CN115572502A - Multifunctional coating based on cation-pi interaction and preparation method and application thereof - Google Patents
Multifunctional coating based on cation-pi interaction and preparation method and application thereof Download PDFInfo
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- CN115572502A CN115572502A CN202211233345.2A CN202211233345A CN115572502A CN 115572502 A CN115572502 A CN 115572502A CN 202211233345 A CN202211233345 A CN 202211233345A CN 115572502 A CN115572502 A CN 115572502A
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- 230000003993 interaction Effects 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000000758 substrate Substances 0.000 claims abstract description 61
- 239000000463 material Substances 0.000 claims abstract description 50
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- 150000008442 polyphenolic compounds Chemical class 0.000 claims abstract description 16
- 235000013824 polyphenols Nutrition 0.000 claims abstract description 16
- 230000003373 anti-fouling effect Effects 0.000 claims abstract description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 56
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 38
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 36
- 239000011550 stock solution Substances 0.000 claims description 34
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 32
- 239000007864 aqueous solution Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 20
- 229940079877 pyrogallol Drugs 0.000 claims description 18
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 16
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- 239000008363 phosphate buffer Substances 0.000 claims description 10
- LEAHFJQFYSDGGP-UHFFFAOYSA-K trisodium;dihydrogen phosphate;hydrogen phosphate Chemical compound [Na+].[Na+].[Na+].OP(O)([O-])=O.OP([O-])([O-])=O LEAHFJQFYSDGGP-UHFFFAOYSA-K 0.000 claims description 10
- 239000007853 buffer solution Substances 0.000 claims description 9
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical group [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 8
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- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 8
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- 239000010703 silicon Substances 0.000 claims description 7
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- 150000002148 esters Chemical class 0.000 claims description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 5
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
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- 239000010935 stainless steel Substances 0.000 claims description 3
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims description 2
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- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 claims description 2
- 108010039918 Polylysine Proteins 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
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- 229940030275 epigallocatechin gallate Drugs 0.000 claims description 2
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 claims description 2
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- IBHWREHFNDMRPR-UHFFFAOYSA-N phloroglucinol carboxylic acid Natural products OC(=O)C1=C(O)C=C(O)C=C1O IBHWREHFNDMRPR-UHFFFAOYSA-N 0.000 claims description 2
- 229920000083 poly(allylamine) Polymers 0.000 claims description 2
- 229920000656 polylysine Polymers 0.000 claims description 2
- 229960001755 resorcinol Drugs 0.000 claims description 2
- ZEDAGFBWUVYFQU-UHFFFAOYSA-M sodium;3-morpholin-4-ylpropane-1-sulfonate;hydrate Chemical compound [OH-].[Na+].OS(=O)(=O)CCCN1CCOCC1 ZEDAGFBWUVYFQU-UHFFFAOYSA-M 0.000 claims description 2
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- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
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- DEGAKNSWVGKMLS-UHFFFAOYSA-N calcein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(CN(CC(O)=O)CC(O)=O)=C(O)C=C1OC1=C2C=C(CN(CC(O)=O)CC(=O)O)C(O)=C1 DEGAKNSWVGKMLS-UHFFFAOYSA-N 0.000 description 1
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4816—Wall or shell material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Plant Pathology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Inorganic Chemistry (AREA)
- Paints Or Removers (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention discloses a multifunctional coating based on a cation-pi interaction, a preparation method and application thereof, and belongs to the technical field of surface modification of biomedical materials. The invention utilizes polyphenol and polyamine to prepare the coating in one step, and the material can be coated on the surfaces of various substrates and has universality. In addition, the coating has outstanding bacteriostatic effect. When the coating is constructed, functional molecules capable of reacting with amino or aldehyde groups are added, so that the coating has multiple functions of biological antifouling and the like.
Description
Technical Field
The invention belongs to the technical field of surface modification of biomedical materials, and particularly relates to a multifunctional coating based on a cation-pi interaction, and a preparation method and application thereof.
Background
The surface modification technology plays an important role in the fields of biological medicine, material manufacturing, industrial production and the like. In recent years, researchers have developed a variety of simple, versatile surface modification techniques, such as coating with polydopamine. However, existing coating techniques suffer from low coating rates; the functional molecules with surface energy to be immobilized are limited in types and require multiple steps; the problems that various functions (such as antibacterial performance and antifouling performance) cannot be realized and the like greatly limit the further application of the antibacterial and antifouling paint.
Chinese patent document CN112587734A discloses a multifunctional coating of biomimetic dopamine, firstly, coating a layer of polydopamine on a substrate, and then further grafting functional molecules containing amino to prepare the coating which has multiple functions of antibiosis, anticoagulation and the like. However, the formation rate of such a coating is low and requires multiple steps, which are time and labor consuming.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a multifunctional coating based on the cation-pi interaction, and a preparation method and application thereof. The invention utilizes polyphenol and polyamine to prepare the coating in one step. The material can be coated on the surfaces of various substrates and has universality. In addition, the coating has a prominent bacteriostatic effect. And functional molecules which react with amino or aldehyde groups can be added while the coating is constructed, so that the coating has multiple functions of biological antifouling and the like.
In order to achieve the purpose, the technical scheme of the invention is as follows:
in a first aspect of the invention, a multifunctional coating based on a cation-pi interaction comprises: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
and adding a substrate into the stock solution, reacting under a stirring condition, and washing after the reaction is finished to obtain the catalyst.
In a second aspect of the present invention, the multifunctional coating obtained by the above preparation method.
In a third aspect of the present invention, the multifunctional coating is applied to biomedical materials.
The invention has the beneficial effects that:
the invention adopts polyphenol and polyamine as raw materials, and water as a solvent to prepare the polyphenol-polyamine coating, and the material is safe and easy to obtain and is environment-friendly. The coating is prepared in one step by a soaking method, a plurality of steps are not needed, and the operation is simple, convenient and easy. The coating material can be coated on the surfaces of various substrates and has universality. Due to the electropositivity of the amino groups and the presence of polyphenols, the coating material has an outstanding bacteriostatic effect. The polyphenol-polyamine coating has high forming speed, and the coating thickness can reach 180nm after 24 hours of reaction.
According to the invention, polyphenol, polyamine and functional molecules are used as raw materials, and water is used as a solvent to prepare the multifunctional coating based on the cation-pi interaction, the functional molecules are grafted through covalent or non-covalent interaction, so that multiple steps are not required, the preparation is realized by a one-step method, and the operation is simple and easy; wherein polyphenol and polyamine realize adhesion through synergistic action without forming an adhesion layer on a substrate in advance; the resulting multifunctional coating was successful in resisting 75% of protein and cell adhesion. The strategy can also be successfully applied to a three-dimensional substrate, and the obtained capsule material can obviously reduce the endocytosis of cells.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a graph showing the growth curves of a polyphenol-polyamine coating and a dopamine coating on a planar substrate prepared in example 1 and comparative example 1 of the present invention;
FIG. 2 is an image of a polyphenol-polyamine coating on a planar substrate prepared in example 2 of the present invention applied to a different substrate;
FIG. 3 is an antibacterial picture of a polyphenol-polyamine coating material on a planar substrate prepared in example 3 of the present invention;
FIG. 4 is an Atomic Force Microscope (AFM) image of a multifunctional coating based on a cation-pi interaction on a planar substrate prepared in example 4 of the present invention;
FIG. 5 shows the protein adsorption amount of the multifunctional coating surface based on the cation- π interaction on a planar substrate prepared in example 5 of the present invention;
FIG. 6 is a fluorescent microscope image of cell adhesion on the surface of a multifunctional coating based on the cation-pi interaction on a planar substrate prepared in example 6 of the present invention;
FIG. 7 is a Transmission Electron Microscope (TEM) image of capsule materials prepared in example 7 of the present invention and comparative example 2;
FIG. 8 is a laser Confocal (CLSM) image of the interaction between the capsule material and the cells prepared in example 7 and comparative example 2 of the present invention;
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an", and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
In view of the low coating rate, complex and complicated modification process of functional molecules and harsh reaction conditions of the existing coating preparation method, the invention provides a multifunctional coating based on the cation-pi interaction, and a preparation method and application thereof.
In an exemplary embodiment of the present invention, a method for preparing a multifunctional coating based on a cation-pi interaction is provided, comprising: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
and adding a substrate into the stock solution, reacting under a stirring condition, and washing after the reaction is finished to obtain the catalyst.
In some embodiments of this embodiment, the stock solution further comprises functional molecules, specifically: dissolving polyphenol, polyamine and functional molecules in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution. By adding functional molecules which react with amino or aldehyde groups, the coating is endowed with various functions such as biological antifouling and the like.
In some embodiments of this embodiment, the substrate comprises a planar substrate, a three-dimensional substrate.
And when the substrate is a plane substrate, adding the plane substrate into the stock solution, reacting under stirring, and washing and drying after the reaction is finished to obtain the functional coating.
Preferably, when the substrate is a planar substrate, the reaction time is 1 to 48 hours, preferably 6 to 24 hours.
Preferably, the planar substrate is one of a silicon wafer, glass, a mica sheet, a gold sheet, a stainless steel substrate, a polystyrene substrate, a polymethyl methacrylate substrate and a 24-pore plate, and is preferably one of a silicon wafer, a gold sheet and a 24-pore plate.
And when the substrate is a three-dimensional substrate, adding the three-dimensional substrate into the stock solution, reacting under stirring, etching to remove the template after the reaction is finished, centrifuging, and washing to obtain the capsule material.
Preferably, when the substrate is a three-dimensional substrate, the reaction time is from 1 to 48 hours, preferably from 6 to 12 hours.
Preferably, the specific centrifugation condition is centrifugation at 1000-10000 rpm for 1-10 min, preferably at 6000-10000 rpm for 5-10 min.
Preferably, the solution used for removing the template by etching is an ethylene diamine tetraacetic acid solution, a hydrofluoric acid-ammonium fluoride solution or a tetrahydrofuran solution, and the ethylene diamine tetraacetic acid solution is preferred. The raw material ethylene diamine can compete with zinc ions in the ZIF-8 nano particles for coordination, so that the template is removed by etching.
Preferably, the three-dimensional substrate is one of calcium carbonate particles, silica particles, polystyrene microspheres and ZIF-8 nanoparticles, preferably calcium carbonate particles or ZIF-8 nanoparticles, and further preferably ZIF-8 nanoparticles.
In some embodiments of this embodiment, the polyphenol is one or a combination of two or more of phenol, catechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, gallic acid, tannic acid, and epigallocatechin gallate, preferably one or a combination of two or more of catechol, hydroquinone, pyrogallol, phloroglucinol, and gallic acid.
The polyamine is one or the combination of more than two of ammonia water, ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine, polyethyleneimine, polylysine and polyallylamine, preferably one or the combination of more than two of ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine and polyethyleneimine.
The functional molecule is one of methoxypolyethylene glycol benzaldehyde, methoxypolyethylene glycol aldehyde group, methoxypolyethylene glycol active ester, methoxypolyethylene glycol amino, methoxypolyethylene glycol hydroxyl, methoxypolyethylene glycol fluorescein isothiocyanate, methoxypolyethylene glycol dopamine, four-arm polyethylene glycol benzaldehyde, four-arm polyethylene glycol aldehyde group, four-arm polyethylene glycol active ester, four-arm polyethylene glycol amino, four-arm polyethylene glycol hydroxyl, four-arm polyethylene glycol fluorescein isothiocyanate, four-arm polyethylene glycol dopamine, eight-arm polyethylene glycol benzaldehyde, eight-arm polyethylene glycol aldehyde group, eight-arm polyethylene glycol active ester, eight-arm polyethylene glycol amino, eight-arm polyethylene glycol hydroxyl, eight-arm polyethylene glycol fluorescein isothiocyanate, eight-arm polyethylene glycol dopamine, fluorescein isothiocyanate, adriamycin and imidazoquinoline, and is preferably one of methoxypolyethylene glycol benzaldehyde, four-arm polyethylene glycol benzaldehyde and eight-arm polyethylene glycol benzaldehyde.
The alkaline buffer solution is one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer aqueous solution, a 3-morpholinopropanesulfonic acid-sodium hydroxide buffer aqueous solution, a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution, a sodium hydroxide aqueous solution, a potassium hydroxide aqueous solution or an ammonia aqueous solution, and is preferably one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer aqueous solution and a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution.
In some examples of this embodiment, the polyphenol concentration in the stock solution is from 0.1 to 100mg/mL, preferably from 1 to 25mg/mL.
The polyamine concentration in the stock solution is 5-100 mmol/L, preferably 15-100 mmol/L.
In some examples of this embodiment, the functional molecule has a molecular weight of 1 to 20kDa, preferably 2 to 10kDa.
In some embodiments of this embodiment, the functional molecule concentration in the stock solution is 1 to 100mg/mL, preferably 2 to 20mg/mL.
In some examples of this embodiment, the alkaline buffer solution has a pH of 7 to 9.5, preferably 7.5 to 9.5.
In another embodiment of the present invention, there is provided a coating material obtained by any one of the above-mentioned preparation methods.
In a third embodiment of the invention, the application of the coating material in preparing biomedical materials is provided.
In order to make the technical solutions of the present invention more clearly understood by those skilled in the art, the technical solutions of the present invention will be described in detail below with reference to specific embodiments.
Example 1
A method of preparing a polyphenol-polyamine coating on a planar substrate comprising the steps of:
dissolving 6mg of Pyrogallol (PG) and 7. Mu.L of Ethylenediamine (EDA) in 4mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to obtain stock solution; immersing the silicon chip into the stock solution, and carrying out immersion reaction for 2 hours, 6 hours, 12 hours and 24 hours under the stirring condition; and washing with water for three times, and drying with nitrogen to obtain the PG-EDA coating material.
Example 2
A method for preparing a polyphenol-polyamine coating on a planar substrate, which is different from that of example 1 in that: the substrates are replaced by mica sheets, glass, gold sheets, stainless steel substrates, polystyrene substrates and polymethyl methacrylate substrates respectively. Other steps and conditions were identical to those of example 1, and a PG-EDA coating material was prepared.
Example 3
A method of preparing a polyphenol-polyamine coating on a planar substrate comprising the steps of:
dissolving 20mg of Pyrogallol (PG) and 30 μ L of Ethylenediamine (EDA) in 1mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to obtain stock solution; adding the stock solution into a 24-hole plate, and carrying out soaking reaction for 12 hours under the stirring condition; and washing with water for three times, and drying with nitrogen to obtain the PG-EDA coating material.
Example 4
A preparation method of a multifunctional coating based on a cation-pi interaction on a planar substrate comprises the following steps:
dissolving 6mg of Pyrogallol (PG), 7 μ L of Ethylenediamine (EDA) and 20mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) in 4mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to obtain stock solution; immersing the silicon chip into the stock solution, and carrying out soaking reaction for 6 hours and 12 hours under the stirring condition; and washing with water for three times, and drying with nitrogen to obtain the PG-EDA-PEG coating material.
Example 5
A preparation method of a multifunctional coating based on cation-pi interaction on a planar substrate comprises the following steps:
dissolving 8mg of Pyrogallol (PG), 14 mu L of triethylene tetramine (TETA) and 40mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) into 4mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH is 8) to prepare stock solution; then, the gold flakes are immersed into the stock solution for immersion reaction for 6 hours; and washing with water for three times, and drying with nitrogen to obtain the PG-TETA-PEG coating material.
Example 6
A preparation method of a multifunctional coating based on a cation-pi interaction on a planar substrate comprises the following steps:
dissolving 2mg of Pyrogallol (PG), 10. Mu.L of Ethylenediamine (EDA) and 5mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) in 1mL of disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8.5) to obtain a stock solution; adding the stock solution into a 24-hole plate, and carrying out soaking reaction for 12 hours under the stirring condition; and washing with water for three times, and drying with nitrogen to obtain the PG-EDA-PEG coating material.
Example 7
A preparation method of a multifunctional coating based on a cation-pi interaction on a three-dimensional substrate comprises the following steps:
dissolving 7mg of Pyrogallol (PG), 6. Mu.L of Ethylenediamine (EDA) and 17.5mg of methoxypolyethylene glycol benzaldehyde (mPEG-PhCHO) in 3.5mL of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer aqueous solution (pH 8.5) to prepare a stock solution; then adding 500 mu L of ZIF-8 nano particles, and carrying out soaking reaction for 6h under the stirring condition; and centrifuging the reaction solution at 8000rpm for 5min, and washing for three times to obtain the PG-EDA-PEG capsule material.
Comparative example 1
To compare the application rates of a polyphenol-polyamine coating to a polydopamine coating, a method of preparing a polydopamine coating on a planar substrate comprising the steps of:
dissolving 6mg Dopamine (DA) in 4mL disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution (pH 8) to obtain stock solution; immersing the silicon chip into the stock solution, and carrying out immersion reaction for 2 hours, 6 hours, 12 hours and 24 hours under the stirring condition; and washing with water for three times, and drying with nitrogen to obtain the polydopamine coating material.
Comparative example 2
In order to compare the degree of cell interaction of the PEG grafted capsule, the preparation method of the polyphenol biological antifouling material on the three-dimensional substrate comprises the following steps:
dissolving 7mg of Pyrogallol (PG) and 6. Mu.L of Ethylenediamine (EDA) in 3.5mL of a tris-hydroxymethyl aminomethane-hydrochloric acid buffer aqueous solution (pH 8.5) to prepare a stock solution; then adding 500 mu L of ZIF-8 nano particles, and carrying out soaking reaction for 6h under the stirring condition; and centrifuging the reaction solution at 8000rpm for 5min, and washing for three times to obtain the PG-EDA capsule material.
Polyphenol-polyamine coating performance testing
(1) AFM tests are carried out on the coating materials obtained in the embodiment 1 and the comparative example 1, the thicknesses of the coating materials obtained in the soaking reactions of 2h, 6h, 12h and 24h are measured, a thickness-time curve is drawn, as shown in figure 1, the coating thickness of the embodiment 1 can reach 180nm after the reaction of 24h, and the forming speed of the coating is high.
(2) Detection of antibacterial property of planar coating material
The coating material obtained in example 3 of the present invention was evaluated for in vitro antibacterial activity against gram-negative escherichia coli (e.coli) and gram-positive staphylococcus aureus (s.aureus). As shown in fig. 3, the coating obtained in example 3 has outstanding antibacterial properties.
Multifunctional coating material performance detection based on cation-pi interaction
(1) AFM testing was performed on the coating material obtained in inventive example 4, and AFM images are shown in FIG. 4, wherein the coating thickness was about 14nm when formed for 6h and about 18nm when formed for 12h, and successful formation of the coating was observed.
(2) Detection of protein adsorption resistance of planar functional coating material
Mounting the PG-TETA-PEG coating material modified gold sheet prepared in example 5 on a Quartz Crystal Microbalance (QCM), and introducing water for three times to clean the surface of the gold sheet; then introducing bovine serum albumin solution (BSA) for 10min; then introducing water to wash off the protein with weak surface adsorption; the protein adsorption resistance of the coating was evaluated by comparing the frequency change before and after protein introduction. As shown in FIG. 5, the PG-TETA-PEG coating material prepared by the invention can resist 75% of protein adsorption compared with the surface of bare gold.
(3) Detection of anti-cell adhesion performance of planar functional coating material
The blank 24-well plate and the PG-EDA-PEG coating material modified 24-well plate prepared in example 6 were seeded with 10X 10 of each 4 MDA-MB-231 cells were cultured for 6 hours at 37 ℃; washing with PBS three times to wash off the cells with weak adhesion; then 100. Mu.L of calcein dye was added and the solution was stained in the dark at room temperature for 15min. The results of inverted fluorescence microscopy are shown in FIG. 6, where the PG-EDA-PEG coating material is resistant to 75% cell adhesion.
(4) The capsule materials obtained in example 7 of the present invention and comparative example 2 were subjected to TEM test, and TEM images are shown in fig. 7, indicating that example 7 succeeded in forming capsules having a hollow structure.
(5) Detection of cell interaction performance of capsule material
Seeding in a confocal dish at 10X 10 4 MDA-MB-231 cells are cultured for 12h at 37 ℃ to adhere to the cells; subsequently, 500. Mu.L of Fluorescein Isothiocyanate (FITC) -labeled capsule materials prepared in example 7 and comparative example 2 were added, and after incubation for 6 hours, washed three times with PBS; fixation with 4% paraformaldehyde, and Hoechst 33342 pairsCell nuclei were stained for 20min and cell membranes were stained with WGA-AF633 for 10min. Confocal microscopy observation results as shown in fig. 8, PG-EDA-PEG capsule material can significantly reduce the degree of endocytosis compared to PG-EDA capsule material.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of a multifunctional coating based on a cation-pi interaction is characterized by comprising the following steps: dissolving polyphenol and polyamine in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution;
and adding a substrate into the stock solution, reacting under a stirring condition, and washing after the reaction is finished to obtain the catalyst.
2. The method for preparing the multifunctional coating based on the cation-pi interaction as claimed in claim 1, wherein the stock solution further comprises functional molecules, specifically: dissolving polyphenol, polyamine and functional molecules in an alkaline buffer solution, and uniformly mixing and dispersing to obtain a stock solution.
3. The method for preparing the multifunctional coating based on the cation-pi interaction as claimed in claim 1, wherein the substrate comprises a planar substrate, a three-dimensional substrate;
preferably, when the substrate is a planar substrate, adding the planar substrate into the stock solution, reacting under stirring, and washing and drying after the reaction is finished to obtain the functional coating material; the reaction time is 1 to 48 hours, preferably 6 to 24 hours;
preferably, when the substrate is a three-dimensional substrate, adding the three-dimensional substrate into the stock solution, reacting under stirring, after the reaction is finished, removing the template by etching, centrifuging and washing to obtain a functional coating material; the reaction time is 1 to 48 hours, preferably 6 to 12 hours; the solution for removing the template by etching is an ethylene diamine tetraacetic acid solution, a hydrofluoric acid-ammonium fluoride solution or a tetrahydrofuran solution, and preferably the ethylene diamine tetraacetic acid solution; the specific centrifugation conditions are 1000-10000 rpm, 1-10 min, preferably 6000-10000 rpm, and 5-10 min.
4. The method for preparing the multifunctional coating based on the cation-pi interaction according to claim 3, wherein the planar substrate is a silicon wafer, glass, mica sheet, gold sheet, stainless steel substrate, polystyrene substrate, polymethyl methacrylate substrate, 24-well plate, preferably a silicon wafer, gold sheet, 24-well plate;
or the three-dimensional substrate is calcium carbonate particles, silica particles, polystyrene microspheres and ZIF-8 nanoparticles, and calcium carbonate particles and ZIF-8 nanoparticles are preferred.
5. The method for preparing the multifunctional coating based on the cation-pi interaction as claimed in claim 1, wherein the polyphenol is one or a combination of more than two of phenol, catechol, resorcinol, hydroquinone, pyrogallol, phloroglucinol, gallic acid, tannic acid and epigallocatechin gallate, preferably one or a combination of more than two of catechol, hydroquinone, pyrogallol, phloroglucinol and gallic acid;
or the polyamine is one or the combination of more than two of ammonia water, ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine, polyethyleneimine, polylysine and polyallylamine, preferably one or the combination of more than two of ethylenediamine, diethylenetriamine, triethylenetetramine, tri (2-aminoethyl) amine and polyethyleneimine;
or the functional molecule is one of methoxypolyethylene glycol benzaldehyde, methoxypolyethylene glycol aldehyde group, methoxypolyethylene glycol active ester, methoxypolyethylene glycol amino group, methoxypolyethylene glycol hydroxyl group, methoxypolyethylene glycol fluorescein isothiocyanate, methoxypolyethylene glycol dopamine, tetrapolyethylene glycol benzaldehyde, tetrapolyethylene glycol aldehyde group, tetrapolyethylene glycol active ester, tetrapolyethylene glycol amino group, tetrapolyethylene glycol hydroxyl group, tetrapolyethylene glycol fluorescein isothiocyanate, tetrapolyethylene glycol dopamine, octapolyethylene glycol benzaldehyde, octapolyethylene glycol aldehyde group, octapolyethylene glycol active ester, octapolyethylene glycol amino group, octapolyethylene glycol hydroxyl group, octapolyethylene glycol fluorescein isothiocyanate, octapolyethylene glycol dopamine, fluorescein isothiocyanate, doxorubicin and imidazoquinoline, preferably one of methoxypolyethylene glycol benzaldehyde, tetraaminopolyethylene glycol benzaldehyde and octapolyethylene glycol benzaldehyde;
or the alkaline buffer solution is one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer aqueous solution, a 3-morpholinopropanesulfonic acid-sodium hydroxide buffer aqueous solution, a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution, a sodium hydroxide aqueous solution, a potassium hydroxide aqueous solution or an ammonia aqueous solution, and is preferably one of a tris (hydroxymethyl) aminomethane-hydrochloric acid buffer aqueous solution and a disodium hydrogen phosphate-sodium dihydrogen phosphate buffer aqueous solution.
6. The method for preparing the multifunctional coating based on the cation-pi interaction according to claim 1, wherein the concentration of polyphenol in the stock solution is 0.1-100 mg/mL, preferably 1-25 mg/mL;
the polyamine concentration in the stock solution is 5-100 mmol/L, preferably 15-100 mmol/L.
7. The method for preparing the multifunctional coating based on the cation-pi interaction according to claim 1, wherein the molecular weight of the functional molecule is 1 to 20kDa, preferably 2 to 10kDa;
the concentration of the functional molecules in the stock solution is 1-100 mg/mL, preferably 2-20 mg/mL.
8. The method for preparing the multifunctional coating based on the cation-pi interaction as claimed in claim 1, wherein the pH value of the alkaline buffer solution is 7-9.5, preferably 7.5-9.5.
9. A multifunctional coating material obtained by the preparation method of the multifunctional coating based on the cation-pi interaction as described in any one of claims 1 to 8; preferably, the multifunctional coating material is a polyphenol-polyamine coating or a biological antifouling coating.
10. Use of the multifunctional coating material according to claim 9 in biomedical materials.
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| CN110016089A (en) * | 2019-04-17 | 2019-07-16 | 西南交通大学 | Rich amine base catecholamine compound and preparation method thereof, rich amine primary surface modified product, material and its dip-coating method |
| CN112691238A (en) * | 2021-01-18 | 2021-04-23 | 成都鼎峰前瞻科技有限公司 | Material with biological anti-fouling function, preparation method and application thereof |
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| CN110016089A (en) * | 2019-04-17 | 2019-07-16 | 西南交通大学 | Rich amine base catecholamine compound and preparation method thereof, rich amine primary surface modified product, material and its dip-coating method |
| CN112691238A (en) * | 2021-01-18 | 2021-04-23 | 成都鼎峰前瞻科技有限公司 | Material with biological anti-fouling function, preparation method and application thereof |
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