CN113563261B - Water-soluble polyurethanediol antibacterial molecule, and preparation method and application thereof - Google Patents
Water-soluble polyurethanediol antibacterial molecule, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a water-soluble multi-urea antibacterial molecule, a preparation method and application thereof. Expands the application of the polyureas in the biological field and provides a new idea for solving the problem of bacterial drug resistance development.
Description
Technical Field
The invention belongs to the technical field of compound synthesis, and particularly relates to a water-soluble polyurethanediol antibacterial molecule, a preparation method and application thereof.
Background
The discovery of antibiotics lays a serious role for people to defeat pathogenic microorganisms. However, for a 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 bacterial resistance has become a significant challenge in the world public health field. However, the development of new antibiotics has far from followed the development of bacterial resistance. Therefore, developing new strategies and means to make up for the inadequacies of traditional antibiotics and to slow down the rate of bacterial resistance development has become one of the main tasks of researchers.
Anions are ubiquitous in biological and environmental systems and play an important role in maintaining normal operation of organisms and in maintaining ecological balance. "anion coordination chemistry" has evolved from a model system of simple molecular recognition to complex and highly ordered molecular self-assembly through decades of development, becoming an important branch of supramolecular chemistry. The extensive development has also led researchers to realize that anion coordination chemistry can well mimic structures and processes in living beings, such as studying the binding properties of phosphate binding proteins, sulfate binding proteins, and the like. The team where the applicant is located has designed and constructed various structures based on multi-urea molecules in earlier work and found that the molecules can identify anions such as phosphate groups in the aqueous phase. However, the problem of water solubility of such molecules has been a bottleneck that prevents their further application in the fields of biology and the like.
It is well known that bacteria, particularly gram-negative bacteria, contain abundant phospholipid molecules in their electronegative cell wall outer membrane, and can achieve efficient binding with urea molecules through non-covalent interactions. Meanwhile, urea structures have been reported to interact non-covalently with DNA molecules. Thus, the DNA in the bacterial cell membrane can be used for constructing a complex structure of urea molecules and DNA through molecular recognition with the multi-urea molecules.
Disclosure of Invention
The invention designs and develops a novel antibacterial material based on the combination of membrane targeting and non-membrane targeting of water-soluble polyurethanes based on bacterial cell walls and DNA in membranes, which can provide rich recognition sites for the polyurethanes, and realizes excellent antibacterial performance by improving the bonding strength of the molecules and bacteria. The preparation of the novel polyurethanes not only can expand the application of the polyurethanes in the biological field, but also provides a new idea for solving the problem of bacterial drug resistance development.
In order to achieve the technical purpose, the invention adopts the following technical scheme:
a water-soluble polyurethanes antibacterial molecule, said water-soluble polyurethanes antibacterial molecule having the structural formula:
the introduction of the terminal quaternary ammonium salt in the water-soluble polyurethanes antibacterial molecules has the effect of increasing the water solubility of the polyurethanes.
In another aspect of the present invention, there is provided a method for preparing the water-soluble polyurethaneantibacterial molecule, comprising the steps of:
1) Dripping tetrahydrofuran solution of amine compound and o-nitro isocyanate together, and heating to react to obtain yellow solid compound;
2) Dissolving the compound obtained in the step 1) and palladium carbon in tetrahydrofuran, dripping hydrazine hydrate, heating, dissolving with N, N-dimethylformamide after the reaction is completed, removing the palladium carbon, and adding anhydrous diethyl ether to obtain a white solid compound;
3) Dropping the N, N-dimethylformamide solution of the compound obtained in the step 2) into tetrahydrofuran solution of 4,4' -methylenebis (phenyl isocyanate), and heating to react to obtain a white compound;
4) Mixing the N, N-dimethylformamide solution of the white compound obtained in the step 3) with the acetonitrile solution of 3-bromo-N, N, N-trimethylpropane-1-ammonium bromide, and heating for reaction to obtain a gray target product.
Further, the amine compound in step 1) 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 invention, there is also provided the use of the water-soluble polyurethaneurea antibacterial molecule described above as an antibacterial agent. The water-soluble polyurethanes antibacterial molecules have excellent antibacterial effects against gram-negative and gram-positive bacteria.
Preferably, the gram-negative bacterium is escherichia coli and the gram-positive bacterium is staphylococcus aureus.
The water-soluble polyurethanediol has the important role of the ureido skeleton and the terminal quaternary ammonium salt in the antibacterial function in the water-soluble polyurethanediol antibacterial molecular structure, and the antibacterial effect is obviously improved along with the increase of the number of the ureido groups in the polyurethanediol molecules. The introduction of quaternary ammonium salt can well increase the water solubility of the polyureas, so that the quaternary ammonium salt plays a certain role in exerting the antibacterial effect.
The invention has the beneficial effects that:
the invention provides a water-soluble multi-urea antibacterial molecule with an antibacterial effect, which can be in effective contact with bacterial cell walls through non-covalent interaction, so that outer membranes and inner membranes of the bacterial cell walls are damaged, and small-molecule contents in cells leak, so that bacteria die; on the other hand, the DNA can also diffuse into cells through broken cell membranes, and can be effectively combined with DNA in the membranes through non-covalent interaction, so that the conformation of the DNA is changed, and the death of the cells is promoted. Provides a new idea for solving the problem of bacterial drug resistance development.
Drawings
FIG. 1 is a fluorescent molecule uptake experiment after the outer membrane (a) and the inner membrane (b) of the cell wall of Escherichia coli of the present invention are broken;
FIG. 2 shows a galactoside hydrolysis assay (a) and a DNA/RNA molecule leakage detection assay (b) according to the invention;
FIG. 3 is a graph showing the change in morphology of (a) after (b) before binding of pDNA to 6U in vitro according to the invention;
FIG. 4 shows agarose gel results after binding of pDNA with 6U in vitro according to the invention;
FIG. 5 shows the result of DNA agarose gel after co-culture of E.coli and 6U according to the invention;
FIG. 6 is the binding strength of the polyureas molecules of the invention to DOPE and DOPG;
FIG. 7 is a graph showing the binding strength of the polyurethanemolecule of the present invention to DA.
Detailed Description
The following description of the present invention will be made more complete and clear in view of the detailed description of the invention, which is to be taken in conjunction with the accompanying drawings that illustrate only some, but not all, of the embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
Synthetic route to water-soluble polyurethaneantibacterial molecule (6U):
1) Synthesis of fragment Compound 3
Amine compound (0.8 g,3.5 mmol) was dissolved in 20ml of THF, ortho-nitroisocyanate (0.433 g,1.75 mmol) was dissolved in 20ml of THF, and two different reactions were added dropwise together and heated to 80 ℃. Reflux with vigorous stirring for 2.5 hours yielded a large amount of yellow solid which was removed by suction filtration. The yellow solid obtained was washed with anhydrous tetrahydrofuran and diethyl ether, respectively, under ultrasonic conditions and dried in a vacuum oven to give pure yellow solid compound 3 (0.98 g,1.4 mmol) in 85% yield.
2) Synthesis of fragment Compound 4
Compound 3 (0.9 g,1.4 mmol) and Pd/C10% (0.09 g, cat.) were suspended in 200mL of THF at room temperature and hydrazine hydrate (1.0 mL) was added dropwise to raise the temperature to 80 ℃. The solid was filtered off with suction, dissolved in DMF (50 mL) and Pd/C was removed by filtration through celite with vigorous stirring at reflux for 5 hours. The DMF solution of the dissolved product was distilled to about 3ml, and after standing at room temperature, 200ml of anhydrous diethyl ether was slowly added, and the white precipitate was collected, and the white solid was washed 3 times with anhydrous tetrahydrofuran and anhydrous diethyl ether under ultrasonic conditions, respectively, and dried in vacuo to give pure white solid compound 4 (0.6 g,0.8 mmol) in 75% yield.
3) Synthesis of fragment Compound 5
Compound 4 (0.6 g,0.8 mmol) was dissolved in 2mL of DMF at normal temperature, and a hot solution of 4,4' -methylenebis (phenylisocyanate) (0.263 g,1.6 mmol) in THF (20.0 mL) was added dropwise, and the temperature was raised to 80 ℃. Refluxing with vigorous stirring for 2.5 hours, filtering and collecting the precipitate, washing 3 times with THF, anhydrous diethyl ether, and drying in vacuo afforded pure white compound 5 (0.6 g,0.58 mmol) in 80% yield.
4) Synthesis of Compound 6U
Compound 5 (0.6 g,0.58 mmol) was weighed into 2.5mL DMF and dissolved completely under heating and ultrasound. 3-bromo-N, N, N-trimethylpropane-1-ammonium bromide (0.756 g,2.9 mmol) was dissolved in 40ml acetonitrile solution, the two reaction solutions were mixed well, the temperature was raised to 120℃and the reaction solution was refluxed for 8 hours, yielding a large amount of grey solid attached to the bottle wall. The solid was collected and washed 3 times with acetonitrile, anhydrous diethyl ether, respectively, and then dried in vacuo to give 6U of crude product.
The crude product was dissolved in 6ml of DMF under heating, and again a solution of 3-bromo-N, N, N-trimethylpropane-1-ammonium bromide (0.35 g,1.4 mmol) in acetonitrile was added, the temperature was raised to 120℃and after 5 hours the grey solid in the bottle was collected and washed three times with acetonitrile and anhydrous diethyl ether, respectively, to give pure grey solid 6U (0.54 g,0.348 mmol) in 60% yield.
Example 2 experiment of bacteriostatic Effect
The compound to be tested is firstly serially diluted in a 96-well plate by 100 mu L of liquid culture medium, and then 100 mu L of bacteria liquid (10) 6 CFU/mL), after incubation, bacterial growth was observed and the lowest concentration at which the medium was clear and no bacterial growth was seen was judged as the lowest inhibitory concentration (MIC) of the drug compared to the blank control. Each strain was repeated 3 times and averaged. The drug and strain without bacterial growth were streaked onto new agar plates for cultivation, and the Minimum Bactericidal Concentration (MBC) of the drug was further determined.
As a result, it was found that the minimum inhibitory concentration of Compound 6U of example 1 against E.coli was 3.75. Mu.M, and as the concentration continued to increase, the minimum inhibitory concentration against E.coli was 7.5. Mu.M. The antibacterial result can be comparable with the antibacterial effect of the antibacterial peptide polymyxin B on the bacteria, the minimum antibacterial concentration of the polymyxin B on the escherichia coli is 3.75 mu M, and the minimum antibacterial concentration is 7.5 mu M.
Example 3
In order to investigate that compound 6U causes breakage of bacterial cell walls, a fluorescent molecule uptake experiment was performed.
1) Preparation of bacterial liquid (OD) 600 150 μl of the bacterial liquid was taken in a 96-well plate, and N-phenyl-2-naphthylamine (NPN) (40 μM,50 μl) was further added thereto, followed by co-culture 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 liquid (OD) 600 =0.34), 150 μl of the above bacterial liquid was taken in a 96-well plate, and Propidium Iodide (PI) (40 μΜ,50 μl) was further added and co-cultured for 5 minutes. Subsequently, 20. Mu.L of Compound 6U (60. Mu.M) was added, and the fluorescence emission intensities at 617nm were observed at various times.
Through NPN and PI uptake experiments, it was demonstrated that addition of compound 6U can lead to breakage of the outer and inner membrane of the cell wall of e.coli (fig. 1).
2) Preparation of bacterial liquid (OD) 600 180 μl of the bacterial liquid was taken in a 96-well plate, and 20 μl of compound 6U (60 μΜ) was added. After co-cultivation for 1 hour, the bacterial solution was centrifuged at 1000rpm for 5 minutes, and the supernatant was collected to measure the absorption intensity at 260 nm.
Preparing 15mM of PBS solution of nitrophenyl galactoside; preparation of bacterial liquid (OD) 600 =0.34), and then the bacterial solution was diluted to a concentration of 10 using PBS solution of nitrophenyl galactoside 6 CFU/mL solution. mu.L of the above bacterial liquid was taken 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 various times.
The galactoside hydrolysis experiments and DNA absorbance experiments demonstrated that breakage of cell wall inner membranes can lead to leakage of small molecules, such as proteins in the membrane, but cannot promote leakage of large molecules, such as DNA and RNA molecules, from the broken 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 with a certain concentration of 6U, standing for 30 minutes, and observing the morphology change of the pDNA before and after the compound is added by AFM.
The results of the AFM experiments showed that the supercoiled structure of pDNA was significantly changed in conformation upon addition of 7.5 μm compound 6U, becoming a granular aggregate (fig. 3). This result demonstrates that there is a non-covalent interaction of the compound 6U molecule with pDNA.
2) The agarose gel electrophoresis experiment steps are as follows: 1% (w/V) agarose gel was prepared, pDNA and 6U compound solutions of different concentrations were added to the electrophoresis tank, and run at 60V for 30 minutes, and the corresponding DNA electrophoresis results were photographed by a gel imager.
Agarose gel electrophoresis experiments revealed that compound 6U forms a complex with pDNA, resulting in a lag phenomenon of DNA electrophoresis (fig. 4).
3) To investigate the interaction of DNA within bacterial cells with the compound 6U molecule, after co-culturing compound 6U with e.coli for 24 hours, DNA within the bacteria was extracted and subjected to agarose gel electrophoresis experiments (fig. 5), which compared to the experimental results of PBS blank experimental groups, were found to have a similar DNA electrophoresis retardation phenomenon as in vitro pDNA, indicating that compound 6U may enter into bacterial cells and form complexes with DNA through non-covalent interactions, resulting in a change in DNA conformation, leading to bacterial death.
Example 5
In order to study the important role of ureido skeletons and terminal quaternary ammonium salts in the 6U structure of the compound in antibacterial, the following series of model compounds are designed:
the minimum inhibitory concentration and the minimum bactericidal concentration of the model compounds were systematically examined, and the results are shown in table 1.
TABLE 1 antibacterial results (concentration units. Mu.M) for 6U and a series of model compounds
The results show that the antibacterial effect is obviously improved along with the increase of the number of ureido groups in the polyurethanes. The introduction of quaternary ammonium salt can well increase the water solubility of the polyureas, so that the quaternary ammonium salt plays a certain role in exerting the antibacterial effect.
EXAMPLE 6 non-covalent interactions of ureido groups with lipid molecules DOPG, DOPE and DNA
1) The DOPG and DOPE are used as the models of lipid molecules on cell membranes, and the combination capacities of the 6U,4U and 2U and DOPG and DOPE containing different urea base numbers are systematically examined by using an ultraviolet titration experiment. The specific experimental steps are as follows: preparing 6U,4U and 2U compound solutions with certain concentration, gradually dripping 1-25 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.
Tables 2 binding constants (K) for 6U,4U and 2U with DOPE, DOPG and DA, respectively a ,M -1 )
2) The binding capacity of the polyurethanemolecules 6U,4U and 2U and DA containing different urea base numbers was systematically examined using ultraviolet titration experiments using herring sperm (DA) as a model of the pentose phosphate backbone on DNA. The specific experimental steps are as follows: preparing 6U,4U and 2U compound solutions with certain concentrations, gradually dripping 0.25-30 equivalent DA solution into the solution, and obtaining the bonding strength of the 6U,4U and 2U and DA by fitting the change of ultraviolet absorption. The specific experimental results are shown in Table 2.
From the uv titration experiments, it is clear from table 2 and fig. 6 to 7 that as the number of ureido groups in the polyureas increases, 2U,4U and 6U significantly increase the binding constants of DOPG and DA for DOPE.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to 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 (6)
1. A water-soluble polyurethaneantibacterial molecule characterized by the following structural formula:
2. the method for preparing the water-soluble polyurethaneantibacterial molecule of claim 1, comprising the steps of:
1) The amine compound and the ortho-nitroisocyanic acidThe tetrahydrofuran solution of the ester is dripped together, and the yellow solid compound is obtained through heating reaction, wherein the structural formula of the amine compound is as follows:the structural formula of the yellow solid compound is as follows:
2) Dissolving the compound obtained in the step 1) and palladium carbon in tetrahydrofuran, dripping hydrazine hydrate, heating, dissolving with N, N-dimethylformamide after the reaction is completed, removing the palladium carbon, and adding anhydrous diethyl ether to obtain a white solid compound with the structural formula:
3) Dropping the N, N-dimethylformamide solution of the compound obtained in the step 2) into tetrahydrofuran solution of 4,4' -methylenebis (phenyl isocyanate), heating to react to obtain a white compound,
4) Mixing the N, N-dimethylformamide solution of the white compound obtained in the step 3) with the acetonitrile solution of 3-bromo-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 heating conditions in steps 1) to 3) are 80 ℃.
4. The process according to claim 2, wherein the heating conditions in step 4) are 120 ℃.
5. The use of the water-soluble polyurethanes antibacterial molecule of claim 1 for the preparation of antibacterial agents.
6. The use according to claim 5, wherein the water-soluble polyurethanes antibacterial molecule is used to inhibit or kill escherichia coli and staphylococcus aureus.
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| JP2006151941A (en) * | 2004-10-26 | 2006-06-15 | Univ Of Tokushima | Bis(quaternary ammonium salt) compound and its manufacturing method |
| 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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| AU2005288519A1 (en) * | 2004-09-27 | 2006-04-06 | Technion Research & Development Foundation Ltd. | Fatty acid modified polylysines as antimicrobial agents |
| US8563558B2 (en) * | 2010-12-06 | 2013-10-22 | Confluence Life Sciences, Inc. | Substituted pyridine urea compounds |
| US9724352B2 (en) * | 2012-05-31 | 2017-08-08 | 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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| JP2006151941A (en) * | 2004-10-26 | 2006-06-15 | Univ Of Tokushima | Bis(quaternary ammonium salt) compound and its manufacturing method |
| 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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| 脲类受体对阴离子的结合、识别和分离;魏梅莹 等;《高等学校化学学报》;第32卷(第09期);第1939-1949页 * |
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