CN110029500A - Functionalization orientation fiber and preparation method thereof for the building of tissue engineering blood vessel bracket - Google Patents
Functionalization orientation fiber and preparation method thereof for the building of tissue engineering blood vessel bracket Download PDFInfo
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
- A61L27/507—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials for artificial blood vessels
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
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- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/342—Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
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- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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Abstract
The functionalization orientation fiber and preparation method thereof that the present invention relates to a kind of for the building of tissue engineering blood vessel bracket, by the way that DOPA amine salt DA and lysine Lys to be added in buffer, obtains DA/Lys solution；Will orientation fiber be immersed in DA/Lys solution react to get.The present invention not only effectively enhances the coating result of PDA by introducing active constituent Lys, also significantly improves the coating modified rear orientation regenerated function of fiber-induction blood vessel endothelium.It is PDA/Lys coating process simple process provided by the invention, high-efficient, the poor biocompatibility of polymer matrix tissue engineering blood vessel bracket can effectively be solved, the defects of inducing endothelial regeneration function is insufficient, the research and development and clinical application of promotion functions tissue engineering blood vessel convert.
Description
Technical field
The invention belongs to functionalization orientation fiber and its preparation fields, in particular to a kind of to be used for tissue engineering blood vessel branch
Functionalization orientation fiber that framework is built and preparation method thereof.
Background technique
The orientation fiber of electrical spinning method preparation is recognized because of the architectural characteristic with bionical native blood vessels tissue extracelluar matrix
For be it is a kind of it is important with modulating vascular cell behavior, promote the biomimetic scaffolds of damage vascular repair and functional regeneration to construct material
Material.The characteristics such as synthetic polymer has easy processing, performance is controllable, material source is extensive are widely used in intravascular tissue engineering field
The preparation of middle orientation fibrous framework, but its poor biocompatibility, do not have modulating vascular cell adherence, proliferation and the energy of differentiation
Power needs to carry out modification appropriate, for example enhances its endothelialization function when applying in intravascular tissue engineering.Endothelial regeneration
It is one of the key factor for determining tissue engineering blood vessel clinical application success or failure, has to the long and short phase patency of remodeling blood vessel
Very important effect.Therefore, the biocompatibility of synthetic polymer base orientation fibrous framework how is easily and efficiently improved,
Enhance the intercellular interaction of bracket-to carry out the functional expression of induction of vascular cell, promote vascular endothelial tissue regeneration, is bionical
Construct tissue engineering blood vessel urgent problem to be solved.
In recent years, it is formed on the surface of the material using dopamine catechol group Chemical Diversity and affine diversity etc.
PDA coating is considered as a kind of method of modifying for efficiently, efficiently improving rack surface biocompatibility, to enhance cell
The tissue affinity (Ding et.al., Acta Biomaterialia, 2015.15:150-163) of adherency and bracket.However,
Since DA can generate non-covalent bond during auto polymerization forms PDA, so that nano-scale PDA aggregation is easily deposited on bracket table
Face forms inhomogenous graininess, this anticoagulation function of intravascular stent is had adverse effect (Liu et.al.,
Composites Science and Technology,2017.151:164-173).The study found that functional group containing polyamino point
The introducing of sub (such as hexamethylene diamine, hexa and polyethyleneimine) can be in the coating result for being effectively improved PDA
On the basis of be further successfully introduced into active group for subsequent bio bioactive molecule grafting (Fu et.al., Journal of
Chromatography A,2015.1416:94-102).But this subsequent process that need to further graft active constituent makes bracket
Preparation process complicate, and introduce molecule of functional group containing polyamino itself often lack bioactivity.If it is possible to
The molecule of functional group containing polyamino of tool bioactivity is selected to improve the coating result of PDA, by the biology to enhancing orientation fiber
Functionality is of great significance.
Summary of the invention
Technical problem to be solved by the invention is to provide one kind is needed on the basis of PDA coating in the prior art further
It introduces active group to be grafted, preparation process is complicated, and the polyamino functional group introduced lacks active defect, invention choosing
The coating result for improving PDA with the Lys of bioactivity is modified modification to the orientation fiber of synthetic polymer preparation, prepares
Obtain the orientation fiber modified through PDA/Lys.
A kind of functionalization of the invention is orientated fiber, which is characterized in that the fiber is poly-dopamine PDA and lysine
Lys modified orientation fiber.
A kind of preparation method of functionalization orientation fiber of the invention, comprising:
(1) it dissolves a polymer in solvent, obtains spinning solution, then carry out Electrospun, orientation fiber is prepared；
(2) dopamine hydrochloride DA, lysine Lys are dissolved in buffer, stirring and dissolving obtains DA/Lys solution；
(3) it will be orientated fiber impregnation DA/Lys solution, reaction obtains functionalization orientation fiber.
The preferred embodiment of above-mentioned preparation method is as follows:
Polymer is the copolymer p LCL of lactic acid and caprolactone, polyurethane PU, polycaprolactone (PCL), gathers in the step (1)
Sebacic acid glyceride PGS, poly- citric acid ethohexadiol ester POC, polylactic acid PLA, polymetylmethacrylate, 3-hydroxybutyrate
One or more of the copolymer p HBV of ester and 3- hydroxyl valerate, lactic acid and copolymer p LGA of hydroxyacetic acid.The step
Suddenly solvent is hexafluoroisopropanol, formic acid, acetic acid, methylene chloride, chloroform, acetone, dimethyl sulfoxide, trifluoroacetic acid, three in (1)
One or more of fluoroethanol, methanol, ethyl alcohol, water.
The mass volume ratio of polymer is 1-100g/mL in spinning solution in the step (1).
Electrospinning process parameter in the step (1) are as follows: spinning rate 0.01-100mL/h applies voltage 1-100kV, uses
Roller receives jet stream monofilament, and receiving distance is 0.01-1m, and it is 1-10000rpm, environment temperature that roller reception device, which winds rate,
It is 0-1000 DEG C, envionmental humidity 0-100%.
The mass ratio of dopamine hydrochloride DA and lysine Lys are 1:0-100 in the step (2)；In DA/Lys solution
The concentration of DOPA amine salt DA is 0.1-10mg/mL.
Buffer is the Tris buffer of alkalinity in the step (2), wherein pH=8.5, concentration 10mM.
Reaction in the step (3) are as follows: reaction time 0-100h；Reaction temperature is 0-100 DEG C.
A kind of functionalization of the method preparation of the invention is orientated fiber.
A kind of application of the functionalization orientation fiber provided by the invention in the building of tissue engineering blood vessel bracket.
Beneficial effect
(1) present invention not only effectively enhances the coating result of PDA by introducing active constituent Lys, also significantly improves
The regenerated function of fiber-induction blood vessel endothelium, PDA/Lys coating process technique letter provided by the invention are orientated after coating modified
It is single, high-efficient, it can effectively solve poor biocompatibility, the inducing endothelial regeneration function of polymer matrix tissue engineering blood vessel bracket
The defects of insufficient, the research and development and clinical application of promotion functions tissue engineering blood vessel convert；
(2) present invention selects Lys to regulate and control PDA coating process, convenient and efficient, economic benefits are high, can be effectively improved the painting of PDA
Layer effect, and as the addition of Lys may make coating to have the distinctive functional activity of Lys；
(3) PDA/Lys coating process of the invention can enhance biomaterial in intravascular tissue engineering field and apply function
Effect, as enhanced bioactivity of the synthetic polymer of biologically inert in injury of blood vessel reparation；
(4) preparation method of the functionalization orientation fiber that can be used for the building of tissue engineering blood vessel bracket of the invention, can
The effective orientation fiber for having bionical native blood vessels extra-cellular matrix structure that improves potentially is applied in intravascular tissue engineering field
Prospect.
Detailed description of the invention
Fig. 1 is that PLCL prepared by the present invention is orientated fiber scanning electron microscope diagram；
Fig. 2 is that the modified PLCL of pure PDA is orientated fiber scanning electron microscope diagram；
Fig. 3 is that PDA/Lys (mass ratio 1:0.1) modified PLCL is orientated fiber scanning electron microscope diagram；
Fig. 4 is that PDA/Lys (mass ratio 1:0.5) modified PLCL is orientated fiber scanning electron microscope diagram；
Fig. 5 is that PDA/Lys (mass ratio 1:1) modified PLCL is orientated fiber scanning electron microscope diagram；
Fig. 6 is the fourier conversion infrared spectrum that the modified PLCL of PLCL, PDA modified PLCL, PDA/Lys is orientated fiber
Scheme FTIR；Wherein PLCL-PDA/Lys (1-1), PLCL-PDA/Lys (1-0.5), PLCL-PDA/Lys (1-0.1) are respectively corresponded
Embodiment 4, embodiment 3 and embodiment 2；
Fig. 7 be endothelial cell ECs be planted in cultivated 3 hours on PLCL fiber after cell adherence fluorescent staining figure；
Fig. 8 be ECs be planted in cultivated 3 hours on the modified PLCL fiber of PDA after cell adherence fluorescent staining figure；
Fig. 9 be ECs be planted in cultivate 3 hours on PDA/Lys (mass ratio 1:0.5) modified PLCL fiber after cell glue
Attached fluorescent staining figure；
Figure 10 be ECs be planted in cultivate 3 days on PLCL fiber after cell-specific proteins VE-Cadherin immunofluorescence dye
Chromatic graph；
Figure 11 be ECs be planted in cultivated 3 days on the modified PLCL fiber of PDA after cell-specific proteins VE-Cadherin
Immunofluorescence dyeing figure；
Figure 12 be ECs be planted in cultivate 3 days on PDA/Lys (mass ratio 1:0.5) modified PLCL fiber after cell spy
Foreign preteins VE-Cadherin immunofluorescence dyeing figure.
Figure 13 is the SEM figure in comparative example before and after PCL/CNF composite fibrous scaffold coating: (left figure a) before coating；After coating
(right figure b).
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Embodiment 1
At room temperature, the PLCL of 0.57g (copolymerization ratios of lactic acid and caprolactone are 50:50, viscosity 2.9dl/g) is molten
In the hexafluoroisopropanol of 6mL, the spinning solution that mass fraction is 10% is obtained after stirring 12h；In room, epidemic disaster is 40-60%
Under conditions of carry out Electrospun, applied voltage is 5kV, and receiving distance is 20cm, and it is 1000rpm, injection that roller, which receives revolving speed,
Rate is 0.5mL/h.
The scanning electron microscope (SEM) photograph of the pure PLCL orientation fiber of preparation, as shown in Figure 1, showing it with height-oriented structure, fibre
Tieing up diameter is 1.67 ± 0.17 μm.
Cell adherence situation after the bracket is planted ECs 3 hours, as shown in fig. 7, bracket plantation ECs is thin after cultivating 3 days
Born of the same parents' functional protein VE-Cadherin expression, as shown in Figure 10, though show that PLCL orientation fiber can maintain ECs functional expression,
But cell adherence situation is unsatisfactory.
It is to be sufficiently stirred in Tris buffer that 10mM, pH are 8.5 that the Lys of the DA of 20mg and 0mg, which is dissolved in 10mL concentration,
Dissolution prepares and obtains DA/Lys solution.The orientation fiber base bracket of 1cm × 1cm is immersed in DA/Lys solution, with 100 times/
The vibration rate room temperature oscillation of minute for 24 hours, obtains the modified orientation fiber of PDA.PDA modified orientation fiber scanning electron microscope (SEM) photograph,
As shown in Figure 2, it was demonstrated that fiber surface has granular agglomerate, and the raising (1.89 ± 0.13 μm) of fibre diameter shows poly-dopamine
Success coating is in fiber surface.The FTIR spectrum figure of the bracket, as shown in fig. 6, the raising of-NH absorption peak further confirms PDA
Successful application.The bracket plant ECs 3 hours after cell adherence situation as shown in figure 8, the bracket plantation ECs cultivate 3 days after
Cell function albumen VE-Cadherin expression is as shown in figure 11, show the adherency that may advantageously facilitate ECs after PDA coating and
Functional expression.
Embodiment 2
At room temperature, the PLCL of 0.57g (copolymerization ratios of lactic acid and caprolactone are 50:50, viscosity 2.9dl/g) is molten
In the hexafluoroisopropanol of 6mL, the spinning solution that mass fraction is 10% is obtained after stirring 12h；In room, epidemic disaster is 40-60%
Under conditions of carry out Electrospun, applied voltage is 5kV, and receiving distance is 20cm, and it is 1000rpm, injection that roller, which receives revolving speed,
Rate is 0.5mL/h.It is to fill in Tris buffer that 10mM, pH are 8.5 that the Lys of the DA of 20mg and 2mg, which is dissolved in 10mL concentration,
Point stirring and dissolving is prepared to obtain DA/Lys solution.The orientation fiber base bracket of 1cm × 1cm is immersed in DA/Lys solution, with
100 beats/min of vibration rate room temperature oscillation for 24 hours, obtains the modified orientation fiber of PDA/Lys.PDA/Lys modified orientation is fine
Scanning electron microscope (SEM) photograph is tieed up, as shown in figure 3, showing that fiber surface granular agglomerate starts to increase, fibre diameter is further increased
(1.98 ± 0.11 μm) show the coating result enhancing of PDA.The FTIR spectrum figure of the bracket, as shown in fig. 6 ,-NH absorption peak
It further increases and demonstrates the enhancing of PDA coating result.
Embodiment 3
At room temperature, the PLCL of 0.57g (copolymerization ratios of lactic acid and caprolactone are 50:50, viscosity 2.9dl/g) is molten
In the hexafluoroisopropanol of 6mL, the spinning solution that mass fraction is 10% is obtained after stirring 12h；In room, epidemic disaster is 40-60%
Under conditions of carry out Electrospun, applied voltage is 5kV, and receiving distance is 20cm, and it is 1000rpm, injection that roller, which receives revolving speed,
Rate is 0.5mL/h.The Lys of the DA of 20mg and 10mg, which is dissolved in 10mL concentration, is in Tris buffer that 10mM, pH are 8.5,
Dissolution preparation is sufficiently stirred and obtains DA/Lys solution.The orientation fiber base bracket of 1cm × 1cm is immersed in DA/Lys solution,
For 24 hours with 100 beats/min of vibration rate room temperature oscillation, the modified orientation fiber of PDA/Lys is obtained.PDA/Lys modified orientation
Fiber scanning electron microscope (SEM) photograph, as shown in figure 4, showing that fiber surface granular agglomerate starts to reduce, but the increase of fibre diameter
The coating result of (2.02 ± 0.16 μm) confirmation PDA is more preferably.The FTIR spectrum figure of the bracket as shown in fig. 6 ,-NH absorption peak after
Continuous raising shows that PDA coating result is further enhanced.Cell adherence situation such as Fig. 9 institute after the bracket is planted ECs 3 hours
Show, cell function albumen VE-Cadherin expression is as shown in figure 12 after which plants ECs culture 3 days, shows PDA/
Further promote adherency and the functional expression of ECs after Lys coating.
Embodiment 4
At room temperature, the PLCL of 0.57g (copolymerization ratios of lactic acid and caprolactone are 50:50, viscosity 2.9dl/g) is molten
In the hexafluoroisopropanol of 6mL, the spinning solution that mass fraction is 10% is obtained after stirring 12h；In room, epidemic disaster is 40-60%
Under conditions of carry out Electrospun, applied voltage is 5kV, and receiving distance is 20cm, and it is 1000rpm, injection that roller, which receives revolving speed,
Rate is 0.5mL/h.The Lys of the DA of 20mg and 20mg, which is dissolved in 10mL concentration, is in Tris buffer that 10mM, PH are 8.5,
Dissolution preparation is sufficiently stirred and obtains DA/Lys solution.The orientation fiber base bracket of 1cm × 1cm is immersed in DA/Lys solution,
For 24 hours with 100 beats/min of vibration rate room temperature oscillation, the modified orientation fiber of PDA/Lys is obtained.PDA/Lys modified orientation
Fiber scanning electron microscope (SEM) photograph is 1.93 ± 0.15 μm, shows the coating of PDA as shown in figure 5, measuring fibre diameter has downward trend
Effect starts to be deteriorated.The FTIR spectrum figure of the bracket is as shown in fig. 6, the reduction of-NH absorption peak shows PDA coating result in now
Drop trend.
Comparative example 1
Comparative example is related to a kind of based on the coating modified polycaprolactone of uniform poly-dopamine (PCL)/natural-nanometer fiber
(CNF) (application number: 201810182493.3), preparation step is as follows: it is molten to weigh 4g PCL for the preparation method of composite fibrous scaffold
In 20mL chloroform: in dimethylformamide (4:1) mixed solution, room temperature concussion dissolution obtains PCL spinning solution；In room epidemic disaster
Electrospun is carried out under conditions of being 40% and obtains the disorderly arranged nano fibrous membrane of PCL, and applied voltage is 15kV, receives distance
For 15cm, injection rate 1mL/h.Weigh 0.08g CNF be placed in 50mL deionized water stir 30min obtain CNF suspension
Liquid；PCL tunica fibrosa is placed in CNF suspension and is ultrasonically treated 10min, obtains PCL/CNF composite cellulosic membrane；By the DA of 0.5g
It is dissolved in 250mL concentration and is in Tris buffer that 10mM, PH are 8.5 dissolution is sufficiently stirred preparing and obtain DA solution.By PCL/
CNF composite cellulosic membrane is immersed in DA solution, and room temperature magnetic agitation 20h obtains the composite fibrous scaffold of PDA uniform coating.Figure
13 give the SEM figure of the PCL/CNF composite fibrous scaffold before and after PDA coating.It can be seen that fibrous framework surface is thick after compound
Rugosity increases, and fibre diameter improves.The result shows that PCL/CNF composite fiber surface has been successfully formed uniform PDA coating.
The preparation method mainly improves PDA painting by introducing natural-nanometer fiber element mode in disorderly arranged fiber surface
The problems such as layer uniformity is poor, coating time period is long, coating stability is poor.But the CNF ultrasonication that this method is related to makes
The defects of PDA coating complicates, and there are the residuals of the unnecessary material composition such as CNF.And a kind of functionalization of the present invention
Be orientated fiber preparation method, be under the background based on engineering blood vessel field introduce can promote the Lys of revascularization at
Point, this method not only successfully solves the problems, such as on PDA coating on the basis of simplifying operating procedure, also further imparts fiber
Bracket promotes the function of revascularization, has more application prospect in field of tissue engineering technology.
Claims (10)
1. a kind of functionalization is orientated fiber, which is characterized in that the fiber, which is that poly-dopamine PDA and lysine Lys is modified, to be taken
To fiber.
2. a kind of preparation method of functionalization orientation fiber, comprising:
(1) it dissolves a polymer in solvent, obtains spinning solution, then carry out Electrospun, orientation fiber is prepared；
(2) dopamine hydrochloride DA, lysine Lys are dissolved in buffer, stirring and dissolving obtains DA/Lys solution；
(3) it will be orientated fiber impregnation DA/Lys solution, reaction obtains functionalization orientation fiber.
3. preparation method according to claim 2, which is characterized in that polymer is lactic acid and caprolactone in the step (1)
Copolymer p LCL, polyurethane PU, polycaprolactone (PCL), poly- sebacic acid glyceride PGS, poly- citric acid ethohexadiol ester POC, poly- cream
Sour PLA, polymetylmethacrylate, 3-hydroxybutyrate ester and 3- hydroxyl valerate copolymer p HBV, lactic acid and hydroxyl
One or more of copolymer p LGA of acetic acid.
4. preparation method according to claim 2, which is characterized in that solvent is hexafluoroisopropanol, first in the step (1)
Acid, acetic acid, methylene chloride, chloroform, acetone, dimethyl sulfoxide, trifluoroacetic acid, trifluoroethanol, methanol, ethyl alcohol, one in water
Kind is several.
5. preparation method according to claim 2, which is characterized in that electrospinning process parameter in the step (1) are as follows: spinning
Rate 0.01-100mL/h applies voltage 1-100kV, receives jet stream monofilament with roller, and receiving distance is 0.01-1m, and roller connects
It is 1-10000rpm that receiving apparatus, which winds rate, and environment temperature is 0-1000 DEG C, envionmental humidity 0-100%.
6. preparation method according to claim 2, which is characterized in that dopamine hydrochloride DA and bad ammonia in the step (2)
The mass ratio of sour Lys is 1:0-100；The concentration of dopamine hydrochloride DA is 0.1-10mg/mL in DA/Lys solution.
7. preparation method according to claim 2, which is characterized in that buffer is that the Tris of alkalinity is slow in the step (2)
Fliud flushing, wherein pH=8.5.
8. preparation method according to claim 2, which is characterized in that reaction in the step (3) are as follows: reaction time 0-
100h；Reaction temperature is 0-100 DEG C.
9. a kind of functionalization of claim 2 the method preparation is orientated fiber.
10. functionalization described in a kind of claim 1 is orientated application of the fiber in the building of tissue engineering blood vessel bracket.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110806402A (en) * | 2019-10-08 | 2020-02-18 | 中国水产科学研究院 | Neuromelanoidin-like nano material and preparation method and application thereof |
| CN111388766A (en) * | 2020-05-09 | 2020-07-10 | 刘成刚 | Biodegradable nano-film for vascular surgery and preparation method thereof |
| CN112316218A (en) * | 2020-10-26 | 2021-02-05 | 西北大学 | Zwitterionic polymer and heparin composite coating, preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112316218A (en) * | 2020-10-26 | 2021-02-05 | 西北大学 | Zwitterionic polymer and heparin composite coating, preparation method and application thereof |
| CN112316218B (en) * | 2020-10-26 | 2021-12-10 | 西北大学 | Zwitterionic polymer and heparin composite coating, preparation method and application thereof |
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