CN104789547A - Preparation method and application of high-density RGD peptide modified material - Google Patents
Preparation method and application of high-density RGD peptide modified material Download PDFInfo
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- CN104789547A CN104789547A CN201510175638.3A CN201510175638A CN104789547A CN 104789547 A CN104789547 A CN 104789547A CN 201510175638 A CN201510175638 A CN 201510175638A CN 104789547 A CN104789547 A CN 104789547A
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- 0 CC(CC(C)(C)C(C)(C)*(*)=O)Br Chemical compound CC(CC(C)(C)C(C)(C)*(*)=O)Br 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N ON(C(CC1)=O)C1=O Chemical compound ON(C(CC1)=O)C1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a preparation method and application of a high-density RGD peptide modified material. The preparation method comprises the following steps: dispersing a material, modified in the way that the surface is provided with an active group, into methylbenzene, adding a catalytic amount of 4-dimethylamino-pyridine, and slowly dropwise adding triethylamine and 2-bromoisobutyryl bromide under ice-bath, so as to prepare an initiator; adding cuprous bromide, 2,2'-dipyridyl and poly(ethylene glycol) methyl ether methacrylate into the initiator, so as to obtain a macromolecular polymer; adding the macromolecular polymer into a dimethylformamide solution containing an activating agent and 4-dimethylamino-pyridine to obtain an activated polymer brush, and adding RGD peptide for performing reaction in the dark at the room temperature for 18 hours; transferring a cell into the RGD peptide modified polymer brush, and performing reaction on a shaking table at the temperature of 4 DEG C for 20 minutes by adopting a phosphate buffer solution as a suspension liquid, so as to obtain the high-density RGD peptide modified material. The method is moderate in reaction conditions, simple, convenient and feasible in procedures, and achieves the purpose of fixing a cell on the surface of a solid material with high concentration and high density.
Description
Technical field
The present invention relates to biomedical sector, the polymer brush layer of application RGD-containg peptide is modified solid material surface, cell is fixed on material surface, is specially a kind of preparation method and application of high-density RGD peptide decorative material.
Background technology
Biomass cells immobilization technology refers to and utilizes the means of chemistry or physics naturally to be fixed by cell or be positioned, in the area of space of restriction, to keep the catalytic activity that it is intrinsic, and can Reusability.Immobilization biological cell energy continuous proliferation, dormancy and decline, its activity remains stable.Immobilized biomass cells except its original identification of maintenance, combination and catalytic activity, also have be easy to be separated, the significant advantage such as reusable and stability raising.If the solid material of avidity can be had as a kind of bio-medical material using with cell, implant when histoorgan is impaired, the normal function of damaged tissue can be repaired, greatly reduce the untoward reaction of body for implant, make the speed of postoperative recovery from illness greatly accelerate simultaneously.
Originally, surgery be cut, removal lesion tissue is the Main Means of curing the disease, and when tissue, organ due to illness hurt ruin, when cannot repair its function by existing medical procedure, then can by a kind of method implanting tissue or organ, replace the function of disease damage histoorgan, keep the normal activities of body.The replacing of human tissue organ has two kinds, a kind of is the transplanting of allohisto compatibility's organ, as renal transplantation, heart transplantation, liver transplantation, corneal transplantation etc., and at present in countries in the world, the limited source of donor organ is all a large bottleneck of restriction allosome organ transplantation; And another kind of method is artificial organ and tissue transplantation, as the implantation etc. of the transplanting of the implantation of heart valve prosthesis, artificial blood vessel, the implantation of joint prosthesis, the implantation of artificial bone and artificial lens.And the displacement of artificial organ is due to the progress of science and technology, the structure and function of artificial organ, also constantly changing nearly raising, successfully at clinical application, considerably improves clinical levels.
Artificial organ is from essence, and be a kind of medical device with artificial material manufacture or instrument, they have a kind of function partly or entirely substituting human body natural's organ.And for the intravital macromolecular material of implantable bioartificial, generally should have two kinds of fundamental propertys, i.e. medicinal functional and biocompatibility.Medicinal functional refers to that material can reach the effect of diagnosis or medical treatment after combining with bio-tissue; And biocompatibility refers to the degree mutually held between material and biological tissue.Whatsoever material implant into body, concerning coenocorrelation in body, it is all a kind of foreign matter outside tissue, and the physical chemical factor that all can produce in various degree for body tissue cell stimulates, as caused the change such as connective tissue proliferation, tissue calcification.Simultaneously the nerve of body, humoral system environment also can produce a series of corrosive effect and rejection to the biomaterial implanted, and this is enorganic a kind of defense mechanism.If this rejection is on body physiological function, cause more serious impact to the physics of material itself and chemical property, even cause the afunction of artificial organs, serious threatens HUMAN HEALTH, and so this material cannot be applied to clinical treatment.It is restrained or be limited in certain spatial dimension that immobilized cell is that phalangeal cell is subject to the factors such as physical chemistry, but cell still retain catalytic activity and have can by the vigor repeatedly or continuously used.At present, this technology has been widely used in the fields such as fermentation, pharmacy, environment protection.Conventional cell fixation methods has absorption method, entrapping method, crosslinking, covalent coupling method, flocculence etc.Entrapping method is by cellular localization in gel network or in polymkeric substance semi-permeable membranes microcapsule, and the structure of formation can prevent cell seepage, but permission substrate enters, product diffuses out.Its shortcoming is the reaction that diffusional resistance is large, be not suitable for catalysis macromolecule substrate and product; Covalent coupling method relies on cell surface and forms chemical covalent bonds connection between functional group and the reactive group of solid support surface, the method cell is combined with carrier closely, difficult drop-off, but reaction is violent, the difficult control of condition, cytoactive loss is large, preparation is more difficult; Mainly there is chemical reaction by the group (as sulfydryl, hydroxyl, amino etc.) of poly functional reagent and cell surface and form covalent linkage in crosslinking the method, realizes the immobilization of cell.The outstanding feature of the method is that cell is combined closely with carrier, but chemical reaction is violent, and cytoactive is reduced greatly, preparation trouble; Absorption method is combined by physical adsorption or ionization the method be fixed on by cell on carrier between cell with carrier.The method is simple to operate, little on the impact of cell, but adsorptive power is little, cell easily comes off.In traditional method for immobilizing cell, during by adsorption fixed cell, general binding ability is weak, and cell easily comes off; By covalent linkage effect, method fixing for cell is then large to cell damage, cannot cytoactive be kept.
Therefore meeting the material implanted most important condition, is exactly that its biocompatibility wants high.The impact of biosystem on biocompatibility comprises the physiological environment etc. of organism kind, implant site, the healthy state of acceptor, heeling-in remaining time, use.In general, on material and the interactional reaction of organism mainly concentrate on that solid bio-material and bioresorbable formed solid-liquid interface.Polymer brush refers to that macromolecular chain one end is fixed on a kind of polymkeric substance packaging assembly that certain interface is formed, and the polymer brush containing RGD peptide, by series of chemical, is grafted on solid material surface by the present invention, forms shallow layer.RGD peptide is the small peptide that a class contains arginine, glycine, aspartic acid sequence, is present in multiple biomass cells epimatrix, can identify cell surface integrin specifically and combine with it, thus mediating multiple important physiological process.And integrin is present in most cells surface, it is the transmembrane receptor of a kind of mediated cell and intercellular interaction and cell and extracellular matrix interphase interaction.By identification and the interaction of cell surface integrin and RGD peptide, cell adhesion can be made at the solid material surface of RGD-containg peptide polymer brush layer, be applied in the biomedical material in all kinds of implant into body, not only greatly strengthen the biocompatibility of material, reduce immunological rejection, and this adhesion, make cells in vivo in the better adaptability of implantation material surface, more easily breed, greatly reduce the untoward reaction of body.And the method also can be used as a kind of synthetic method of new chromatographic filler, the interaction of Study of Exogenous drug molecule and the functional protein entrained by it on a cellular level.Cell is the primitive reaction device of organism vital movement, functional protein entrained by it and exogenous drugs molecule, the interaction of endogenous cytokine, chemokine and somatomedin, be the prerequisite starting and complete later stage compact cascade type intracellular signaling process, also determine each physiological processes in organisms in itself.What is more important, the specificity interaction process of this complexity and the pathology and disease mechanism of disease have close relationship, are also often carried out the research and development of new drug and the treatment of disease by as foundation.If whole cell reactor can be fixed carrier surface by special antigen-antibody physiological response, as chromatographic media, then can not only inherit the advantage of classical affinity chromatography method, and the deficiency that it can not embody functional protein intracellular signaling process can be overcome, thus by chromatographic process obtain on a cellular level functional protein and Drug Ligand interact and in organoid produced thus physiological processes more accurately, abundanter information.
Summary of the invention
The object of the invention is to put forward a kind of active immobilized method of high-density cells, its preparation method reaction conditions is gentle, and step is simple and easy to do, and farthest can preserve cell integrity with active, adsorptive power is strong, cell difficult drop-off.
The present invention is by the following technical solutions for achieving the above object:
A preparation method for high-density RGD peptide decorative material, comprises the following steps:
(1) preparation of initiator
Amino microballoon is scattered in toluene, ultrasonic 10 minutes, add the DMAP of catalytic amount, slowly be added dropwise to triethylamine and 2-bromine isobutyl acylbromide under ice bath, continue stirring under ice bath after 2 hours, be warming up to stirred at ambient temperature fully reaction in 12 hours, use sand core funnel suction filtration, after using dry methylene chloride, acetone, methanol wash successively, drying 12 hours under temperature 60 C vacuum, obtained initiator;
Reaction scheme is as follows:
(2) synthesis of polymer brush
Amino for step (1) gained initiator microballoon is added in the mixing solutions containing polyethylene glycol methacrylate-styrene polymer, cuprous bromide, 2-2 dipyridyl and methanol solvate, stop surperficial transition free radical polymerization reaction at nitrogen protection stirring reaction after 6 hours, wash successively with pure water and methyl alcohol; Reaction scheme is as follows:
(3) activation of polymer brush
Step (2) reaction resulting polymers brush is added in the dimethyl formamide solution containing the drying of carbonyl dimidazoles and DMAP, pass into nitrogen and at room temperature react 6 hours, reaction terminates the washing of rear dimethyl formamide solution, obtains the polymer brush of activation;
Reaction scheme is as follows:
(4) grafting of RGD
The polymer brush of activation is put into the dimethyl formamide solution containing RGD peptide and DMAP, 18 hours are reacted in lucifuge at room temperature condition, wash successively with dimethyl formamide and phosphate buffered saline buffer, suction filtration, obtain the polymer brush that RGD peptide is modified;
(5) immigration of cell
The polymer brush that step (4) gained RGD peptide is modified is kept in phosphate buffered saline buffer, cell is moved in the EGMA polymer brush of RGD-containg peptide modification, take phosphate buffered saline buffer as suspension, shaking bed reaction 20 minutes at temperature 4 DEG C, obtain the solid material containing immobilized cell coating.
The material that described surface band active group is modified is micro-any one of amino microballoon, carboxyl microballoon, polystyrene microsphere, polyvinyl alcohol microparticles, polymethylmethacrylate.
The methanol solvate of described step (2) is the mixed solution of first alcohol and water, and methyl alcohol and water volume ratio are 4:1.
Described step (3) activating reagent be carbonyl dimidazoles, N-base N-Hydroxysuccinimide, maleimide any one.
The high-density RGD peptide decorative material that the preparation method that present invention also offers a kind of high-density RGD peptide decorative material obtains.This high-density RGD peptide decorative material is applied to the making of body implanting material (as artificial blood vessel, man-made support, heart valve prosthesis etc.), makes the screening that chromatograph packing material is applied to active ingredient of Chinese herbs.
Compared with prior art, beneficial effect of the present invention: the method reaction conditions is gentle, step is simple and easy to do, what the method adopted is that surperficial Atom Transfer Radical Polymerization reactive applications is driven polymer brush in the albumen of preparation grafting polyethylene glycol methacrylate-styrene polymer (OEGMA), again RGD peptide is grafted on polymer brush layer, enable cell be adsorbed in coating by the specificity affinity interaction of integrin on RGD peptide and film; The polymer brush that RGD peptide can be made to modify to greatest extent with cells contacting, farthest preserve cell integrity with active, adsorptive power is strong, and cell difficult drop-off, achieves cell high density, the object being fixed on solid material surface to high-density.This cell fixation methods is used for the preparation of chromatograph packing material, the screening of activeconstituents in complex system can be realized on a cellular level.
Accompanying drawing explanation
Fig. 1 is embodiment of the present invention Ligusticum wallichii extracting solution color atlas.
Embodiment
Below in conjunction with the drawings and specific embodiments, the present invention is further elaborated.
A preparation method for high-density RGD peptide decorative material, comprises the following steps:
(1) preparation of initiator
Amino for 1g microballoon (30 μm) is scattered in 30mL toluene, ultrasonic 10 minutes, add the DMAP of catalytic amount (0.08g), slowly be added dropwise to 1.25mL triethylamine and 0.75mL 2-bromine isobutyl acylbromide under ice bath, continue stirring under ice bath after 2 hours, be warming up to stirred at ambient temperature fully reaction in 12 hours, use sand core funnel suction filtration, after using toluene, acetone, methanol wash successively, drying 12 hours under temperature 60 C vacuum, obtained initiator;
Reaction scheme is as follows:
(2) synthesis of polymer brush
Amino for step (1) gained initiator microballoon is added containing polyethylene glycol methacrylate-styrene polymer (17.5mL, 63mmol), cuprous bromide CuBr (180mg, 1.26mmol), 2-2 dipyridyl (490mg, 3.15mmol) and methanol solvate (V
water: V
methyl alcohol=1:4) mixing solutions in, stop surperficial transition free radical polymerization reaction at nitrogen protection stirring reaction after 6 hours, wash successively with pure water and methyl alcohol;
Reaction scheme is as follows:
(3) activation of polymer brush
Step (2) reaction resulting polymers brush is added in the dimethyl formamide solution containing the drying of 0.32g carbonyl dimidazoles and 0.24g DMAP (DMAP), pass into nitrogen and at room temperature react 6 hours, reaction terminates the washing of rear dimethyl formamide solution, obtains the polymer brush of activation;
Reaction scheme is as follows:
(4) grafting of RGD
The polymer brush of activation is put into the dimethyl formamide solution containing 1mM RGD peptide and 2.5mM DMAP (DMAP), 18 hours are reacted in lucifuge at room temperature condition, wash successively with dimethyl formamide and 50mM phosphate buffered saline buffer, suction filtration, obtains the polymer brush that RGD peptide is modified;
(5) immigration of cell
The polymer brush that step (4) gained RGD peptide is modified is kept in 20mM phosphate buffered saline buffer, the Human umbilical vein endothelial cells that cell cultures obtains is moved in the polymer brush of RGD-containg peptide modification, with 20mM phosphate buffered saline buffer for suspension, shaking bed reaction 20 minutes at temperature 4 DEG C, obtain immobilization vascular endothelial cell.Dress column condition is with 50.0mM phosphate buffer soln for homogenate and displacer, and dress column pressure is 200bar, and the dress post time is 30 minutes, wet method dress post.The reaction scheme figure that cell is fixed on solid material surface is as follows:
This high-density RGD peptide decorative material is applied to the making of body implanting material, makes the screening that chromatograph packing material is applied to active ingredient of Chinese herbs.Such as make the screening that chromatograph packing material is applied to Bai mustard seed active ingredients of medicinal materials, in Ligusticum wallichii extracting solution, the activeconstituents of vasoactive endothelial cell growth factor receptor 2 body screens, as shown in Figure 1, there is the active substance of 3 vasoactive endotheliocytes in visible extracting solution.
The method, under the prerequisite ensureing cytoactive and integrity, by the affinity interaction of part acceptor corresponding on cytolemma, by high cell densities ground, is fixed on solid material surface firmly.This polymer brush can be used as the surface that coating is wrapped in artificial organ, organ, is significant to its biocompatibility of increase.This cell fixation methods is used for the preparation of chromatograph packing material, the screening of activeconstituents in complex system can be realized on a cellular level.
Claims (6)
1. a preparation method for high-density RGD peptide decorative material, is characterized in that, comprises the following steps:
(1) preparation of initiator
The dispersion of materials of being modified by surface band active group is in toluene, ultrasonic 10 minutes, add the DMAP of catalytic amount, slowly be added dropwise to triethylamine and 2-bromine isobutyl acylbromide under ice bath, continue stirring under ice bath after 2 hours, be warming up to stirred at ambient temperature fully reaction in 12 hours, use sand core funnel suction filtration, successively after toluene, acetone, methanol wash, drying 12 hours under temperature 60 C vacuum, obtained initiator;
(2) synthesis of polymer brush
Step (1) gained initiator is added in the mixing solutions containing polyethylene glycol methacrylate-styrene polymer, cuprous bromide, 2-2 dipyridyl and MeOH methanol solvent, stop surperficial transition free radical polymerization reaction at nitrogen protection stirring reaction after 6 hours, wash successively with pure water and methyl alcohol;
(3) activation of polymer brush
Step (2) reaction resulting polymers brush is added in the dimethyl formamide solution containing the drying of activating reagent and DMAP, pass into nitrogen and at room temperature react 6 hours, reaction terminates the washing of rear dimethyl formamide solution, obtains the polymer brush of activation;
(4) grafting of RGD
The polymer brush of activation is put into the dimethyl formamide solution containing RGD peptide and DMAP, 18 hours are reacted in lucifuge at room temperature condition, wash successively with dimethyl formamide and phosphate buffered saline buffer, suction filtration, obtain the polymer brush that RGD peptide is modified;
(5) immigration of cell
The polymer brush that step (4) gained RGD peptide is modified is kept in phosphate buffered saline buffer, cell is moved in the polymer brush of RGD-containg peptide modification, take phosphate buffered saline buffer as suspension, shaking bed reaction 20 minutes at temperature 4 DEG C, obtaining high-density RGD peptide decorative material.
2. the preparation method of a kind of high-density RGD peptide decorative material as claimed in claim 1, it is characterized in that, the material that described surface band active group is modified is micro-any one of amino microballoon, carboxyl microballoon, polystyrene microsphere, polyvinyl alcohol microparticles, polymethylmethacrylate.
3. the preparation method of a kind of high-density RGD peptide decorative material as claimed in claim 1, is characterized in that, the methanol solvate of described step (2) is the mixed solution of first alcohol and water, and methyl alcohol and water volume ratio are 4:1.
4. the preparation method of a kind of high-density RGD peptide decorative material as claimed in claim 1, is characterized in that, described step (3) activating reagent be carbonyl dimidazoles, N-base N-Hydroxysuccinimide, maleimide any one.
5. the high-density RGD peptide decorative material obtained by the preparation method of the arbitrary described a kind of high-density RGD peptide decorative material of claim 1-4.
6. the application of the high-density RGD peptide decorative material obtained by the preparation method of the arbitrary described a kind of high-density RGD peptide decorative material of claim 1-4, this high-density RGD peptide decorative material is applied to the making of body implanting material, makes the screening that chromatograph packing material is applied to active ingredient of Chinese herbs.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108176384A (en) * | 2018-01-17 | 2018-06-19 | 四川大学 | It is grafted magnetic nano-balls of arginine polymer brush and preparation method and application |
| CN109575309A (en) * | 2018-12-20 | 2019-04-05 | 左国幼 | A kind of preparation method of biological high molecular material |
| CN113462640A (en) * | 2021-06-16 | 2021-10-01 | 成都微沃科技有限公司 | Preparation method of caging ligand for regulating and controlling cell spreading rate |
| CN115531614A (en) * | 2022-09-22 | 2022-12-30 | 新乡医学院 | RGD coupled cross-linked PVA scaffold for promoting endothelial differentiation and preparation method thereof |
-
2015
- 2015-04-13 CN CN201510175638.3A patent/CN104789547B/en active Active
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108176384A (en) * | 2018-01-17 | 2018-06-19 | 四川大学 | It is grafted magnetic nano-balls of arginine polymer brush and preparation method and application |
| CN108176384B (en) * | 2018-01-17 | 2020-08-14 | 四川大学 | Magnetic nanosphere of grafted arginine polymer brush as well as preparation method and application of magnetic nanosphere |
| CN109575309A (en) * | 2018-12-20 | 2019-04-05 | 左国幼 | A kind of preparation method of biological high molecular material |
| CN113462640A (en) * | 2021-06-16 | 2021-10-01 | 成都微沃科技有限公司 | Preparation method of caging ligand for regulating and controlling cell spreading rate |
| CN113462640B (en) * | 2021-06-16 | 2024-03-22 | 成都微沃科技有限公司 | Preparation method of caged ligand for regulating cell spreading rate |
| CN115531614A (en) * | 2022-09-22 | 2022-12-30 | 新乡医学院 | RGD coupled cross-linked PVA scaffold for promoting endothelial differentiation and preparation method thereof |
| CN115531614B (en) * | 2022-09-22 | 2023-03-17 | 新乡医学院 | RGD coupled cross-linked PVA scaffold for promoting endothelial differentiation and preparation method thereof |
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