CN108815529A - The ball-type conjugated polymer nanoparticle and its antibacterial applications of quaternary ammonium salt functionalization - Google Patents
The ball-type conjugated polymer nanoparticle and its antibacterial applications of quaternary ammonium salt functionalization Download PDFInfo
- Publication number
- CN108815529A CN108815529A CN201810699457.4A CN201810699457A CN108815529A CN 108815529 A CN108815529 A CN 108815529A CN 201810699457 A CN201810699457 A CN 201810699457A CN 108815529 A CN108815529 A CN 108815529A
- Authority
- CN
- China
- Prior art keywords
- conjugated polymer
- quaternary ammonium
- ammonium salt
- nanoparticle
- ball
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- MYEAZIWJNFLWLK-UHFFFAOYSA-N BrCCCCCC(CCCCCBr)(c1c2)c3cc(Br)ccc3-c1ccc2Br Chemical compound BrCCCCCC(CCCCCBr)(c1c2)c3cc(Br)ccc3-c1ccc2Br MYEAZIWJNFLWLK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1412—Saturated aliphatic units
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/146—Side-chains containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/18—Definition of the polymer structure conjugated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
- C08G2261/3142—Condensed aromatic systems, e.g. perylene, anthracene or pyrene fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3246—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing nitrogen and sulfur as heteroatoms
Abstract
The invention discloses a kind of ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization and its antibacterial applications, the nanoparticle is using hydrophobicity conjugated polymer as kernel, quaternary ammonium salt functional group molecule is formed on its surface shell by hydrophobic effect, the conjugated polymer nanoparticle of ball-type is finally obtained, wherein the structural formula of hydrophobicity conjugated polymer isThe structural formula of quaternary ammonium salt functional group molecule isConjugated polymer nanoparticle of the present invention is under the conditions of being protected from light, broad-spectrum high efficacy antibacterial can be realized without light source or other energy, its antibiotic rate is significantly larger than the antibiotic rate of same concentrations functional group molecule, and is not likely to produce drug resistance, and the exploitation for the following antimicrobial nano material provides new thinking.
Description
Technical field
The invention belongs to nanoparticle antimicrobial technology fields, and in particular to a kind of novel conjugated polymer nanoparticle,
And application of the nanoparticle as anti-biotic material.
Background technique
With the appearance of drug-resistant type bacterium in recent years, development is not influenced by bacterial resistance and has the new of high-efficiency antimicrobial performance
Type antibacterial agent and antibiotic method are of great significance.Nano anti-biotic material due to advantages such as size is small, large specific surface areas significantly
Improve antibacterial activity.And compared with traditional antibacterial agent, nano anti-biotic material, which has, to be not likely to produce drug resistance, can persistently resist
The advantages that bacterium and broad-spectrum antiseptic.Although common antimicrobial nano material anti-microbial property is good at present, photocatalysis and right is needed mostly
Mammalian cell has bio-toxicity, especially heavy metal nanoparticle, therefore limits them in biomedical aspect
Using.
Conjugated polymer nanoparticle (CPNs) is the novel nano-material quickly grown in recent years, is based on conjugated polymer
The nanoparticle being prepared generally has that bright fluorescence, colloidal stability are good, biocompatibility is high and cytotoxicity is low
The advantages that, it is therefore widely used in bio-imaging, diagnosis, treatment etc..
Summary of the invention
Technical problem to be solved by the present invention lies in provide a kind of ball-type conjugated polymers of novel quaternary ammonium salt functionalization
The application of object nanoparticle and the conjugated polymer nanoparticle in antibiosis.
The ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization used by solution above-mentioned technical problem is will be hydrophobic
Property conjugated polymer and quaternary ammonium salt functional group molecule by hydrophobic effect formed using hydrophobicity conjugated polymer as kernel, quaternary ammonium
Salt functional group's molecule is the nanosphere of shell.
The structural formula of above-mentioned hydrophobicity conjugated polymer is as follows：
Wherein R is selected from C1~C20Alkyl,In it is any one
Kind, the integer that m is 1~19, X1Br or I is represented, n represents the degree of polymerization；The number-average molecular weight of the hydrophobicity conjugated polymer is
10000~50000, preparation method is：It is in molar ratio 1 by compound of formula I and Formula II compound, palladium acetate:1:0.036 is added
The in the mixed solvent of dimethylformamide and triethylamine reacts 4 hours at 100 DEG C, isolates and purifies product, and it is total to obtain hydrophobicity
Conjugated polymer.
The structural formula of above-mentioned quaternary ammonium salt functional group molecule is as follows：
X represents Cl or Br, p 3,4,6,8,9,10,12,14,16 or 18 in formula.
The preparation method of conjugated polymer nanoparticle of the present invention is：The nanoparticle be by hydrophobicity conjugated polymer with
Quaternary ammonium salt functional group molecule is dispersed in tetrahydrofuran under ultrasonic condition of ice bath, and acquired solution is rapidly injected deionized water
In, continue ultrasound 10~20 minutes, removes tetrahydrofuran and portions of de-ionized water then to get ball-type conjugated polymer nanoparticle
Son.
In above-mentioned preparation method, the molar ratio of the hydrophobicity conjugated polymer and quaternary ammonium salt functional group molecule is 1:1~
5, the tetrahydrofuran of addition and the volume ratio of deionized water are 1:1~3.
Purposes of the conjugated polymer nanoparticle of the present invention as anti-biotic material, the bacterium are Escherichia coli, golden yellow
Staphylococcus etc..
Conjugated polymer nanoparticle of the present invention is using hydrophobicity conjugated polymer as kernel, the cation with quaternary ammonium group
Surfactant forms shell on surface by hydrophobic effect, finally obtains the conjugated polymer nanoparticle of ball-type.The present invention
By control hydrophobicity conjugated polymer and the molar ratio of quaternary ammonium salt functional group molecule, the volume ratio of water phase and tetrahydrofuran and
The concentration of hydrophobicity conjugated polymer and quaternary ammonium salt functional group molecule in system, regulates and controls the partial size of the nanoparticle of generation.This
Broad-spectrum high efficacy antibacterial can be realized under the conditions of being protected from light, without light source or other energy in invention nanoparticle, and antibiotic rate is much
Higher than the antibiotic rate of same concentrations quaternary ammonium salt functional group molecule, and it is not likely to produce drug resistance, for opening for the following antimicrobial nano material
Hair provides new thinking.
Detailed description of the invention
Fig. 1 is the transmission electron microscope picture of conjugated polymer nanoparticle prepared by embodiment 1.
Fig. 2 is bactericidal activity of the conjugated polymer nanoparticle to Escherichia coli of the preparation of embodiment 1 under the conditions of being protected from light.
Fig. 3 is sterilization of the conjugated polymer nanoparticle of the preparation of embodiment 1 under the conditions of being protected from light to staphylococcus aureus
Activity.
Specific embodiment
The present invention is described in more detail with reference to the accompanying drawings and examples, but protection scope of the present invention is not limited only to
These embodiments.
Embodiment 1
Under ultrasonic condition of ice bath, by 0.1mg hydrophobicity conjugated polymer c-1 and 0.1mg cetyl trimethyl bromination
Ammonium is added in 5mL tetrahydrofuran, and ultrasonic disperse is uniform, and gained mixed solution is quickly poured into the flask equipped with 15mL secondary water
In, jog makes its mixing, continues ultrasound 15 minutes.After the completion of ultrasound, restore to room temperature, respectively with syringe needle drum nitrogen in room temperature item
The tetrahydrofuran in mixed solution is removed under part, removes portions of de-ionized water in a heated condition, so that solution is concentrated into 5mL, is obtained
To conjugated polymer nanoparticle.As seen from Figure 1, the partial size of gained nanoparticle is 50nm or so.
The synthetic route and synthetic method of above-mentioned hydrophobicity conjugated polymer c-1 is as follows：
1, into 50mL round-bottomed flask be added 7.2mL (50mmol) hexyl bromide 1 bromohexane, 0.33g (1mmol) Tetrabutylammonium bromide,
Reaction mixture after deoxygenation 30 minutes, is warming up to 75 DEG C, 1.62g is added by the KOH aqueous solution that 20mL mass fraction is 50%
(5mmol) 2,7- dibromo fluorenes continues 75 DEG C and flows back 15 minutes.Column chromatography for separation after reaction mixture is extracted, dried and concentrated,
Obtain compound a -1.
2,738.5mg (1.5mmol) compound a -1,10mL toluene are added into 25mL round-bottomed flask, after deoxygenation 30 minutes
Sequentially add 1.43mL (4.5mmol) tributylvinyl tin, 2mg (0.0095mmol) 2,6- di-tert-butylphenol and 47.4mg
(0.0675mmol) bis- (triphenylphosphine) palladium chlorides, reaction mixture flow back 7 hours at 100 DEG C, are cooled to room temperature, and 10mL is added
The KF aqueous solution that mass fraction is 10% is stirred overnight, and is extracted after removing solid residue, dries and concentrates rear pillar chromatography point
From obtaining compound b-1.
3, into 25mL round-bottomed flask be added 96.7mg (0.25mmol) compound b-1,1.67mL dimethylformamide,
0.83mL triethylamine sequentially adds 73.5mg (0.25mmol) 4,7- bis- bromo- 2,1,3- diazosulfide, 2mg after deoxygenation 30min
(0.009mmol) palladium acetate, 15mg (0.049mmol) tricresyl phosphate p-methylphenyl ester, reaction mixture flow back 4 hours at 100 DEG C
By centrifugation after extraction, drying, concentration, hydrophobicity conjugated polymer c-1 is obtained.It is detected through gel permeation chromatography, it is hydrophobic
The M of property conjugated polymer c-1n=44810, Mw=47827, PDI=1.07.
Embodiment 2
Under ultrasonic condition of ice bath, by 0.1mg hydrophobicity conjugated polymer c-2 and 0.1mg cetyl trimethyl bromination
Ammonium is added in 5mL tetrahydrofuran, and ultrasonic disperse is uniform, and gained mixed solution is quickly poured into the flask equipped with 15mL secondary water
In, jog makes its mixing, continues ultrasound 15 minutes.After the completion of ultrasound, restore to room temperature, respectively with syringe needle drum nitrogen in room temperature item
The tetrahydrofuran in mixed solution is removed under part, removes portions of de-ionized water in a heated condition, so that solution is concentrated into 5mL, is obtained
To conjugated polymer nanoparticle.
The synthetic route and synthetic method of above-mentioned hydrophobicity conjugated polymer c-2 is as follows：
In its synthetic method, need to only use equimolar 1, the hexyl bromide 1 bromohexane in 1 is implemented in the replacement of 6- dibromo-hexane, for his step with
The synthetic method of c-1 is identical, obtains hydrophobicity conjugated polymer c-2.It is detected through gel permeation chromatography, hydrophobicity conjugated polymer
The M of c-2n=13958, Mw=15078, PDI=1.08.
Embodiment 3
Under ultrasonic condition of ice bath, by 0.1mg hydrophobicity conjugated polymer e-3 and 0.1mg cetyl trimethyl bromination
Ammonium is added in 5mL tetrahydrofuran, and ultrasonic disperse is uniform, and gained mixed solution is quickly poured into the flask equipped with 15mL secondary water
In, jog makes its mixing, continues ultrasound 15 minutes.After the completion of ultrasound, restore to room temperature, respectively with syringe needle drum nitrogen in room temperature item
The tetrahydrofuran in mixed solution is removed under part, removes portions of de-ionized water in a heated condition, so that solution is concentrated into 5mL, is obtained
To conjugated polymer nanoparticle.
The synthetic route and synthetic method of above-mentioned hydrophobicity conjugated polymer e-3 is as follows：
1,6mL (75mmol) triethylene glycol monomethyl ether, 10mL CH are added into 100mL round-bottomed flask2Cl2, and in ice bath
1.42g (7.5mmol) p-methyl benzene sulfonic chloride is dissolved in 10mL CH by lower addition 2.07mL (15mmol) triethylamine2Cl2In and drip
After normal-temperature reaction is added in above-mentioned solution overnight, column chromatography for separation after being extracted, being dried and concentrated obtains compound a -3.
2,30mL anhydrous propanone, 1.27g (4mmol) compound a -3,1.4g (16mmol) is added to 100mL round-bottomed flask
LiBr, mixed solution are warming up to 85 DEG C, after back flow reaction is stayed overnight, are cooled to room temperature, and are extracted, dry and concentrate rear pillar chromatography point
From obtaining compound b-3.
3,0.4g (1.76mmol) compound b-3,0.23g (0.71mmol) 2,7- dibromo is added into 50mL round-bottomed flask
Fluorenes, 0.02g (0.06mmol) Tetrabutylammonium bromide, 2mL DMSO, the KOH aqueous solution that 0.56mL mass fraction is 50%, heating
To 100 DEG C, after back flow reaction is stayed overnight, it is cooled to room temperature, column chromatography for separation after being extracted, being dried and concentrated obtains compound c-
3。
4,924.6mg (1.5mmol) compound c-3,10mL toluene is added into 25mL round-bottomed flask, after deoxygenation 30 minutes
Sequentially add 1.43mL (4.5mmol) tributylvinyl tin, 2mg (0.0095mmol) 2,6- di-tert-butylphenol and 47.4mg
(0.0675mmol) bis- (triphenylphosphine) palladium chlorides, reaction mixture flow back 7 hours at 100 DEG C, are cooled to room temperature, and 10mL is added
The KF aqueous solution that mass fraction is 10% is stirred overnight, and is extracted after removing solid residue, dries and concentrates rear pillar chromatography point
From obtaining compound d-3.
5, into 25mL round-bottomed flask be added 127.7mg (0.25mmol) compound d-3,1.67mL dimethylformamide,
0.83mL triethylamine sequentially adds 73.5mg (0.25mmol) 4,7- bis- bromo- 2,1,3- diazosulfide, 2mg after deoxygenation 30min
(0.009mmol) palladium acetate, 15mg (0.049mmol) tricresyl phosphate p-methylphenyl ester, reaction mixture flow back 4 hours at 100 DEG C
By centrifugation after extraction, drying, concentration, conjugated polymer e-3 is obtained.It is detected through gel permeation chromatography, hydrophobicity conjugation
The M of polymer e-3n=16589, Mw=23420, PDI=1.41.
Embodiment 4
The application of conjugated polymer nanoparticle prepared by embodiment 1 as anti-biotic material
Subzero 80 DEG C of staphylococcus aureus will be stored in and Escherichia coli are transferred to TSB agar plate with method of scoring respectively
On LB agar plate, the progress first generation activation that is incubated overnight is placed in 37 DEG C of water-impermeable incubator.On picking agar plate
Single colonie is placed in 25mL culture medium, is put into 37 DEG C of shaking table and is incubated for about 12 hours to its logarithmic growth phase.It is received by centrifugation
Collect the bacterium of logarithmic growth phase, then washed twice with 0.9%NaCl solution, removes supernatant, it is molten to be eventually adding 0.9%NaCl
Liquid obtains bacterial suspension.
By conjugated polymer nanoparticle (ultimate density is respectively 0,0.2,0.5,0.8,1.0,1.5,2.0 μ g/mL) and
Bacterial suspension (final concentration of 2 × 107Cfu/mL it after) mixing, is placed in light protected environment and is incubated for 30 minutes and 60 minutes respectively.
After the completion of incubation, handled with SYTO 9/PI mixed dye dyeing, with the survival rate of flow cytomery bacterium.Sampling amount is
100000 signals, signal collection select the channel (530 ± 15nm) FL1 to collect green florescent signal, and FL2 (585 ± 20nm) is logical
Collect red fluorescent in road.The cetyl trimethyl bromination of blank control experiment and same concentrations is done in each processing simultaneously
The antibacterial experiment of ammonium (CTAB).Bacteriostasis rate result is shown in Fig. 2 and Fig. 3.
From Figure 2 it can be seen that Escherichia coli and conjugated polymer nanoparticle are incubated for 30 minutes and 60 minutes under the conditions of being protected from light
Antibacterial effect it is almost consistent, illustrate that nanoparticle has been completed in conjunction with bacterium in 30 minutes and destroyed the full mistake of bacterial membrane
Journey, and the concentration of antibacterial activity and nanoparticle is positively correlated, when the concentration of nanoparticle is 0.8 μ g/mL, bacterium it is dead
The rate of dying reaches 91%.
As seen from Figure 3, conjugated polymer nanoparticle also can be in 30 minutes to the antibacterial process of staphylococcus aureus
Complete, the variation tendency of antibacterial activity and anti-Escherichia coli are almost the same, due to gram-positive bacteria in structure its cell wall
Intensity it is more tough and tensile than Gram-negative bacteria, but the nanoparticle of 1.0 μ g/mL is incubated for and can also make antibacterial in 30 minutes under the conditions of being protected from light
Rate reaches 96%.And from figure we can also be seen that 0 to 1.0 μ g/mL CTAB almost without antibacterial activity, and this concentration
The antibiotic rate of lower nanoparticle can be more than 90%, illustrate that the anti-microbial property of conjugated polymer nanoparticle is not to derive from
CTAB but by with conjugated polymer formed nanoparticle collective effect realize.These are the experimental results showed that the present invention is conjugated
Polymer nano-particle has efficient broad spectrum antibiotic activity under the conditions of being protected from light.
Claims (6)
1. a kind of ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization, it is characterised in that：The nanoparticle is will be hydrophobic
Property conjugated polymer and quaternary ammonium salt functional group molecule by hydrophobic effect formed using hydrophobicity conjugated polymer as kernel, quaternary ammonium
Salt functional group's molecule is the nanosphere of shell；
The structural formula of above-mentioned hydrophobicity conjugated polymer is as follows：
Wherein R is selected from C1~C20Alkyl ,-(CH2)mCH2X1、In any one, m 1
~19 integer, X1Br or I is represented, n represents the degree of polymerization；The number-average molecular weight of the hydrophobicity conjugated polymer be 10000~
50000；
The structural formula of above-mentioned quaternary ammonium salt functional group molecule is as follows：
X represents Cl or Br, p 3,4,6,8,9,10,12,14,16 or 18 in formula.
2. the ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization in surface according to claim 1, it is characterised in that：
The nanoparticle is that hydrophobicity conjugated polymer and quaternary ammonium salt functional group molecule are dispersed in four under ultrasonic condition of ice bath
In hydrogen furans, acquired solution is rapidly injected in deionized water, continues ultrasound 10~20 minutes, then removes tetrahydrofuran and part
Deionized water is to get ball-type conjugated polymer nanoparticle.
3. the ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization in surface according to claim 2, it is characterised in that：
The molar ratio of the hydrophobicity conjugated polymer and quaternary ammonium salt functional group molecule is 1:1~5.
4. the ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization in surface according to claim 2, it is characterised in that：
The tetrahydrofuran of addition and the volume ratio of deionized water are 1:1~3.
5. use of the ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization in surface described in claim 1 as anti-biotic material
On the way.
6. the ball-type conjugated polymer nanoparticle of quaternary ammonium salt functionalization in surface according to claim 5 is as anti-biotic material
Purposes, it is characterised in that：The bacterium is Escherichia coli or staphylococcus aureus.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810699457.4A CN108815529B (en) | 2018-06-29 | 2018-06-29 | Spherical conjugated polymer nano particle functionalized by quaternary ammonium salt and antibacterial application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810699457.4A CN108815529B (en) | 2018-06-29 | 2018-06-29 | Spherical conjugated polymer nano particle functionalized by quaternary ammonium salt and antibacterial application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108815529A true CN108815529A (en) | 2018-11-16 |
| CN108815529B CN108815529B (en) | 2021-07-09 |
Family
ID=64133999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810699457.4A Active CN108815529B (en) | 2018-06-29 | 2018-06-29 | Spherical conjugated polymer nano particle functionalized by quaternary ammonium salt and antibacterial application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108815529B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110522955A (en) * | 2019-09-27 | 2019-12-03 | 淮阴工学院 | A kind of preparation method of antimicrobial nano synthesis and antimicrobial coating |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103053517A (en) * | 2013-01-18 | 2013-04-24 | 陕西师范大学 | Synthesis method and application of fluorescence DNA-polyphenylene acetylene hydrogel |
| CN105001193A (en) * | 2015-07-15 | 2015-10-28 | 陕西师范大学 | Cationic water-soluble oligothiophene acetylene compound, and preparation method and application thereof |
| CN105963697A (en) * | 2016-05-31 | 2016-09-28 | 陕西师范大学 | Composite antibacterial agent based on fluorescent conjugated polymer and upconversion nanometer material and using method thereof |
-
2018
- 2018-06-29 CN CN201810699457.4A patent/CN108815529B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103053517A (en) * | 2013-01-18 | 2013-04-24 | 陕西师范大学 | Synthesis method and application of fluorescence DNA-polyphenylene acetylene hydrogel |
| CN105001193A (en) * | 2015-07-15 | 2015-10-28 | 陕西师范大学 | Cationic water-soluble oligothiophene acetylene compound, and preparation method and application thereof |
| CN105963697A (en) * | 2016-05-31 | 2016-09-28 | 陕西师范大学 | Composite antibacterial agent based on fluorescent conjugated polymer and upconversion nanometer material and using method thereof |
Non-Patent Citations (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110522955A (en) * | 2019-09-27 | 2019-12-03 | 淮阴工学院 | A kind of preparation method of antimicrobial nano synthesis and antimicrobial coating |
Also Published As
| Publication number | Publication date |
|---|---|
| CN108815529B (en) | 2021-07-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9809476B2 (en) | Biological composite material loaded with magnetic nanoparticles with core-shell structure, the preparation therefore and the application | |
| Sun et al. | Self-enriched mesoporous silica nanoparticle composite membrane with remarkable photodynamic antimicrobial performances | |
| CN104472538A (en) | Functional graphene oxide loaded nano-silver antibacterial material as well as preparation method and application thereof | |
| Agnihotri et al. | Synthesis and antimicrobial activity of aminoglycoside-conjugated silica nanoparticles against clinical and resistant bacteria | |
| CN112056310B (en) | DFNS (double-walled carbon nanotubes) loaded carbon quantum dot/molybdenum disulfide quantum dot as well as preparation method and application thereof | |
| CN109942751B (en) | Preparation method of plastic antibacterial material | |
| Yin et al. | A multifunctional upconverting nanoparticle incorporated polycationic hydrogel for near-infrared triggered and synergistic treatment of drug-resistant bacteria | |
| CN101864078B (en) | Polyethyleneimine-chitosan-octadecanoic acid grafting, preparation and application | |
| CN113413462B (en) | Nano material for simulating natural killer cells to efficiently treat intracellular bacteria and preparation method and application thereof | |
| Hu et al. | More is less: creation of pathogenic microbe-related theranostic oriented AIEgens | |
| Zhang et al. | One-pot synthesis of bio-functionally water-soluble POSS derivatives via efficient click chemistry methodology | |
| Zhou et al. | High thermal stability Cu2O@ OZrP micro-nano hybrids for melt-spun excellent antibacterial activity polyester fibers | |
| CN108815529A (en) | The ball-type conjugated polymer nanoparticle and its antibacterial applications of quaternary ammonium salt functionalization | |
| Yu et al. | Therapeutic nanoplatforms with bacteria-specific activation for directional transport of antibiotics | |
| CN112841221A (en) | Silver-loaded polyphosphazene microsphere with mesoporous core-shell structure as well as preparation method and application thereof | |
| CN109223761A (en) | A kind of dihydromyricetin/multi-walled carbon nanotube compound and its preparation method and application | |
| Li et al. | Photosensitizer doped zeolitic imidazolate framework-8 nanocomposites for combined antibacterial therapy to overcome methicillin-resistant Staphylococcus aureus (MRSA) | |
| Wang et al. | Bacteria-triggered radical anions amplifier of pillar [5] arene/perylene diimide nanosheets with highly selective antibacterial activity | |
| CN109603906B (en) | Anthraquinone-2-sodium sulfonate/graphene oxide composite photocatalytic bactericide and preparation method and application thereof | |
| Ouyang et al. | Reversible environmental impacts of iron-based metal-organic framework MIL-53 (Fe) on nitrogen-fixing bacterium Azotobacter vinelandii | |
| Foulady-Dehaghi et al. | Drug delivery with solvent-free synthesized polyimide-COF/amino-functionalized MCM-41 nanohybrid | |
| Cao et al. | Designing of membrane-active nano-antimicrobials based on cationic copolymer functionalized nanodiamond: Influence of hydrophilic segment on antimicrobial activity and selectivity | |
| Magadla et al. | Evaluation of the antibacterial activity of gallic acid anchored phthalocyanine-doped silica nanoparticles towards Escherichia coli and Staphylococcus aureus biofilms and planktonic cells | |
| Zhang et al. | Functional Silver nanoparticles as broad-spectrum antimicrobial agents | |
| CN112618716A (en) | Photodynamic combined lysozyme antibacterial method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |