CN106336829A - Preparation method for DA (Dopamine)-based adhesive - Google Patents
Preparation method for DA (Dopamine)-based adhesive Download PDFInfo
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- CN106336829A CN106336829A CN201610806795.4A CN201610806795A CN106336829A CN 106336829 A CN106336829 A CN 106336829A CN 201610806795 A CN201610806795 A CN 201610806795A CN 106336829 A CN106336829 A CN 106336829A
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- dopamine
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- macromolecular
- binder
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J105/00—Adhesives based on polysaccharides or on their derivatives, not provided for in groups C09J101/00 or C09J103/00
- C09J105/08—Chitin; Chondroitin sulfate; Hyaluronic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
- C09J177/04—Polyamides derived from alpha-amino carboxylic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a preparation method for a DA (Dopamine)-based adhesive, and belongs to the field of high polymer materials. According to the preparation method for the DA-based adhesive, biological macromolecular hyaluronic acid and polyglutamic acid are taken as raw materials, and DA is taken as a functional group; the DA is grafted to biological macromolecules to obtain biologically modified macromolecules; the grafting rate of the biologically modified macromolecules on the DA can be controlled by adjusting a feed ratio. Sodium periodate is added into the biologically modified macromolecules, and the sodium periodate and the DA can perform oxidative cross linking, so that the adhesion strength is improved. Compared with a plurality of base materials, the adhesive prepared by the invention has excellent adhesion property, has very good biocompatibility, and can be applied to adhesion of a plurality of materials, adhesion of a skin wound, and adhesion repair of in-vivo tissues.
Description
Technical field
A kind of preparation method of DOPA amido binder, belongs to functional high polymer material field.
Background technology
The mussel adhesion protein of marine organisms mussel secretion has superpower Adhesion property, can be formed very at short notice
Strong adhesive force, and adhesion effect can also be realized under wet condition well.Byssus attachment proteins have multiple, but
Their common features are exactly all to contain very abundant dihydroxyphenylalanine (dopa, DOPA).Mussel attachment proteins sticks
Action principle is to provide effective bonding group by a kind of poly- phenol albumen, and the general molecular mass of this kind of poly- phenol albumen exists
130kda about, this kind of albumen, rich in the amino acid with hydroxyl, wherein contains substantial amounts of hydroxylating tyrosine, forms dihydroxy
Phenylalanine structure, this structure is exactly DOPA, and this structure serves vital effect, this knot for its adhesive property
Structure also provides the performance of the combination for kinds of surface so as to for many kinds of substance while providing powerful adhesive property
All there is adhesive property, there is the function of uniqueness.Dopamine (da) is a kind of derivative of DOPA, its have with DOPA as
Adhesion property.
Da has adhesion property for kinds of surface, and its adhesive mechanism is also not quite similar.Catechol group in da
Itself can form very powerful complex bonds with metal ion；Irreversible organic gold can also be formed with substrate surface simultaneously
The base material belonging to complex compound or carrying hydroxyl with surface forms chemical bond；Again because its phenolic hydroxyl group is that a kind of have very highly polar base
Group is it is possible to mutually form hydrogen bond with the organic matter such as polymer such as protein, polysaccharide.And, da is that one kind is easy to by oxygen
The group changed, can generate ortho position diquinone, due on the highly unstable meeting of this structure and hydroxyl, amino or sulfydryl after da oxidation
Active hydrogen reaction；The structure of ortho position diquinone can also carry out chemistry instead with mutually isostructural ortho position diquinone group or dopa group
The chemical bonding of complexity should be formed.
Hyaluronic acid (ha) shows multiple important physiology with its unique molecular structure and physicochemical property in body
Function, such as lubricating joint, adjust the permeability of vascular wall, regulatory protein matter, Water-Electrolyte diffusion and operating, promote wound healing
Deng.Polyglutamic acid (pga) is a kind of macromolecular material with good biocompatibility and biodegradability, in organism
Interior, pga biocompatibility is good, can be degraded to glutamic acid and be absorbed by direct organism, have as bio-medical material bright
Aobvious advantage.
The present invention accesses dopamine in hyaluronic acid (ha) and polyglutamic acid (pga) large biological molecule, and preparation has glutinous
Close the biological adhesive of performance, this binder can be applied to the bonding of multiple material, skin wound reparation and tissue wounds
Reparation field.
Content of the invention
It is an object of the invention to provide a kind of preparation method of DOPA amido binder, the material obtaining to various metals,
Nonmetallic, macromolecule and raw body tissue have higher cohesive.
The mentality of designing of the present invention is: from have excellent cement properties dopamine be functional group, by its with transparent
Matter acid, polyglutamic acid large biological molecule carry out amidation process, obtain the large biological molecule of dopamine graft modification；In dopamine
Add sodium metaperiodate in base bio-modification macromolecular so as to carry out oxidation cross-linked with da, obtain the dopamine with high adhesion
Base binder.
The technical scheme is that with n- HOSu NHS (nhs) and 1- (3- dimethylamino-propyl) -3- ethyl
Carbodiimide hydrochloride (edc) is catalyst, by the amidation process between carboxyl in amino in dopamine and large biological molecule,
Prepare the large biological molecule of dopamine graft modification；Remove excessive dopamine and catalyst with dialysis membrane again, chilled
White cotton fluffy solid is obtained after drying；Add sodium metaperiodate so as to carry out with da in DOPA amido bio-modification macromolecular
Oxidation cross-linked, obtain the DOPA amido binder with high adhesion.
Wherein, large biological molecule is hyaluronic acid, and dopamine is 1:4～1:2 with the mol ratio of hyaluronic acid, dopamine
Percent grafting be 3%～11%, the structure of gained bio-modification macromolecular is:
It is expressed as ha-da.
Large biological molecule is polyglutamic acid, and the mol ratio of dopamine and polyglutamic acid is 1:2～1:1, the connecing of dopamine
Branch rate is 13%～30%, and the structure of gained bio-modification macromolecular is:
It is expressed as pga-da.
Beneficial effects of the present invention: the binder of gained is applicable to metal material steel plate, aluminium sheet, nonmetallic materials
Glass, macromolecular material bakelite plate, polyurethane sheet and polyvinyl chloride panel, organism pigskin, it is respectively provided with higher adhesion.
The binder preparing has excellent biocompatibility；The good macromolecular of this adhesion can be used for multiple material, skin
Skin wound is repaired and promotion organization wound healing art.
Brief description
The nuclear magnetic spectrogram of Fig. 1 hyaluronic acid-dopamine bio-modification macromolecular.
The nuclear magnetic spectrogram of Fig. 2 polyglutamic acid-dopamine modified macromer.
Specific embodiment
The preparation of embodiment 1, hyaluronic acid-dopamine modified macromer
Weigh 4gha, be placed in the there-necked flask of three 250ml, then take 100ml deionized water to pour in bottle respectively,
Ha is made to dissolve under conditions of mechanical agitation 270rpm/min.The edc weighing nhs and 1g of 0.6g respectively pours three three mouthfuls burnings into
In bottle.30min is activated under conditions of mechanical agitation.Ph will be reacted with the hydrochloric acid of 1mol/l to adjust to 5.0.Weigh 1g dopamine
And use 15ml deionized water dissolving, from constant pressure funnel, dopamine solution is instilled in flask.After the completion of logical nitrogen
20min it is ensured that reacting under an inert gas, a length of 24h during reaction.After the completion of reaction, product is poured into the dialysis of 3500 molecular weight
In bag, it is placed on dialysis in the pbs cushioning liquid of ph=5.0, dialyses 6 times altogether, each 4h；Again bag filter is placed in deionization
Dialyse in water, dialyse 4 times altogether, each 6h.
Product is poured into freeze overnight in the centrifuge tube of multiple 50ml by dialysis after terminating, further take out freeze-drying and obtain white
The ha-da of floccule, forms ha-da adhesive after adding a small amount of water.
The preparation of embodiment 2, polyglutamic acid-dopamine modified macromer
Weigh 4gpga, be placed in the there-necked flask of three 250ml, then take 100ml deionized water to pour bottle into respectively
In, so that pga is dissolved under conditions of mechanical agitation 190rpm/min.The edc weighing nhs and 2g of 1.2g respectively pours three three into
In mouth flask.30min is activated under conditions of mechanical agitation.Ph will be reacted with the hydrochloric acid of 1mol/l to adjust to 5.0.Weigh 2g many
Bar amine simultaneously uses 20ml deionized water dissolving, is instilled dopamine solution in flask from constant pressure funnel.After the completion of logical nitrogen
20min it is ensured that reacting under an inert gas, a length of 24h during reaction.After the completion of reaction, product is poured into the dialysis of 3500 molecular weight
In bag, it is placed on dialysis in the pbs cushioning liquid of ph=5.0, dialyses 6 times altogether, each 4h；Again bag filter is placed in deionization
Dialyse in water, dialyse 4 times altogether, each 6h.
Product is poured into freeze overnight in the centrifuge tube of multiple 50ml by dialysis after terminating, further take out freeze-drying and obtain white
The pga-da of floccule, forms pga-da adhesive after adding a small amount of water.
Embodiment 3, binder oxidation cross-linked
The ha-da (or pga-da) weighing 0.2g is placed in 6 sample bottles, then weighs 5mg, 10mg, 15mg, 20mg respectively
Naio with 25mg4, after wiring solution-forming, use the volumetric flask constant volume of 250ml.Then with the naio of this 5 kinds of variable concentrations4Solution and super
Fully dissolving DOPA amido binder, it is ensured that gluing agent concentration is as 0.03g/ml, places 12h at 30 DEG C to pure water respectively, many
Occur oxidation cross-linked, to improve bonding strength between bar amido binder.
Claims (5)
1. a kind of preparation method of DOPA amido binder, is characterized in that from the dopamine with excellent cement properties be function
Group, itself and hyaluronic acid, polyglutamic acid large biological molecule is carried out amidation process, obtains the biology of dopamine graft modification
Macromolecular；Remove excessive dopamine and catalyst with dialysis membrane again, freeze-dried after obtain white cotton fluffy solid；Many
Add sodium metaperiodate in bar amido bio-modification macromolecular so as to carry out oxidation cross-linked with da, obtain that there are the many of high adhesion
Bar amido binder.
2. preparation method according to claim 1, is characterized in that large biological molecule is hyaluronic acid, dopamine and hyalomitome
The mol ratio of acid is 1:4～1:2, and the percent grafting of dopamine is 3%～11%, and the structure of gained bio-modification macromolecular is:
It is expressed as ha-da.
3. preparation method according to claim 1, is characterized in that large biological molecule is polyglutamic acid, dopamine and polyglutamic
The mol ratio of acid is 1:2～1:1, and the percent grafting of dopamine is 13%～30%, and the structure of gained bio-modification macromolecular is:
It is expressed as pga-da.
4. preparation method according to claim 1 is it is characterised in that the binder of gained is applicable to metal material steel
Plate, aluminium sheet, nonmetallic materials glass, macromolecular material bakelite plate, polyurethane sheet and polyvinyl chloride panel, organism pig
Skin.
5. preparation method according to claim 1 is it is characterised in that gained binder has excellent biocompatibility；This
Plant the good macromolecular of adhesion and can be used for multiple material, skin wound reparation and promotion organization wound healing art.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610806795.4A CN106336829A (en) | 2016-09-07 | 2016-09-07 | Preparation method for DA (Dopamine)-based adhesive |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610806795.4A CN106336829A (en) | 2016-09-07 | 2016-09-07 | Preparation method for DA (Dopamine)-based adhesive |
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| CN201610806795.4A Pending CN106336829A (en) | 2016-09-07 | 2016-09-07 | Preparation method for DA (Dopamine)-based adhesive |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107158453A (en) * | 2017-06-02 | 2017-09-15 | 武汉纺织大学 | A kind of preparation method of hyaluronic acid tissue adhesive |
| CN107596429A (en) * | 2017-09-29 | 2018-01-19 | 南京轩凯生物科技有限公司 | A kind of blood protein response type γ polyglutamic acid hydrogel hemostatic materials and its preparation method and application |
| CN107619645A (en) * | 2017-11-01 | 2018-01-23 | 江南大学 | A kind of method that dopamine enhancing starch-based adhesive is prepared based on holoenzyme method |
| CN109355057A (en) * | 2018-11-07 | 2019-02-19 | 哈尔滨工程大学 | A kind of bionical tissue adhesive of poly-amino acid-based mussel and preparation method thereof |
| CN109627942A (en) * | 2018-11-12 | 2019-04-16 | 安徽江南泵阀有限公司 | A kind of rare earth enhancing chemical pump surface staining-proof coating |
| CN109705707A (en) * | 2018-11-12 | 2019-05-03 | 安徽江南泵阀有限公司 | A kind of modification infusorial earth enhancing chemical pump surface corrosion-resistant erosion coating |
| CN110041719A (en) * | 2019-05-06 | 2019-07-23 | 山东交通学院 | A kind of dopamine and sodium hyaluronate composite modified emulsification asphalt mist sealing material |
| CN110464870A (en) * | 2019-07-18 | 2019-11-19 | 福建农林大学 | A kind of soft tissue adhesives and preparation method thereof based on modified collagen |
| CN111939142A (en) * | 2020-08-13 | 2020-11-17 | 诺一迈尔（苏州）医学科技有限公司 | A patch for treating oral ulcer and its preparation method |
| CN112442140A (en) * | 2019-08-29 | 2021-03-05 | 上海其胜生物制剂有限公司 | Mussel-imitated enhanced adhesive and preparation method thereof |
| CN113425890A (en) * | 2021-07-16 | 2021-09-24 | 华东理工大学 | Bionic hydrogel tissue adhesive and preparation method thereof |
| CN113512133A (en) * | 2021-05-26 | 2021-10-19 | 江苏诺瓦立医疗用品有限公司 | Preparation method of biological tissue adhesive |
| CN113999630A (en) * | 2021-09-24 | 2022-02-01 | 广东省科学院健康医学研究所 | Adhesive and preparation method and application thereof |
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Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107158453B (en) * | 2017-06-02 | 2020-02-18 | 武汉纺织大学 | Preparation method of hyaluronic acid tissue adhesive |
| CN107158453A (en) * | 2017-06-02 | 2017-09-15 | 武汉纺织大学 | A kind of preparation method of hyaluronic acid tissue adhesive |
| CN107596429A (en) * | 2017-09-29 | 2018-01-19 | 南京轩凯生物科技有限公司 | A kind of blood protein response type γ polyglutamic acid hydrogel hemostatic materials and its preparation method and application |
| CN107596429B (en) * | 2017-09-29 | 2020-09-29 | 南京轩凯生物科技有限公司 | Blood protein response type gamma-polyglutamic acid hydrogel hemostatic material and preparation method and application thereof |
| CN107619645A (en) * | 2017-11-01 | 2018-01-23 | 江南大学 | A kind of method that dopamine enhancing starch-based adhesive is prepared based on holoenzyme method |
| CN107619645B (en) * | 2017-11-01 | 2021-09-03 | 江南大学 | Method for preparing dopamine-enhanced starch-based adhesive based on holoenzyme method |
| CN109355057B (en) * | 2018-11-07 | 2021-03-30 | 哈尔滨工程大学 | Polyamino acid-based mussel bionic tissue adhesive and preparation method thereof |
| CN109355057A (en) * | 2018-11-07 | 2019-02-19 | 哈尔滨工程大学 | A kind of bionical tissue adhesive of poly-amino acid-based mussel and preparation method thereof |
| CN109705707A (en) * | 2018-11-12 | 2019-05-03 | 安徽江南泵阀有限公司 | A kind of modification infusorial earth enhancing chemical pump surface corrosion-resistant erosion coating |
| CN109627942A (en) * | 2018-11-12 | 2019-04-16 | 安徽江南泵阀有限公司 | A kind of rare earth enhancing chemical pump surface staining-proof coating |
| CN110041719A (en) * | 2019-05-06 | 2019-07-23 | 山东交通学院 | A kind of dopamine and sodium hyaluronate composite modified emulsification asphalt mist sealing material |
| CN110464870A (en) * | 2019-07-18 | 2019-11-19 | 福建农林大学 | A kind of soft tissue adhesives and preparation method thereof based on modified collagen |
| CN110464870B (en) * | 2019-07-18 | 2021-10-26 | 福建农林大学 | Soft tissue adhesive based on modified collagen and preparation method thereof |
| CN112442140A (en) * | 2019-08-29 | 2021-03-05 | 上海其胜生物制剂有限公司 | Mussel-imitated enhanced adhesive and preparation method thereof |
| CN111939142A (en) * | 2020-08-13 | 2020-11-17 | 诺一迈尔（苏州）医学科技有限公司 | A patch for treating oral ulcer and its preparation method |
| CN113512133A (en) * | 2021-05-26 | 2021-10-19 | 江苏诺瓦立医疗用品有限公司 | Preparation method of biological tissue adhesive |
| CN113425890A (en) * | 2021-07-16 | 2021-09-24 | 华东理工大学 | Bionic hydrogel tissue adhesive and preparation method thereof |
| CN113999630A (en) * | 2021-09-24 | 2022-02-01 | 广东省科学院健康医学研究所 | Adhesive and preparation method and application thereof |
| CN113999630B (en) * | 2021-09-24 | 2023-11-28 | 广东省科学院健康医学研究所 | Adhesive, and preparation method and application thereof |
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