CN107441490A - Possess composite nano antibacterial agent and its application of bacterium specific recognition capability - Google Patents
Possess composite nano antibacterial agent and its application of bacterium specific recognition capability Download PDFInfo
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- CN107441490A CN107441490A CN201710639308.4A CN201710639308A CN107441490A CN 107441490 A CN107441490 A CN 107441490A CN 201710639308 A CN201710639308 A CN 201710639308A CN 107441490 A CN107441490 A CN 107441490A
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- galactolipin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/38—Silver; Compounds thereof
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
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Abstract
The invention discloses a kind of composite nano antibacterial agent for possessing bacterium specific recognition capability and its application, belong to technical field of high-molecular polymer.It is made up of Nano silver grain, the pyrroles's molecule of boron fluoride two and poly- galactolipin, Nano silver grain forms silver nanoparticle ball, poly- galactolipin is poly- galactolipin chain, silver nanoparticle ball connects one end of several poly- galactolipin chains respectively, the other end of each poly- galactolipin chain is all connected with a pyrroles's molecule of boron fluoride two, all pyrroles's molecules of boron fluoride two around silver nanoparticle ball, also form spheroidal structure.Composite nano antibacterial agent particle prepared by the present invention possesses selective recognition capability to pseudomonas aeruginosa, Escherichia coli, clostridium tetani and staphylococcus aureus, and not by or few adsorbed by normal human cell, therefore on the basis of to the less toxic side effect of human body, antibacterial purpose is optionally realized.
Description
Technical field
The present invention relates to composite nano antibacterial agent, belongs to technical field of high-molecular polymer, possesses more particularly to one kind
The composite nano antibacterial agent of bacterium specific recognition capability and its application.
Background technology
Pathogenic microorganism wide variety and make a variation rapid so that antimicrobial therapy is faced with huge challenge always.Although
Antibiotic has clear and definite therapeutic effect to numerous cause pathogeny imcrobe infections, but in the game of antibiotic and pathogenic microorganism, resists
Raw element no longer has overwhelming dominance, and drug resistance all occur in many pathogenic microorganisms easily resisted in the past, cause to infect
The caused incidence of disease is continuously increased.Also in the new antibiotic of exploitation of trying one's best, although it researches and develops speed and lagged far behind people
In the speed of mutation of pathogenic microorganism；Severeer is that drug resistance problems show no sign of being resolved, increasingly severe on the contrary, is gone out
Having showed has " superbacteria " of drug resistance to several antibiotic, and it is even panic to cause global vigilance.Therefore, exploitation is new
Type possess bacterium specific recognition antibacterials and antibiotic method it is extremely urgent.
The content of the invention
To solve the technical problem of above-mentioned bacterial drug resistance, the invention discloses one kind to possess bacterium specific recognition capability
Composite nano antibacterial agent and its application.
To achieve the above object, the invention discloses a technical scheme, i.e. one kind to possess bacterium specific recognition capability
Composite nano antibacterial agent, be made up of Nano silver grain, the pyrroles's molecule of boron fluoride two and poly- galactolipin, the Nano silver grain structure
Into silver nanoparticle ball, the poly- galactolipin is poly- galactolipin chain, and the silver nanoparticle ball connects several poly- galactolipin chains respectively
One end, the other end of each poly- galactolipin chain is all connected with a pyrroles's molecule of boron fluoride two, all boron fluorides two
Pyrroles's molecule around silver nanoparticle ball, also forms spheroidal structure.
Further, the length of the poly- galactolipin chain is 30~60nm.
Yet further, the monomer of the poly- galactolipin is the full acetic acid esters of 2- methyacryloxyethyl galactolipins.
Yet further, the structural formula of the pyrroles's molecule of boron fluoride two is as shown in formula B：
Yet further, a diameter of 40~50 nm of the Nano silver grain.
Meanwhile present invention also offers another technical scheme, i.e., a kind of composite nano antibacterial agent is in bacterium specificity
Application in identification.
Further, the bacterium is pseudomonas aeruginosa, Escherichia coli, clostridium tetani or staphylococcus aureus
In one kind.
The selection principle of each component of composite nano antibacterial agent of the present invention：
1st, select poly- galactolipin and be because sugar can between albumen between interact, poly- galactolipin in itself but also with
Good biocompatibility so that the composite nano antibacterial agent being prepared can Intelligent Recognition bacterium, but also with higher thin
Born of the same parents' compatibility；The length for selecting poly- galactolipin chain is 30~60 nm, is one end connection sensitising agent because poly- galactolipin chain
Molecule, it is long, can not be made by resonance energy transfer nano-particle still have enhancing photodynamics antibacterial ability, it is too short then
Feature glycosyl molecular amounts are insufficient, and weaker to the targeting of various bacteria；
2nd, Nano silver grain is selected, is due to silver ion haptoreaction, causes microorganism to share component damage or produces work(
Can obstacle so as to realizing the purpose of antibacterial；To the diameter control of Nano silver grain between 40~50nm, reason is nano grain of silver
It may be easy to be directly entered cell interior by processes such as endocytosis if son is too small, and make Nano silver grain to the special of bacterium
Property recognition reaction weaken；
3rd, photosensitizer molecule possesses the photodynamics antibacterial effect of self-reinforcing in itself.
Therefore, under conditions of no light, poly- galactolipin chain carries Nano silver grain and realizes selectivity to cell
Targeting is identified, under conditions of having illumination, it is thin to targetting that poly- galactolipin chain carries Nano silver grain, photosensitizer molecule
Bacterium realizes stronger antibacterial action.
Beneficial effect：
Composite nano antibacterial agent particle prepared by the present invention to pseudomonas aeruginosa, Escherichia coli, clostridium tetani and
Staphylococcus aureus possesses selective recognition capability, and not by or it is few adsorbed by normal human cell, therefore
On the basis of the less toxic side effect of human body, antibacterial purpose is optionally realized.
Brief description of the drawings
Fig. 1 is the structural representation of composite nano antibacterial agent of the present invention；
Wherein, label is as follows in figure：
Nano silver grain 1, poly- galactolipin 2, the pyrroles's molecule of boron fluoride two.
Embodiment
In order to preferably explain the present invention, below in conjunction with the specific embodiment main contents that the present invention is furture elucidated, but
Present disclosure is not limited solely to following examples.
The preparation method of the composite nano antibacterial agent of the present invention, including following preparation process：
1) room temperature, nitrogen protective atmosphere enclose and stirring under, benzyl chlorobenzoyl chloride (1.5g, 8mmol) will be added
Into 2,4- dimethyl pyrroles (2.2mL) dichloromethane (90mL) solution, and 2,4- dimethyl pyrrole make with dichloromethane
Water process is removed with passing through before, obtains reaction system；Reaction system is heated to 25 DEG C, and reacts 6h；Again to the reaction system
It is interior addition triethylamine (3.88g, 38mmol), continue react 20min, then add boron trifluoride etherate (7.82g,
55mmol), reaction time 4h, the material of chemical formula shown in formula A is obtained；
2) under stirring, pyrroles (0.17mL, 2.38mmol) is added to sodium hydride (57.1mg2.38mmol)
In dimethyl sulfoxide (DMSO) suspension, after solution is colourless be changed into brown color after, reaction time 20min, add carbon disulfide
(0.14mL, 2.38mmol), continue stirring reaction, reaction time 25min, add chemistry shown in the formula A of step 1) preparation
The material (1.02g, 2.38mmol) of formula, reaction temperature are 40 DEG C, reaction time 15h, and post processing preparation is carried out to reaction solution
The pyrroles's molecule of boron fluoride two that there is reversible addion-fragmentation chain transfer polymerization to trigger activity is obtained, and molecular formula is as shown in B；
The operating process post-processed in the step 2) to reaction solution is：500ml water is added into reaction solution, then is used
Chloroform (50mL) is extracted, and extraction three times, then extract is merged and concentrated, and silica gel chromatographic column point is carried out to concentrate
From obtaining the pyrroles's molecule of boron fluoride two.
3) the full acetic acid esters of galactose monomers 2- methyacryloxyethyl galactolipins is added into Isosorbide-5-Nitrae-dioxane
(AcGEMA) the galactolipin polymerized monomer solution that mass concentration is 45~55%, is obtained；Then under ice water bath environment, add respectively
Enter azodiisobutyronitrile and the pyrroles's molecule of boron fluoride two of step 2) preparation, the mole of the azodiisobutyronitrile is galactolipin
The 0.8~1.2% of polymerized monomer, then in the case where nitrogen protective atmosphere encloses, reaction system is gradually heating to 70~75 DEG C, the reaction time
For 8~12h, ether is eventually adding as precipitating reagent, obtains solid polymer, and molecular formula is as shown in formula C；
The span of n in above-mentioned molecular formula C is controlled between 170~340, and the length for ensureing poly- galactolipin chain is
10~60nm.
4) dissolution of solid polymer for preparing the step 3) is into dichloromethane, obtain mass concentration be 20% it is poly-
Polymer solution；N- N-iodosuccinimides are added, and the mole of N- N-iodosuccinimides is 10 times of polymer, in room
Temperature stirring, nitrogen protective atmosphere enclose and dark condition under, react untill system is changed into red, reaction time 3h；Then add
Precipitating reagent n-hexane, reaction obtain iodo macromolecular sensitising agent；
5) the iodo macromolecular sensitising agent polymer 100mg and hydrazine hydrate 10mmol co-dissolves prepared step 4) is arrived
In 20mL DMSO, and polymer deacetylation is reacted into 24h under 25 DEG C of nitrogen atmospheres, 1mL third is added into reaction system
Ketone terminating reaction, then reactant solution is placed in distilled water and dialysed, freeze-drying obtains polymer；
6) polymer prepared by step 5) is dissolved into deionized water, it is molten is configured to the polymerization that concentration is 250mg/mL
Liquid；By 100ml polymeric solutions and isometric silver nitrate solution (concentration 8mg/mL), low whipping speed is 800r/min bar
Be added separately under part in the aqueous solution, and the volume of the aqueous solution is 10000ml, then add sodium borohydride (2.34mmol,
89.9mg), stirring reaction 35min, composite nano antibacterial agent is obtained.
Preparation process is as follows：
Composite nano antibacterial agent as shown in Figure 1 is prepared, as shown in Figure 1, possesses the Nano silver grain 1 of antibacterial ability
Form silver nanoparticle ball, one end connection silver nanoparticle ball of each poly- galactolipin chain 2, the other end connection one of poly- galactolipin chain 2
The individual pyrroles's molecule 3 of boron fluoride two, all pyrroles's molecules of boron fluoride two around silver nanoparticle ball, also form spheroidal knot
Structure.
Antibiotic property test illustrates：
1st, cytotoxicity test：
With MEC, pass through MTT colorimetric method for determining polymethylacrylic acid N, N- dimethylamino ethyl esters
Galactolipin functional nanoparticle (composite nano antibacterial agent) prepared by functional nanoparticle and the present invention is giving illumination
(15min) and without cytotoxicity test is carried out under the conditions of care, using blanc cell culture as negative control experiments, and by survival rate
It is set as 100%, obtains such as table 1 below.
The cytotoxicity test data of table 1
As shown in Table 1, cell survival rate is higher represents weaker to the toxic side effect of cell, i.e., composite Nano of the invention resists
Microbial inoculum is smaller to the toxic side effect of cell.
2nd, antibacterial test：
Illumination and the non-illuminated conditions for giving same time respectively with above-mentioned concentration identical sample are taken, are obtained such as table 2 below
Shown bacteriostasis test data；
The bacteriostasis test data of table 2
As shown in Table 2, the bacteriostasis under non-illuminated conditions is weaker, and reason is that there was only silver particles in itself under non-illuminated conditions
Antibacterial action, without photodynamics antibacterial action, so the antibacterial ability under non-illuminated conditions is weaker than when having illumination condition.
Above two nano-particle possesses similar high-efficiency antimicrobial ability in the case where there is illumination condition, and reason is probably can be by
Bacterial adsorption, so as to effectively play the synergetic antibacterial effect of photodynamics and silver.Understood with reference to table 1, under equal conditions, galactolipin
The cytotoxicity of the nano-particle of functionalization is significantly lower than polymethylacrylic acid N, N- dimethylamino ethyl ester functionalized nano grain
Son；I.e. the nano-particle of galactolipin functionalization can keep effectively reducing antiseptic to human body while high-efficiency antimicrobial ability again
Side effect.
3rd, the antibacterial test of selectivity：
Using the composite nano antibacterial agent of non-iodo as fluorescence molecule, by 5nmol/mL fluorescence molecule solution respectively with
Laser confocal imaging test is carried out after HepG2 cells, NIH3T3 cell culture 30min, has obtained the selectivity suppression shown in table 3
Bacterium aptitude tests data；
The selective bacteriostasis test data of table 3
As shown in Table 3, pseudomonas aeruginosa and staphylococcus aureus inhale to the composite nano antibacterial agent fluorescence molecule
Attached is more, therefore strong to the selective antibiotic ability of this kind of bacterium, and people's renal epithelial cell, human lung cancer cell A549 are to compound
The absorption of nano antibacterial agent fluorescence molecule it is less, therefore not by or it is few adsorbed by normal human cell, reduce to people
The toxic side effect of body.
Claims (7)
- A kind of 1. composite nano antibacterial agent for possessing bacterium specific recognition capability, it is characterised in that：By Nano silver grain, fluorination The pyrroles's molecule of boron two and poly- galactolipin are formed, and the Nano silver grain forms silver nanoparticle ball, and the poly- galactolipin is poly- galactolipin Chain, the silver nanoparticle ball connect one end of several poly- galactolipin chains respectively, and each the poly- galactolipin chain is another End is all connected with a pyrroles's molecule of boron fluoride two, and all pyrroles's molecules of boron fluoride two also form class around silver nanoparticle ball Like chondritic.
- 2. the composite nano antibacterial agent according to claim 1 for possessing bacterium specific recognition capability, it is characterised in that：Institute The length for stating poly- galactolipin chain is 30~60nm.
- 3. the composite nano antibacterial agent according to claim 2 for possessing bacterium specific recognition capability, it is characterised in that：Institute The monomer for stating poly- galactolipin is the full acetic acid esters of 2- methyacryloxyethyl galactolipins.
- 4. the composite nano antibacterial agent according to claim 1 for possessing bacterium specific recognition capability, it is characterised in that：Institute The structural formula of the pyrroles's molecule of boron fluoride two is stated as shown in formula B：
- 5. according to the composite nano antibacterial agent for possessing bacterium specific recognition capability described in claim 1 or 2 or 3 or 4, it is special Sign is：A diameter of 40~50nm of the Nano silver grain.
- 6. application of the composite nano antibacterial agent in bacterium specific recognition according to any one in Claims 1 to 5.
- 7. application of the composite nano antibacterial agent according to claim 6 in bacterium specific recognition, it is characterised in that：Institute Bacterium is stated as one kind in pseudomonas aeruginosa, Escherichia coli, clostridium tetani or staphylococcus aureus.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1822867A (en) * | 2003-07-16 | 2006-08-23 | 诺瓦提斯公司 | Antimicrobial medical devices |
| WO2011104497A1 (en) * | 2010-02-24 | 2011-09-01 | University Of Exeter | Method for the preparation of a novel nanoparticle conjugate |
| CN105994358A (en) * | 2016-05-25 | 2016-10-12 | 武汉纺织大学 | Preparation method of composite nanometer antibacterial agent |
| CN106039310A (en) * | 2016-05-25 | 2016-10-26 | 武汉纺织大学 | Composite nano antibacterial agent and application thereof |
| US20160311877A1 (en) * | 2013-12-18 | 2016-10-27 | President And Fellows Of Harvard College | Crp capture/detection of gram positive bacteria |
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2017
- 2017-07-31 CN CN201710639308.4A patent/CN107441490B/en active Active
Patent Citations (5)
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|---|---|---|---|---|
| CN1822867A (en) * | 2003-07-16 | 2006-08-23 | 诺瓦提斯公司 | Antimicrobial medical devices |
| WO2011104497A1 (en) * | 2010-02-24 | 2011-09-01 | University Of Exeter | Method for the preparation of a novel nanoparticle conjugate |
| US20160311877A1 (en) * | 2013-12-18 | 2016-10-27 | President And Fellows Of Harvard College | Crp capture/detection of gram positive bacteria |
| CN105994358A (en) * | 2016-05-25 | 2016-10-12 | 武汉纺织大学 | Preparation method of composite nanometer antibacterial agent |
| CN106039310A (en) * | 2016-05-25 | 2016-10-26 | 武汉纺织大学 | Composite nano antibacterial agent and application thereof |
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