CN108434514A - It is a kind of to have both antibacterial and biological inducing action collagen hydrogel preparation method - Google Patents
It is a kind of to have both antibacterial and biological inducing action collagen hydrogel preparation method Download PDFInfo
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- CN108434514A CN108434514A CN201810348985.5A CN201810348985A CN108434514A CN 108434514 A CN108434514 A CN 108434514A CN 201810348985 A CN201810348985 A CN 201810348985A CN 108434514 A CN108434514 A CN 108434514A
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- collagen
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- collagen hydrogel
- antibacterial
- inducing action
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- 102000008186 Collagen Human genes 0.000 title claims abstract description 135
- 108010035532 Collagen Proteins 0.000 title claims abstract description 135
- 229920001436 collagen Polymers 0.000 title claims abstract description 135
- 239000000017 hydrogel Substances 0.000 title claims abstract description 76
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 230000001939 inductive effect Effects 0.000 title claims abstract description 28
- 239000004475 Arginine Substances 0.000 claims abstract description 16
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 16
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000012805 post-processing Methods 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000007987 MES buffer Substances 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 230000001954 sterilising effect Effects 0.000 claims description 12
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910017052 cobalt Inorganic materials 0.000 claims description 10
- 239000010941 cobalt Substances 0.000 claims description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 150000003384 small molecules Chemical class 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000000502 dialysis Methods 0.000 claims description 4
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- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
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- 231100000135 cytotoxicity Toxicity 0.000 claims description 2
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- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract description 9
- 235000013824 polyphenols Nutrition 0.000 abstract description 9
- 238000004925 denaturation Methods 0.000 abstract description 4
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- 229910001385 heavy metal Inorganic materials 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
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- 239000003431 cross linking reagent Substances 0.000 abstract description 2
- 230000002779 inactivation Effects 0.000 abstract description 2
- 239000007822 coupling agent Substances 0.000 abstract 1
- 239000003292 glue Substances 0.000 description 8
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 239000007853 buffer solution Substances 0.000 description 4
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- -1 guanidine radicals Chemical class 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
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- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical class OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229960000686 benzalkonium chloride Drugs 0.000 description 3
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
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- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 description 3
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
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- 244000269722 Thea sinensis Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000012620 biological material Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
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- 102000004169 proteins and genes Human genes 0.000 description 2
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- 230000029663 wound healing Effects 0.000 description 2
- HNXGGWNCFXZSAI-UHFFFAOYSA-N 2-morpholin-2-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCC1CNCCO1 HNXGGWNCFXZSAI-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- CAQWNKXTMBFBGI-UHFFFAOYSA-N C.[Na] Chemical compound C.[Na] CAQWNKXTMBFBGI-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 102000012422 Collagen Type I Human genes 0.000 description 1
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- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 1
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- 235000019082 Osmanthus Nutrition 0.000 description 1
- 241000333181 Osmanthus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
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- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- 239000002245 particle Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229940032171 plum preparation Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 230000036560 skin regeneration Effects 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/008—Hydrogels or hydrocolloids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0009—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form containing macromolecular materials
- A61L26/0028—Polypeptides; Proteins; Degradation products thereof
- A61L26/0033—Collagen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L26/00—Chemical aspects of, or use of materials for, wound dressings or bandages in liquid, gel or powder form
- A61L26/0061—Use of materials characterised by their function or physical properties
- A61L26/0066—Medicaments; Biocides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/78—Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin, cold insoluble globulin [CIG]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/252—Polypeptides, proteins, e.g. glycoproteins, lipoproteins, cytokines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
Abstract
Antibacterial and biological inducing action collagen hydrogel preparation method is had both the invention discloses a kind of, is included the following steps：The preparation of unmodified collagen hydrogel；The post-processing of collagen hydrogel；It is triangle Planting Patterns that male parent, which takes vertical view,.The advantage of the invention is that：Inactivation and denaturation of the heavy metal to collagen itself are avoided, by introducing arginine needed by human, guanidinated reaction is carried out, while keeping bacteriostasis efficacy, remains the good biological inducing action of collagen；Avoid influence of the polyphenol to collagen hydrogel biocompatibility, the coupling agent of use is also the good crosslinking agent EDCHCl and NHS of biocompatibility academicly approved already and reaction condition is mild, temperature is at 4~10 DEG C, in collagen itself denaturation temperature hereinafter, the biological inducing action that collagen has been effectively ensured is not destroyed.
Description
Technical field
The present invention relates to technical field of biological materials, more particularly to a kind of to have both antibacterial and biological inducing action collagen
Hydrogel preparation method.
Background technology
Every year because of a large amount of Skin preparation sufferer of the initiations such as burn and diabetes, such as treatment can be led not in time
Skin histology necrosis is caused then to cause serious whole body acute reaction, therefore the clinically various skin regeneration materials of generally use
Repair process is carried out to defect point.Document and a large amount of patents now shows hydrogel because comprising hydrophilic polymer chain
Three-dimensional network has regulatable physics, chemistry and biological property, and structure is similar to natural extracellular matrix, thus wide
It is general to be used for Skin preparation reparation.Hydrogel can be divided into synthesis macromolecule hydrogel and natural polymer according to its constituent
Sub- hydrogel etc..Wherein synthesis macromolecule mainly has polyacrylic acid, polyurethane, polyvinylpyrrolidone etc., natural polymer master
There are collagen, gelatin, chitosan, fibroin albumen, alginate etc..Particularly, the main component in skin histology is I type glue
Original, from the angle of material biomimetics, to patient skin tissue defect repair using type i collagen hydrogel becomes vast
The emphasis that scientific worker competitively studies.Such as Chen Xin is prepared for being based on collagen and two kinds of polysaccharide derivates --- and oxidation Portugal is poly-
The collagen hydrogel of sugar and oxycellulose is to host material (the rosy clouds oxidation of polysaccharides modified adhesive raw waters as organizational project
Gel [D] Fudan University, Master's thesis, 2014).Diversiform-leaved poplar etc., which has been invented, a kind of to be interacted based on collagen and dopamine
(diversiform-leaved poplar, Zhu Shichen, bear are apt to bionical adhesion hydrogels of a kind of collagen-based mussels of such as cypress and preparation method thereof to collagen hydrogel
[P] Chinese patents, 2018, patent No. ZL201610050 568.3).But in recent years, in wound repair, due to debridement
Be not thorough, reasons, the wound such as cross-infection can be invaded by microorganism, if the quantity of microorganism is more than certain limit,
Wound will form clinical infection, increase the pain of wound, and the surface of a wound is made to form a large amount of useless fellows, influence wound healing.Common
Collagen hydrogel material does not often have bacteria resistance function, therefore study and produce and have both although tissue inducing action is excellent
The antibacterial collagen hydrogel with biological inducing action has highly important theoretical and realistic meaning for tissue injury reparation.
Existing patent discloses several collagen-based materials with bacteriostasis, such as Zhou Jiucai discloses one kind with suppression
Collagen-DNA-Ag compounds of bacterium effect and preparation method thereof, by collagen, DNA and soluble silver salt AgNO3Solution mixes
Having arrived a kind of clinical medicine biological dressing of antibacterial type, (Zhou Jiucai, Liu Zhanlong, gold osmanthus chrysanthemum wait to have the collagen-of bacteriostasis efficacy
DNA-Ag compounds and preparation method thereof [P] Chinese patents, 2003, publication number 1406489A)；But defending China etc. discloses one
Collagen aggregate composite type medical fiber of the kind with antibacterial/bacteriostasis efficacy, by acid-soluble collagen aggregate, dialdehyde acid methyl
Sodium cellulosate and the organic mixing of chitin, the technological processes such as agitated, deaeration, spinning are prepared for the compound doctor of collagen aggregate
(but China is defended, Liu Xinhua, but time waits to have the collagen aggregate composite type medical fiber of antibacterial/bacteriostasis efficacy with fiber
[P] Chinese patents, 2015, publication number 104711702B)；King's Zhe etc. discloses a kind of collagen-tea polyphenols antibacterial film, will
Collagen, which is dissolved in distilled water and is heat-treated at 20-60 DEG C after 5-30mi n, to be mixed progress vacuum outgas in tea polyphenols, is cast into
Film can (king's Zhe, Ye Chen, Wang Huai rain a kind of collagen-tea polyphenols antibacterial film and preparation method thereof [P] Chinese patents,
2016, application number 201610131170.2)；But it defends China etc. and discloses a kind of oxidation chitosan oligosaccharide crosslinked with collagen and in-situ preparation is received
Rice silvery is re-introduced into silver ion, and in amino for the method for antibacterial Collagen Type VI using excessive oxidation chitosan oligosaccharide crosslinked with collagen
Under the action of stablize nano-Ag particles, to prepare with excellent performance, biocompatibility and dual antibacterial effect glue
Raw material (but time, Chen Yining, but China is defended, wait a kind of oxidation chitosan oligosaccharide crosslinked with collagen of and in-situ preparation nano silver to prepare anti-
Method [P] Chinese patents of bacterial type collagen, 2016, application number 201610529368.6)；
Wang Yulu etc. discloses a kind of preparation method of antibiotic property collagen, right at 2 5~50 DEG C using modified triclosan
Collagen is modified, dialyse and be freeze-dried to obtain antibiotic property collagen-based materials (a kind of antibiotic property collagens of the strong of Wang Yulu, Jin Li
Preparation method [P] Chinese patents, 2016, application number 201610935790.1)；Wei Kun etc. disclose a kind of silver-colored mesoporous silicon of load/
(Wei Kun is a kind of silver-colored mesoporous silicon/collagen/acetal of loads of health to the preparation method of collagen/polyvinyl alcohol of acetalization antiseptic dressing perhaps
Preparation method [P] Chinese patents of change polyvinyl alcohol antiseptic dressing, 2014, application number 2014104 is 60969.7)；
Wang Xuemei etc. discloses a kind of antibacterial repairing type electrostatic spinning collagen-bacteria cellulose composite nano fiber
The preparation method of holder, using electrostatic spinning technique to containing AgNO3Or the bacterium of the fluorescent nano materials such as gold, silver nano-cluster
Cellulose and collagen mixed solution carry out spinning, and contain AgNO using UV Light reduction3Or gold, silver nano-cluster
Deng nano fiber scaffold, by related compound nano fiber scaffold for cell culture prepare tissue engineering material (Wang Xuemei,
Liu Xiaoli carrys out a kind of blue systems of antibacterial repairing type electrostatic spinning collagen-bacteria cellulose composite nano fiber scaffold of plum
Preparation Method and its application [P] Chinese patents, 2014,20141003892 6.X)；Amp- Cole Nei Liualupeiyi etc. in Hu
Disclose it is a kind of from disinfection, antibacterial collagen preparations, by the salt of free Chlorhexidine, the salt of Win-41464, benzalkonium chloride etc.
Collagen preparations (the amp- Cole in Hu that can be obtained from disinfection, antibacterial is added in collagen solution in cationic antibacterial agent
Nei Liualupeiyi, Mali in this-Thomas Ge Erka, Peter's rood, wait from disinfection, antibacterial collagen system
Agent and application thereof and preparation method [P] Chinese patents, 2006,2 00680012963.7).
By existing literature and disclosed patented method it is found that current antibacterial or antibacterial collagen-based materials are mainly to introduce
Ag+Being combined by enzyme containing sulfhydryl reactive group in fish bacterial body makes it lose activity, to make bacterial growth breeding by
To inhibition, but as heavy metal ion, it can also make protein lose bioactivity.Or certainly using introducing tea polyphenols etc.
Polyphenols of the body with antibacterial action makes final product with bacteriostasis property, but the addition of polyphenol can be to a certain degree
It is upper to influence the biocompatibility of final product, and confirmed by numerous scientific workers.Or introducing benzalkonium chloride etc. is with anti-
The ingredient of bacterium effect, but the biological inducing action for also resulting in collagen weakens, while also having other introducing antimicrobial components
Method, such as using modified triclosan modified collagen, but reaction condition is not mild, and the biology that can also influence final product lures
Lead effect.Therefore, develop and prepare it is a kind of have both antibacterial with biological inducing action collagen hydrogel, have highly important
Theory value and realistic meaning.It is worth pointing out that constitute protein more than 20 a amino acid in, arginine because
To contain guanidine radicals (under neutral, acid or alkaline condition positively charged), protonation structure type can make guanidine radicals in vivo
The interaction of specificity is generated to promote with electronegative group such as phosphate radical, carboxylic acid group and Atomic oxygen radical anion etc.
Make the progress of biological respinse, while also can inhibit bacterial growth with electronegative bacterial action.Therefore the spy can be utilized
Arginine is introduced collagen hydrogel by point, and under mild action condition, preparation has both antibacterial and biological inducing action glue
Raw water gel.
The professional term of the present invention is as follows：
Half sodium salt buffer solution of 2-morpholine ethane sulfonic acid is abbreviated as：MES buffer solutions；
1- (3- dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides are abbreviated as：EDC·HCl；
N-hydroxysuccinimide is abbreviated as：NHS.
Invention content
The present invention in view of the drawbacks of the prior art, provide it is a kind of have both it is antibacterial with biological inducing action collagen water-setting
Glue preparation method.The hydrogel material should be a kind of not only with good biological inducing action but also with good bacteriostasis
Wound healing and reparation biomaterial.
In order to realize the above goal of the invention, the technical solution adopted by the present invention is as follows：
A kind of to have both antibacterial and biological inducing action collagen hydrogel preparation method, preparation process is as follows：
Step 1, the preparation of unmodified collagen hydrogel：Collagenolysis is obtained in 0. 5M acetic acid at 4~10 DEG C
The collagen solution of 5mg/ml~20mg/ml, then at 4 DEG C using N aOH solution slowly adjust collagen solution pH value to 6.5~
8.5, then collagen solution is placed in 3 7~42 DEG C of insulating box and hatches 1~4h to get to unmodified collagen hydrogel；Institute
State the mixture that collagen is one or more of Animal Skin Collagens such as acid soluble pigskin, ox-hide, sheepskin, fish-skin, donkey hide；
Step 2, arginine is introduced into unmodified collagen hydrogel：The unmodified collagen water of 10~20g of dry weight is weighed first
Gel is immersed under conditions of 0~10 DEG C in the MES buffer solutions that volume is 1L, a concentration of 2 5~50mmol/L, pH=
5.0；Then EDCHCl and NHS is weighed, dosage n (EDC) in molar ratio：n(NHS)：The n (- COO in collagen hydrogel
H)=5:3:2 ratio is added in above-mentioned MES buffer solutions；Then, by arginine according to the 1/4 of EDC HCl object molal weights
~1/2 is added in MES buffer solutions, and after stirring 12h~48h under conditions of 4 DEG C, the hydrochloric acid of 1~10wt% of dry weight is added
Azanol terminates reaction, and adjusts pH to 9.0 using NaOH solution；
The post-processing of step 3 collagen hydrogel：The collagen hydrogel of above-mentioned preparation is retained in 6000~8000 dalton
Dialyse 12-36h in the bag filter of molecular weight, further removes unreacted chemical small molecule reagent, and be freeze-dried, cobalt -60
Ray sterilizing pack obtains having both antibacterial and biological inducing action collagen hydrogel material, and -60 ray sterilizing intensity of cobalt is
15~30KG y；
Preferably, the collagen in the step 1 is human evolution distal end, the lower fish skin collagen of immunogenicity；
Preferably, preferably 4 DEG C, the preferred 10mg/ml of collagen solution concentration of collagenolysis temperature, collagen solution pH value is excellent
Select 7.5, preferably 40 DEG C of calorstat temperature, brooding time 3h.
Preferably, the unmodified collagen hydrogel quality in the step 2 is 15g, hydrogel bath temperature is 4 DEG C,
MES buffer concentrations are 35mmol/L, and arginine and EDCH Cl object molal weight ratios are 1/3, and mixing time is salt for 24 hours
Sour azanol dosage is the 5wt% of unmodified collagen hydrogel dry weight.
Preferably, the dialysis bag retention molecular weight in the step 3 is 8000 dalton, dialysis time 36h, cobalt-
60 ray sterilizing intensity are 25KGy.
It is above-mentioned have both the antibacterial key performance with the collagen hydrogel of biological inducing action should meet it is claimed below：
Appearance：White or light yellow water-setting jelly；
Content of beary metal：≤8μg/g(m/m)；
Elasticity modulus：50~500Pa；
Swelling ratio：100%~500%；
Cytotoxicity：0 grade；
Sterility test：It is sterile；
Sensitivity response：Without delayed type hypersensitivity, DTH.
Compared with prior art the advantage of the invention is that：
(1) with existing report using heavy metal Ag or Ag+Antibacterial difference is carried out, the invention avoids heavy metals to glue
The inactivation of original itself and denaturation carry out guanidinated reaction, are keeping antibacterial work(by introducing arginine needed by human
While effect, the good biological inducing action of collagen is remained；
(2) collagen is modified and then is made using polyphenol or benzalkonium chloride or modified triclosan with existing report
Standby antibacterial collagen-based materials are different, the influence the invention avoids polyphenol to collagen hydrogel biocompatibility, the coupling of use
Agent is also two Asia of biocompatibility good crosslinking agent 1- (3- dimethylamino-propyls) -3- ethyls carbon academicly approved already
Amine hydrochlorate (EDCH Cl) and n-hydroxysuccinimide (NHS) and reaction condition is mild, temperature is at 4~10 DEG C, in glue
Itself former denaturation temperature is not hereinafter, the biological inducing action that collagen has been effectively ensured is destroyed.
Description of the drawings
Fig. 1 has both antibacterial linear with the elasticity modulus of the collagen hydrogel of biological inducing action for the embodiment of the present invention 1
Figure；
Fig. 2 is that the embodiment of the present invention 2 has both the antibacterial swelling ratio Line Chart with the collagen hydrogel of biological inducing action.
Specific implementation mode
To make the objectives, technical solutions, and advantages of the present invention more comprehensible, develop simultaneously embodiment referring to the drawings,
The present invention is described in further details.
Embodiment 1
(1) preparation of unmodified collagen hydrogel：Pigskin collagen is dissolved in 0.5 M acetic acid at 4 DEG C, obtains 5mg/
The collagen solution of ml then slowly adjusts collagen solution pH value to 6.5, then by collagen solution at 4 DEG C using NaOH solution
It is placed in 37 DEG C of insulating box and hatches 1h to get to unmodified collagen hydrogel；
(2) arginine is introduced into unmodified collagen hydrogel：The above-mentioned unmodified collagen hydrogels of 10g are weighed first at 0 DEG C
Under conditions of be immersed in volume be 1L, a concentration of 25mmol/L half sodium salt of 2- morpholino b acids (MES) buffer solution in (pH=
5.0)；Then 1- (3- the dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides (EDCHCl) and N- of certain mass are weighed
HOSu NHS (NHS), dosage n (EDC) in molar ratio：n(NHS)：The n (- COOH in collagen hydrogel)=5:
3:2 ratio is added in above-mentioned MES buffer solutions；Then, by the arginine of certain mass according to EDCHCl amount of substance (mole)
1/3 be added in MES buffer solutions, after stirring 12h under conditions of 4 DEG C, unmodified collagen hydrogel dry weight is added
The hydroxylamine hydrochloride of 1wt% terminates reaction, and adjusts pH to 9.0 using NaOH solution；
(3) post-processing of collagen hydrogel：By the collagen hydrogel of above-mentioned preparation in 6000 dalton molecular cut offs
Dialyse 12h in bag filter, further removes unreacted chemical small molecule reagent, and is freeze-dried, -60 ray sterilizing of cobalt,
- 60 ray sterilizing intensity of cobalt is 15KGy, and pack obtains having both antibacterial and biological inducing action collagen hydrogel material, real
Apply one prepared by example 1 group have both it is antibacterial as shown in Figure 1 with the elasticity modulus of the collagen hydrogel of biological inducing action.
Embodiment 2
(1) preparation of unmodified collagen hydrogel：Ox-hide collagen is dissolved in 0.5 M acetic acid at 6 DEG C, is obtained
The collagen solution of 10mg/ml then slowly adjusts collagen solution pH value to 7.5, then by glue at 4 DEG C using NaOH solution
Original solution, which is placed in 40 DEG C of insulating box, hatches 3h to get to unmodified collagen hydrogel；
(2) arginine is introduced into unmodified collagen hydrogel：The above-mentioned unmodified collagen hydrogels of 15g are weighed first at 4 DEG C
Under conditions of be immersed in volume be 1L, a concentration of 35mmol/L half sodium salt of 2- morpholino b acids (MES) buffer solution in (pH=
5.0)；Then 1- (3- the dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides (EDCHCl) and N- of certain mass are weighed
HOSu NHS (NHS), dosage n (EDC) in molar ratio：n(NHS)：The n (- COOH in collagen hydrogel)=5:
3:2 ratio is added in above-mentioned MES buffer solutions；Then, by the arginine of certain mass according to EDCHCl amount of substance (mole)
1/4 be added in MES buffer solutions, after stirring 36h under conditions of 4 DEG C, unmodified collagen hydrogel dry weight is added
The hydroxylamine hydrochloride of 5wt% terminates reaction, and adjusts pH to 9.0 using NaOH solution；
(3) post-processing of collagen hydrogel：By the collagen hydrogel of above-mentioned preparation in 8000 dalton molecular cut offs
Dialyse 36h in bag filter, further removes unreacted chemical small molecule reagent, and is freeze-dried, -60 ray sterilizing of cobalt,
- 60 ray sterilizing intensity of cobalt is 20KGy, and pack obtains having both antibacterial and biological inducing action collagen hydrogel material, real
Apply one prepared by example 2 group have both it is antibacterial as shown in Figure 2 with the swelling ratio of the collagen hydrogel of biological inducing action.
Embodiment 3
(1) preparation of unmodified collagen hydrogel：Fish skin collagen is dissolved in 0.5 M acetic acid at 4 DEG C, is obtained
The collagen solution of 20mg/ml then slowly adjusts collagen solution pH value to 8.5, then by glue at 4 DEG C using NaOH solution
Original solution, which is placed in 42 DEG C of insulating box, hatches 4h to get to unmodified collagen hydrogel；
(2) arginine is introduced into unmodified collagen hydrogel：The above-mentioned unmodified collagen hydrogels of 20g are weighed first at 4 DEG C
Under conditions of be immersed in volume be 1L, a concentration of 40mmol/L half sodium salt of 2- morpholino b acids (MES) buffer solution in (pH=
5.0)；Then 1- (3- the dimethylamino-propyls) -3- ethyl-carbodiimide hydrochlorides (EDCHCl) and N- of certain mass are weighed
HOSu NHS (NHS), dosage n (EDC) in molar ratio：n(NHS)：The n (- COOH in collagen hydrogel)=5:
3:2 ratio is added in above-mentioned MES buffer solutions；Then, by the arginine of certain mass according to EDCHCl amount of substance (mole)
1/2 be added in MES buffer solutions, after stirring 48h under conditions of 4 DEG C, unmodified collagen hydrogel dry weight is added
The hydroxylamine hydrochloride of 10wt% terminates reaction, and adjusts pH to 9.0 using NaOH solution；
(3) post-processing of collagen hydrogel：By the collagen hydrogel of above-mentioned preparation in 7000 dalton molecular cut offs
It dialyses in bag filter for 24 hours, further removes unreacted chemical small molecule reagent, and be freeze-dried, -60 ray sterilizing of cobalt,
- 60 ray sterilizing intensity of cobalt is 30KGy, and pack obtains having both antibacterial and biological inducing action collagen hydrogel material.
Those of ordinary skill in the art will understand that in each method embodiment of the present invention, the sequence of each step
The sequencing that number can not be used to limit each step is not paying creative labor for those of ordinary skill in the art
Under the premise of dynamic, the priority of each step is changed also within protection scope of the present invention.The embodiments described herein be in order to
Reader is helped to understand the implementation of the present invention, it should be understood that protection scope of the present invention is not limited to such special
Statement and embodiment.Those skilled in the art can be made according to the technical disclosures disclosed by the invention it is various not
Various other specific variations and combinations of present invention essence are detached from, these variations and combinations are still in protection scope of the present invention
It is interior.
Claims (6)
1. a kind of having both antibacterial and biological inducing action collagen hydrogel preparation method, which is characterized in that preparation process is as follows：
Step 1, the preparation of unmodified collagen hydrogel：Collagenolysis is obtained into 5mg/ml in 0.5M acetic acid at 4~10 DEG C
The collagen solution of~20mg/ml then slowly adjusts collagen solution pH value to 6.5~8.5 using NaOH solution at 4 DEG C, connects
It collagen solution being placed in 37~42 DEG C of insulating box and hatches 1~4h to get to unmodified collagen hydrogel；The collagen is
The mixture of one or more of the Animal Skin Collagens such as acid soluble pigskin, ox-hide, sheepskin, fish-skin, donkey hide；
Step 2, arginine is introduced into unmodified collagen hydrogel：The unmodified collagen hydrogel of 10~20g of dry weight is weighed first
It is immersed under conditions of 0~10 DEG C in the MES buffer solutions that volume is 1L, a concentration of 25~50mmol/L, pH=5.0；So
After weigh EDCHCl and NHS, dosage n (EDC) in molar ratio：n(NHS)：The n (- COOH in collagen hydrogel)=5:3:2
Ratio be added in above-mentioned MES buffer solutions；Then, arginine is added to according to the 1/4~1/2 of EDCHCl object molal weights
In MES buffer solutions, after stirring 12h~48h under conditions of 4 DEG C, the hydroxylamine hydrochloride that 1~10wt% of dry weight is added terminates instead
It answers, and pH to 9.0 is adjusted using NaOH solution；
The post-processing of step 3 collagen hydrogel：The collagen hydrogel of above-mentioned preparation is retained into molecule in 6000~8000 dalton
Dialyse 12-36h in the bag filter of amount, further removes unreacted chemical small molecule reagent, and is freeze-dried, -60 ray of cobalt
Sterilizing pack obtains having both antibacterial with biological inducing action collagen hydrogel material, and -60 ray sterilizing intensity of cobalt is 15~
30KGy。
2. according to the method described in claim 1, it is characterized in that：Collagen in the step 1 is human evolution distal end, is immunized
The lower fish skin collagen of originality.
3. according to the method described in claim 1, it is characterized in that：Preferably 4 DEG C of collagenolysis temperature, collagen solution concentration is preferred
10mg/ml, collagen solution pH value preferably 7.5, preferably 40 DEG C of calorstat temperature, brooding time 3h.
4. according to the method described in claim 1, it is characterized in that：Unmodified collagen hydrogel quality in the step 2 is
15g, hydrogel bath temperature are 4 DEG C, and MES buffer concentrations are 35mmol/L, arginine and EDCHCl objects molal weight ratio
Example is 1/3, and mixing time is that for 24 hours, hydroxylamine hydrochloride dosage is the 5wt% of unmodified collagen hydrogel dry weight.
5. according to the method described in claim 1, it is characterized in that：Dialysis bag retention molecular weight in the step 3 is 8000
Dalton, dialysis time 36h, -60 ray sterilizing intensity of cobalt are 25KGy.
6. according to the method described in claim 1-5, it is characterised in that：It is described to have both antibacterial and biological inducing action collagen water
The key performance of gel should meet claimed below：
Appearance：White or light yellow water-setting jelly；
Content of beary metal：≤8μg/g(m/m)；
Elasticity modulus：50~500Pa；
Swelling ratio：100%~500%；
Cytotoxicity：0 grade；
Sterility test：It is sterile；
Sensitivity response：Without delayed type hypersensitivity, DTH.
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