with Escherichia coli for 24 hours, the DNA in the bacteria is extracted and subjected to an agarose gel electrophoresis experiment (figure 5), compared with the experiment result of a PBS blank experiment group, the DNA electrophoresis delay phenomenon similar to that of in vitro pDNA is found, which indicates that the compound 6U can enter the bacterial cells and form a compound with the DNA through non-covalent interaction, so that the conformation of the DNA is changed, and the bacteria die.
Example 5
In order to research the important function of the carbamido skeleton and the terminal quaternary ammonium salt in the 6U structure of the compound in antibiosis, the following series of model compounds are designed:
the system examined the minimum inhibitory and bactericidal concentrations of the model compounds and the results are shown in table 1.
TABLE 16U antibacterial results (concentration in. mu.M) for a series of model compounds
The result shows that the antibacterial effect is obviously improved along with the increase of the number of carbamido groups in the polyurea molecule. The introduction of the quaternary ammonium salt can well increase the water solubility of the polyurea molecule, so the quaternary ammonium salt also has a certain effect in the exertion of the antibacterial effect.
Example 6 non-covalent interaction of ureido groups with lipid molecules DOPG, DOPE and DNA
1) The method adopts DOPG and DOPE as a model of lipid molecules on a cell membrane, and utilizes an ultraviolet titration experiment to systematically investigate the binding capacity of 6U, 4U and 2U of polyurea molecules containing different urea groups and the DOPG and DOPE. The specific experimental steps are as follows: preparing 6U, 4U and 2U compound solutions with certain concentrations, gradually dropwise adding 1 to 25 equivalents of DOPG or DOPE solution, and obtaining the bonding strength of 6U, 4U and 2U and DOPG or DOPE by fitting the change of ultraviolet absorption. The specific experimental results are shown in table 2.
TABLE 26 binding constants (K) of U, 4U and 2U with DOPE, DOPG and DA, respectivelya,M-1)
2) Herring sperm (DA) is used as a model of pentose phosphate skeleton on DNA, and the combination capability of 6U, 4U and 2U polyurea molecules containing different urea groups and DA is systematically examined by using an ultraviolet titration experiment. The specific experimental steps are as follows: preparing 6U, 4U and 2U compound solutions with certain concentrations, gradually dropwise adding 0.25-30 equivalents of DA solution, and obtaining the bonding strength of 6U, 4U and 2U and DA by fitting the change of ultraviolet absorption. The specific experimental results are shown in table 2.
Through ultraviolet titration experiments, as shown in table 2 and fig. 6-7, the binding constants of 2U, 4U and 6U to DOPE, DOPG and DA are remarkably increased along with the increase of the number of carbamido groups in a polyurea molecule.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (7)
1. A water-soluble, polyurethaneurea antimicrobial molecule, characterized by the structural formula:
2. a method of preparing a water-soluble polyurea antimicrobial molecule according to claim 1, comprising the steps of:
1) dropwise adding an amine compound and a tetrahydrofuran solution of o-nitroisocyanate together, and heating for reaction to obtain a yellow solid compound;
2) dissolving the compound obtained in the step 1) and palladium carbon in tetrahydrofuran, then dripping hydrazine hydrate into the tetrahydrofuran for heating, dissolving the mixture by using N, N-dimethylformamide after the reaction is finished, removing the palladium carbon, and adding anhydrous ether to obtain a white solid compound;
3) dripping the N, N-dimethylformamide solution of the compound obtained in the step 2) into the tetrahydrofuran solution of 4,4' -methylene bis (phenyl isocyanate), and heating for reaction to obtain a white compound;
4) mixing the N, N-dimethylformamide solution of the white compound in the step 3) with the acetonitrile solution of 3-bromine-N, N, N-trimethylpropane-1-ammonium bromide, and heating for reaction to obtain a gray target product.
3. The method according to claim 2, wherein the amine compound in step 1) is selected from 4,4' -diaminodiphenylmethane.
4. The method according to claim 2, wherein the heating conditions in steps 1) to 3) are 80 ℃.
5. The method according to claim 2, wherein the heating condition in the step 4) is 120 ℃.
6. Use of the water-soluble polyurea antibacterial molecule of claim 1 as an antibacterial agent.
7. Use according to claim 6, wherein the water-soluble polyurea antibacterial molecule is used to inhibit or kill Escherichia coli and Staphylococcus aureus.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060074021A1 (en) * | 2004-09-27 | 2006-04-06 | Amram Mor | Novel antimicrobial agents |
| JP2006151941A (en) * | 2004-10-26 | 2006-06-15 | Univ Of Tokushima | Bis(quaternary ammonium salt) compound and its manufacturing method |
| US20120142708A1 (en) * | 2010-12-06 | 2012-06-07 | Selness Shaun R | Substituted pyridine urea compounds |
| CN105503711A (en) * | 2016-01-30 | 2016-04-20 | 山西大学 | Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof |
| US20170000800A1 (en) * | 2012-05-31 | 2017-01-05 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pyrrolo[2,1-f[1,2,4]triazine compounds, preparation methods and applications thereof |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060074021A1 (en) * | 2004-09-27 | 2006-04-06 | Amram Mor | Novel antimicrobial agents |
| JP2006151941A (en) * | 2004-10-26 | 2006-06-15 | Univ Of Tokushima | Bis(quaternary ammonium salt) compound and its manufacturing method |
| US20120142708A1 (en) * | 2010-12-06 | 2012-06-07 | Selness Shaun R | Substituted pyridine urea compounds |
| US20170000800A1 (en) * | 2012-05-31 | 2017-01-05 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Pyrrolo[2,1-f[1,2,4]triazine compounds, preparation methods and applications thereof |
| CN105503711A (en) * | 2016-01-30 | 2016-04-20 | 山西大学 | Pyridylurea biquaternary ammonium salt as well as preparation method and application thereof |
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| Title |
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| 魏梅莹 等: "脲类受体对阴离子的结合、识别和分离", 《高等学校化学学报》, vol. 32, no. 09, pages 1939 - 1949 * |
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