CN104208761B - A kind of anticoagulant material preparation method with inducing catalysis endogenous NO release function - Google Patents
A kind of anticoagulant material preparation method with inducing catalysis endogenous NO release function Download PDFInfo
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- CN104208761B CN104208761B CN201410394981.2A CN201410394981A CN104208761B CN 104208761 B CN104208761 B CN 104208761B CN 201410394981 A CN201410394981 A CN 201410394981A CN 104208761 B CN104208761 B CN 104208761B
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- material preparation
- anticoagulant
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- 239000003146 anticoagulant agent Substances 0.000 title claims abstract description 29
- 229940127219 anticoagulant drug Drugs 0.000 title claims abstract description 28
- 238000006555 catalytic reaction Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 230000001939 inductive effect Effects 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- -1 phenol structure compound Chemical group 0.000 claims abstract description 17
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- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 12
- 239000007853 buffer solution Substances 0.000 claims abstract description 11
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Abstract
The invention discloses a kind of anticoagulant material preparation method with inducing catalysis endogenous NO release function.Its step comprises the Tris-buffer buffer solution of configuration alkalescence, and add wherein certain density there is adjacent phenol structure compound and there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl; Base material is inserted in reaction solution, take out substrate after controlling reaction temperature and reaction 1-24h, after cleaning, after drying, obtain object material.The inventive method has simple to operate, the gentle easy advantage of reaction condition; the compound component unit content in the material of preparation with the two ends amino-contained of disulfide bond or two selenium keys or sulfydryl is controlled; the modified coating adopting the inventive method to obtain has excellent adhesion; and by the NO donor sustained release NO molecule in situ catalytic blood; suppress hematoblastic activation and gathering; suppress smooth muscle cell proliferation, protection Ink vessel transfusing cortex.
Description
Technical field
The present invention relates to biomedical engineering functional material, especially there is superior anti-coagulant technical field of material.
Background technology
Cardiovascular implantation instrument, as angiocarpy bracket, Cardiac valve prosthesis, IVCF, artificial blood vessel etc., faces an anticoagulant difficult problem for a long time.The anticoagulant material surface with excellent properties is also investigation means and the object of contacting blood class material practical function always.Nitric oxide (NO) is as human body first signaling molecule, play extremely important biological function, years of researches show, NO can suppress hematoblastic activation and gathering, antithrombotic ability can greatly be promoted, and there is the multiplication capacity suppressing smooth muscle cell.At present, NO donator type material loads the material that can discharge NO molecule mainly through preparing polymeric coating layer, and in blood environment, sustained release NO reaches anticoagulant object.But this NO release type pattern, rate of release can be brought too fast, and initial stage burst size is excessive, and the persistent period is too short causes corresponding blood pathological condition and the problem such as anticoagulation timeliness is limited, which also limits its application in anticoagulation.Containing a large amount of reproducible NO donor in blood of human body, the glutathion peroxidase (GPx) in human body has can the effect of catalysis donor release NO, therefore, situ catalytic NO regeneration mode be configured to a kind of novel anticoagulation scheme.In recent years research shows, the compound of the two ends amino-contained or sulfydryl with disulfide bond or two selenium keys has catalyzing N O donor release NO ability.Research also shows, some polyphenol compounds (as EGCG) can consume active oxygen fragment due to its good oxidation resistance, protects vascular endothelial cell to avoid oxidative stress toxicity, can promote vascular endothelial cell proliferation in finite concentration scope.Therefore research and inquirement obtains a kind of convenient effective process, there is the compound of adjacent phenol structure and there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl prepare modified coating with the assembling of the pattern of chemical crosslinking and be achieved, there is obvious necessity.
Summary of the invention
The object of this invention is to provide is the novel anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release, prepares modified coating with the assembling of the pattern of selenocystamine chemical crosslinking, and make it to have simple to operate, cost is lower, the advantage that universality is wide.
The anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release of the present invention, comprises the steps:
1, will the base material of modifying and decorating be needed to carry out polishing, cleaning, drying;
2, step A gained sample is positioned over the Tris-buffer buffer system of pH=5-12, then add in system the compound with adjacent phenol structure that concentration is 0.01mg/ml-10mg/ml and concentration be 0.01mg/ml-10mg/ml there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl, at 10-30 DEG C, reaction 1-24h;
3, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Adopt the inventive method, by the compound of the two ends amino-contained or sulfydryl with disulfide bond or two selenium keys is assembled into contacting blood class material surface, on the one hand can the rate of release of control NO, long-acting NO sustained release can be obtained on the other hand, there is very high using value.Polyphenol compound is easier to oxidized dehydrogenation, catechol in its structure easily changes into adjacent benzene two quinone structure, this structure can further with containing amino compound generation Michael addition reaction and schiff base reaction, therefore the compound containing two or more amino in polyphenol compound and molecular structure is reacted, can polymer coated or crosslinked polymer coated film be formed.Cystamine and selenocystamine have the molecular structure of two Amino End Group, can with polyphenol compound generation Michael addition reaction and schiff base reaction, cross-linked polymeric coating can be formed at material surface, therefore just can realize the load of organic selenium compounds at metal contacting blood material surface, obtain the catalytically active surface with situ catalytic NO regeneration.Polyphenol compound in this anticoagulant coatings material is excessive relative to cystamine and selenocystamine; except forming crosslinked film with cystamine or selenocystamine; remaining polyphenolic substance also has excellent non-oxidizability and the ability of scavenging activated oxygen, has protective effect to cardiovascular and cerebrovascular vessel.Containing a large amount of ortho position phenolic hydroxyl groups in the molecular structure of polyphenol compound, these ortho position phenolic hydroxyl groups can form stable chelation with metal, therefore polyphenol compound can form more stable fixing or combination in metal surface, and such coating and metal, ceramic bases have excellent adhesion.In addition this cross-linked polymeric coating also interacts and hydrogen bond action by intermolecular hydrophobic, has good combination power with polymeric base material.Therefore, this coating can be widely used in nearly all biomaterial surface.
The novel anticoagulant material surface adopting the inventive method to prepare, has the ability of excellent catalysis human endogenous property NO donor release, platelet effectively can be suppressed in the activation of material surface and gathering, play good anticoagulant functions.
Compared with prior art, usefulness of the present invention is:
1) traditional anticoagulant biomolecule (as heparin, hirudin, bivalirudin), be no matter with covalence graft or electrostatic assembly to material surface, all must rely on the size of molecule, conformation, activity and its play stability and the persistency of anticoagulation at material surface.Biomolecule, once inactivation or lose in a large number in process under arms, just can not effectively play its biological function.The present invention utilizes the function of NO signaling molecule, and its approach playing function is not by the impact of above-mentioned biomolecule confined condition;
2) traditional NO donator type material surface, owing to being the mode of loading with coating parcel, need thicker coating to load NO, can be subject to certain restrictions at the thickness of the equipment surfaces coating of reality, this also means that the sustained release of NO is restricted.The rate of release time to time change of NO, and there is the factors such as initial stage NO rate of release is too fast, also can cause negative biological effect.The organic catalysis coating that this method is prepared by chemical crosslinking, can discharge NO molecule sustainedly and stably by the NO donor in situ catalytic blood, suppress hematoblastic activation and gathering, suppress neointimal hyperplasia;
3) once had relevant surfaces grafting organic selenium compounds, the technology report on the anticoagulation surface that catalyzing endogenous property NO discharges, but grafting density is usually lower, is difficult to provide enough suppression platelet activations and the NO concentration of neointimal hyperplasia.The present invention passes through chemical crosslinking, there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl---cystamine, selenocystamine, selenocystine, cystine and the copolymerization of micromolecule sulfhydryl compound are in modified coating, modulation process parameter, rationally mixing of organic catalysis molecular weight can be realized, ensure that the release efficiency of safe NO and rational release concentration, play its biological function.
4) coating of preparation required for the present invention is usually less than 50nm, and gained coating is comparatively even, and raw material drops into seldom, and can modify in surfaces of various materials.Compared with traditional anticoagulation means, simple to operate, cost is lower, and universality is wide.
5) some the Polyphenols components related in material of the present invention; all there is excellent non-oxidizability; there is the ability removing oxygen-derived free radicals in blood vessel; to blood vessel, there is protective effect; by the copolymerize discharged with catalyzing N O; good anticoagulation function can be obtained, good Ink vessel transfusing cortex repairing performance can be obtained again.
Accompanying drawing explanation
Below in conjunction with accompanying drawing and case study on implementation, the present invention is described in further detail.
Fig. 1 is x-ray photoelectron power spectrum (XPS) result on 316LSS surface of functional coating coating prepared by the present invention, is the degree of full spectral element under technological parameter and Se element in figure.
Fig. 2 a contacts the stereoscan photograph of cultivating 120min with the novel anticoagulant material with situ catalytic NO release prepared by the present invention with Freshman platelet rich plasma.Organic selenium coating is prepared in 316L medical stainless steel surface (316LSS), in figure, and Co (EGCG-Se): the 316LSS of epigallocatechin gallate (EGCG) and selenocystamine copolymerization coating modifying; Donor: add S-Nitroso-N-acetyl-DL-penicillamine (SNAP) in blood plasma, the endogenous NO donor environment in simulation human blood; No-donor: do not add SNAP in blood plasma, as the contrast without catalytic substrate.
Fig. 2 b is that 316LSS surface contacts the stereoscan photograph of cultivating 120min with Freshman platelet rich plasma, left for not add donor group, right for adding donor group.Donor and No-Donor and same meaning shown in Fig. 2 a.
Detailed description of the invention
Below in conjunction with embodiment, enforcement of the present invention is further described.
In reality is implemented:
The described compound with adjacent phenol structure is the one of dopamine, gallic acid, epigallocatechin gallate (EGCG) EGCG, L-Epicatechin gallate ECG, epicatechin EC, epigallo catechin EGC, catechol.
The compound of described the two ends amino-contained or sulfydryl with disulfide bond or two selenium keys is the one of cystamine, selenocystamine, selenocystine, cystine and micromolecule sulfhydryl compound.
The novel anticoagulant material preparation method of described a kind of inducing catalysis endogenous NO release, is characterized in that, described base material can be polymeric biomaterial, the hybrid biomaterials of metallic biomaterial, ceramic biomaterial, natural and synthesis.Described metallic biomaterial comprises rustless steel, cobalt-base alloys, titanium and titanium alloys, gold, magnesium and alloy thereof, kirsite, tantalum and alloy, pure iron and alloy thereof.Described ceramic biomaterial comprises medical inorganic material and thin film-TiO2, isotropic pyrolytic carbon LTIC, hydroxyapatite, calcium phosphate, diamond and diamond like carbon.Described polymeric biomaterial that is natural and synthesis comprises: natural biologic material-collagen, gelatin, fibroin albumen, cellulose, chitosan, alginic acid, hyaluronic acid, synthetic macromolecular material-terylene PET, polytetrafluoroethylene PTFE, polyurethane PU, polyformaldehyde POM, silicone rubber, polylactic acid PLA, glycolide-lactide copolymer PLGA, PTMC PTMC, polycaprolactone (PCL).Described hybrid biomaterials comprises polylactic acid/hydroxy apatite, chitosan/hydroxyapatite.
In the examples below, the chemical reagent beyond matrix is chemical pure except special declaration.
Embodiment 1
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the pure iron material of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=5, then in system, adds the compound that concentration is the dopamine of 0.01mg/ml and concentration is the cystamine of 0.01mg/ml, at 10 DEG C, reaction 1h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 2
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the mg-based material of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=12, in system, then adds epigallocatechin gallate (EGCG) (EGCG) that concentration is 10mg/ml and concentration is the selenocystamine of 10mg/ml, at 30 DEG C, reaction 24h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 3
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the medical 316L stainless steel of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=7, in system, then adds L-Epicatechin gallate (ECG) that concentration is 2mg/ml and concentration is the selenocystine of 3mg/ml, at 15 DEG C, reaction 4h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 4
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the Co-base alloy material of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=9, then in system, adds the gallic acid that concentration is 5mg/ml and concentration is the cystine of 5mg/ml, at 20 DEG C, reaction 8h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 5
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the titanium of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=10, then add in system the compound with epicatechin (EC) that concentration is 6mg/ml and concentration be 7mg/ml there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl, at 25 DEG C, reaction 10h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 6
There is the novel anticoagulant material preparation method of inducing catalysis endogenous NO release function, obtained by following steps:
A, will the pure iron material of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the buffer system of pH=8, then in system, adds the epigallo catechin that concentration is 0.1mg/ml and concentration is the cystamine of 0.3mg/ml, at 12 DEG C, reaction 16h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 7
There is the novel anticoagulant material preparation method of inducing catalysis endogenous NO release function, obtained by following steps:
A, clean needing the terylene of modifying and decorating (PET) material to carry out, dry;
B, step A gained sample is positioned over the buffer system of pH=6, then add in system the compound with catechol structure that concentration is 7mg/ml and concentration be 9mg/ml there are two selenocystamines, at 6 DEG C, reaction 9h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Embodiment 8
There is a novel anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, clean needing the politef of modifying and decorating (PTFE) material to carry out, dry;
B, step A gained sample is positioned over the buffer system of pH=11, then add in system concentration be 1mg/ml there is the selenocystamine acid that epigallocatechin gallate (EGCG) (EGCG) and concentration are 1mg/ml, at 18 DEG C, reaction 4h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material.
Claims (5)
1. there is an anticoagulant material preparation method for inducing catalysis endogenous NO release function, obtained by following steps:
A, will the base material of modifying and decorating be needed to carry out polishing, cleaning, drying;
B, step A gained sample is positioned over the Tris-buffe buffer system of pH=5-12, then add in system the compound with adjacent phenol structure that concentration is 0.01mg/ml-10mg/ml and concentration be 0.01mg/ml-10mg/ml there is the two ends amino-contained of disulfide bond or two selenium keys or the compound of sulfydryl, at 10-30 DEG C, reaction 1-24h;
C, to step B gained sample, deionized water submergence, ultrasonic cleaning 3 times, each 5min, then at N
2dry under condition, obtain target material;
The described compound with adjacent phenol structure is the one of dopamine, gallic acid, epigallocatechin gallate (EGCG) EGCG, L-Epicatechin gallate ECG, epicatechin EC, epigallo catechin EGC, catechol;
The compound of described the two ends amino-contained or sulfydryl with disulfide bond or two selenium keys is the one of cystamine, selenocystamine, selenocystine, cystine and micromolecule sulfhydryl compound.
2. the anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release as claimed in claim 1, it is characterized in that, described base material is metal based biomaterial, ceramic base biomaterial, polymer-based biomaterial, hybrid material.
3. the anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release as claimed in claim 5, it is characterized in that, described metal based biomaterial comprises:, cobalt-base alloys, titanium and titanium alloys, gold, magnesium and alloy thereof, kirsite, pure iron and alloy thereof.
4. the anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release as claimed in claim 5, it is characterized in that, described polymeric biomaterial that is natural and synthesis comprises: natural biologic material---collagen, gelatin, fibroin albumen, cellulose, chitosan, alginic acid, hyaluronic acid, synthetic macromolecular material---terylene PET, polytetrafluoroethylene PTFE, polyurethane PU, polyformaldehyde POM, silicone rubber, polylactic acid PLA and glycolide-lactide copolymer PLGA, PTMC PTMC, polycaprolactone (PCL).
5. the anticoagulant material preparation method of a kind of inducing catalysis endogenous NO release as claimed in claim 5, it is characterized in that, described hybrid biomaterials comprises polylactic acid/hydroxy apatite, chitosan/hydroxyapatite.
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| US11253794B2 (en) * | 2015-05-28 | 2022-02-22 | Proprietary Technology Assets, Llc | Universal blood product and methods of preparing and using same |
| CN106581742B (en) * | 2016-11-22 | 2019-06-21 | 成都迈德克科技有限公司 | A method of NO catalytic type nano coating is constructed in titanium alloy surface |
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| CN108578772B (en) * | 2018-05-23 | 2020-09-08 | 西南交通大学 | Preparation method of blood contact material for improving biocompatibility and blood contact material |
| CN108969805B (en) * | 2018-07-05 | 2019-06-11 | 四川大学 | A kind of anticoagulation hydrogel coating and preparation method thereof being catalyzed nitric oxide releasing |
| CN109651586A (en) * | 2018-12-19 | 2019-04-19 | 中国科学院长春应用化学研究所 | The polyurethane containing selenium and the preparation method and application thereof of stable, controllable nitric oxide releasing |
| CN110354308A (en) * | 2019-05-31 | 2019-10-22 | 苏州大学附属第一医院 | A kind of bioactive bracket and preparation method thereof |
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| CN114129780B (en) * | 2020-09-03 | 2022-06-28 | 天津大学 | Preparation and application of light-operated nitric oxide releasing composite hydrogel |
| CN113041409B (en) * | 2021-03-25 | 2021-11-09 | 西南交通大学 | Hydrogel drug-loaded coating for treatment in oxidative stress environment and preparation method thereof |
| CN113230464B (en) * | 2021-04-01 | 2022-04-12 | 暨南大学 | Anti-restenosis 3D printing self-expanding degradable intravascular stent and preparation method thereof |
| CN113332491A (en) * | 2021-05-11 | 2021-09-03 | 淮阴工学院 | Anticoagulation hydrogel material for inducing NO release and preparation method and application thereof |
| CN113599581B (en) * | 2021-08-20 | 2022-10-04 | 安徽省立医院(中国科学技术大学附属第一医院) | Cardiovascular stent high polymer coating with controllable nitric oxide generation catalyzing function, and preparation method and application thereof |
| CN114588314B (en) * | 2022-03-31 | 2022-12-20 | 东莞市人民医院 | Intravascular stent and preparation method and application thereof |
| CN114632194B (en) * | 2022-04-11 | 2023-05-23 | 东莞市人民医院 | Coating material with long-acting NO catalytic release and preparation method and application thereof |
| CN115089773A (en) * | 2022-07-19 | 2022-09-23 | 中国科学院长春应用化学研究所 | Intravascular stent bionic coating, intravascular stent and preparation method thereof |
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Effective date of registration: 20191012 Address after: Room 306, building B, Beidou Industrial Park, No. 23, Nanxiang Second Road, Science City, Huangpu District, Guangzhou City, Guangdong Province Patentee after: Guangzhou Nanchuang Everest Medical Technology Co.,Ltd. Address before: 610000 Office Building 308, Modern Industrial Center, Southwest Jiaotong University, 111 North Section of Second Ring Road, Jinniu District, Chengdu City, Sichuan Province Co-patentee before: BEIJING NATON TECHNOLOGY GROUP Co.,Ltd. Patentee before: Chengdu Dingfeng Forward-looking Technology Co.,Ltd. |