CN107417520A - A kind of Burkholderia cepacia antimicrobial compound and preparation method and application - Google Patents
A kind of Burkholderia cepacia antimicrobial compound and preparation method and application Download PDFInfo
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- CN107417520A CN107417520A CN201710332225.0A CN201710332225A CN107417520A CN 107417520 A CN107417520 A CN 107417520A CN 201710332225 A CN201710332225 A CN 201710332225A CN 107417520 A CN107417520 A CN 107417520A
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- methyl
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/03—Monocarboxylic acids
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Abstract
The present invention discloses a kind of Burkholderia cepacia antimicrobial compound and preparation method and application.The pentadecylenic acid of 14 methyl of entitled Z 2 of the compound, shown in molecular formula such as formula (I).The present invention carries out bromo-reaction using 11 methyl lauryl alcohols as substrate, generates the methyl dodecane of bromo 11;Then with propiolic acid in organic solvent, the pentadecynic acid of 14 methyl 2 is generated in the presence of catalyst I;Organic solvent II is eventually adding, hydrogenation reaction, the pentadecylenic acid of 14 methyl of generation Z 2 are carried out in the presence of catalyst II.The compound has good interference suppressioning effect to Burkholderia cepacia BDSF intervention school-baseds, and shows obvious antibacterial effect;Grown because the compound does not suppress Burkholderia cepacia directly, selection pressure will not be produced to Burkholderia cepacia, would not also cause the generation of pathogenic bacteria of drug-resistant.
Description
Technical field
The invention belongs to biomedicine technical field, more particularly to a kind of Burkholderia cepacia antimicrobial compound and its
Preparation method and application.
Background technology
Burkholderia cepacia (Burkholderia cepacia) is a kind of important conditioned pathogen, is usually caused
The inside-hospital infections such as respiratory tract infection, pneumonia, urethral infection, and cause cystic fibrosis (Cystic fibrosis,
CF), main causes of death occur for immuuoeorapromised host, seriously endanger the health and life of the mankind.With antibiotic
A large amount of widely use, it will continue to provide selection pressure to high drug-fast bacteria, promote it to replicate, group structure and enjoy resistance base jointly
Cause, accelerate multi-drug resistant (Multidrug resistance, MDR) generation.
Can be antibacterial therefore, it is necessary to study one kind, B.cepacia will not be made to produce the antibacterials of drug resistance again.
The content of the invention
The shortcomings that primary and foremost purpose of the present invention is to overcome prior art and deficiency, there is provided a kind of Burkholderia cepacia
Antimicrobial compound.
Another object of the present invention is to provide the preparation method of described Burkholderia cepacia antimicrobial compound.
It is still another object of the present invention to provide the application of described Burkholderia cepacia antimicrobial compound.
The purpose of the present invention is achieved through the following technical solutions:A kind of Burkholderia cepacia antimicrobial compound, title
For Z-14- methyl -2- pentadecylenic acid (English names:(Z) -14-methylpentadec-2-enoic acid), molecular formula such as formula
(I) shown in:
The preparation method of described Burkholderia cepacia antimicrobial compound, preferably comprises following steps:With 11- first
Base-lauryl alcohol is substrate, carries out bromo-reaction, generates bromo 11- methyl-dodecanoics;Then with propiolic acid in organic solvent,
14- methyl -2- pentadecynic acids are generated in the presence of catalyst I;Organic solvent II is eventually adding, in the presence of catalyst II
Hydrogenation reaction is carried out, generates Z-14- methyl -2- pentadecylenic acids.
The reaction raw materials of described bromo-reaction are preferably phosphonium bromide (PBr3)。
Described 11- methyl-lauryl alcohol and described phosphonium bromide are preferably in molar ratio 1:1 proportioning.
The dosage of described propiolic acid is preferably excessive relative to described bromo 11- methyl-dodecanoics, so as to react more
To be complete;Preferably, the dosage of described propiolic acid and described bromo 11- methyl-dodecanoics in molar ratio 1.1~1.5:1
Proportioning.
Described organic solvent I is preferably HPT (HMPT).
Described catalyst I is preferably n-BuLi (n-BuLi).
Described catalyst I dosage is catalytic amount;Preferably, described catalyst I dosage is relative to described
Bromo 11- methyl-dodecanoics are excessive;Described catalyst I and described bromo 11- methyl-dodecanoics in molar ratio 2~
2.5:1 proportioning.
Described organic solvent II is preferably polyether diols.
The dosage of described polyether diols is excessive relative to described 14- methyl -2- pentadecynic acids;Described dihydroxy
The mole dosage of base polyethers is preferable over 50~60 times equivalent to described 14- methyl -2- pentadecynic acid moles.
Described catalyst II is preferably barium sulfate.
Described catalyst II dosage is catalytic amount;Preferably, the dosage of described barium sulfate is relative to described
14- methyl -2- pentadecynic acids are excessive;The mole dosage of described barium sulfate is preferable over equivalent to described 14- methyl -2- ten
50~60 times of five acetylenic acid moles.
Described Burkholderia cepacia antimicrobial compound is preparing the medicine for treating Burkholderia cepacia disease
Application in thing.
The present invention is had the following advantages relative to prior art and effect:
Compound Z-14- methyl -2- pentadecylenic acids provided by the invention have carried out antibacterial reality to Burkholderia cepacia
To test, as a result show, the compounds of this invention has good interference effect to Burkholderia cepacia BDSF intervention school-baseds, and
And there is pharmacological activity, it, when concentration is 20 μM, just shows to press down in the case where not suppressing strains tested H111 growth
The effect of strains tested H111 motilities processed and biofilm formation;When compound concentration is up to 100 μM, its motility and biomembrane
Inhibition is consistent with rpfFBC mutant (BDSF signals synzyme) decrease effect.In addition, in the experiment of A549 cytotoxicities,
When Z-14- methyl -2- pentadecylenic acids concentration is up to 50 μM, it significantly suppress virulence of the strains tested H111 to A549 cells,
To sum up, compound Z-14- methyl -2- pentadecylenic acids have dry well to Burkholderia cepacia BDSF intervention school-baseds
Inhibition is disturbed, and shows obvious antibacterial effect.
Due to compound Z-14- methyl -2- pentadecylenic acids directly suppress Burkholderia cepacia growth, will not be to ocean
Green onion burkholderia produces selection pressure, would not also cause the generation of pathogenic bacteria of drug-resistant.
Brief description of the drawings
Fig. 1 is the chemical synthesis flow chart of compound Z-14- methyl -2- pentadecylenic acids in the present invention.
Fig. 2 is the result figure of microwell plate Dilution bacteriostatic experiment in embodiment 2.
Fig. 3 is the result figure that compound Z-14- methyl -2- pentadecylenic acids suppress bacterial strain H111 motilities in embodiment 3.
Fig. 4 is the result figure that compound Z-14- methyl -2- pentadecylenic acids suppress bacterial strain H111 biomembranes in embodiment 3.
Fig. 5 is that compound Z-14- methyl -2- pentadecylenic acids suppress cells of the bacterial strain H111 to A549 cells in embodiment 4
The result figure of virulence.
Embodiment
With reference to embodiment and accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are unlimited
In this.
Embodiment 1
The synthesis of Z-14- methyl -2- pentadecylenic acids, is comprised the following steps that (also as shown in Figure 1):
(1) using 10.02g (0.05mol) 11- methyl-lauryl alcohol as substrate, 16.7g (0.06mol) phosphorus tribromide is added
(PBr3) bromo-reaction is carried out, generates bromo 11- methyl-dodecanoics, crude product 7.9g, purity is about 96% (gas-chromatography inspection
Survey);Then, under the conditions of -70 DEG C, foregoing bromo 11- methyl-dodecanoics are with 3g (0.04mol) propiolic acids in hexamethyl phosphoric acid
In triamide (HMPT) solvent, the n-BuLi (n-BuLi) that 31mL concentration is 2M is added, after reaction terminates, generation 14- methyl-
2- pentadecynic acids, crude product 4.2g, purity 94% (gas chromatographic detection);It is eventually adding 1mol polyether diols and 1mol sulfuric acid
Barium (Pd/BaSO4) hydrogenation reaction is carried out, generate Z-14- methyl -2- pentadecylenic acids.Crude product is 2.3g, and purity is about 92% (gas
Phase chromatogram detects), crude product after purification, obtains 1.5g, purity about 98.8% by column chromatography, and there is Dehua in compound commission Shanghai
Work company is synthesized, and through Mass Spectrometer Method, determines structural formula shown in formula I.
Embodiment 2
Z-14- methyl -2- pentadecylenic acids determine to Burkholderia cepacia growth effect:
(1) test method:
(1) activation of Burkholderia cepacia:Choosing bacterial strain H111, (bacterial strain is in document " Carlier A., et
al.Genome Sequence of Burkholderia cenocepacia H111,a Cystic Fibrosis Airway
Isolate.Genome Announcements,2014,2(2):1-2 " is open) strains tested is used as, strains tested is put down in LB
Activate, be placed in 37 DEG C of incubators on plate (tryptone 10g/L, yeast extract 5g/L, NaCl 10g/L, agar 15g/L)
It is incubated overnight.
(2) compound Z-14- methyl -2- pentadecylenic acids are prepared:Weigh the dissolving of 0.254g Z-14- methyl -2- pentadecylenic acids
In 10mL methanol, concentration 100mM mother liquor is configured to, it is then with methanol that the sample of the diluted chemical compound into various concentrations is standby
With (100mM, 50mM, 20mM, 5mM).
(3) various concentrations Z-14- methyl -2- pentadecylenic acids are to bacterial strain H111 growth effects:Picking LB plated growths
H111 bacterial strains, it is inoculated in 10mL LB nutrient solutions (tryptone 10g/L, yeast extract 5g/L, NaCl 10g/L), 37 DEG C,
200rpm shaken cultivations are stayed overnight, measure bacterium solution OD600, bacterium solution is then diluted to OD with LB nutrient solutions600=0.01, and press volume
Than 1:1000 ratio adds the Z-14- methyl -2- pentadecylenic acids of above-mentioned various concentrations in the bacterium solution of dilution, sets at 6
Reason:
Processing 1:It is not added with compound and methanol;
Processing 2:By volume 1:1000 ratios add methanol into bacterium solution, i.e., 1mL methanol is added in 1L bacterium solutions;
Processing 3:By volume 1:1000 ratios add 5mM Z-14- methyl -2- pentadecylenic acids into bacterium solution;
Processing 4:By volume 1:1000 ratios add 20mM Z-14- methyl -2- pentadecylenic acids into bacterium solution;
Processing 5:By volume 1:1000 ratios add 50mM Z-14- methyl -2- pentadecylenic acids into bacterium solution;
Processing 6:By volume 1:1000 ratios add 100mM Z-14- methyl -2- pentadecylenic acids into bacterium solution;
Each processing sets 8 repetitions, then adds in 96 orifice plates each processing bacterium solution, is placed in growth curve analyzer
In, 37 DEG C, 200rpm cultures, an OD is determined per 2h600It is worth, observation experiment result after 2d, GraphPad Prism 6 handle number
According to.
(2) result of the test
As a result as shown in Fig. 2 finding the Z-14- methyl -2- pentadecylenic acids of various concentrations does not influence primary gram of Hall of onion
Moral bacterium H111 normal growth.
Embodiment 3
Z-14- methyl -2- pentadecylenic acids determine to the Phenotype of Burkholderia cepacia BDSF system regulations:
(1) test method:
(1) activation of Burkholderia cepacia:By onion Burkholderia bacterial strain H111, Δ rpfFBCMutant strain (bacterial strain
In document " Deng YY, et al.Cis-2-dodecenoic acid receptor RpfR links quorum-
sensing signal perception with regulation of virulence through cyclic dimeric
guanosine monophosphate turnover.PNAS,2012,109(38):15479-15484 " is open) in LB flat boards
Activation, is placed in 37 DEG C of incubators and is incubated overnight.
(2) influence of the various concentrations Z-14- methyl -2- pentadecylenic acids to bacterial strain H111 motilities:It will be configured to different dense
Spend the Z-14- methyl -2- pentadecylenic acids by volume 1 of (100mM, 50mM, 20mM, 5mM):1000 ratio adds motility training
Support in base (tryptone 8g/L, glucose 5g/L, agar 3g/L), be down flat plate, per ware 15mL, with the thalline that toothpick picking is fresh
Flat board center is inoculated in, each handles 5 repetitions, and set and be not added with compound and Δ rpfFBCMutant strain is placed in 28 as reference
Cultivated in DEG C incubator, strains tested is determined after 18h and is moved about on plate distance, records experimental data.
(3) influence of the various concentrations Z-14- methyl -2- pentadecylenic acids to bacterial strain H111 biofilm formations:Picking activation
Onion Burkholderia bacterial strain H111, Δ rpfFBCMutant strain is in LB fluid nutrient mediums (tryptone 10g/L, yeast extract 5g/
L, NaCl 10g/L) it is incubated overnight, measure bacterium solution OD600Value, with MM culture mediums (K2HPO4 10.5g/L、KH2PO4 4.5g/L、
(NH4)2SO4 2g/L、MgSO4.7H2O 0.2g/L、FeSO4 0.005g/L、CaCl2 0.01g/L、MnCl2It is 0.002g/L, sweet
Reveal alcohol 2g/L, glycerine 2g/L) bacterium solution is diluted to OD600=0.01, by various concentrations (100mM, 50mM, 20mM, 5mM) Z-
14- methyl -2- pentadecylenic acids and by volume 1:1000 ratio is added in bacterium solution, respectively takes 150 μ L to add in 96 orifice plates, each
6 repetitions are handled, and sets and is not added with compound and Δ rpfFBCMutant is placed in 37 DEG C, vibrated in 200rpm shaking tables as control
Cultivate, bacterium solution is abandoned after 12h, add the crystal violet that 200 μ L concentration are mass volume ratio 0.1%, room temperature treatment 20min, use ddH2O
96 orifice plates are cleaned, totally 3 times, drying in oven is placed in, adds the ethanol of 200 μ L 95%, determine OD570, with GraphPad Prism
6 software data processings.
(2) result of the test
As shown in Figure 3 and Figure 4, Z-14- methyl -2- pentadecylenic acids have to bacterial strain H111 biofilm formation and motility
Significantly affect, and as the rise of concentration, its inhibition are also more obvious.When concentration is more than 20 μM, the compound is to motion
Property inhibition and Δ rpfFBCMutation type surface is similar;When concentration reaches 100 μM, the suppression of the compound on organism film
Effect and Δ rpfFBCThe degree that mutant weakens, illustrates BDSF of the compound Z-14- methyl -2- pentadecylenic acids to bacterial strain H111
Intervention school-based has interference well and suppressed.
Embodiment 4
Z-14- methyl -2- pentadecylenic acids influence measure to the virulence of Burkholderia cepacia BDSF system regulations:
(1) recovery and culture of A549 cells:The Non-small cell lung carcinoma A549 cells of freeze thawing are transferred to containing 10% (v/
V) in FBS DMEM culture mediums (Gioco companies), 37 DEG C, 5%CO2Under the conditions of be incubated overnight.
(2) A549 cells prepare:A549 cells in the high glucose medium DMEM of the hyclone containing percent by volume 10%,
With 1.5 × 104The cell concentration in individual/hole overnight incubation in 96 orifice plates.When treating that cell is covered with 96 orifice plate bottom 80%, abandon
Nutrient solution is removed, cell is cleaned 3 times with 1 × PBS (pH=7.4,0.1M).
(3) Burkholderia cepacia prepares:Picking fresh H111 and Δ rpfFBCMutants which had is inoculated in LB nutrient solutions
In, shaken cultivation is stayed overnight under the conditions of 37 DEG C, 200rpm;Thalline is collected by centrifugation in 5000rpm, 5min, with 1 × PBS thalline 3
It is secondary, with 109Cfu/mL concentration is dispersed in the DMEM cell maintenance mediums of the 1%FBS containing percent by volume.
(4) cytotoxicity bioassay:By the Z-14- methyl -2- pentadecylenic acids of various concentrations (100mM, 50mM, 20mM, 5mM)
And press percent by volume 1:1000 ratio is added in the cell maintenance medium containing bacterium, takes 100 μ L to add ready A549 cells
In, it is placed in 37 DEG C, 5%CO2Culture 8h in cell culture incubator, 6 repetitions are often handled, while set and be not added with compound and Δ
rpfFBCMutant is as control.With reference to Promega company CytoToxNonRadioactive Cytotoxicity
Assay operating methods determine cell LDH activity, then carry out data analysis.
(2) result of the test
Z-14- methyl -2- pentadecylenic acids have certain influence to bacterial strain H111 to A549 cytotoxicities, as shown in figure 5, and
With the rise of compound concentration, H111 bacterial strains also substantially weaken to the virulence of A549 cells, the H111 bacterium when concentration is up to 50 μM
Strain virulence attenuation of degree and Δ rpfFBCMutant is consistent, also further illustrates the onion of Z-14- methyl -2- pentadecylenic acids pair
Burkholderia BDSF signal pathways have interference well and suppressed.
Above-described embodiment is the preferable embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any Spirit Essences without departing from the present invention with made under principle change, modification, replacement, combine, simplification,
Equivalent substitute mode is should be, is included within protection scope of the present invention.
Claims (6)
- A kind of 1. Burkholderia cepacia antimicrobial compound, it is characterised in that:Entitled Z-14- methyl -2- pentadecylenic acids, point Shown in minor such as formula (I):
- 2. the preparation method of the Burkholderia cepacia antimicrobial compound described in claim 1, it is characterised in that comprising as follows Step:Using 11- methyl-lauryl alcohol as substrate, bromo-reaction is carried out, generates bromo 11- methyl-dodecanoics;Then and propiolic acid In organic solvent, 14- methyl -2- pentadecynic acids are generated in the presence of catalyst I;Organic solvent II is eventually adding, is being urged Hydrogenation reaction is carried out in the presence of agent II, generates Z-14- methyl -2- pentadecylenic acids.
- 3. the preparation method of Burkholderia cepacia antimicrobial compound according to claim 2, it is characterised in that:It is described The reaction raw materials of bromo-reaction be phosphonium bromide;Described organic solvent I is HPT;Described catalyst I is n-BuLi;Described organic solvent II is polyether diols;Described catalyst II is barium sulfate.
- 4. the preparation method of Burkholderia cepacia antimicrobial compound according to claim 3, it is characterised in that:It is described 11- methyl-lauryl alcohol and described phosphonium bromide in molar ratio 1:1 proportioning;Described n-BuLi and described bromo 11- methyl-dodecanoics in molar ratio 2~2.5:1 proportioning;50~60 times of the mole dosage of described polyether diols equivalent to described 14- methyl -2- pentadecynic acid moles;50~60 times of the mole dosage of described barium sulfate equivalent to described 14- methyl -2- pentadecynic acid moles.
- 5. the preparation method of Burkholderia cepacia antimicrobial compound according to claim 2, it is characterised in that:The dosage of described propiolic acid and described bromo 11- methyl-dodecanoics in molar ratio 1.1~1.5:1 proportioning.
- 6. the Burkholderia cepacia antimicrobial compound described in claim 1 is being prepared for treating Burkholderia cepacia Application in the medicine of disease.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108739860A (en) * | 2018-05-02 | 2018-11-06 | 华南农业大学 | Bacterium and its application as biocontrol microorganisms is quenched in a kind of micropopulation inductive signal |
CN109942397A (en) * | 2019-04-30 | 2019-06-28 | 嘉兴学院 | A kind of preparation method of royal jelly acid |
CN114588148A (en) * | 2022-03-18 | 2022-06-07 | 中山大学 | Application of oridonin in preparation of CepR and RqpR protein binding preparation |
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WO2011142724A1 (en) * | 2010-05-14 | 2011-11-17 | Agency For Science, Technology And Research | Novel antimicrobial compounds and uses thereof |
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BRETT D. SCHWARTZ: "Structure and absolute configuration of mycobactin J", 《TETRAHEDRON LETTERS》 * |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108739860A (en) * | 2018-05-02 | 2018-11-06 | 华南农业大学 | Bacterium and its application as biocontrol microorganisms is quenched in a kind of micropopulation inductive signal |
CN109942397A (en) * | 2019-04-30 | 2019-06-28 | 嘉兴学院 | A kind of preparation method of royal jelly acid |
CN109942397B (en) * | 2019-04-30 | 2022-03-08 | 嘉兴学院 | Preparation method of royal jelly acid |
CN114588148A (en) * | 2022-03-18 | 2022-06-07 | 中山大学 | Application of oridonin in preparation of CepR and RqpR protein binding preparation |
CN114588148B (en) * | 2022-03-18 | 2023-12-29 | 中山大学 | Application of oridonin in preparation of CepR and RqpR protein binding preparation |
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