CN103881010B - A kind of high-molecular anti-bacteria material based on borneol - Google Patents
A kind of high-molecular anti-bacteria material based on borneol Download PDFInfo
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- CN103881010B CN103881010B CN201410081967.7A CN201410081967A CN103881010B CN 103881010 B CN103881010 B CN 103881010B CN 201410081967 A CN201410081967 A CN 201410081967A CN 103881010 B CN103881010 B CN 103881010B
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Abstract
The present invention relates to a kind of high-molecular anti-bacteria material based on borneol, this high-molecular anti-bacteria material taking the acryloyl derivatization borneol monomer of four kinds of different chiral configurations as raw material, forms macromolecule as anti-biotic material by polymerisation respectively. This chiral polymer material has good anti-adhesive and suppresses growth gram-positive bacteria, Gram-negative bacteria, fungi, this macromolecular material has good biocompatibility, non-toxic feature simultaneously, can be used as anti-biotic material for comprising medical science, food, health and field of Environment Protection, development potentiality is huge.
Description
Technical field
The present invention relates to a kind of high-molecular anti-bacteria material based on borneol. Belong to medical high polymer technical field, be applicable toComprising medical science, food, health and field of Environment Protection, is the antibacterial material of a kind of novel high polymer that suppresses microorganism adhering and growth thereofMaterial.
Background technology
In recent years, along with the increase year by year of bacterial infection disease example, the hospital infection control of medicine equipment is more and more subject to boundaryInterior personage's common concern, seems particularly urgent so prepare eco-friendly, to have high-efficiency antimicrobial performance macromolecular materialCut.
On the one hand, the atom of borneol compound forms polyhedron or multiring structure with hollow three-dimensional structural arrangement, is structureUnique chiral molecules. The borneol molecule with this unique texture belongs to natural terpenes compounds, is extensively present in plant,Also be widely used clinically, have the effects such as pain relieving, anticorrosion, calm, anti-inflammatory, to staphylococcus, streptococcus, pneumonia is twoCoccus, Escherichia coli etc. have inhibitory action, and the pathogenic dermatophyte of part is also had to obvious inhibitory action. On the other hand, chiralityBe the essential characteristic of life process, the organic molecule overwhelming majority who forms life entity is chiral molecules. When a chirality chemical combinationWhen thing enters life entity, its two enantiomters can show different biologically actives conventionally. For chiral drug, oneChiral isomer may be effectively, and another chiral isomer may be invalid or even harmful. For chiral material,Microorganism or cell also can perception material surface by surface receptor molecule chirality difference, and then produce whether to express and stickBehavior. So, the macromolecule material that chirality borneol molecule is prepared into by acryloyl group derivatization and then with covalent bond polymerizationMaterial, effectively the adhesion property of anti-bacteria to material surface, has important practical significance.
The application for a patent for invention of application number 03127103 relates to 2-phenyl-bornyl propionate derivative and synthetic method thereof,Reacting with borneol under catalyst action by 2-phenyl-propionic acid and derivative thereof, is that core texture has carried out entering one to borneolStep, to reach the selective inhibiting object to COX-2. Design and made borneol load have anti-inflammatory structural compounds, shouldCompound can and show the effect of higher pharmacologically active with COX-2 selectively acting.
Application number is that 98113045 application for a patent for invention relates to a kind of pure Chinese medicine external paste skin-cleaning medicine (Jiefuning), by root of Chinese trichosanthes,Rhizoma Sparganii, spina gleditsiae, pangolin, lycopodium calvatum, madder, akebi, the coptis, rheum officinale, the root of large-flowered skullcap, kelp, rosin, borneol 13 taste Chinese medicines and plantThing oil and beeswax composition, forming for scar is due to qi depression to blood stasis, and train of thought is obstructed, and knot is polymerized to the reason of shape, establishes invigorating blood circulationThe stasis of blood, dredges through promoting blood circulation, anti-inflammatory sterilization, and profit is supported the medication theory of skin, has go out spot, anti-inflammatory of blood circulation and channel invigorating, soft perpendicular dissipating bind, the scar that disappears and killsBacterium, profit are supported the effect of skin.
Above-mentioned prior art is not all mentioned chirality borneol molecule by acryloyl group derivatization and then with radical polymerizationClose the macromolecular material being prepared into.
Summary of the invention
The object of the invention is to prepare a kind of macromolecular material with anti-microbial property, this material is anti-bacteria effectivelyAdhere to and growth, be with a wide range of applications comprising on medical science, food, health and field of Environment Protection.
For solving the problems of the technologies described above, the invention provides a kind of high-molecular anti-bacteria material based on borneol, this macromolecule is anti-Bacterium material taking four kinds not the borneol compound of isomorphism type and acryloyl group derivative as raw material, the borneol list of synthesizing propylene acidylateBody, and then form described high-molecular anti-bacteria material by polymerisation, its structure is as shown in the formula shown in (1):
Wherein R represents hydrogen atom or alkyl, n ∈ [10,5000], and formula (1) is chirality borneol polymer.
As preferred embodiment of the present invention, the configuration of borneol compound comprises D-borneol, L-Borneol, Iso-dragonBrain.
As preferred embodiment of the present invention, selected borneol is one-component or mixture.
As preferred embodiment of the present invention, acryloyl group derivative comprises acryloyl chloride, methacrylic chloride, thirdOlefin(e) acid, methacrylic acid.
As preferred embodiment of the present invention, in alkaline environment, borneol rubs with reacting of acryloyl group derivativeYou are than being 1:2-2:1, and reaction temperature is 30-60 DEG C, and the reaction time is 6-24h, after reaction finishes, make acryloyl by purifyingThe borneol monomer of changing.
As preferred embodiment of the present invention, polymerisation is radical polymerization, and the initator using is for producingThe initator of raw free radical, preferably includes persulfate system, azo-compound system, diphenyl peroxide methyl amine system, withAnd photo-thermal system.
As preferred embodiment of the present invention, the initator that polymerisation adopts be preferably azodiisobutyronitrile orAmmonium persulfate solution, solvent adopts methyl alcohol or carrene.
The present invention lays special stress on protecting the antibacterial application of the described high-molecular anti-bacteria material based on borneol.
The preparation-obtained high-molecular anti-bacteria material of the present invention has gram-positive bacteria, Gram-negative bacteria, fungiAnti-adhesion and inhibition growth preferably, this macromolecular material has good biocompatibility, non-toxic feature simultaneously,Can be used as anti-biotic material for comprising medical science, food, health and field of Environment Protection, development potentiality is huge.
Brief description of the drawings
Below in conjunction with accompanying drawing, the present invention is further described
Fig. 1 is the CD collection of illustrative plates of the L-Borneol polymer that is prepared from of the embodiment of the present invention 1;
Fig. 2 is that experimental example 1 bacterium liquid of the present invention is cultivated PMMA and the PBA material inhibition Escherichia coli of 5 days in antibacterial experiment altogetherAdhesiving effect figure;
Fig. 3 is that experimental example 2 bacterium liquid of the present invention are cultivated PMMA and the golden yellow Portugal of the PBA material inhibition of 4 days in antibacterial experiment altogetherGrape coccus adhesiving effect figure;
Fig. 4 is PMMA and the PBA material inhibition Escherichia coli of 3 days in experimental example 3 confinement growth antibacterial experiments of the present inventionGrowth result figure.
Detailed description of the invention
Below in conjunction with embodiment, the invention will be further described:
Embodiment 1
Get the propylene acidylate L-Borneol monomer of 200 μ g in reaction bulb, add the methyl alcohol of 200 μ L that solvent environment is provided, thenAdd concentration be the ammonium persulfate solution 10 μ L of 0.1mg ∕ mL as initator, under 60 DEG C of conditions, react 4h. This polymerization toolHave simple to operate, the advantage that extent of polymerization is high, the molecular weight of polymer can reach 250,000.
Accompanying drawing 1 is prepared synthetic L-Borneol polymer CD collection of illustrative plates for the embodiment of the present invention 1. Find out from CD map analysis, institute closesThe polymer becoming has optical activity.
Embodiment 2
The propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of getting 200 μ g inIn reaction bulb, add the methyl alcohol of 400 μ L that solvent environment is provided, then add concentration be 0.1mg ∕ mL ammonium persulfate solution 20 μ L doFor initator, under 70 DEG C of conditions, react 6h. The molecular weight of this polymerization polymer can reach 530,000.
Embodiment 3
The propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of getting 200 μ g inIn reaction bulb, add the methyl alcohol of 300 μ L that solvent environment is provided, then add the azodiisobutyronitrile of 1.32mg as initator, 60Under DEG C condition, react 4h. The molecular weight of this polymerization polymer can reach 200,000.
Embodiment 4
The propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of getting 200 μ g inIn reaction bulb, add the methyl alcohol of 400 μ L that solvent environment is provided, then add the azodiisobutyronitrile of 1.58mg as initator, 70Under DEG C condition, react 5h. This polymerization has simple to operate, the advantage that extent of polymerization is high, the molecule of this polymerization polymerMeasure and the highlyest can reach 740,000.
Embodiment 5
The propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of getting 200 μ g inIn reaction bulb, add the carrene of 300 μ L that solvent environment is provided, then add the azodiisobutyronitrile of 1.58mg as initiationAgent, reacts 4h under 60 DEG C of conditions. This polymerization has simple to operate, the advantage that extent of polymerization is high, this polymerization polymerMolecular weight the highlyest can reach 180,000.
Embodiment 6
Take L-Borneol 1.00g, add the oxolane of 0.98g triethylamine and 15mL, stirring and dissolving under 35 DEG C of conditions.The acryloyl chloride of 0.88g is added drop-wise in above-mentioned system to stirring reaction 18h under 35 DEG C of conditions. After reaction finishes, purify and make thirdThe L-Borneol monomer (LBA) of alkene acidylate. Product purity 94%, productive rate 95%.
Embodiment 7
Take D-borneol 1.00g, add the oxolane of 0.90g triethylamine and 20mL, stirring and dissolving under 40 DEG C of conditions.The methacrylic chloride of 1.02g is added drop-wise in above-mentioned system to stirring reaction 15h under 40 DEG C of conditions. After reaction finishes, the system of purifyingObtain the D-borneol monomer (DBA) of propylene acidylate. Product purity 97%, productive rate 95%.
Embodiment 8
Take Iso-borneol 1.00g, add the oxolane of 1.05g triethylamine and 25mL, under 30 DEG C of conditions, stir moltenSeparate. The acrylic acid of 0.98g is added drop-wise in above-mentioned system to stirring reaction 24h under 30 DEG C of conditions. After reaction finishes, purification makesThe Iso-borneol monomer (IBA) of propylene acidylate. Product purity 95%, productive rate 95%.
Experimental example:
The prepared anti-biotic material of experimental example 1 the present invention carries out bacterium liquid and cultivates altogether antibacterial experiment.
Get the above-mentioned three kinds of not macromolecular material of isomorphism type (synthetic gathering of arbitrary routine method in embodiment 1 to embodiment 5Compound) make respectively film, be placed in 107In the physiological saline of the e. coli concentration of CFU ∕ mL, leave standstill cultivate, respectively at 10min,1h, 12h, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 day time period take out and use aseptic water washing three times, and dry, microscopy is observed.
Experiment showed, that borneol polymeric material can suppress colibacillary adhesion, film transparent pollution, microscopic examinationFilm surface does not have microorganism adhering, and the antibacterial time can reach 5 days. With kind polyester PMMA polymeric film material in 10min justFind that there is Escherichia coli and adhere to surface.
Accompanying drawing 2 is cultivated in antibacterial experiment not isomorphism type PBA material 5 days of PMMA and three kinds altogether for experimental example 1 bacterium liquid of the present inventionInhibition Escherichia coli adhesiving effect figure. As can be seen from Figure, the polymeric material of synthesized of the present invention has stronger inhibitionThe effect that Escherichia coli adhere to.
The prepared anti-biotic material of experimental example 2 the present invention carries out bacterium liquid and cultivates altogether antibacterial experiment.
Get the above-mentioned three kinds of not macromolecular material of isomorphism type (synthetic gathering of arbitrary routine method in embodiment 1 to embodiment 5Compound) make respectively film, be placed in 107In the physiological saline of the staphylococcus aureus concentration of CFU ∕ mL, leave standstill and cultivate, respectively at10min, 1h, 12h, 1 day, 2 days, 3 days, 4 days, 5 day time period take out and use aseptic water washing three times, and dry, microscopy is observed.
Experiment showed, that borneol polymeric material can suppress the adhesion of staphylococcus aureus, film transparent pollution, micro-Sem observation film surface does not have microorganism adhering, and the antibacterial time can reach 4 days. And there is part similar structures with borneol polymerPMMA polymeric film material just finds that there is staphylococcus aureus and adheres to surface in 10min.
Accompanying drawing 3 is cultivated in antibacterial experiment not isomorphism type PBA material 4 days of PMMA and three kinds altogether for experimental example 2 bacterium liquid of the present inventionInhibition staphylococcus aureus adhesiving effect figure. As can be seen from Figure, the polymeric material of synthesized of the present invention has inhibitionThe effect that staphylococcus aureus adheres to.
The prepared anti-biotic material of experimental example 3 the present invention carries out confinement growth antibacterial experiment.
Above-mentioned macromolecular material (the synthetic polymer of arbitrary routine method in embodiment 1 to embodiment 5) is made to film, cut outBe cut into toroidal, be fixed on sterile solid culture medium, it is 10 that Huan center splashes into concentration7The bacterium liquid of CFU ∕ mL, cultivates oneThe section time, observe colony growth situation.
Experiment showed, that borneol polymer ring film can suppress the extension life of Escherichia coli, staphylococcus aureus preferablyLong, film transparent pollution, the antibacterial time was up to 3 days. With kind polyester PMMA polymeric film material, in 1 day, annulus outside is justOvergrow with bacterium colony.
Accompanying drawing 4 is PMMA and the PBA material inhibition large intestine bar of 3 days in experimental example 3 confinement growth antibacterial experiments of the present inventionBacteria growing design sketch. As can be seen from Figure, the polymeric material of synthesized of the present invention has stronger inhibition Escherichia coli extensionThe fungistatic effect of growth.
The prepared anti-biotic material of experimental example 4 the present invention carries out the experiment of OD pH-value determination pH.
Get above-mentioned macromolecular material (the synthetic polymer of arbitrary routine method in embodiment 1 to embodiment 5) and make film, putIn 107In the bacteria suspension of CFU ∕ mL concentration, leave standstill and cultivate after a period of time, phosphate buffer cleans three times, blots membrane materialMoisture, is placed in respectively the concussion of 50mL aseptic culture fluid by homalographic membrane material and cultivates. Respectively 0h, 3h, 6h, 9h, 12h,15h, 24h respectively take out 1mL bacterium liquid, measure its OD value.
Found that the Escherichia coli that PMMA membrane material is corresponding, the bacterium liquid OD value of staphylococcus aureus increase fast, andThe Escherichia coli that polymeric material of the present invention is corresponding, the bacterium liquid OD value of staphylococcus aureus are lower.
The prepared anti-biotic material of experimental example 5 the present invention carries out colony counting method determination experiment.
Get above-mentioned macromolecular material (the synthetic polymer of arbitrary routine method in embodiment 1 to embodiment 5) and make film, putIn 107In the certain volume bacteria suspension of CFU ∕ mL concentration, after standing cultivation a period of time, take out membrane material, super with phosphate bufferSound cleans, and after gradient dilution, gets the dull and stereotyped coating of bacterium liquid of 100 μ L dilutions and cultivates, and calculates dull and stereotyped single clump count, anti-to measure materialBacterium performance.
Found that the obviously flat board more corresponding than polymeric material of the present invention of flat board list bacterium colony that PMMA membrane material is correspondingSingle bacterium colony is wanted a how upper order of magnitude. Further illustrate polymeric material of the present invention to Escherichia coli, staphylococcus aureusAnd fungi has stronger anti-adhesion effect, antibiotic rate reaches 92%.
Above embodiment shows and has described general principle of the present invention and principal character and advantage of the present invention. The industryTechnical staff should understand, the present invention is not restricted to the described embodiments, in above-described embodiment and description, describe justPrinciple of the present invention is described, instead of limits the scope of the invention by any way, without departing from the scope of the invention,The present invention also has various changes and modifications, and these changes and improvements all fall in claimed scope.
Claims (9)
1. the high-molecular anti-bacteria material based on borneol, is characterized in that, this high-molecular anti-bacteria material is with four kinds of isomorphism types notBorneol compound and acryloyl group derivative be raw material, the borneol monomer of synthesizing propylene acyl derivatization, and then anti-by polymerizationShould form described high-molecular anti-bacteria material, its structure is as shown in the formula shown in (1):
Wherein R represents hydrogen atom or alkyl, n ∈ [10,5000], and formula (1) is chirality borneol polymer.
2. high-molecular anti-bacteria material according to claim 1, is characterized in that, the configuration of borneol compound comprises D-dragonBrain, L-Borneol, Iso-borneol.
3. high-molecular anti-bacteria material according to claim 1 and 2, is characterized in that, selected borneol is one-component or mixedCompound.
4. high-molecular anti-bacteria material according to claim 1, is characterized in that, acryloyl group derivative comprises acryloylChlorine, methacrylic chloride, acrylic acid, methacrylic acid.
5. high-molecular anti-bacteria material according to claim 1, is characterized in that, in alkaline environment, and borneol and acryloylThe reaction mol ratio of radical derivative is 1:2-2:1, and reaction temperature is 30-60 DEG C, and the reaction time is 6-24h, and reaction finishes rear logicalCross the borneol monomer that purifying makes propylene acidylate.
6. high-molecular anti-bacteria material according to claim 1, is characterized in that, polymerisation is radical polymerization.
7. high-molecular anti-bacteria material according to claim 6, is characterized in that, the initator that polymerisation adopts comprisesPersulfate system, azo-compound system or diphenyl peroxide methyl amine system.
8. high-molecular anti-bacteria material according to claim 7, is characterized in that, the initator adopting is azo two isobutylsNitrile or ammonium persulfate solution, solvent adopts methyl alcohol or carrene.
9. according to the antibacterial application of the high-molecular anti-bacteria material described in claim 1-6 any one.
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| CN113121810B (en) * | 2019-12-31 | 2022-05-24 | 华南理工大学 | Borneol-based polymer and preparation method and application thereof |
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| CN115124652A (en) * | 2022-04-28 | 2022-09-30 | 李柏欣 | Polymer with antibacterial effect and composite material thereof |
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