CN114344570A - Copper porphyrin @ polydopamine film and preparation method thereof - Google Patents
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- 229920001690 polydopamine Polymers 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 58
- 229960003638 dopamine Drugs 0.000 claims abstract description 29
- NUSORQHHEXCNQC-UHFFFAOYSA-N [Cu].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical compound [Cu].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 NUSORQHHEXCNQC-UHFFFAOYSA-N 0.000 claims abstract description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 238000004140 cleaning Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000008367 deionised water Substances 0.000 claims description 13
- 229910021641 deionized water Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 239000007983 Tris buffer Substances 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 18
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract description 14
- 238000012986 modification Methods 0.000 abstract description 9
- 230000004048 modification Effects 0.000 abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 4
- 239000010408 film Substances 0.000 description 48
- 230000000052 comparative effect Effects 0.000 description 29
- 238000012360 testing method Methods 0.000 description 25
- 239000000203 mixture Substances 0.000 description 8
- 238000005530 etching Methods 0.000 description 6
- 239000010949 copper Substances 0.000 description 5
- -1 copper (II) tetracarboxyphenyl porphyrin Chemical compound 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 229920006254 polymer film Polymers 0.000 description 1
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- 238000011002 quantification Methods 0.000 description 1
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- 210000002460 smooth muscle Anatomy 0.000 description 1
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- 239000011343 solid material Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
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- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/04—Macromolecular materials
- A61L31/06—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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/08—Materials for coatings
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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
- A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
- A61L31/14—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
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/18—Modification of implant surfaces in order to improve biocompatibility, cell growth, fixation of biomolecules, e.g. plasma treatment
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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
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/02—Methods for coating medical devices
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Abstract
The invention discloses a copper porphyrin @ polydopamine film and a preparation method thereof, belonging to the technical field of film materials, wherein the preparation method mainly comprises the following steps: adding copper porphyrin and tris (hydroxymethyl) aminomethane into a solvent, dissolving in the dark at room temperature, adding dopamine, standing in the dark after the dopamine is dissolved, cleaning, and drying to obtain the copper porphyrin @ polydopamine film. The invention overcomes the technical difficulty that copper porphyrin is insoluble in water, successfully dopes the copper porphyrin into the polydopamine film, and stably fixes the polydopamine film on the surface of the material, thereby preparing the copper porphyrin @ polydopamine film with excellent nitric oxide catalytic release capacity; meanwhile, the copper porphyrin @ polydopamine film contains rich amino and carboxyl, forms a multifunctional modification layer on the surface of the material, provides a good material modification platform, and can be widely applied to the technical fields of preparation of cardiovascular stent materials and the like.
Description
Technical Field
The invention relates to the technical field of film materials, in particular to a copper porphyrin @ polydopamine film and a preparation method thereof.
Background
NO can play a role in regulating vasodilation, inhibiting platelet aggregation and activation of damaged parts, inhibiting release of immune cytokines, increasing the content of cGMP in smooth muscle cells and reducing the activity of the smooth muscle in a cardiovascular system. NO has a wide range of chemical reactivity and sites of action, mediating and regulating the physiological and pathological functions of many organ systems. With the physiological research on nitric oxide, researchers not only stay in the mechanism research aspect, but also pay attention to the application research in the fields of cardiovascular stent materials, new drug research and the like.
The multifunctional modification layer is prepared on the surface of the material, so that different functions of the material are the basis of a new material surface modification technology. Dopamine (Dopamine) is a neurotransmitter which is extremely important in brain, can initiate mild self-polymerization-crosslinking reaction under aerobic and alkaline conditions, and can perform chelation and self-polymerization reaction with almost any solid material to form a stable Dopamine polymer film (PDA). In order to enable the PDA to have wider application, a simple and effective method is developed to realize the modification and preparation of the PDA, and the method has important significance for future research and application.
Disclosure of Invention
Aiming at the defects, the invention aims to provide a copper porphyrin @ polydopamine film and a preparation method thereof, overcomes the technical difficulty that copper porphyrin (copper (II) tetracarboxyphenyl porphyrin, CuTCPP) is insoluble in water, successfully dopes the copper porphyrin into the polydopamine film, and stably fixes the polydopamine film on the surface of a material to prepare the copper porphyrin @ polydopamine film with excellent nitric oxide catalytic release capacity; meanwhile, the copper porphyrin @ polydopamine film has rich amino and carboxyl, forms a multifunctional modification layer on the surface of the material, provides a good material modification platform, and can be widely applied to the technical fields of preparation of cardiovascular stent materials and the like.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a preparation method of a copper porphyrin @ polydopamine film, which comprises the following steps: adding copper porphyrin (copper (II) tetracarboxyphenylporphyrin, CuTCPP) and Tris into a solvent, dissolving in the dark at room temperature, adding Dopamine (DA), standing until the DA is dissolved in the dark, cleaning, and drying to obtain a copper porphyrin @ polydopamine film; wherein the mass ratio of the copper porphyrin to the trihydroxymethyl aminomethane to the dopamine is 1-2: 25-35: 8-12.
Further, the mass ratio of the copper porphyrin, the tris (hydroxymethyl) aminomethane and the dopamine is preferably 1-2: 30: 9-10; more preferably 1:30: 10.
Further, the solvent is a mixed solvent consisting of deionized water and ethanol; preferably, the mixed solvent consists of ethanol and deionized water in a volume ratio of 2-5: 1-2; more preferably a mixed solvent consisting of ethanol and deionized water in a volume ratio of 3: 1.
Further, the standing time is 1-24 hours.
Further, the pH value of a mixed solution obtained after dissolving the copper porphyrin, the tris and the dopamine is 8-9.
The invention also provides the copper porphyrin @ polydopamine film prepared by the preparation method.
In summary, the invention has the following advantages:
1. the invention provides a preparation method of a copper porphyrin @ polydopamine film, which overcomes the technical difficulty that copper porphyrin (copper (II) tetracarboxyphenyl porphyrin, CuTCPP) is insoluble in water, successfully dopes the copper porphyrin into the polydopamine film, and stably fixes the polydopamine film on the surface of a material to prepare the copper porphyrin @ polydopamine film with excellent nitric oxide catalytic release capacity; and the preparation method is simple and easy to implement and can be widely popularized and applied.
2. The copper porphyrin @ polydopamine film disclosed by the invention has excellent nitric oxide catalytic release capacity, also contains rich amino and carboxyl, forms a multifunctional modification layer on the surface of the material, provides a good material modification platform, and can be widely applied to the technical fields of preparation of cardiovascular stent materials and the like.
Drawings
FIG. 1 is a graph showing IR spectrum measurements of film samples obtained in examples 1 to 3 and comparative examples 1 to 3 of the present invention;
FIG. 2 is a Fe element test of film samples obtained in examples 2 to 3 and comparative examples 2 to 3 according to the present invention;
FIG. 3 is a Cu element test of thin film samples obtained in examples 2 to 3 and comparative examples 2 to 3 according to the present invention;
FIG. 4 is a nitric oxide test of film samples obtained in examples 1-3 and comparative examples 1-3 of the present invention;
FIG. 5 is a graph showing amino group quantitative measurements of film samples obtained in examples 1 to 3 and comparative examples 1 to 3 according to the present invention;
FIG. 6 is a carboxyl group quantitative test of film samples obtained in examples 1 to 3 and comparative examples 1 to 3 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention.
Thus, the following detailed description of the embodiments of the present invention is not intended to limit the scope of the invention as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The embodiment provides a preparation method of a copper porphyrin @ polydopamine film, which comprises the following steps: taking 20ml of ethanol and deionized water, mixing the ethanol and the deionized water in a ratio of 3:1 to prepare a solvent, adding 2mg of copper porphyrin (copper (II) tetracarboxyphenylporphyrin, CuTCPP) and 60mg of Tris (hydroxymethyl) aminomethane (Tris), dissolving the mixture at room temperature in a dark place, then adding 20mg of Dopamine (DA), dissolving the DA in a dark place, standing the mixture for 1 hour, ultrasonically cleaning the mixture by using deionized water, and drying the mixture to prepare a copper porphyrin @ polydopamine film (marked as CuTCPP @ PDA.1h); wherein the pH value of the mixed solution of copper porphyrin, tris (hydroxymethyl) aminomethane and dopamine after dissolution is 8.5.
Example 2
This example provides a method for preparing a copper porphyrin @ polydopamine film (denoted as CuTCPP @ pda.5h), which differs from example 1 only in that: standing for 5 hours in a dark place; the rest steps and parameters are the same.
Example 3
This example provides a method for preparing a copper porphyrin @ polydopamine film (denoted as CuTCPP @ pda.24h), which differs from example 1 only in that: standing for 24 hours in dark; the rest steps and parameters are the same.
Example 4
This example provides a method for preparing a copper porphyrin @ polydopamine film, which is different from example 1 only in that: adjusting the dosage of Tris to 70 mg; the rest steps and parameters are the same.
Comparative example 1
This example provides a method for preparing a polydopamine film (denoted as pda.1h) comprising the following steps: adding 60mg of Tris into 20ml of solvent prepared by mixing ethanol and deionized water in a ratio of 3:1, dissolving in the dark at room temperature, then adding 20mg of Dopamine (DA), standing for 1 hour after the DA is dissolved in the dark, ultrasonically cleaning with deionized water, and drying to prepare a polydopamine film; wherein the pH value of the mixed solution of copper porphyrin, tris (hydroxymethyl) aminomethane and dopamine after dissolution is 8.5.
Comparative example 2
This example provides a method for preparing a polydopamine film (denoted pda.5h) which differs from comparative example 1 only in that: standing for 5 hours in a dark place; the rest steps and parameters are the same.
Comparative example 3
This example provides a method for preparing a polydopamine film (denoted pda.24h) which differs from comparative example 1 only in that: standing for 24 hours in dark; the rest steps and parameters are the same.
Comparative example 4
The embodiment provides a preparation method of a copper porphyrin @ polydopamine film, which comprises the following steps: taking 20ml of ethanol and deionized water, mixing the ethanol and the deionized water in a ratio of 3:1 to prepare a solvent, adding 2mg of copper porphyrin (copper (II) tetracarboxyphenyl porphyrin, CuTCPP) and 60mg of Tris (hydroxymethyl) aminomethane (Tris), dissolving the mixture at room temperature in a dark place, adding 20mg of Dopamine (DA), dissolving the DA in a dark place, standing the mixture for 24 hours, ultrasonically cleaning the mixture by using deionized water, and drying the mixture to prepare a copper porphyrin @ polydopamine film; wherein the pH value of the mixed solution of copper porphyrin, tris (hydroxymethyl) aminomethane and dopamine after dissolution is 8.5.
Experimental example 1
In this example, the film samples obtained in examples 1 to 3 and comparative examples 1 to 3 were transferred onto a transparent glass plate substrate by an LB (Langmuir-Blgett) transfer method to perform an ultraviolet spectrophotometer UV-Vis test, the test results are shown in FIG. 1; wherein, three groups of test charts in fig. 1 are the test results corresponding to example 1/comparative example 1, example 2/comparative example 2 and example 3/comparative example 3 from left to right, and two curves in each group of test charts correspond to the test results of the examples and the comparative examples from top to bottom. As a result, a characteristic absorption peak of copper porphyrin appears at 406nm, which indicates that CuTCPP and dopamine are successfully copolymerized.
Experimental example 2
This example prepares examples 2-3 and comparative examples 2-3 by using the film samples obtained in examples 2-3 and comparative examples 2-3 on a stainless steel sheet substrate. The XPS test was performed as shown in FIG. 2, in which PDA-5 represents the test results of the sample obtained in comparative example 2, PDA-24 represents the test results of the sample obtained in comparative example 3, Cu-5 represents the test results of the sample obtained in example 2, and Cu-24 represents the test results of the sample obtained in example 3; 10s etching is respectively carried out on the example 2 (standing for 5h) and the example 3 (standing for 5h), and Cu element high resolution is analyzed, and the test result is shown in figure 3; wherein Cu-5-0s and Cu-5-10s represent test results obtained in example 2 in which etching was not performed and 10s etching was performed, and Cu-24-0s and Cu-24-10s represent test results obtained in example 3 in which etching was not performed and 10s etching was performed. The results show that: according to the high resolution of the Fe element, the Fe element can be detected when the film is deposited for 5 hours, the film is relatively thin, and after the film is deposited for 24 hours, the Fe element signal cannot be detected, so that the film is continuously deposited between 5 and 24 hours, the coverage is more sufficient, and the thickness of the film is increased. Cu element high-resolution tests are carried out on copper porphyrin @ polydopamine films (CuTCPP @ PDA) deposited for 5h and 24h, etching is carried out for 10s, and obvious Cu element signals exist in samples, so that the copper porphyrin is successfully copolymerized in the polydopamine films.
Experimental example 3
In this example, examples 1 to 3 and comparative examples 1 to 3 were prepared by using the film samples obtained in examples 1 to 3 and comparative examples 1 to 3 on a stainless steel foil substrate, and NO test was performed using a NO chemiluminescence detector. The test results are shown in fig. 4, wherein three groups of NO test charts in fig. 4 sequentially correspond to the test results of example 1/comparative example 1, example 2/comparative example 2, and example 3/comparative example 3 from top to bottom, and two curves in each group of NO test charts sequentially correspond to the test results of the example and the comparative example from top to bottom; tests show that films copolymerized with copper porphyrin have the capability of catalyzing and releasing nitric oxide, the capability of catalyzing and releasing NO is different according to different deposition time, and the capability is probably caused by different amounts of copper elements on the outermost surfaces of the films.
Experimental example 4
Examples 1-3 and comparative examples 1-3 were prepared by using the film samples obtained in examples 1-3 and comparative examples 1-3 on a stainless steel foil upper substrate, and the films were subjected to amino group quantification using an acid orange solution and measured for absorbance value at 485nm using a microplate reader, as shown in FIG. 5. The film was quantified for carboxyl groups using toluidine blue solution and its absorbance at 631nm was measured using a microplate reader, as shown in FIG. 6. The quantitative results of amino and carboxyl indicate that a large number of amino and carboxyl groups still exist on the surface after the copper porphyrin is copolymerized, and the carboxyl groups are obviously more than those of the dopamine film within 1 hour and 5 hours.
The foregoing is merely exemplary and illustrative of the present invention and it is within the purview of one skilled in the art to modify or supplement the embodiments described or to substitute similar ones without the exercise of inventive faculty, and still fall within the scope of the claims.
Claims (7)
1. A preparation method of a copper porphyrin @ polydopamine film is characterized by comprising the following steps: adding copper porphyrin and tris (hydroxymethyl) aminomethane into a solvent, dissolving in the dark at room temperature, adding dopamine, standing in the dark after the dopamine is dissolved, cleaning, and drying to obtain a copper porphyrin @ polydopamine film; wherein the mass ratio of the copper porphyrin to the trihydroxymethyl aminomethane to the polydopamine is 1-2: 25-35: 8-12.
2. The preparation method of the copper porphyrin @ polydopamine film as claimed in claim 1, wherein the mass ratio of the copper porphyrin, the tris and the dopamine is 1-2: 30: 9-10.
3. The method for preparing copper porphyrin @ polydopamine film as claimed in claim 1, wherein the solvent is a mixed solvent of deionized water and ethanol.
4. The preparation method of the copper porphyrin @ polydopamine film as claimed in claim 1 or 3, wherein the solvent is a mixed solvent composed of ethanol and deionized water in a volume ratio of 2-5: 1-2.
5. The method for preparing copper porphyrin @ polydopamine film as claimed in claim 1, wherein the standing time is 1-24 hours.
6. The method for preparing the copper porphyrin @ polydopamine film as claimed in claim 1, wherein the pH value of a mixed solution obtained by dissolving copper porphyrin, tris (hydroxymethyl) aminomethane and dopamine is 8-9.
7. A copper porphyrin @ polydopamine film, which is characterized by being prepared by the preparation method of the copper porphyrin @ polydopamine film as claimed in any one of claims 1-6.
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| CN117186764A (en) * | 2023-03-23 | 2023-12-08 | 南昌师范学院 | Polydopamine/porphyrin coating and preparation method thereof |
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| CN109663151A (en) * | 2018-12-19 | 2019-04-23 | 西南交通大学 | A kind of preparation method and application of the rich amino timbering material of tetracarboxylic phenyl porphyrin copper modification and a kind of vascular stent material and application |
| EP3523020A1 (en) * | 2016-10-04 | 2019-08-14 | Aarhus Universitet | Flexible and multi-functional coacervates and hydrogel materials |
| CN112625277A (en) * | 2020-12-01 | 2021-04-09 | 吉林大学 | Preparation method of metal organic framework @ polydopamine film |
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