CN110693869B - Application of 2- (methylamino) methyl benzoate - Google Patents
Application of 2- (methylamino) methyl benzoate Download PDFInfo
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Abstract
The invention discloses an application of 2- (methylamino) methyl benzoate, and relates to the technical field of compound application. The 2- (methylamino) methyl benzoate has strong inhibitory activity on the generation of pseudomonas aeruginosa quorum sensing virulence factors and the formation of biofilms, and experimental results show that the 2- (methylamino) methyl benzoate has no significant inhibition on the growth of pseudomonas aeruginosa, but has significant inhibition (p <0.05) on the virulence factors (including pyocyanin, elastase and rhamnolipid) and the biofilm formation, can be used for preparing health care products or medicines for preventing and/or treating pseudomonas aeruginosa infection, and is suitable for large-scale popularization. The effective dose of the methyl 2- (methylamino) benzoate for inhibiting the quorum sensing of the pseudomonas aeruginosa is small, the potential side effect is small, and the use is safer; can be prepared into different health products and pharmaceutical formulations with different additives and excipients, and can be conveniently eaten by people and clinically applied.
Description
Technical Field
The invention relates to the technical field of application of compounds, in particular to the technical field of application of citrus volatile oil compounds, and especially relates to application of methyl 2- (methylamino) benzoate in preparation of products for preventing and/or treating pseudomonas aeruginosa infection.
Background
Pseudomonas aeruginosa (Pseudomonas aeruginosa, PA) is one of the common conditional pathogens in nature (existing in water, air, normal human skin, respiratory tract, intestinal tract and the like), can cause infection of important systems of organisms such as respiratory system, chronic wound, urinary system, soft tissue and the like, and seriously harms human health. Currently, the treatment of pseudomonas aeruginosa infection is mainly based on the treatment of multiple antibiotics, however, with the abuse of antibiotics, the resistance variation caused by pseudomonas aeruginosa is caused, so that the traditional antibacterial drugs can not meet the clinical requirement any more. The natural plant active ingredients derived from the traditional Chinese medicinal materials have the advantages of good specificity, wide sources, small side effects and the like, so that the functional quorum sensing inhibitor health-care products and the medicines added with the natural plant active ingredients are the key focus of the current research on the treatment of resisting the infection of the pseudomonas aeruginosa.
Methyl 2- (methylamino) benzoate (Methyl N-methylinathanite) is a nitrogen-containing compound in volatile oil extracted from fruit (Citrus reticulata Blanco) and pericarp of Citrus of Rutaceae, and has the following structural formula:
2- (methylamino) benzoic acid Methyl ester (Methyl N-methylinathralate)
At present, pericarpium citri reticulatae volatile oil has proven to have biological activities such as antioxidant activity, antibacterial activity and antiviral activity, and reports of the antibacterial activity mainly aim at escherichia coli, staphylococcus aureus, mould and the like, but the unique component methyl 2- (methylamino) benzoate in the volatile oil is not used for treating pseudomonas aeruginosa infection or is developed together with traditional antibacterial drugs to prevent and treat the pseudomonas aeruginosa infection.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention aims to provide an application of methyl 2- (methylamino) benzoate in preparing a product for preventing and/or treating pseudomonas aeruginosa infection.
The purpose of the invention is realized by the following technical scheme:
the invention provides an application of methyl 2- (methylamino) benzoate in preparation of a product for preventing and/or treating pseudomonas aeruginosa infection. The 2- (methylamino) methyl benzoate has good inhibitory activity on the generation of pseudomonas aeruginosa quorum sensing virulence factors and biofilm formation, can be used for preparing products for preventing and/or treating pseudomonas aeruginosa infection, and is suitable for large-scale popularization and application.
The product comprises a medicament or a health-care product;
specifically, 2- (methylamino) methyl benzoate and one or more pharmaceutically acceptable carriers or excipients can be prepared into the medicaments in the dosage forms of injection, tablets, powder injection, granules, capsules, ointment, cream or oral liquid, and the dosage forms of the medicaments are not limited.
The health care product is used for preventing or treating pseudomonas aeruginosa infection.
The health product is in the form of liquid spray, collutory, powder, paste or throat lozenge.
The methyl 2- (methylamino) benzoate is methyl 2- (methylamino) benzoate monomer extracted from fruit (Citrus reticulata Blanco) and pericarp of Rutaceae.
The effective concentration of the methyl 2- (methylamino) benzoate is 2.5-6.25 mg/mL of bacterial suspension, wherein the concentration of the bacterial suspension is 1 x 106One per mL.
Compared with the prior art, the invention has the following advantages and effects:
(1) the 2- (methylamino) methyl benzoate has strong inhibitory activity on the generation of pseudomonas aeruginosa quorum sensing virulence factors and the formation of biofilms: through experiments such as growth curves, pyocyanin, elastase, rhamnolipid, biomembranes, real-time fluorescence quantitative PCR and the like, the results show that the 2- (methylamino) methyl benzoate has no obvious inhibition on the growth of the pseudomonas aeruginosa, but has obvious inhibition (p is less than 0.05) on the formation of virulence factors (including the pyocyanin, the elastase and the rhamnolipid) and biomembranes thereof, can be used for preparing health care products or medicines for preventing and/or treating the infection of the pseudomonas aeruginosa, and is suitable for large-scale popularization.
(2) The effective dose of the methyl 2- (methylamino) benzoate for inhibiting the quorum sensing of the pseudomonas aeruginosa is small, the potential side effect is small, and the use is safer.
(3) The 2- (methylamino) methyl benzoate has wide resources, easy acquisition and lower cost.
(4) The 2- (methylamino) methyl benzoate can be prepared into different health care products and pharmaceutical formulations with different additives and excipients, and can be convenient for people to eat and clinically apply.
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FIG. 1 is a graph of growth inhibition by P.aeruginosa by methyl 2- (methylamino) benzoate at various concentrations.
FIG. 2 is a graph showing the real-time fluorescent quantitative PCR effect of methyl 2- (methylamino) benzoate on genes associated with virulence factors (including pyocin, elastase, rhamnolipid) and biofilm formation inhibition in the Pseudomonas aeruginosa quorum sensing system. Wherein the different letters on the gene expression histogram indicate that the difference between the groups is significant (p <0.05) and significant (p <0.001), respectively.
FIG. 3 is a graph showing the effect of methyl 2- (methylamino) benzoate on the metabolite clustering analysis of Pseudomonas aeruginosa, where Blank is a Blank background group, Control is a Control group, Quality Control is a Quality Control group, and Sample is an experimental group.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
The present invention is exemplified by extracts with concentrations of 2- (methylamino) benzoic acid methyl ester (abbreviated as PCR-M) all being > 95% purity of active ingredient, but not limited to extract or extractum. When applied in other forms, such as an extract, the amounts used should be converted to the amounts disclosed in the present invention as pure extracts.
The experimental materials used in the following examples are as follows:
the strain (pseudomonas aeruginosa ATCC 9027) is a commercial product; LB medium was purchased from Biotechnology engineering (Shanghai) GmbH; cell RNA extraction kit, reverse transcription kit and real-time fluorescent quantitative PCR kit are all purchased from Takara company.
The experimental methods used in the following examples are as follows:
growth curve experiments: pseudomonas aeruginosa was activated, centrifuged and resuspended in PBS to make 1 × 106Bacteria suspension per mL. Adding 100 μ L of bacterial suspension into each well of 96-well plate, culturing in a full-automatic growth curve tester at 37 deg.C, and shakingThe speed is adjusted to the middle level and is continued, and the absorbance values of the methyl 2- (methylamino) benzoate treatment group and the control group at the wavelength of 600nm are detected every 1h, and the growth curves of the pseudomonas aeruginosa under the PCR-M action of 0, 1.25mg/mL, 2.5mg/mL, 3.75mg/mL, 5mg/mL and 6.25mg/mL are drawn.
Pyocin assay: 2.5mg/mL PCR-M was selected for Pseudomonas aeruginosa pyocin inhibition assay. Activating pseudomonas aeruginosa, and preparing into 1 x 10 pseudomonas aeruginosa6Adding PCR-M into each mL of bacterial suspension, enabling the final concentration to be 2.5mg/mL, culturing for 24 hours in an LB liquid culture medium at 37 ℃ and 200rpm, taking 2.0mL of bacterial liquid, adding 2.0mL of chloroform into supernatant after centrifugation at 10000rpm and 5min, shaking for 30min, centrifuging, taking 1mL of chloroform layer, adding 1mL of hydrochloric acid with the volume concentration of 0.2mol/L, shaking for 30min, centrifuging, layering, detecting the light absorption value of the bacteria by using an enzyme labeling instrument at the wavelength of 520nm, calculating the inhibition rate of the PCR-M on pseudomonas aeruginosa pyocin, repeating each group of samples for 3 times, and replacing the PCR-M with PBS in a control group. Inhibition rate [ (OD)Control group－ODExperimental group)/ODControl group]X 100%, the same applies below.
Elastase assay: 2.5mg/mL PCR-M was selected for the Pseudomonas aeruginosa elastase inhibition assay. Activating pseudomonas aeruginosa to prepare 1 x 10 pseudomonas aeruginosa6Adding PCR-M into each mL of bacterial suspension, enabling the final concentration of the bacterial suspension to be 2.5mg/mL, culturing the bacterial suspension in an LB liquid culture medium for 24 hours at 37 ℃ and 200rpm, taking 1.0mL of bacterial liquid, adding 800 mu L of 2% Congo red elastin solution (PH is 7.2) into supernatant after centrifugation at 5000rpm and 5 minutes, performing shake culture for 6 hours, centrifuging, detecting the light absorption value of the bacterial suspension at the wavelength of 495nm by using a microplate reader, calculating the inhibition rate of the PCR-M on pseudomonas aeruginosa elastase, repeating the samples of each group for 3 times, and replacing the PCR-M with PBS in a control group.
Rhamnolipid assay: 2.5mg/mL of PCR-M was selected for the analysis of P.aeruginosa rhamnolipid inhibition. Activating pseudomonas aeruginosa, and preparing into 1 x 10 pseudomonas aeruginosa6Adding PCR-M into bacterial suspension of each mL to make the final concentration 2.5mg/mL, culturing at 37 deg.C and 200rpm in LB liquid culture medium for 24h, centrifuging 2.0mL bacterial solution, adjusting pH of supernatant to 2.0 with hydrochloric acid, adding 2.0mL ethyl acetate, shaking for 15MCentrifuging and layering after in, taking 1.5mL of ethyl acetate mixed liquid, volatilizing, re-dissolving the precipitate with 1.0mL of sterile water, taking 200 mu L of 0.19% orcinol-concentrated sulfuric acid solution, carrying out water bath at 80 ℃ for 40min, centrifuging at the wavelength of 421nm, detecting the light absorption value by using an enzyme labeling instrument, calculating the inhibition rate of PCR-M on pseudomonas aeruginosa rhamnolipid, repeating each group of samples for 3 times, and replacing the PCR-M with PBS in a control group.
And (3) biological membrane experiment: 2.5mg/mL of PCR-M was selected for the analysis of Pseudomonas aeruginosa biofilm inhibition. Activating pseudomonas aeruginosa, and preparing into 1 x 10 pseudomonas aeruginosa6Adding PCR-M into a 96-well plate to enable the final concentration to be 2.5mg/mL, carrying out standing culture in an LB liquid culture medium at 37 ℃ for 24h, washing the culture medium and the planktonic pseudomonas aeruginosa by deionized water, adding 200 mu L of 0.1% crystal violet solution for dyeing for 10min, adding 200 mu L of 95% ethanol for dissolving, detecting the absorbance value by a microplate reader at 590nm wavelength, calculating the inhibition rate of the PCR-M on the pseudomonas aeruginosa biofilm, repeating the samples of each group for 3 times, and replacing the PCR-M with PBS in a control group.
Real-time quantitative PCR experiment: 2.5mg/mL PCR-M is selected to analyze the inhibition of the virulence factors of the pseudomonas aeruginosa quorum sensing system and the expression level of the genes related to biofilm formation. Extracting total RNA of the pseudomonas aeruginosa cell after the PCR-M treatment, performing reverse transcription to form cDNA, and detecting the expression levels of different genes by utilizing real-time fluorescence quantitative PCR.
Metabonomics experiments: 2.5mg/mL PCR-M was selected for P.aeruginosa metabolite dynamics analysis. Extracting total metabolites of the pseudomonas aeruginosa cells after the PCR-M treatment, and detecting the change information of the pseudomonas aeruginosa metabolites by using an ultrahigh pressure liquid chromatography-mass spectrometer after the total metabolites are redissolved by using methanol.
Example 1: effect of methyl 2- (methylamino) benzoate on growth of Pseudomonas aeruginosa
The growth curve is drawn by adding different concentrations of methyl 2- (methylamino) benzoate to pseudomonas aeruginosa for 48 hours, the PCR-M with different concentrations has no obvious inhibition to the growth of the pseudomonas aeruginosa as shown in figure 1.
Example 2: effect of methyl 2- (methylamino) benzoate on pyocyanin, elastase, rhamnolipids and biofilms of Pseudomonas aeruginosa
The inhibition of Pseudomonas aeruginosa by PCR-M was examined according to the experimental methods of pyocin, elastase, rhamnolipid and biofilm, and the results are shown in Table 1. The experimental result shows that the inhibition rates of 2.5mg/mL PCR-M on pseudomonas aeruginosa pyocin, elastase, rhamnolipid and biomembrane are respectively 86.4%, 20.5%, 40.5% and 46.8%, and single-factor anova analysis shows that the PCR-M has significant inhibition on pseudomonas aeruginosa virulence factors (including pseudomonas aeruginosa, elastase and rhamnolipid) and biomembrane formation (P < 0.05).
TABLE 1 inhibition of pyocyanin, elastase, rhamnolipids and biofilms of Pseudomonas aeruginosa by methyl 2- (methylamino) benzoate
Wherein the different letters and in the table indicate that the difference between the groups is significant (p <0.05) and (p <0.001), respectively.
Example 3: real-time fluorescent quantitative PCR (polymerase chain reaction) influence of methyl 2- (methylamino) benzoate on genes related to virulence factors and biofilm formation in pseudomonas aeruginosa quorum sensing system
The real-time quantitative PCR experiment detects that PCR-M regulates the transcription level of the related genes of the pseudomonas aeruginosa quorum sensing system, and the genes with obvious changes are shown in figure 2.
The experimental result shows that the relative expression quantities of virulence factors or biofilm formation related genes lasA, pqsA, phzM, mvfR, pelF, lasR, chiC, lasI, lasB, rhlI, rhlR, pslA, rpoS and the like in the growth process of pseudomonas aeruginosa are all reduced, and the difference is very obvious (P < 0.001); the result shows that the PCR-M has obvious regulation and control effect on the transcription level of a pseudomonas aeruginosa quorum sensing system, so that the probability of generating virulence factors and forming a biological membrane after the pseudomonas aeruginosa is infected is reduced, the toxicity of the pseudomonas aeruginosa is weakened, and the effect of preventing and treating the infection of the pseudomonas aeruginosa is achieved.
Example 4: effect of methyl 2- (methylamino) benzoate on metabolites of Pseudomonas aeruginosa
The dynamic change of pseudomonas aeruginosa at the metabolite level by the PCR-M through the non-targeted metabolomics experiment is detected, and the clustering result of the different metabolite expression amounts with significant changes on each group (including the blank background group, the control group, the quality control group and the experimental group) samples is shown in fig. 3. The result shows that after the cluster analysis of the differential metabolites, the control group and the experimental group added with the PCR-M can be obviously distinguished, which shows that the PCR-M has obvious regulation and control effect on the metabolite level of the pseudomonas aeruginosa quorum sensing system, thereby reducing the probability of generating virulence factors and forming a biofilm after infecting the pseudomonas aeruginosa, weakening the toxicity of the pseudomonas aeruginosa and generating the effect of preventing and treating the infection of the pseudomonas aeruginosa.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (6)
- Use of methyl 2- (methylamino) benzoate for the preparation of a product for the prophylaxis and/or treatment of Pseudomonas aeruginosa infections.
- 2. Use according to claim 1, characterized in that:the product comprises a medicament.
- 3. Use according to claim 2, characterized in that:the medicine can be prepared into injection, tablets, powder injection, granules, capsules, ointment, cream or oral liquid.
- 4. Use according to claim 2, characterized in that:the medicine contains one or more pharmaceutically acceptable carriers.
- 5. Use according to claim 2, characterized in that:the medicament contains one or more pharmaceutically acceptable excipients.
- 6. Use according to any one of claims 1 to 5, characterized in that:the effective concentration of the methyl 2- (methylamino) benzoate is 2.5-6.25 mg/mL of bacterial suspension, wherein the concentration of the bacterial suspension is 1 x 106one/mL.
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