CN108410766A - Conjugated polymer PMNT is promoting intestinal beneficial bacterium adherency and its application of biofilm formation - Google Patents
Conjugated polymer PMNT is promoting intestinal beneficial bacterium adherency and its application of biofilm formation Download PDFInfo
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Abstract
The invention discloses a kind of conjugated polymer PMNT to promote enteric bacteria adherency and its application of biofilm formation.The solution of polymer shown in polymer or Formulas I shown in claimed Formulas I is in following application in any one or a few：A, promote the adherency of enteric bacteria；B, promote the formation of enteric bacteria biomembrane；C, preparation can promote the product of the adherency of enteric bacteria；D, preparation can promote the product of the formation of enteric bacteria biomembrane.The present invention utilizes polymer shown in Formulas I so that bacterium increases the interaction between bacterium bacterium by electrostatic interaction and hydrophobic effect formation conjugated polymer-bacterium compound population in connection.These aggregations be more likely to it is irreversible be adhered to substrate surface, form microcolony, lay a good foundation for the formation of biomembrane.It after beneficial bacterium forms biomembrane, is not easy to be interfered by ambient enviroment, there is great significance for maintaining intestinal flora to stablize.
Description
Technical field
The invention belongs to chemical field, it is related to a kind of conjugated polymer PMNT and is promoting intestinal beneficial bacterium adherency and its biology
The application that film is formed.
Background technology
Mankind's Colonization inside plants a large amount of microorganisms, and the overwhelming majority lives in gastrointestinal tract, and type is more than 1000 kinds or more,
Sum about 1014It is a, it is 10 times of human body own cells.The enteric bacteria of symbiosis forms a huge and complicated intestinal flora system
System, evolves together with host, directly the participation digestion of human body, nutrient absorption, energy supply, fat metabolism, immunological regulation, disease-resistant
Etc. all various aspects.It includes Bacteroides, clostridium subgroup, Bifidobacterium to study the more relevant specific flora of four classes health at present
Category and Lactobacillus.Intestinal flora and host are mostly symbiosis, and normal Bacterial community can promote body health, and intestines
Road Flora Disturbance can cause disease, such as colon cancer, non-inflammation enteropathy, metabolic disease are such as fat, diabetes.Research
Show that fat and diabetes patient intestinal flora diversity significantly reduces, the beneficial bacteriums such as clostridium, Bifidobacterium and Bacillus acidi lactici subtract
Few, harmful bacteria increases, and the intestinal flora of patient is caused to be lacked of proper care.In addition, the abuse of antibiont, causes harmful bacteria in enteron aisle to produce
Raw drug resistance, to influence intestinal flora balance.Probiotic supplemented is a kind of effective means to prevent and treat disease, prebiotic
Bacterium plays its beneficial function and needs field planting or a large amount of proliferation in enteron aisle, enhances its competitive advantage in enteron aisle, but some
The probiotics of food source is difficult to be resistant to intestine microenvironment and lead to its effect unobvious.Therefore, promote the increasing of beneficial bacterium
Metabolism and its adherency are grown, and then maintains intestinal flora balance, intestinal flora is understood in host disease occurrence and development for people
Effect have a very important significance.
Invention content
The object of the present invention is to provide a kind of conjugated polymer PMNT to promote enteric bacteria adherency and its biofilm formation
Application.
The solution of polymer shown in polymer (namely PMNT) shown in claimed Formulas I or Formulas I is following arbitrary
Application in one or more：
A, promote the adherency of enteric bacteria；
B, promote the formation of enteric bacteria biomembrane；
C, preparation can promote the product of the adherency of enteric bacteria；
D, preparation can promote the product of the formation of enteric bacteria biomembrane；
In the Formulas I, n 20-40, X F, Cl, Br or I；
R is methyl or ethyl.
In above application, the growth of the promotion enteric bacteria includes：Polymer shown in the Formulas I is trained altogether with microorganism
It supports.
It is described promote enteric bacteria biomembrane formation include：By polymer and microculture shown in the Formulas I；
In the solution of polymer shown in the Formulas I, solvent is water；The concentration of the solution of polymer described in the Formulas I is not high
In 100 μm of ol/L.
A kind of method of promotion enteric bacteria adherency is also claimed in the present invention, including：By polymer shown in the Formulas I with
Microbial co culture；
A kind of method for the formation promoting enteric bacteria biomembrane is also claimed in the present invention, including：Shown in the Formulas I
Polymer and microbial co culture.
In above application or method, the microorganism is enteric bacteria, concretely Escherichia coli, enterococcus faecalis, bifid
At least one of bacillus and lactobacillus acidophilus；More specifically Escherichia coli ATCC 25922, enterococcus faecalis ATCC29212 and double
At least one of discrimination bacillus ATCC 15697.
The condition of culture is that conventional microculture condition is cultivated such as Escherichia coli and enterococcus faecalis
Temperature be 37 DEG C, aerobic condition；For Bifidobacterium and lactobacillus acidophilus, cultivation temperature is 37 DEG C, anaerobic condition.
The formation of bacterial biof iotalm includes two steps：First part is that bacterium is non-specific, reversible adheres to substrate
Surface, second part are the further proliferation of bacterium, this part needs the interaction between bacterium and bacterium.Enteric bacteria table
The main component in face is polysaccharide, protein, lipoid etc., carries negative electrical charge.The present invention utilizes polymerization shown in the Formulas I with positive charge
Object so that bacterium is combined closely by electrostatic interaction and hydrophobic effect with polymer shown in Formulas I, and conjugated polymer-bacterium is formed
Compound population increases the interaction between bacteria-bacteria.These aggregations are more likely to irreversible be adhered to substrate table
Face forms microcolony, lays a good foundation for the formation of biomembrane.After beneficial bacterium forms biomembrane, it is not easy to be interfered by ambient enviroment,
There is great significance for maintaining intestinal flora to stablize.
Description of the drawings
Fig. 1 is the growth curve of bacterium.
Fig. 2 is the biofilm formation situation of bacterium.
Fig. 3 is the fluorescence microscope figure of bacterium and polymer P MNT effects.
Fig. 4 is the influence that PMNT forms bacterial biof iotalm.
Fig. 5 is the influence that PMNT forms Escherichia coli biofilm under different time.
Specific implementation mode
With reference to specific embodiment, the present invention is further elaborated, but the present invention is not limited to following embodiments.Institute
It is conventional method to state method unless otherwise instructed.Test material as used in the following examples is unless otherwise specified certainly
What routine biochemistry reagent shop was commercially available.Quantitative test in following embodiment is respectively provided with three repeated experiments, as a result makes even
Mean value.
In following embodiments, 3- methyl -4- (3- (N, N- diethylamino) propoxyl group) thiophene is made as follows:
Under nitrogen protection, anhydrous 1, the 2- dimethyl second diether (DME) of 15mL, N, N- lignocaine -1- propyl alcohol are sequentially added at 0 DEG C
(524mg, 4.0mmol), sodium hydride (96mg, 4.0mmol), then reaction solution is warmed to room temperature, and addition 3- is bromo- after reacting 20min
The DME solution 6mL of 4- methylthiophenes (531mg, 3mmol), cuprous iodide (287mg, 1.5mmol) rise to 105 DEG C, reacted
Night.Reaction solution is cooled to room temperature, dichloromethane dilution is added, filtering, three times, organic phase is dried with anhydrous magnesium sulfate for washing,
It is concentrated to give crude product, is CH2Cl2/CH3OH (30 with silica gel column chromatography, eluant, eluent:1) crude product is purified, dry product (328mg,
48%).
1H NMR(400MHz,CDCl3):δ=6.80 (s, 1H), 6.14 (s, 1H), 3.98 (t, J=6.0Hz, 2H),
2.62 (t, J=7.2Hz, 2H), 2.55 (m, J=7.2Hz, 4H), 2.09 (s, 3H), 1.93 (m, 2H), 1.04 (t, J=
7.2Hz,6H)；13C NMR (100MHz, CDCl3) δ=156.1,129.1,119.7,96.0,68.2,49.3,47.0,26.7,
12.7,11.6。
3- methyl -4- (3- (N, N, N- triethyl group ammonium) propoxyl group) thiophene is made as follows：In reaction bulb
Sequentially add 20mL acetonitriles, 3- methyl -4- (3- (N, N- diethylamino) propoxyl group) thiophene (114mg, 0.5mmol), 1.9mL
Bromoethane under nitrogen protection, is warming up to 70 DEG C and reacts 3 days.Reaction solution is cooled to room temperature, and solvent under reduced pressure is removed, and is added a little
Chloroform dissolves, and is then recrystallized through ethyl acetate, crystal is filtered, and washs, and product (164mg, 98%) is obtained after dry.
1H NMR(400MHz,CDCl3):δ=6.84 (d, J=2Hz, 1H), 6.22 (d, J=3.2H, 1H), 4.12 (t, J
=5.2Hz, 2H), 3.60 (t, J=7.2Hz, 8H), 2.38 (m, 2H), 2.05 (s, 3H), 1.43 (t, J=7.2Hz, 9H)；13C
NMR (75MHz, CDCl3) δ=153.6,132.1,127.1,119.3,96.1,64.6,53.6,52.5,21.5,11.6,6. 8.
Polymer PMNT used in following embodiments (wherein, R is ethyl, X Cl) are made as follows：It is reacting
10mL chloroforms are sequentially added in bottle, anhydrous ferric trichloride (194mg, 1.2mmol) leads to half an hour N2, 3- methyl -4- is then added dropwise
The chloroformic solution of (3- (N, N, N- triethyl group ammonium) propoxyl group) thiophene (101mg, 0.3mmol) reacts at room temperature two days.Decompression removes
Chloroform is removed, is filtered, methanol washs 3 times, then excessive tetrabutylammonium chloride is added in obtained solid acetone solution, generates
Red precipitate.Precipitation is filtered, the dissolving of filter cake again with methanol adds 5-6 drop hydrazine hydrates, Fe3+ is deprotected, solution is spin-dried for, and is obtained
Solid add the saturation acetone soln washing of a small amount of tetrabutylammonium chloride, with acetone Soxhlet extraction 6h, vacuum drying obtains product
48mg, yield 47%.
1H NMR(400MHz,D2O):δ=4.04 (br), 3.19 (br), 2.27 (br), 1.62 (s), 1.32 (br),
0.92(t)；TGA:Thermal weight loss 5% (210 DEG C).
Embodiment 1, bacterium (Escherichia coli, enterococcus faecalis) growth curve
(1), the recovery culture of bacterium
Using Escherichia coli ATCC 25922, enterococcus faecalis ATCC 29212 and Bifidobacterium ATCC15697 as template, super
It is filled after germy ampere bottle outer surface carries out disinfection with 75% alcohol absorbent cotton to purchasing in net workbench, it is heated with flame
The ampoule bottle top on top, drop 300-400 μ L sterile waters to heating is allowed to rupture.Draw the suitable liquid trainings of 300-500 μ L
Base (can be replaced with sterile water) is supported, is instilled in ampoule bottle, gently oscillation piping and druming, it is in suspension to make the dissolving of freeze-drying thalline, is drawn complete
Portion's bacteria suspension, transplants that (Escherichia coli correspond to LB solid mediums, and it is solid that enterococcus faecalis corresponds to TSA in two solid mediums respectively
Body culture medium, Bifidobacterium correspond to MRS solid mediums) in, 37 DEG C are cultivated 24 hours.Appropriate thalline, which is scraped, with oese draws Z
Type is inoculated into new solid medium, and 37 DEG C are continued to cultivate, and the so continuous 3-4 that passes is commissioned to train foster, obtains stable bacterial strain, puts 4
It is spare DEG C to make strain.Wherein Bifidobacterium ATCC15697 is anaerobic bacteria, need to be placed in anaerobic jar and cultivate.
The LB solid mediums constituent is by weight percentage：1.0% tryptone, 0.5% yeast extract,
1%NaCl, 1.2%-1.5% agar, 97.5% distilled water；TSB the and TSA culture mediums are purchased from U.S. company BD；The MRS is solid
Body culture medium bacterium is purchased from Beijing overpass technical concern Co., Ltd；Escherichia coli ATCC 25922 and enterococcus faecalis ATCC 29212
Purchased from China General Microbiological culture presevation administrative center (CGMCC), number is：CGMCC1.2385 and CGMCC 1.2135.It is double
Discrimination bacillus ATCC 15697 is purchased from Chinese industrial Microbiological Culture Collection administrative center (CICC), and number is CICC 6069.
(2), the measurement of growth curve of bacteria
In fluid nutrient medium, (Escherichia coli correspond to LB liquid medium, excrement intestines ball to appropriate thalline in picking solid medium
Bacterium corresponds to TSB fluid nutrient mediums) in, rotating speed 180rpm shake cultures are to OD at 37 DEG C600Value is 0.7-1.2.Take a small amount of bacterium solution
After diluting 1000 times with culture medium, PMNT polymer shown in final concentration of 20 μM of Formulas I is added, blank control is that peer is added
Long-pending aqua sterilisa, rotating speed 180rpm shake cultures at 37 DEG C, its OD was surveyed every 30 minutes600It is worth (Fig. 1).
The LB liquid medium constituent is by weight percentage：1.0% tryptone, 0.5% yeast extract,
1%NaCl, 97.5% distilled water；The TSB fluid nutrient mediums are purchased from U.S. company BD.
It can be obtained from Fig. 1, PMNT does not have an impact the growth of Escherichia coli and enterococcus faecalis.
Embodiment 2, the optimization of the formation condition of bacterial biof iotalm
Appropriate thalline (Escherichia coli, enterococcus faecalis and Bifidobacterium) is in fluid nutrient medium in picking solid medium,
Rotating speed 180rpm shake culture 5-10h, Bifidobacterium are placed in anaerobic jar and cultivate for 24 hours at 37 DEG C.It is washed twice with PBS, adjusts OD600
Value is 1.0.After taking a small amount of bacterium solution culture medium to dilute 100 times, the glucose of various concentration is added, blank control is to be added on an equal basis
The aqua sterilisa of volume, remaining operation is consistent with experimental group, at 37 DEG C stationary culture for 24 hours after, take out survey its OD590It is worth (Fig. 2), it is double
Discrimination bacillus need to be placed in anaerobic jar and cultivate 48h.
From figure 2 it can be seen that Escherichia coli biofilm formation ability when concentration of glucose is 0.25% is most strong, excrement intestines
Coccus biofilm formation ability when concentration of glucose is 0.5% is most strong, and concentration of glucose is to Bifidobacterium biofilm formation
Do not influence.
Embodiment 3, bacterium and conjugated polymer PMNT imaging experiments
Appropriate thalline is in fluid nutrient medium in picking solid medium, rotating speed 180rpm shake cultures 5- at 37 DEG C
10h, Bifidobacterium are placed in anaerobic jar and cultivate for 24 hours.It is washed twice with PBS, adjusts OD600Value is 1.0.Take a small amount of bacterium solution culture medium
After 100 times of dilution, PMNT polymer shown in final concentration of 20 μM of Formulas I being added, is placed 30 minutes at 37 DEG C, supernatant is abandoned in centrifugation,
After being washed once with PBS, 10 μ L is taken to mix liquid in fluorescence microscopy microscopic observation.
Under fluorescence microscope it can be seen that light field Escherichia coli, enterococcus faecalis and Bifidobacterium with shown in Formulas I
PMNT polymer forms good complex, and the wherein fluorescent places of PMNT are completely superposed (Fig. 3) with complex, formula I institutes
Show that PMNT polymer can interact with various bacteria.
Embodiment 4, conjugated polymer PMNT form bacterium the influence of biomembrane
Appropriate thalline is in fluid nutrient medium in picking solid medium, rotating speed 180rpm shake cultures 5- at 37 DEG C
10h, Bifidobacterium are placed in anaerobic jar and cultivate for 24 hours.It is washed twice with PBS, adjusts OD600Value is 1.0.Take a small amount of bacterium solution culture medium
After 100 times of dilution, PMNT polymer shown in final concentration of 20 μM of Formulas I being added and is placed in 96 orifice plates, control group is not added with PMNT,
Remaining operation is consistent with experimental group.It is placed for 24 hours in 37 DEG C of incubators, Bifidobacterium, which is placed in anaerobic jar, places 48h.
Figure 4, it is seen that after PMNT is added, Escherichia coli biofilm increases 216.5%, enterococcus faecalis biomembrane
47.6% is increased, the biomembrane that Bifidobacterium is formed increases 130.7%.Illustrate that PMNT can promote enteric bacteria biomembrane
It is formed.
The influence of embodiment 5, conjugated polymer PMNT to bacterium initial adherence
By taking Escherichia coli as an example, appropriate thalline is in fluid nutrient medium in picking solid medium, rotating speed at 37 DEG C
180rpm shake cultures 5-10h.It is washed twice with PBS, adjusts OD600Value is 1.0.After taking a small amount of bacterium solution culture medium to dilute 100 times,
PMNT polymer shown in final concentration of 20 μM of Formulas I is added to be placed in 8 orifice plates, control group is not added with PMNT, remaining operation and experiment
Group is consistent.After placing 2h, 4h and 6h respectively, solution is discarded supernatant, after being washed twice with PBS, is dyed and is tried with BacLight life or death bacterium
Agent box is dyed.CLSM characterizations are finally carried out, light field and the fluorescence field of sample is acquired, is for SYTO9 excitation wavelengths
488nm, PI 559nm, the results are shown in Figure 5.
With the extension of time, blank group bacterial population increases.And within the same time, the bacterium of PMNT groups is thinner than blank group
Bacterium number is more, illustrates that PMNT can promote bacterial adhesion in a short time, and then promote the formation of biomembrane.
Claims (7)
1. the solution of polymer shown in polymer or Formulas I shown in Formulas I is in following application in any one or a few：
A, promote the adherency of enteric bacteria；
B, promote the formation of enteric bacteria biomembrane；
C, preparation can promote the product of the adherency of enteric bacteria；
D, preparation can promote the product of the formation of enteric bacteria biomembrane；
In the Formulas I, n 20-40, X F, Cl, Br or I；
R is methyl or ethyl.
2. application according to claim 1, it is characterised in that：In the solution of polymer shown in the Formulas I, solvent is water.
3. according to any application in claim 1-2, it is characterised in that：The solution of polymer is dense described in the Formulas I
Degree is not higher than 100 μm of ol/L.
4. a kind of method promoting enteric bacteria adherency, including：By polymer and microbial co culture shown in the Formulas I；
In the Formulas I, n 20-40, X F, Cl, Br or I；
R is methyl or ethyl.
5. a kind of method of the formation of promotion enteric bacteria biomembrane, including：Polymer shown in the Formulas I is trained altogether with microorganism
It supports；
In the Formulas I, n 20-40, X F, Cl, Br or I；
R is methyl or ethyl.
6. according to any application or method in claim 1-5, it is characterised in that：The microorganism is enteric bacteria.
7. application according to claim 6 or method, it is characterised in that：The microorganism is selected from Escherichia coli, excrement intestines ball
At least one of bacterium, Bifidobacterium and lactobacillus acidophilus.
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| CN111180742A (en) * | 2018-11-09 | 2020-05-19 | 中国科学院化学研究所 | Microbial electrode, preparation method thereof and microbial fuel cell |
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| CN109788760A (en) * | 2016-07-28 | 2019-05-21 | 艾克森实验室有限公司 | Antimicrobial photoreactive composition comprising organic and inorganic more knot composite materials |
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| CN111180742A (en) * | 2018-11-09 | 2020-05-19 | 中国科学院化学研究所 | Microbial electrode, preparation method thereof and microbial fuel cell |
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