CN106215239B - A kind of preparation method of crosslinked antimicrobial type acellular matrix material - Google Patents
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Abstract
The invention discloses a kind of preparation methods of antimicrobial form acellular matrix material.The present invention is crosslinked acellular matrix material using oxidation chitosan quaternary ammonium salt, crosslinking is formed using between the active group on the multiple aldehyde radicals and acellular matrix on oxidation chitosan quaternary ammonium salt, improve the structural stability of material, chitosan quaternary ammonium salt is grafted in acellular matrix material simultaneously, to assign acellular matrix material excellent antibacterial bacteriostasis property.The crosslinking of material and endowing antibacterial can be combined into one by this method, are a kind of preparation methods of novel functional acellular matrix material, be can be widely applied to technical field of biological material.
Description
Technical field
The present invention relates to a kind of preparation methods of antimicrobial form acellular matrix material, are applied to technical field of biological material.
Background technique
Acellular matrix material is to handle host material by the method for physics, chemistry and biology, carry out de- cell processing,
Remove the material obtained after relevant antigen.It eliminates the cell component in natural material, remains matrix components, effectively drops
The low immunogenicity of natural material, while being able to maintain the basic structure and performance (such as macroscopical braiding structure, micro- of host material
View hole gap structure, physical mechanical strength etc.).Common acellular matrix material has acellular dermal matrix, de- cell cornea base
It is taken off under matter, human acellular amniotic membrane matrix, porcine aorta acellular matrix, ox (or pig) pericardium acellular matrix, intestinal mucosa thin
Cytoplasmic matrix, urethra acellular matrix, de- cellular cartilage, the reparation or tissue that can be used for skin, blood vessel, valve, the urinary tract etc. are filled out
It fills, is widely used to medical field (Zhang Chen, Wang Zhijun, the progress University Of Dalian of Gao Jingheng acellular tissue matrices
Journal, 2007,28(3): 57-60).
Immunogenicity, improvement physical mechanical property, raising degradation resistant ability can be eliminated or reduce by being crosslinked, preferably
Meet the needs used.Physical crosslinking method (such as hot dehydrogenation) fails extensively due to being confined to material surface and degree of cross linking degree is low
Using.Synthetic cross-linking agent is from a wealth of sources, can obtain specific molecular structure by the method for MOLECULE DESIGN, introduce multiple chemistry
Active group is crosslinked high into cross-linker molecules；But synthetic cross-linking agent (such as glutaraldehyde) is insufficient due to by-product and purity
Etc. reasons, be easy to cause crosslinking after Biocompatibility it is poor.Natural products and its derivative crosslinking agent (such as Geniposide), phase
Of less types to good biocompatibility, but often, the cost is relatively high for preparation and purification, can not extensive industrial application.
In recent years, with the progress of science, to aoxidize natural products derivative crosslinking agent of the natural polysaecharides as representative, at
For research hotspot.Such crosslinking agent forms multiple aldehyde radicals using natural carbohydrate as parent, by oxidation, so that carbohydrate be made to have crosslinking
Performance.Due to polysaccharide good biocompatibility, after being introduced into biomaterial, still ensure that crosslinking after material have good life
Object compatibility.For example, the oxidized sodium alginate that alginate oxidation is prepared is used as bio-medical material crosslinking agent, take
Obtained preferable effect (Hu, Y, Lju, L, Gu ZP, Dan, WH et al. Modification of collagen
With a natural derived cross-linker, alginate dialdehyde [J] CARBOHYDRATE
POLYMERS, 2014,102:324-332.) such crosslinking agent possesses the higher degree of cross linking, it is low to overcome physical crosslinking degree
Disadvantage；The shortcomings that possessing preferable biocompatibility, overcoming synthetic cross-linking agent poor biocompatibility.Since polysaccharide is with respect to valence
Honest and clean to be easy to get, preparation cost is relatively low, thus has broad application prospects, and is more satisfactory Biological cross-linker.
For biomaterial while treating disease, there is also some problems.It is found that either staying for a long time or in short term
It sets in the intracorporal biomaterial of people, can often cause various bacterium infections.It is reported that the catheter in blood vessel sense that the U.S. occurs in 1 year
Example of catching an illness just has 50,000 to 200,000, and the death rate is up to 20%.Moreover, these infection once occur, even if using on normal dose
Hundred times of drug can not be treated effectively, and the immune system of human body itself can not remove these bacteriums.According to statistics, 45% doctor
Institute's infection and biomaterial using it is related (progress [J] the macromolecule notification of Luo Jianbin antibacterial biological material, 2009,
3:58-60).And for the biomaterial for the treatment of body surface wound, burn, infection is also one of complication the most universal, its meeting
Cause wound a large amount of diffusate occur, decompose extracellular matrix protein and a variety of growth factors, hinders promoting epidermization and wound
Closure, to significantly affect the process of rehabilitation, it could even be possible to leading to the death of burning trauma patient, (Zhou Ying, zero, antiseptic dressing is ground perhaps
Study carefully the damage of progress China and repairs magazine, 2012,7(3): 307-310).As it can be seen that being either applied to body surface or intracorporal
Biomaterial has the function of that antibacterial bacteriostatic is the Premium Features that biomaterial needs to have, the improvement of biomaterial anti-microbial property
As one of the key technology for guaranteeing biomaterial service performance.
Now widely used anti-biotic material includes antibiotic, metal ion, quaternary ammonium salt, natural antibacterial material etc..Antibiosis
The use of element, is easy to produce drug resistance；That there may be cells if metal ion (as silver) is perishable, performance is unstable, at high cost
Etc. various problems；Common quaternary ammonium salt possesses good broad spectrum antibacterial, but often biocompatibility is bad；Natural antibacterial material
(such as chitosan) biocompatibility is excellent, and anti-microbial property is good, but dissolubility is poor, limits its application.
Chitosan quaternary ammonium salt is that the amino of chitosan is changed into quaternary ammonium salt group or grafting low molecule quaternary ammonium salt and is obtained
The product arrived.It belongs to polycationic compounds, have good water solubility, flocculability, biocompatibility, moisture absorbability and moisture retentivity and
The features such as better antibiotic property, therefore its application range is quite extensive.(Zhong Jing, Hong Yan, Chen Yong chitosan quaternary ammonium salt it is newest
Progress China's Tissue Engineering Study and clinical rehabilitation, 2008,12(6): 1115-1118).
Using the method for physical blending, chitosan quaternary ammonium salt is added in biomaterial, can assign biomaterial with
Antibacterial bacteriostatic function, is currently widely used method.However, lacking in chitosan quaternary ammonium molecules of salt with chemical reactivity
Group, it is difficult to form firm Covalent bonding together with biomaterial.The chitosan quaternary ammonium salt that physical blending is added is easy from life
Migration is generated in object material, is lost, and cannot generate permanent antibacterial bacteriostatic performance, it is difficult to achieve the desired results.
Therefore current biomaterial, it on the one hand needs to be crosslinked using the excellent crosslinking agent of biocompatibility,
Need to assign biomaterial simultaneously with good antibacterial bacteriostatic function.Current method can only often meet one of them.It can
Crosslinking is combined into one with antibacterial, biomaterial is assigned with antibiotic property while crosslinking? we hand in long-term biomaterial
In connection research, the new viewpoint of " crosslinking of functionalization scale " is proposed: i.e. while crosslinking, assigning biomaterial with other function
Energy.The viewpoint is found and is prepared functional form crosslinking agent of new generation for us and provides new approaches.Using having both bridging property and antibacterial
The crosslinking agent of property, not only can satisfy the needs of crosslinking, but also can assign material with anti-microbial property.
Chitosan quaternary ammonium salt is aoxidized, parent is chitosan, itself has good biocompatibility；Chitosan quaternary ammonium salt
After selective oxidation, the active aldehyde radical of multiple chemistry is generated, it is thus possible to firm crosslinking is formed between biomaterial,
Improve the degradation resistant ability of material；Chitosan quaternary ammonium salt structure has been accessed in biomaterial simultaneously, thus has been resisted with excellent
Bacterium bacteriostasis property due to generating firm covalent bond in cross-linking process, thus effectively prevents the migration and loss of antibacterial agent,
The shortcomings that overcoming previous methods.The crosslinking of biomaterial and endowing antibacterial can be combined into one by this method, while be reached
The dual purpose for generating cross-linking effect and endowing antibacterial is a kind of preparation side of novel functional acellular matrix material
Method can be widely applied to technical field of biological material.
Summary of the invention
The purpose of the present invention is provide a kind of preparation of antimicrobial form acellular matrix material in view of the deficiencies of the prior art
Method, it is realized by following technical measures.
A kind of preparation method of antimicrobial form acellular matrix material, it is characterized in that: weighing the acellular matrix of 100 parts by weight
Material is added the buffer that the pH value of 100~1000 parts by weight is 3.0~10.5, handles 10~60min at 20~65 DEG C；
Then the oxidation chitosan quaternary ammonium salt that the oxidizability of 1~20 parts by weight is 1~98% is added, handles 0.5~24.0 hour；It discards
The water of 200~1000 parts by weight is added in waste reaction solution, cleans 10~30 minutes；Cleaning waste liquid is discarded, 100~1000 weights are added
The buffer that the pH value of part is 3.0~10.5 is measured, the amino acid of 0.5~2.0 parts by weight is added, at 20~65 DEG C, processing 0.5
~4.0 hours；Waste liquid is discarded, the water of 200~1000 parts by weight is added, is cleaned 20~60 minutes；Discard waste liquid, it is added 100~
The lactic acid or sodium lactate of 0.1~1.0 parts by weight is added in the water of 300 parts by weight, at 20~35 DEG C, handles 30~90 minutes, will
Bath foam pH is adjusted to neutrality；Waste liquid is discarded, 30~42 DEG C of injection water of 200~1000 parts by weight is added, cleans 1~4h；It abandons
Waste liquid is removed, 30~42 DEG C of injection water of 200~1000 parts by weight is added, cleans 1~4h.
The preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the oxidation shell is poly-
Sugared quaternary ammonium salt refers to the chitosan quaternary ammonium salt for containing multiple aldehyde radicals in the structure formed after the chosen property oxidation of chitosan quaternary ammonium salt.
The preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the amino acid, is
Refer to glycine, arginine, lysine and histidine.
The preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the pH value is 3.0
~10.5 buffer, the pH are by using acetic acid-hydrochloric acid buffer solution, phosphate buffer solution, boric acid-borax buffering
Solution, NaHCO3- NaOH buffer solution reaches.
A kind of preparation method of antimicrobial form acellular matrix material described in claim 1, it is characterised in that this method is available
Cell is taken off in acellular dermal matrix, cell-eliminating coanea matrix, human acellular amniotic membrane matrix, porcine aorta acellular matrix, pericardium
Under matrix, intestinal mucosa in the preparation of acellular matrix, urethra acellular matrix, de- cellular cartilage.
Oxidation chitooligosaccharidequaternary quaternary ammonium salt used is pharmaceutical grade in the present invention, and other materials are to analyze pure or biological reagent.
This cross-linking method has the advantage that
(1) crosslinking degree is high:, can be with acellular matrix material since oxidation chitosan quaternary ammonium molecules of salt contains multiple aldehyde radicals
Amino in material etc. generates multiple spot and combines, and forms the crosslinking of higher degree.The antigenicity that acellular matrix material can be reduced, changes
Kind physical mechanical property and degradation resistance；
(2) antibacterial bacteriostatic performance is good: due to the stronger positive electricity of chitosan quaternary ammonium salt, having broad spectrum antibacterial, antibiotic property
Can be excellent, chitosan quaternary ammonium salt is introduced in the acellular matrix material after crosslinking, thus just impart acellular matrix material
With good antibacterial bacteriostatic function；
(3) antibacterial bacteriostatic performance is lasting: by the aldehyde radical and acellular matrix material in oxidation chitosan quaternary ammonium salt
The firm covalent bond of the formation such as amino, bond energy is big, and stability is high, thus effectively prevents the chitosan that physical blending process is also easy to produce
The migration of quaternary ammonium salt and the defect being lost, can keep its antibacterial bacteriostatic performance for a long time；
(4) good biocompatibility: in oxidation chitosan quaternary ammonium salt after aldehyde radical reaction, remaining chitosan quaternary ammonium alkali in structure
Group, and chitosan quaternary ammonium salt derives from chitosan, thus inherit the good biocompatibility of chitosan.After amino acid
Reason, it would be possible to which remaining aldehyde radical removes, and ensure that the good biocompatibility of cross-linked material；
(5) Modulatory character is good: can pass through the type of selective oxidation chitosan, control degree of oxidation, control crosslinking agent
Dosage, to control crosslinking degree and anti-microbial property；
(6) biodegradable: since chitosan quaternary ammonium salt has biodegradability, after being linked into biomaterial, still
The biological degradability of cross-linked material can be kept, its degradation property can be adjusted by crosslinking degree；
(7) biomaterial is assigned with good hydrophilic performance of keeping humidity: chitosan quaternary ammonium salt is introduced in biomaterial, it will
The performance of keeping humidity of chitosan quaternary ammonium salt is given to biomaterial, so that the material after crosslinking be made to have good hydrophilic, moisture retention
Energy；
(8) color is light: the collagen through oxidation chitosan quaternary ammonium salt crosslinking can keep white, after no glutaraldehyde cross-linking
Buff, also without the navy blue after genipin cross-linked；
(9) low in raw material price, can extensive industrialization: the oxidation excellent crosslinking agent phase such as chitosan quaternary ammonium salt and Geniposide
Than, cheaper, thus, this method can be applied to industrialized production, be widely used in technical field of biological material.
In conclusion the present invention is applied to the friendship of acellular matrix material to aoxidize chitosan quaternary ammonium salt as raw material
Connection, on the one hand can reduce the antigenicity of material, improve the structural stability and degradation resistant ability of material；Material can be assigned simultaneously
Material is a kind of preparation method of novel functional acellular matrix material, can widely be answered with good antibacterial bacteriostatic function
For technical field of biological material.
Specific embodiment
The present invention is specifically described below by example, it is necessary to which indicated herein to be, this example is served only for pair
Further explanation of the invention, and should not be understood as limiting the scope of the invention, the person skilled in the art in the field can
Some nonessential modifications and adaptations are made with the content according to foregoing invention.
Embodiment 1
(1) acellular allodermis matrix for weighing 100 parts by weight, is added in reactor；
(2) boric acid-borax buffer solution that the pH value of 130 parts by weight is 8.5 is added, rotates 30 points of kinds；
(3) 8 parts by weight of oxidation N- hydroxypropyltrimethylammonium chloride chitosan that oxidizability is 8% are weighed, 20 weight are dissolved in
In the distilled water of part；
(4) aqueous solution for aoxidizing chitosan quaternary ammonium salt is added in reactor, is warming up to 37 DEG C, react 16 hours,
Dereaction waste liquid；
(5) pure water of 300 parts by weight is added, cleans 20 minutes, removes waste liquid；
(6) boric acid-borax buffer solution that 37 DEG C of pH value of 100 parts by weight is 8.5 is added, 1.5 parts by weight are added
Lysine rotates 2 hours, removes waste liquid；
(7) pure water of 1000 parts by weight is added, cleans 30 minutes, removes waste liquid；
(8) pure water of 200 parts by weight is added, the lactic acid of 0.5 parts by weight is added, handles 1.5 hours, discards waste liquid；
(9) 37 DEG C of injection water of 500 parts by weight is added, cleans 1 hour；Cleaning solution is removed, addition 1000 is added
37 DEG C of injection water of parts by weight cleans 3 hours.
Embodiment 2
(1) the bovine pericardium acellular matrix for weighing 100 parts by weight, is added in reactor；
(2) acetic acid-hydrochloric acid buffer solution that the pH value of 200 parts by weight is 4.8 is added, rotates 60 points of kinds；
(3) 4 parts by weight of oxidation N, N, N- trimethyl chitin quaternary ammonium salt that oxidizability is 80% are weighed, 50 weight are dissolved in
In acetic acid-hydrochloric acid buffer solution that the pH value of part is 4.8；
(4) solution for aoxidizing chitosan quaternary ammonium salt is added in reactor, is warming up to 42 DEG C, rotated 8 hours, gone anti-
Answer waste liquid；
(5) pure water of 500 parts by weight is added, rotates 20 minutes, removes waste liquid；
(6) acetic acid-hydrochloric acid buffer solution that the pH value of 150 parts by weight is 4.8 is added, the smart ammonia of 0.5 parts by weight is added
Acid rotates 4 hours at 42 DEG C, removes waste liquid；
(7) pure water of 800 parts by weight is added, rotates 20 minutes, removes waste liquid；
(8) pure water of 100 parts by weight is added, the sodium lactate of 1.0 parts by weight is added, rotates 90 minutes, removes waste liquid；
(9) 42 DEG C of injection water of 1000 parts by weight is added, cleans 2 hours；Cleaning solution is removed, addition 500 is added
42 DEG C of injection water of parts by weight cleans 4 hours.
Embodiment 3
(1) human acellular amniotic membrane matrix for weighing 100 parts by weight, is added in reactor；
(2) NaHCO that the pH value of 100 parts by weight is 9.4 is added3- NaOH buffer solution rotates 20 points of kinds；
(3) 16 parts by weight of oxidation O- hydroxypropyl-trimethyl ammonium chloride N- trimethyl chitin that oxidizability is 5% are weighed, it is molten
Solution is in the pure water of 50 parts by weight；
(4) solution for aoxidizing chitosan quaternary ammonium salt is added in reactor, is warming up to 32 DEG C, rotated 24 hours, go
Waste reaction solution；
(5) pure water of 800 parts by weight is added, rotates 40 minutes, removes waste liquid；
(6) NaHCO that 150 parts by weight pH value are 9.4 is added3The glycine of 2.0 parts by weight is added in-NaOH buffer solution,
It is reacted 1 hour at 32 DEG C, removes waste liquid；
(7) pure water of 300 parts by weight is added, rotates 15 minutes, discards waste liquid；
(8) pure water of 300 parts by weight is added, the lactic acid of 1.0 parts by weight is added, rotates 40 minutes, discards waste liquid；
(9) 37 DEG C of injection water of 600 parts by weight is added, cleans 2 hours；Cleaning solution is removed, addition 1000 is added
32 DEG C of injection water of parts by weight cleans 4 hours；
(10) human acellular amniotic membrane matrix, freeze-drying are taken out.
Claims (5)
1. a kind of preparation method of antimicrobial form acellular matrix material, it is characterized in that: weighing the acellular matrix material of 100 parts by weight
Material is added the buffer that the pH value of 100~1000 parts by weight is 3.0~10.5, handles 10~60min at 20~65 DEG C；So
The oxidation chitosan quaternary ammonium salt that the oxidizability of 1~20 parts by weight is 1~98% is added afterwards, handles 0.5~24.0 hour；It discards anti-
Waste liquid is answered, the water of 200~1000 parts by weight is added, is cleaned 10~30 minutes；Cleaning waste liquid is discarded, 100~1000 weight are added
The amino acid of 0.5~2.0 parts by weight is added in the buffer that the pH value of part is 3.0~10.5, at 20~65 DEG C, processing 0.5~
4.0 hour；Waste liquid is discarded, the water of 200~1000 parts by weight is added, is cleaned 20~60 minutes；Waste liquid is discarded, is added 100~300
The lactic acid or sodium lactate of 0.1~1.0 parts by weight is added in the water of parts by weight, at 20~35 DEG C, handles 30~90 minutes, will bathe
Liquid pH is adjusted to neutrality；Waste liquid is discarded, 30~42 DEG C of injection water of 200~1000 parts by weight is added, cleans 1~4h；It discards
30~42 DEG C of injection water of 200~1000 parts by weight is added in waste liquid, cleans 1~4h.
2. the preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the oxidation chitosan
Quaternary ammonium salt refers to the chitosan quaternary ammonium salt for containing multiple aldehyde radicals in the structure formed after the chosen property oxidation of chitosan quaternary ammonium salt.
3. the preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the amino acid, refers to
Glycine, arginine, lysine and histidine.
4. the preparation method of antimicrobial form acellular matrix material according to claim 1, wherein the pH value be 3.0~
10.5 buffer, the pH are molten by using acetic acid-hydrochloric acid buffer solution, phosphate buffer solution, boric acid-borax buffering
Liquid, NaHCO3- NaOH buffer solution reaches.
5. a kind of preparation method of antimicrobial form acellular matrix material described in claim 1, it is characterised in that this method is for taking off
Acellular dermal matrix, cell-eliminating coanea matrix, human acellular amniotic membrane matrix, porcine aorta acellular matrix, pericardium acellular matrix,
The preparation of acellular matrix, urethra acellular matrix, de- cellular cartilage under intestinal mucosa.
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| CN107823717B (en) * | 2017-11-29 | 2020-11-27 | 四川大学 | Preparation method of anti-calcification biological patch |
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