CN110408038A - A kind of chitosan oligosaccharide base bioadhesive and preparation method thereof that performance is controllable - Google Patents
A kind of chitosan oligosaccharide base bioadhesive and preparation method thereof that performance is controllable Download PDFInfo
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- CN110408038A CN110408038A CN201910681976.2A CN201910681976A CN110408038A CN 110408038 A CN110408038 A CN 110408038A CN 201910681976 A CN201910681976 A CN 201910681976A CN 110408038 A CN110408038 A CN 110408038A
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- Prior art keywords
- chitosan oligosaccharide
- propionic acid
- dihydroxy benzenes
- benzenes propionic
- bioadhesive
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- 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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/08—Polysaccharides
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- 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
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- 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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/04—Materials for stopping bleeding
Abstract
The present invention provides a kind of chitosan oligosaccharide base bioadhesive and preparation method thereof that performance is controllable, belongs to high molecular material and technical field of biological materials.The present invention is using large biological molecule chitosan oligosaccharide as basis material, utilize 3,4- dihydroxy benzenes propionic acid obtains chitosan oligosaccharide -3 to its modification, 4- dihydroxy benzenes propionic acid modified macromer, it is subjected to cross-linking reaction by amino open loop epoxy group with polyethyleneglycol diglycidylether again, chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether bioadhesive is prepared.The present invention prepares resulting adhesive material with good tissue adhesion performance, higher mechanical strength, suitable degradation cycle and no cytotoxicity, it can be used for the various types of materials surface bonding such as glass, metal and its oxide, plastics, it can also be used to the bonding of the animal body epidermis, in-vivo tissue organ of clinical medical field of surgery.
Description
Technical field
The present invention relates to a kind of chitosan oligosaccharide base bioadhesives and preparation method thereof that performance is controllable, belong to high molecular material
And technical field of biological materials.
Background technique
Today of medical item prosperity, the whole world increase there are about 4,000,000 surgical operations and year by year every year.Current operation
Suturing secured technology mostly uses the materials such as suture, rivet to sew up a wound, but often brings secondary pain and wound infection very
Can extremely function of organization be interfered to restore.The bioadhesive that wound can be bonded by thus developing has important theory significance and reality
Border application value.
For the regeneration issues for effectively solving repair deficiency tissue, domestic and international numerous scholars carried out a large amount of basic research with
Clinical practice achieves major progress, and bio-adhesive materials is made to have obtained strong expansion in field of tissue engineering technology.Currently,
Material for bioadhesive mainly has chemical classes (polyurethane and cyanoacrylate etc.), degradable synthetic macromolecule (poly-
Vinyl alcohol and polycaprolactone etc.), large biological molecule polysaccharide (chitosan, alginic acid and hyaluronic acid etc.), large biological molecule it is more
Peptides (polyglutamic acid, polylysine and fibrin etc.).Wherein, the above two intensity is higher, but its biocompatibility, with
The associativity and degradability at surrounding tissue interface are all poor.Large biological molecule polysaccharide and polypeptide are adjustable due to its preferable structure
The advantages that property, biocompatibility and degradability, widely is used to construct bio-adhesive materials.However it is obtained at present biological
The viscosity of adhesive is universal weaker, so that its use is restricted.Therefore, it develops a kind of with more strongly adherent bioadhesive
Material is that have the urgent market demand.
Catechu phenolic group is considered as the main functional group that mussel can be adhered to surfaces of various materials, is a kind of highly polar base
Group, can occur with different materials hydrogen bond, covalent bond, coordinate bond and the effects of pi-pi accumulation power and there is strongly adherent, and easily quilt
Oxidation forms quinone, and further cross-linked polymeric forms the high strength polymer with network structure.Meanwhile catechu phenol-based compounds have
Have excellent biocompatibility, can promote cell stick and proliferative capacity, and for a long time keep relative stability in temperature
The human body environment of sum, thus, with using catechu phenolic group to modify degradable synthetic macromolecule or large biological molecule in more research, with
Improve the adhesion strength and regeneration of modified macromer.And in addition to that should have high adhesion strength in bio-adhesive materials
Outside, how to improve the internal stress inside adhesive is also a research emphasis.It is mostly non-total by electrostatic etc. in existing research
Valence link interacts to improve internal stress, and right few researchs are directly improved by open loop epoxy group formation covalent bond effect and are somebody's turn to do
The research of performance.Thus, the present invention is based on the modified large biological molecules of catechu phenolic group, are contracted by amino open loop in large biological molecule
Water glycerin ether epoxide epoxy group group and the covalent cross-linking network formed, to improve the adhesion strength of bioadhesive.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of chitosan oligosaccharide base tissue repair adhesive that performance is controllable, make
It is expected to excellent tissue adhesion performance, higher mechanical strength, suitable degradation cycle and no cytotoxicity as group
Reparation adhesive is knitted, sealant and hemostatic material etc. are applied to clinical medical field of surgery.
Technical solution of the present invention: chitosan oligosaccharide modification is changed using the 3,4- dihydroxy benzenes propionic acid with excellent adhesion
Property, modified macromer chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid with adhesion property is prepared；Then few using modified shell
Amino on sugar -3,4- dihydroxy benzenes propionic acid forms covalent cross-linking net to the epoxy group on polyethyleneglycol diglycidylether
Chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether bioadhesive is prepared in network.
Include the following steps:
(1) 3,4- dihydroxy benzenes propionic acid and chitosan oligosaccharide under the effect of the catalyst, in acid medium (pH 4.5~6.0)
10~15h of reaction obtains modified macromer chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid；Its reaction equation is as follows:
(2) the resulting chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of step (1) and polyethyleneglycol diglycidylether are passed through into amine
Base open loop epoxy group reacts to obtain chitosan oligosaccharide based adhesive, and reaction equation is as follows:
Wherein, a, n, m are 2-20, and n > m；Represent chitosan oligosaccharide sugar chain.
In one embodiment of the invention, the molecular weight of chitosan oligosaccharide is 2000 in the step (1), ammonia on chitosan oligosaccharide
Base and 3, the molar ratio of carboxyl is amino in 4- dihydroxy benzenes propionic acid: carboxyl=5:1~1:1, gained chitosan oligosaccharide -3,4- dihydroxy
The access amount of 3,4- dihydroxy benzenes propionic acid is 5%-26% in base benzenpropanoic acid, i.e. 3,4- dihydroxy benzenes propionic acid unit compares chitosan oligosaccharide
Mole accounting of single-stranded upper saccharide ring unit is 5%~26%.
In one embodiment of the invention, the catalyst is carbodiimide and n-hydroxysuccinimide.
In one embodiment of the invention, the amino in the step (2) in chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid
Molar ratio with polyethyleneglycol diglycidylether epoxy group is 10:3~10:5, and water bath with thermostatic control is reacted for 24 hours at 37 DEG C.
In one embodiment of the invention, chitosan oligosaccharide -3, the 4- dihydroxy benzenes propionic acid-polyethylene glycol diglycidyl is sweet
Oily ether bioadhesive can by changing access amount, constituent, the conditions such as the extent of reaction, temperature, time of amino and epoxy,
The degree of cross linking of adhesive is adjusted, and realizes the regulation to adhesion property.
Beneficial effects of the present invention
Chitosan oligosaccharide -3,4- dihydroxy benzenes the propionic acid produced according to the present invention for obtaining having cross-linked structure-polyethylene glycol two contracts
Water glycerin ether bioadhesive has the advantages that preparation method is simple mildly, performance is controllable.By changing bio-adhesive materials
Structure, organize in pairs its properties regulated and controled；Chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether
Bioadhesive adhesive strength is higher to can reach 157kPa, and this bioadhesive can be used for glass, metal and its oxide, modeling
The various types of materials surface bondings such as material, and have potential using value in clinical medical field of surgery.
Detailed description of the invention
The UV-visible spectrum (a) and nuclear magnetic resonance map (b) of Fig. 1 chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid
Shear adhesive strength between Fig. 2 bio-adhesive materials and pigskin tissue
Specific embodiment
The preparation of 1 modified macromer chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of embodiment
0.5g (3mmol) chitosan oligosaccharide (molecular weight 2000) is dissolved in the pH=5.5 ultrapure water of 10mL hydrochloric acid acidification, In
Wherein be added 0.284g (1.5mmol) 3,4- dihydroxy benzenes propionic acid ethanol solution 10mL, add 0.622g carbodiimide,
The mixed solution of 0.076g n-hydroxysuccinimide and 10mL morpholino b acid sodium buffer, utilizes 0.1mol/L dilute hydrochloric acid
Regulate and control pH=5.5, the lower 25 DEG C of reactions 12h of nitrogen atmosphere of reaction system, stops the product obtaining after reaction in deionized water
It dialyses 3 days and is freeze-dried to obtain flower-shaped modified macromer chitosan oligosaccharide -3, the 4- dihydroxy benzenes propionic acid (CSA) of brown cotton, wherein 3,4-
The access amount of dihydroxy benzenes propionic acid is 26%.
It should be noted that under the same conditions, when the dosage of 3,4- dihydroxy benzenes propionic acid replaces with 0.114g respectively
When (0.6mmol), 0.142g (0.75mmol), 0.189g (1mmol) and 0.237g (1.25mmol), connecing for CSA is prepared
Entering amount is respectively 5%, 8%, 12% and 18%.
The structure of prepared modified macromer is proved with access amount by ultraviolet-visible spectrum and nuclear magnetic spectrogram, such as Fig. 1 institute
Show.
Probe into influence of the chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of different access amounts to adhesive:
Select fresh pigskin simulated human tissue, from local market buy fresh pigskin be cut into it is evenly sized rectangular
Shape, size are about 5.0cm × 1.0cm, remove the extra fat of pigskin tissue, thickness control is in 1-2mm.The pig that will be cut
The sodium chloride solution of Pi Xianyong 0.9% cleans, then with the PBS buffer solution soaked overnight of pH=7.4, filter paper dries pigskin after taking-up
The solution on surface.
Taking 0.128g access amount respectively is 0,5%, 8%, 12%, 18% and 26% chitosan oligosaccharide -3,4- dihydroxy phenylpropyl alcohol
Acid is used as one-package adhesive, it is uniformly coated in a piece of pigskin tissue endosexine, area is about 2.5cm × 1.0cm, so
After cover another pigskin and two panels force together.It is placed in 37 DEG C crosslinking curing again for 24 hours.Pressure member is surveyed using 10kN
The universal tensile testing machine of part carries out tension test, and sample is fixed between two fixtures, sets rate of extension as 1mm/
min.The pigskin bonded is taken out and carries out tensile shear(ing) test, until completely pulling open two panels pigskin, maximum pulling force
Bonding force as between adhesive and tissue, the results are shown in Table 1.
The adhesive strength of the chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of the different access amounts of table 1
It is viscous as one pack system because having contained the catechu phenolic group of adhesive attraction in chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid
Mixture investigates the bonding effect between the CSA adhesive and pigskin tissue of 3,4- of difference dihydroxy benzenes propionic acid access amount.With 3,4-
The raising of dihydroxy benzenes propionic acid access amount, adhesive strength between CSA adhesive and tissue can maximum be increased to 67.5kPa, can be with
It proves that catechu phenolic group plays a leading role to bond properties, can make its modified macromer that there is certain adhesiveness.
The preparation of 2 chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of embodiment-polyethyleneglycol diglycidylether bioadhesive
By 0.064g (4mmol) chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid (26%3,4- dihydroxy benzenes propionic acid in embodiment 1
Access amount) be dissolved in 250 μ L ultrapure waters be configured to concentration be 25wt% chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid solution, add
0.12g polyethyleneglycol diglycidylether (amino: molar ratio=10:3 of epoxy group) Yu Shangshu chitosan oligosaccharide -3,4- dihydroxy benzenes
In the aqueous solution of propionic acid, magnetic agitation 5min is to being uniformly mixed, and water bath with thermostatic control reaction for 24 hours, obtains chitosan oligosaccharide -3,4- bis- at 37 DEG C
Hydroxy phenylpropionic acid-polyethyleneglycol diglycidylether bioadhesive, is denoted as CSA-PEG0.30.The adhesive strength of gained adhesive
For 110kPa.
The preparation of 3 chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of embodiment-polyethyleneglycol diglycidylether bioadhesive
Referring to embodiment 2,3, the 4- dihydroxy benzenes propionic acid access amount of chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid is replaced with
5%, other conditions are constant, and chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether bioadhesive is prepared
Agent.The adhesive strength of gained adhesive is 40kPa.
The adhesive strength of the different crosslinking degree adhesives of embodiment 4
Referring to embodiment 2, under the same conditions, when the dosage of polyethyleneglycol diglycidylether replaces with 0.08g respectively
With 0.10g (amino: epoxy group molar ratio is respectively 10:5 and 10:4), chitosan oligosaccharide -3,4- dihydroxy of different crosslinking degrees is prepared
Base benzenpropanoic acid-polyethyleneglycol diglycidylether bioadhesive, is denoted as CSA-PEG respectively0.20、CSA-PEG0.25。
Adhesive test is carried out to gained bioadhesive, step 2 in method such as embodiment 1, test result is as shown in table 2.
Chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid is mixed with polyethyleneglycol diglycidylether in certain condition, it may occur that crosslinking curing,
Network structure is formed, its internal stress is greatly improved, to improve the adhesive strength of bio-adhesive materials.The result shows that shell is few
Sugar -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether bioadhesive optimum adhesion intensity can reach 157kPa.
The adhesive strength of the different crosslinking degree adhesives of table 2
In addition, the adhesive of common commercial-Fibrin Glue Fibrin glue adhesive strength is 8.0KPa, this hair
The adhesive strength of bright prepared adhesive improves 5-20 times, is much higher than commercially available fibrin viscose binder.
Claims (9)
1. a kind of preparation method of chitosan oligosaccharide base bioadhesive, which is characterized in that the method is to utilize 3,4- dihydroxy benzenes
Propionic acid forms modified macromer chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid to chitosan oligosaccharide modification, then contracts with polyethylene glycol two
Water glycerin ether is crosslinked to obtain chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid-polyethyleneglycol diglycidylether bioadhesive.
2. the method according to claim 1, wherein amino and 3 in the chitosan oligosaccharide, in 4- dihydroxy benzenes propionic acid
The molar ratio of carboxyl is 5:1~1:1.
3. the method according to claim 1, wherein modified macromer chitosan oligosaccharide -3,4- dihydroxy phenylpropyl alcohol
3,4- dihydroxy benzenes propionic acid unit is 5%~26% compared to mole accounting of the single-stranded upper saccharide ring unit of chitosan oligosaccharide in acid.
4. the method according to claim 1, wherein modified macromer chitosan oligosaccharide -3,4- dihydroxy phenylpropyl alcohol
The molar ratio of amino and polyethyleneglycol diglycidylether epoxy group is 10:3~10:5 in acid.
5. the method according to claim 1, wherein described method includes following steps:
(1) 3,4- dihydroxy benzenes propionic acid and chitosan oligosaccharide under the effect of the catalyst, react 10~15h in acid medium and are changed
Property macromolecular chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid；
(2) by the resulting modified macromer chitosan oligosaccharide -3,4- dihydroxy benzenes propionic acid of step (1) and polyethyleneglycol diglycidylether
Reaction obtains chitosan oligosaccharide based adhesive.
6. according to the method described in claim 5, it is characterized in that, the pH of the acid medium is 4.5~6.0.
7. the chitosan oligosaccharide based adhesive that any the method for claim 1-6 is prepared.
8. the application of chitosan oligosaccharide based adhesive as claimed in claim 7 in the field of medicine, the application includes: to repair as tissue
It is multiplexed adhesive, sealant or hemostatic material.
9. chitosan oligosaccharide based adhesive as claimed in claim 7 is viscous on the surface of glass, metal and its oxide or plastic material
Application in conjunction.
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