CN111848457B - Guanidyl modified oligophenylacetylene as well as preparation method and antibacterial application thereof - Google Patents
Guanidyl modified oligophenylacetylene as well as preparation method and antibacterial application thereof Download PDFInfo
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Abstract
The invention discloses a guanidino-modified oligophenylacetylene, a preparation method and an antibacterial application thereof, wherein the middle of the guanidino-modified oligophenylacetylene is a benzene ring and triple bond conjugated system with different substituents, and two ends of the guanidino-modified oligophenylacetylene are connected with guanidino structures with different chain lengths. The guanidino modified oligomeric phenylacetylene can be applied to preparation of disinfectant for resisting staphylococcus aureus and escherichia coli.
Description
Technical Field
The invention belongs to the technical field of oligomeric phenylacetylene compounds, and particularly relates to guanidino modified oligophenylacetylene, a preparation method and an antibacterial application thereof.
Background
Bacterial infections represent a great health threat to humans, and the use of antibiotics saves a large number of patients, but with the abuse of antibiotics, various resistant bacteria have emerged. The development of new antibacterial agents, preferably with different antibacterial mechanisms, is becoming of great importance. Among them, the photodynamic sterilization is a sterilization technology with important prospect, which is not easy to generate drug resistance and has broad spectrum sterilization effect.
The large conjugated system formed by alternating benzene ring and acetylene triple bond is used for Oligomeric Phenylacetylene (OPE), and the large conjugated system can generate Reactive Oxygen Species (ROS) under illumination, and the ROS has strong oxidizability and can break cell membrane, cytoplasm and DNA structure of cells, thereby killing the cells. Whitten and Schanze et al have conducted systematic studies on the cytotoxicity of oligophenylacetylenes and found that oligophenylacetylenes of quaternary ammonium salts are very toxic to both gram-negative and gram-positive bacteria under light, but their excitation light is near ultraviolet light, and does not utilize any technology (J.Phys.chem.Lett.2010, 1, 3207-3212;). Recently, wang Jing et al found that neutral oligophenylacetylene has better antibacterial activity, and can be excited by visible light to obtain good antibacterial activity. However, the intensity of the visible excitation light used was 90mW/cm 2 Stronger than the general natural light irradiation conditions, difficult to use in natural environments, and free from bacterial toxicity in dark places (ACS appl. In addition, the neutral oligomeric phenylacetylene has low solubility in aqueous solution, which limits the application of the neutral oligomeric phenylacetylene.
Guanidyl is widely present in natural polypeptides with antibacterial activity, and researches show that the guanidyl has a transmembrane effect, can assist a compound to have a transmembrane effect, has a certain destructive effect on bacterial cell membranes, and is considered as an antibacterial effective site of the natural antibacterial polypeptides (Biomacromolecules 2014, 15, 812-820). In addition, the guanidino group is present in protonated form in aqueous solution, which helps to increase the water solubility of the compound.
Disclosure of Invention
The invention aims to solve a technical problem of providing guanidino modified oligophenylacetylene, and the invention aims to solve another technical problem of providing a preparation method of guanidino modified oligophenylacetylene.
The invention specifically adopts the following technical scheme:
the guanidino modified oligomeric phenylacetylene is characterized in that the middle of the guanidino modified oligomeric phenylacetylene is a benzene ring and triple bond conjugated system with different substituents, two ends of the guanidino modified oligomeric phenylacetylene are connected with guanidino structures with different chain lengths, and the chemical structural formula is as follows;
R＝H，O(CH 2 ) m CH 3 ，OCH 2 (CH 2 ) m N(CH 3 ) 2 (m＝0～9)
n＝0～9。
the invention also provides a preparation method of the guanidino modified oligophenylacetylene, which is characterized in that the reaction formula in the preparation method is as follows:
the preparation method also comprises the following reaction steps:
a. synthesis of compound S4: dissolving the compound S3 in dichloromethane, adding an organic base, dropwise adding a solution of the compound S2 into the dichloromethane, washing an organic phase by using water and saturated saline solution in sequence after the reaction is finished, drying by using a drying agent, filtering, and separating by using column chromatography to obtain a compound S4.
b. Synthesis of compound S6: under the protection of inert gas, dissolving the compounds S4 and S5 and a catalyst in a solvent, heating, removing the solvent by vacuum rotary evaporation after the heating reaction is finished, and then separating by using column chromatography to obtain a compound S6.
c. Synthesis of compound S1: and mixing the compound S6 with acid, stirring for reaction, and then carrying out vacuum rotary evaporation to remove the solvent to obtain a compound S1, namely the guanidino modified oligomeric phenylacetylene.
Further, the organic base in the step a is one of triethylamine, diethylamine, diisopropylamine, trimethylamine or pyridine.
Further, the catalyst in the step b is Pd (P)Ph 3 ) 2 Cl 2 CuI and PPh 3 Mixture of (1), pd (PPh) 3 ) 4 And a mixture of CuI, pd 2 (dba) 3 CuI and dppf or Pd 2 (dba) 3 CuI and PPh 3 One of the mixtures of (a).
Further, the heating temperature in the step b is 20-100 ℃.
Further, the solvent in the step b is any one of tetrahydrofuran, dichloromethane or toluene, and is a mixed solvent mixed with any one of triethylamine, diisopropylamine, trimethylamine or pyridine according to different proportions.
Further, the acid in the step c is one of formic acid, trifluoroacetic acid, hydrochloric acid or acetic acid.
The invention also provides application of the guanidino-modified oligophenylacetylene prepared by the preparation method based on the guanidino-modified oligophenylacetylene or the guanidino-modified oligophenylacetylene in preparation of a disinfectant for resisting staphylococcus aureus and escherichia coli.
In the invention, the guanidino is introduced into the oligophenylacetylene structure, so that the water solubility of the compound can be improved, and the compound with stronger antibacterial effect can be obtained through the dual antibacterial effect of the guanidino and oligophenylacetylene structures.
Detailed Description
The present invention will be described in detail with reference to examples.
It is to be noted that the examples are given solely for the purpose of illustration and are not to be construed as limitations on the scope of the invention, as those skilled in the art will be able to make insubstantial modifications and adaptations of the invention in light of the present disclosure.
Example 1
The preparation method of guanidino-modified oligophenylacetylene in this example 1 is as follows:
step a. Synthesis of compound S4 (n = 1)
Compound S3 (5.1g, 13mmol) was dissolved in 200mL of dichloromethane, triethylamine (2.0mL, 14.33mmol) was added thereto, 10mL of a dichloromethane solution of compound S2 (3.77g, 14.33mmol) was added dropwise thereto, and after completion of the reaction, the organic phase was washed with water and saturated brine in this order, dried over anhydrous sodium sulfate, filtered, and separated by column chromatography to give compound S4.
Step b. Synthesis of Compound S6 (n =1, R = H)
Under the protection of nitrogen, compounds S4 (120mg, 0.951mmol), S5 (1.15g, 2.28mmol) and Pd 2 (dba) 3 (44mg, 0.048mmol), dppf (53mg, 0.095mmol) and CuI (18mg, 0.095mmol) were dissolved in a mixed solvent of tetrahydrofuran and triethylamine, and the mixture was reacted by heating, after completion of the reaction, the solvent was removed by vacuum rotary evaporation, and then the reaction product was separated by column chromatography to obtain compound S6.
Step c. Synthesis of compound S1 (n =1, r = h)
And (3) mixing the compound S6 (650 mg, 0.774mmol) with 10ml of formic acid, stirring for reaction, and then carrying out vacuum rotary evaporation to remove the solvent to obtain a compound S1, namely the guanidino modified oligomeric phenylacetylene.
Example 2
The procedure for the preparation of guanidino-modified oligophenylacetylene of this example was the same as that of example 1 except that the procedure of step a for the synthesis of compound S4 was as follows:
step b. Synthesis of compound S6 (n =1, r = och) 3 )
Under the protection of nitrogen, compound S4 (100mg, 0.537mmol), S5 (765mg, 1.29mmol) and Pd (PPh) 3 ) 2 Cl 2 (38mg，0.054mmol)，PPh 3 (28mg, 0.11mmol) and CuI (21mg, 0.11mmol) were dissolved in diisopropylamine, and after completion of the reaction, the solvent was removed by vacuum rotary evaporation, followed by separation by column chromatography to obtain Compound S6.
Step c. Synthesis of compound S1 (n =1, r = och) 3 )
And mixing the compound S6 (570mg, 0.606mmol) with 10ml of formic acid, stirring for reaction, and then removing the solvent by vacuum rotary evaporation to obtain the compound S1, namely the guanidino modified oligophenylacetylene.
Example 3
This example was tested for the antibacterial effect of the compound S1 prepared in example 1, i.e., the phototoxicity and dark toxicity of escherichia coli (n =1,r = h) were tested.
Culturing Escherichia coli in LB culture medium at 37 deg.C for 12 hr, centrifuging, pouring off supernatant, adding sterilized normal saline, blowing to disperse bacteria, centrifuging again, pouring off supernatant, and repeating for three times. The bacteria were divided in physiological saline and adjusted to OD 600 =1, and then the bacterial solution was diluted 100 times for use. Compound S1 was formulated as a 1mg/mL DMSO solution. To a 2mL centrifuge tube, 800. Mu.L of the cell suspension was added, followed by addition of the DMSO solution of S1, so that the final concentrations of compound S1 were 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL, respectively (control). Two sets were prepared for each concentration, each in visible light (5 mW/cm) 2 ) The cells were irradiated and left in the dark for 1 hour, and then stained with a mixed dye of SYTO9 and PI for 15 minutes, and the bacterial mortality was measured using a flow counter.
Experimental results; the bacterial mortality rates under dark conditions of 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL (control) were 96.7%,73.2%,15.6% and 2.5%, respectively; under the illumination condition, the bacterial mortality rates of 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL (control group) were 99.4%, 82.55%, 21.6% and 1.6%, respectively.
Therefore, the guanidino modified oligophenylacetylene prepared by the method has obvious bactericidal effect on escherichia coli under illumination and dark places.
Example 4
This example was tested for antibacterial effect of compound S1 prepared in example 1, i.e., phototoxicity and dark toxicity to staphylococcus aureus (n =1,r = h).
Culturing Staphylococcus aureus in LB culture medium at 37 deg.C for 12 hr, centrifuging, pouring off supernatant, adding sterilized normal saline, blowing to disperse bacteria, centrifuging again, pouring off supernatant, and repeating for three times. The bacteria were divided in physiological saline and adjusted to OD 600 =1, and then the bacterial solution was diluted 100 times for use. Compound S1 was formulated as a 1mg/mL DMSO solution. To a 2mL centrifuge tube, 800. Mu.L of the cell suspension was added, followed by addition of the DMSO solution of S1, so that the final concentrations of compound S1 were 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL, respectively (control). Two sets of samples were prepared for each concentration,respectively in visible light (5 mW/cm) 2 ) The cells were irradiated and left in the dark for 1 hour, and then stained with a mixed dye of SYTO24 and PI for 15 minutes, and the bacterial mortality was measured using a flow counter.
Experimental results; the bacterial mortality rates under dark conditions of 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL (control) were 99.3%,99.1%,19.1% and 2.6%, respectively; under light conditions, the bacterial mortality rates of 9. Mu.g/mL, 3. Mu.g/mL, 1. Mu.g/mL and 0. Mu.g/mL (control) were 99.9%,99.8%,98.8% and 1.9%, respectively.
Therefore, the guanidino modified oligophenylacetylene prepared by the method has obvious bactericidal effect on staphylococcus aureus under both illumination and dark places.
Claims (7)
1. The guanidino modified oligomeric phenylacetylene is characterized in that the guanidino modified oligomeric phenylacetylene has the following chemical structural formula;
wherein R = H, OCH 3 ；n＝1～9。
2. A preparation method of guanidyl modified oligophenylacetylene is characterized in that the reaction formula in the preparation method is as follows:
wherein R = H, OCH in the reaction formula 3 ；n＝1～9；
The preparation method also comprises the following reaction steps:
a. synthesis of compound S4: dissolving a compound S3 in dichloromethane, adding an organic base, dropwise adding a solution of a compound S2 into the dichloromethane, washing an organic phase with water and saturated saline solution in sequence after the reaction is finished, drying the organic phase with a drying agent, filtering the organic phase, and separating the organic phase with column chromatography to obtain a compound S4;
b. synthesis of compound S6: under the protection of inert gas, dissolving the compounds S4 and S5 and a catalyst in a solvent, heating, removing the solvent by vacuum rotary evaporation after the heating reaction is finished, and then separating by using column chromatography to obtain a compound S6; wherein the catalyst is Pd (PPh) 3 ) 2 C1 2 CuI and PPh 3 Mixture of (1), pd (PPh) 3 ) 4 And a mixture of CuI, pd 2 (dba) 3 CuI and dppf or Pd 2 (dba) 3 CuI and PPh 3 One of the mixtures of (a);
c. synthesis of compound S1: and mixing the compound S6 with acid, stirring for reaction, and then carrying out vacuum rotary evaporation to remove the solvent to obtain a compound S1, namely the guanidino modified oligomeric phenylacetylene.
3. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the organic base in step a is one of triethylamine, diethylamine, diisopropylamine, trimethylamine or pyridine.
4. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the solvent in step b is one of tetrahydrofuran, dichloromethane or toluene, or a mixed solvent mixed with one of triethylamine, diisopropylamine, trimethylamine or pyridine in different proportions.
5. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the heating temperature in step b is 20 to 100 ℃.
6. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the acid in step c is one of formic acid, trifluoroacetic acid, hydrochloric acid or acetic acid.
7. Use of the guanidino-modified oligophenylacetylene according to claim 1 or the guanidino-modified oligophenylacetylene according to any one of claims 2 to 6 for the preparation of a disinfectant against staphylococcus aureus and escherichia coli.
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| Biocidal Activity and Mechanism Study of Unsymmetrical Oligo-Phenylene-Ethynylenes;Jing Wang et al;《ACS Appl. Bio Mater.》;20200802;第3卷;5644-5651 * |
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