CN111848457A - Guanidyl modified oligophenylacetylene, and preparation method and antibacterial application thereof - Google Patents

Guanidyl modified oligophenylacetylene, and preparation method and antibacterial application thereof Download PDF

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CN111848457A
CN111848457A CN202010810402.3A CN202010810402A CN111848457A CN 111848457 A CN111848457 A CN 111848457A CN 202010810402 A CN202010810402 A CN 202010810402A CN 111848457 A CN111848457 A CN 111848457A
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廖伟
王静
卓连刚
赵鹏
杨夏
王关全
魏洪源
杨宇川
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
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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

Guanidyl modified oligophenylacetylene, and preparation method and antibacterial application thereof
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.
Oligomeric Phenylacetylene (OPE) forms a large conjugated system through a benzene ring and acetylene triple bonds alternately, can generate Reactive Oxygen Species (ROS) under illumination, and the reactive oxygen species has strong oxidability and can break cell membranes, cytoplasm and DNA structures of cells, so that the cells are killed. Whitten and Schanze et al have conducted systematic studies on the cytotoxicity of oligophenylacetylene, and found that oligophenylacetylene of quaternary ammonium salt type has excellent toxicity to both gram-negative bacteria and gram-positive bacteria under light irradiation, but their excitation light is near ultraviolet light, and does not utilize the popularization and utilization of the technology (J.Phys.chem.Lett.2010, 1, 3207-. 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/cm2Stronger than the general natural light irradiation conditions, is difficult to use in natural environments, and has no 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 damage effect on bacterial cell membranes, and is considered as an antibacterial effective site of the natural antibacterial polypeptides (Biomacromolecules 2014, 15, 812-. 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;
Figure BDA0002630702690000021
R＝H，O(CH2)mCH3，OCH2(CH2)mN(CH3)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:
Figure BDA0002630702690000022
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, washing the organic phase with water and saturated brine in sequence after the reaction is finished, drying the organic phase with a drying agent, filtering the organic phase, and separating the organic phase by using column chromatography to obtain the 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 step b is Pd (PPh)3)2Cl2CuI and PPh3Mixture of (1), Pd (PPh)3)4And a mixture of CuI, Pd2(dba)3CuI and dppf or Pd2(dba)3CuI and PPh3One of the mixtures of (a).
Further, the heating temperature in the step b is 20-100 ℃.
Further, the solvent in the step b is a mixed solvent of any one of tetrahydrofuran, dichloromethane or toluene and any one of triethylamine, diisopropylamine, trimethylamine or pyridine in 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.
The invention introduces guanidino into the oligophenylacetylene structure, which not only can improve the water solubility of the compound, but also can obtain the compound with stronger antibacterial effect through the dual antibacterial effect of the guanidino and the oligophenylacetylene structure.
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 the reaction was completed, the organic phase was washed successively with water and saturated brine, 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 nitrogen protection, compound S4(120mg, 0.951mmol), S5(1.15g, 2.28mmol) and Pd2(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 reaction was heated, after completion of the reaction, the solvent was removed by vacuum rotary evaporation, followed by separation by column chromatography to give compound S6.
Step c. synthesis of compound S1 (n ═ 1, R ═ H)
And (3) mixing the compound S6(650mg, 0.774mmol) with 10ml formic acid, stirring for reaction, and then removing the solvent by vacuum rotary evaporation to obtain a compound S1, namely the guanidino modified oligomeric phenylacetylene.
Example 2
In the preparation method of guanidino-modified oligophenylacetylene of this example, the method for synthesizing the compound S4 in step a is the same as that in example 1, except that:
step b. synthesis of compound S6 (n ═ 1, R ═ OCH3)
Under nitrogen protection, compound S4(100mg, 0.537mmol), S5(765mg, 1.29mmol) and Pd (PPh)3)2Cl2(38mg，0.054mmol)，PPh3(28mg, 0.11mmol) and CuI (21mg, 0.11mmol) were dissolved in diisopropylamine, heated to react, and after completion of the reaction, the solvent was removed by rotary evaporation in vacuo, followed by separation by column chromatography to give compound S6.
Step c. synthesis of compound S1 (n ═ 1, R ═ OCH3)
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 a compound S1, namely the guanidino modified oligomeric phenylacetylene.
Example 3
This example was conducted to test the antibacterial effect of the compound S1 prepared in example 1, i.e., to test the phototoxicity and dark toxicity (n ═ 1, R ═ H) of escherichia coli.
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 OD600After that, 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 a DMSO solution of S1 to give final concentrations of compound S1 of 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, 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 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 99.4%, 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 in dark.
Example 4
This example was tested for the 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 out supernatant, adding sterilized normal saline, blowing to disperse bacteria, centrifuging again, pouring out supernatant, and repeating for three times. The bacteria were divided in physiological saline and adjusted to OD600After that, 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 a DMSO solution of S1 to give final concentrations of compound S1 of 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, 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 illumination and dark places.

Claims (8)

1. The guanidino modified oligomeric phenylacetylene is characterized in that a benzene ring and triple bond conjugated system with different substituents is arranged in the middle of the guanidino modified oligomeric phenylacetylene, 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;
Figure FDA0002630702680000011
wherein R is H, O (CH)2)mCH3，OCH2(CH2)mN(CH3)2(m＝0～9)
n＝0～9。
2. A preparation method of guanidyl modified oligophenylacetylene is characterized in that the reaction formula in the preparation method is as follows:
Figure FDA0002630702680000012
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 the 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 by using a drying agent, filtering the organic phase, and separating the organic phase 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.
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 catalyst in step b is Pd (PPh)3)2Cl2CuI and PPh3Mixture of (1), Pd (PPh)3)4And a mixture of CuI, Pd2(dba)3CuI and dppf or Pd2(dba)3CuI and PPh3One of the mixtures of (a).
5. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the solvent in step b is a mixed solvent of tetrahydrofuran, dichloromethane or toluene, and triethylamine, diisopropylamine, trimethylamine or pyridine in different proportions.
6. The method for preparing guanidino-modified oligophenylacetylene according to claim 2, wherein the heating temperature in step b is 20-100 ℃.
7. 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.
8. Use of the guanidino-modified oligophenylacetylene according to claim 1 or the guanidino-modified oligophenylacetylene according to any one of claims 2 to 7 for the preparation of a disinfectant against staphylococcus aureus and escherichia coli.
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CN114478834A (en) * 2022-02-28 2022-05-13 江南大学 Guanidino hyaluronic acid antibacterial polymer and preparation method and application thereof

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Publication number Priority date Publication date Assignee Title
CN113336675A (en) * 2021-04-14 2021-09-03 湖南大学 Antibacterial guanidine oligomer with anti-drug resistance and preparation method and application thereof
CN114478834A (en) * 2022-02-28 2022-05-13 江南大学 Guanidino hyaluronic acid antibacterial polymer and preparation method and application thereof
CN114478834B (en) * 2022-02-28 2023-08-08 江南大学 Guanidine hyaluronic acid antibacterial polymer and preparation method and application thereof

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