CN103881010A - Borneol-based macromolecule antibacterial material - Google Patents
Borneol-based macromolecule antibacterial material Download PDFInfo
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- CN103881010A CN103881010A CN201410081967.7A CN201410081967A CN103881010A CN 103881010 A CN103881010 A CN 103881010A CN 201410081967 A CN201410081967 A CN 201410081967A CN 103881010 A CN103881010 A CN 103881010A
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Abstract
The invention relates to a borneol-based macromolecule antibacterial material. According to the macromolecule antibacterial material, four acrylyl-derivative borneol monomers of different chiral configurations are taken as raw materials, and macromolecules are generated by virtue of a polymerization reaction to be taken as the antibacterial material. A chiral macromolecule material has good anti-adhesive and growth-inhibiting effects on gram-positive bacterium, gram-negative bacterium and fungus, also has the characteristics of good biocompatibility and nontoxicity, can be taken as the antibacterial material applied to the fields of medicines, foods, health, and environmental protection and has a huge development potential.
Description
Technical field
The present invention relates to a kind of high-molecular anti-bacteria material based on borneol.Belonging to medical polymer technical field, be applicable to comprise medical science, food, health and field of Environment Protection, is a kind of novel high polymer anti-biotic material that suppresses microorganism adhering and growth thereof.
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 the common concern of personage in boundary, seems particularly urgent so prepare eco-friendly, to have high-efficiency antimicrobial performance macromolecular material.
On the one hand, the atom of borneol compound forms polyhedron or polynuclear plane with hollow three-dimensional structural arrangement, is the chiral molecules of structure uniqueness.The borneol molecule with this unique texture belongs to natural terpenes compounds, extensively be present in plant, also be widely used clinically, there is the effects such as pain relieving, anticorrosion, calm, anti-inflammatory, to staphylococcus, suis, pneumococcus, intestinal bacteria etc. have restraining effect, and the pathogenic dermatophytes of part is also had to obvious restraining effect.On the other hand, chirality is the essential characteristic of vital process, and the organic molecule overwhelming majority who forms life entity is chiral molecules.In the time that a chipal compounds enters life entity, its two enantiomers can show different biological activitys conventionally.For chiral drug, a chiral isomer may be effectively, and another chiral isomer may be invalid or even harmful.For chiral material, the chirality difference that microorganism or cell also can perception material surfaces by surface receptor molecule, and then produce the behavior of sticking of whether expressing.So, the macromolecular material that chirality borneol molecule is prepared into by acryl derivatize and then with covalent linkage polymerization, 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, react with borneol under catalyst action by 2-phenyl-propionic acid and derivative thereof, be that core texture has carried out further to borneol, to reach the selective inhibiting object to COX-2.Designed and made borneol load have anti-inflammatory structural compounds, this compound 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), formed with vegetables oil and beeswax by Snakegourd Root, Rhizoma Sparganii, spina gleditsiae, Squama Manis, Herba Lycopodii, madder, akebi, the coptis, rheum officinale, the root of large-flowered skullcap, kelp, rosin, borneol 13 taste Chinese medicines, due to qi depression to blood stasis for cicatrization, train of thought is obstructed, knot is polymerized to the reason of shape, establish promoting blood circulation and removing blood stasis, dredge through promoting blood circulation, anti-inflammatory sterilization, profit is supported the medication theory of skin, has go out spot, anti-inflammatory sterilization, profit of blood circulation and channel invigorating, soft perpendicular dissipating bind, the scar that disappears and supports the effect of skin.
Above-mentioned prior art is not all mentioned chirality borneol molecule by acryl derivatize and then the macromolecular material prepared with radical polymerization.
Summary of the invention
The object of the invention is to prepare a kind of macromolecular material with anti-microbial property, this material effectively anti-bacteria adheres to and growth, is 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 high-molecular anti-bacteria material taking four kinds not the borneol compound of isomorphism type and acryl derivative as raw material; the borneol monomer of synthesizing propylene acidylate; and then form described high-molecular anti-bacteria material by polyreaction, 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 polymkeric substance.
As preferred embodiment of the present invention, the configuration of borneol compound comprises D-borneol, L-Borneol, Iso-borneol.
As preferred embodiment of the present invention, selected borneol is one-component or mixture.
As preferred embodiment of the present invention, acryl derivative comprises acrylate chloride, methacrylic chloride, vinylformic acid, methacrylic acid.
As preferred embodiment of the present invention, in alkaline environment, borneol is 1:2-2:1 with the mol ratio of reacting of acryl derivative, and temperature of reaction is 30-60 DEG C, and the reaction times is 6-24h, makes the borneol monomer of propylene acidylate after reaction finishes by purifying.
As preferred embodiment of the present invention, polyreaction is radical polymerization, and the initiator using is the initiator that can produce free radical, preferably includes persulphate system, azo-compound system, diphenyl peroxide methylamine system, and photo-thermal system.
As preferred embodiment of the present invention, the initiator that polyreaction adopts is preferably Diisopropyl azodicarboxylate or ammonium persulfate solution, and solvent adopts methyl alcohol or methylene dichloride.
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 good anti-adhesion and suppresses growth gram-positive microorganism, Gram-negative bacteria, fungi, this macromolecular material has good biocompatibility, nontoxicity 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 polymkeric substance 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 intestinal bacteria adhesiving effect figure of 5 days in antibacterial experiment altogether;
Fig. 3 is that experimental example 2 bacterium liquid of the present invention are cultivated PMMA and the PBA material inhibition streptococcus aureus adhesiving effect figure of 4 days in antibacterial experiment altogether;
Fig. 4 is PMMA and the PBA material inhibition Escherichia coli Growth design sketch of 3 days in experimental example 3 confinement growth antibacterial experiments of the present invention.
Embodiment
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 flask, add the methyl alcohol of 200 μ L that solvent environment is provided, then add concentration be the ammonium persulfate solution 10 μ L of 0.1mg ∕ mL as initiator, under 60 DEG C of conditions, react 4h.This polymerization process has simple to operate, the advantage that extent of polymerization is high, and the molecular weight of polymkeric substance can reach 250,000.
Accompanying drawing 1 is prepared synthetic L-Borneol polymkeric substance CD collection of illustrative plates for the embodiment of the present invention 1.Find out from CD map analysis, the polymkeric substance of synthesized has opticity.
Embodiment 2
Get the propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of 200 μ g in reaction flask; add the methyl alcohol of 400 μ L that solvent environment is provided; add again concentration be the ammonium persulfate solution 20 μ L of 0.1mg ∕ mL as initiator, under 70 DEG C of conditions, react 6h.The molecular weight of this polymerization process polymkeric substance can reach 530,000.
Embodiment 3
Get the propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of 200 μ g in reaction flask; add the methyl alcohol of 300 μ L that solvent environment is provided; add again the Diisopropyl azodicarboxylate of 1.32mg as initiator, under 60 DEG C of conditions, react 4h.The molecular weight of this polymerization process polymkeric substance can reach 200,000.
Embodiment 4
Get the propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of 200 μ g in reaction flask; add the methyl alcohol of 400 μ L that solvent environment is provided; add again the Diisopropyl azodicarboxylate of 1.58mg as initiator, under 70 DEG C of conditions, react 5h.This polymerization process has simple to operate, the advantage that extent of polymerization is high, and the molecular weight of this polymerization process polymkeric substance is the highest can reach 740,000.
Embodiment 5
Get the propylene acidylate borneol monomer (the synthetic monomer of arbitrary routine method in embodiment 6 to embodiment 8) of 200 μ g in reaction flask; add the methylene dichloride of 300 μ L that solvent environment is provided; add again the Diisopropyl azodicarboxylate of 1.58mg as initiator, under 60 DEG C of conditions, react 4h.This polymerization process has simple to operate, the advantage that extent of polymerization is high, and the molecular weight of this polymerization process polymkeric substance is the highest can reach 180,000.
Embodiment 6
Take L-Borneol 1.00g, add the tetrahydrofuran (THF) of 0.98g triethylamine and 15mL, stirring and dissolving under 35 DEG C of conditions.The acrylate 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 the L-Borneol monomer (LBA) of propylene acidylate.Product purity 94%, productive rate 95%.
Embodiment 7
Take D-borneol 1.00g, add the tetrahydrofuran (THF) 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, purify and make the D-borneol monomer (DBA) of propylene acidylate.Product purity 97%, productive rate 95%.
Embodiment 8
Take Iso-borneol 1.00g, add the tetrahydrofuran (THF) of 1.05g triethylamine and 25mL, stirring and dissolving under 30 DEG C of conditions.The vinylformic 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, purify and make the 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 above-mentioned three kinds not the macromolecular material of isomorphism type (the synthetic polymkeric substance of arbitrary routine method in embodiment 1 to embodiment 5) make respectively film, be placed in 10
7in the physiological saline of the e. coli concentration of CFU ∕ mL, leave standstill and cultivate, take out and use aseptic water washing three times respectively at 10min, 1h, 12h, 1 day, 2 days, 3 days, 4 days, 5 days, 6 days, 7 day time period, dry, microscopy is observed.
Experiment showed, that borneol polymer materials can suppress colibacillary adhesion, film transparent pollution, microscopic examination film surface does not have microorganism adhering, and the antibacterial time can reach 5 days.In 10min, just find that there is intestinal bacteria with kind polyester PMMA polymeric film material and adhere to surface.
Accompanying drawing 2 is cultivated in antibacterial experiment the not isomorphism type PBA material inhibition intestinal bacteria adhesiving effect figure of 5 days of PMMA and three kinds altogether for experimental example 1 bacterium liquid of the present invention.As can be seen from Figure, the polymer materials of synthesized of the present invention has the effect that stronger inhibition intestinal bacteria adhere to.
The prepared anti-biotic material of experimental example 2 the present invention carries out bacterium liquid and cultivates altogether antibacterial experiment.
Get above-mentioned three kinds not the macromolecular material of isomorphism type (the synthetic polymkeric substance of arbitrary routine method in embodiment 1 to embodiment 5) make respectively film, be placed in 10
7in the physiological saline of the streptococcus aureus concentration of CFU ∕ mL, leave standstill and cultivate, take out and use aseptic water washing three times respectively at 10min, 1h, 12h, 1 day, 2 days, 3 days, 4 days, 5 day time period, dry, microscopy is observed.
Experiment showed, that borneol polymer materials can suppress the adhesion of streptococcus aureus, film transparent pollution, microscopic examination film surface does not have microorganism adhering, and the antibacterial time can reach 4 days.The PMMA polymeric film material that has a part similar structures with borneol polymkeric substance just finds that there is streptococcus aureus and adheres to surface in 10min.
Accompanying drawing 3 is cultivated in antibacterial experiment the not isomorphism type PBA material inhibition streptococcus aureus adhesiving effect figure of 4 days of PMMA and three kinds altogether for experimental example 2 bacterium liquid of the present invention.As can be seen from Figure, the polymer materials of synthesized of the present invention has the effect that streptococcus aureus adheres to that suppresses.
The prepared anti-biotic material of experimental example 3 the present invention carries out confinement growth antibacterial experiment.
Above-mentioned macromolecular material (the synthetic polymkeric substance of arbitrary routine method in embodiment 1 to embodiment 5) is made to film, be cut into toroidal, be fixed on sterile solid substratum, it is 10 that Huan center splashes into concentration
7the bacterium liquid of CFU ∕ mL, cultivates for some time, observes colony growth situation.
Experiment showed, that borneol polymer ring film can suppress the epitaxy of intestinal bacteria, streptococcus aureus preferably, film transparent pollution, the antibacterial time was up to 3 days.With kind polyester PMMA polymeric film material in 1 day annulus outside just overgrow with bacterium colony.
Accompanying drawing 4 is PMMA and the PBA material inhibition Escherichia coli Growth design sketch of 3 days in experimental example 3 confinement growth antibacterial experiments of the present invention.As can be seen from Figure, the polymer materials of synthesized of the present invention has the stronger epitaxially grown fungistatic effect of inhibition intestinal bacteria.
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 polymkeric substance of arbitrary routine method in embodiment 1 to embodiment 5) and make film, be placed in 10
7in the bacteria suspension of CFU ∕ mL concentration, leave standstill and cultivate after for some time, phosphoric acid buffer cleans three times, blots the moisture of mould material, homalographic mould material is placed in respectively to the concussion of 50mL aseptic culture fluid and cultivates.Respectively take out 1mL bacterium liquid at 0h, 3h, 6h, 9h, 12h, 15h, 24h respectively, measure its OD value.
The bacterium liquid OD value that found that intestinal bacteria that PMMA mould material is corresponding, streptococcus aureus increases fast, and the bacterium liquid OD value of intestinal bacteria corresponding to polymer materials of the present invention, streptococcus aureus is 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 polymkeric substance of arbitrary routine method in embodiment 1 to embodiment 5) and make film, be placed in 10
7in the certain volume bacteria suspension of CFU ∕ mL concentration, after standing cultivation for some time, take out mould material, use phosphoric acid buffer ultrasonic cleaning, after gradient dilution, get the dull and stereotyped coating cultivation of bacterium liquid of 100 μ L dilutions, calculate dull and stereotyped single colony number, to measure material anti-microbial property.
Found that the obviously flat board list bacterium colony how upper order of magnitude more corresponding than polymer materials of the present invention of flat board list bacterium colony that PMMA mould material is corresponding.Further illustrate polymer materials of the present invention intestinal bacteria, streptococcus aureus and fungi are had to stronger anti-adhesion effect, antibiotic rate reaches 92%.
Above embodiment shows and has described ultimate principle of the present invention and principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; that in above-described embodiment and specification sheets, describes just illustrates principle of the present invention; instead of limit 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; it is characterized in that; this high-molecular anti-bacteria material taking four kinds not the borneol compound of isomorphism type and acryl derivative as raw material; the borneol monomer of synthesizing propylene acyl derivatize; and then form described high-molecular anti-bacteria material by polyreaction, 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 polymkeric substance.
2. high-molecular anti-bacteria material according to claim 1, is characterized in that, the configuration of borneol compound comprises D-borneol, 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 mixture.
4. high-molecular anti-bacteria material according to claim 1, is characterized in that, acryl derivative comprises acrylate chloride, methacrylic chloride, vinylformic acid, methacrylic acid.
5. high-molecular anti-bacteria material according to claim 1, is characterized in that, in alkaline environment; borneol is 1:2-2:1 with the mol ratio of reacting of acryl derivative; temperature of reaction is 30-60 DEG C, and the reaction times is 6-24h, makes the borneol monomer of propylene acidylate after reaction finishes by purifying.
6. high-molecular anti-bacteria material according to claim 1, is characterized in that, polyreaction is radical polymerization.
7. radical polymerization according to claim 6, is characterized in that, the initiator that polyreaction adopts comprises persulphate system, azo-compound system, diphenyl peroxide methylamine system and photo-thermal system.
8. polyreaction according to claim 7, is characterized in that, the initiator adopting is Diisopropyl azodicarboxylate or ammonium persulfate solution, and solvent adopts methyl alcohol or methylene dichloride.
9. according to the antibacterial application of the high-molecular anti-bacteria material described in claim 1-6 any one.
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| JPH01180514A (en) * | 1988-01-13 | 1989-07-18 | Hitachi Chem Co Ltd | Resin composition for spectacle lens and spectacle lens |
| CN1488620A (en) * | 2003-08-22 | 2004-04-14 | 中国科学院长春应用化学研究所 | 2-phenyl-camphol propionate derivativ and synthesizing method thereof |
| US20060115448A1 (en) * | 2004-08-18 | 2006-06-01 | Tew Gregory N | Amphiphilic polynorbornene derivatives and methods of using the same |
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