生物可降解导电聚膦腈高分子的合成及性能研究
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摘要
导电高分子是一类新兴的功能聚合物,近年来的研究发现,导电高分子不仅具有良好的生物相容性,而且能调节细胞的多重功能(如黏附、增殖、迁移和分化、DNA的合成、蛋自质的分泌等),在生物医学工程领域具有广泛的应用前景和重要的研究价值。本论文以周围神经修复为研究背景,设计合成既具有电活性,同时又具有良好生物相容性和可生物降解性的聚膦腈高分子材料,并对其结构和性能进行表征。通过体外RSC96细胞与材料作用,并辅以电刺激对其进行生物学和电活性评价。本文将电活性和生物降解性的概念同时引入高分子材料的合成,为周围神经组织工程材料的研究开辟了一条新的途经。主要内容如下：
合成了两种苯胺低聚体：苯胺四聚体和苯胺五聚体。探讨了苯胺四聚体合成过程中的反应温度、氧化剂的用量、质子酸的种类和浓度等因素对产率的影响。对合成苯胺五聚体的双向增长和单向增长两种方法进行比较,单向增长法能制备产率和纯度均较高的苯胺五聚体。利用傅立叶红外光谱(FT-IR)、核磁共振(~1H-NMR、~(13)C-NMR)、紫外可见光谱(UV-Vis)表征了苯胺四聚体和五聚体结构,分别采用循环伏安法(CV)和四点探针法表征了电化学性能和电导率。以六氯环三膦腈为原料,通过热开环聚合方法,合成线性聚二氯膦腈,并研究了聚合过程中的温度、聚合时间等因素对产率的影响。
通过亲核取代反应,首先制备两种由可降解基团单取代的聚膦腈高分子材料：聚[双(甘氨酸乙酯)]膦腈(PGEE)和聚甲基苯氧基膦腈(PMPP)。在此基础上,将导电苯胺低聚物和可降解基团与聚二氯膦腈接枝,合成两种由导电基团和可降解基团混合取代的聚膦腈导电高分子材料：聚[(甘氨酸乙酯／苯胺五聚体)膦腈](PGAP)、聚[(对甲基苯氧基)／(苯胺四聚体)膦腈](PMAP)。研究了混合取代聚膦腈合成过程中取代基加入顺序、反应温度等对产率的影响。采用FT-IR、~1H-NMR、UV-Vis、~(31)P-NMR等分析方法表征合成聚合物的结构,利用CV、四点探针法对合成的导电聚合物的电化学性能进行测试和表征。结果表明：合成的导电聚膦腈高分子具有类似苯胺低聚体的化学氧化特征,并能进行质子酸的掺杂；四点探针法测得PGAP的电导率为2×10~(-5)S/cm,PMAP的电导率为1.45×10~(-6)S/cm。前者比后者具有更好的电化学性能,与生物电的电导率相近。采用凝胶渗透色谱法(GPC)测试PGAP的分子量：(?)w=2.1×10~5,(?)n=6.2×10~4,分子量分布d=3.42。
对合成的聚合物PGEE、PMPP、PGAP、PMAP进行体外降解研究。测定降解过程中降解介质pH值、失重率变化和采用扫描电子显微镜(SEM)观察材料微观结构变化表明：聚膦腈的降解性能与侧基的性质有密切的关系,PGAP、PGEE材料比PMAP和PMPP材料具有更好的降解性能。PGAP、PGEE材料在降解过程中溶液的pH值略呈上升的趋势,基本处于中性。
将RSC96细胞与PGAP、PMAP材料体外联合培养,通过细胞增殖、细胞毒性、溶血试验、SEM观察进行生物学评价。噻唑蓝(MTT)比色法表明PGAP材料能促进细胞的增殖；荧光探针技术测试细胞毒性表明导电材料PGAP与对照组PDLLA一致；溶血试验表明PGAP材料的溶血率符合医用材料的溶血要求；SEM观察表明两种材料都具有良好的神经细胞亲和性。
设计和制备了电刺激装置,通过设计的电刺激实验,研究PGAP材料在有无电刺激以及电刺激不同方式下,对RSC96细胞生长、增殖的影响。比较了不导电材料PDLLA、PGEE在有无电刺激的条件下对RSC96细胞生长情况。探讨了不同电压和时间的电刺激对细胞的增殖。结果表明：电极与导电材料PGAP接触,能促进细胞增殖和片状伪足的生长；当电极不接触材料,电流从培养液中通过时,与无电刺激相比,细胞伪足的平均长度无显著性差异；不导电材料有电刺激与无电刺激相比,细胞伪足平均长度无显著性差异；电压超过100 mV,电刺激时间超过72 h时,细胞的增殖不再具有显著性差异。
As a new kind of functional material, conducting polymers not only possess good biocompatiblity but also can modulate cellular activities, including cell adhesion, migration, DNA synthesis, and protein secretion, implying a promising application in biomedical field. In this dissertation, a novel electroactive, biocompatible and biodegradable polyphosphazenes were designed and synthesized for peripheral nerve regeneration. The structure and properties of the synthesized polymer were characterized by different methods. Biological evaluation and electrical activation of materials were carried out, via electrical stimulation, by cultivating RSC96 Schwann cells on the surface of the materials. The idea of tethering conducting polymer and biodegradable materials together to create a new kind of polymer explores a new way for regenerating nerve tissue engineering. The major work is summarized as the following:
Oligoaniline of aniline tetramer and pentamer were synthesized successfully in this part. The influences of reaction temperature, dosage of oxidant and concentration of different proton acid on yield of aniline tetramer were investigated. Two synthetic routes for the preparation of aniline pentamer had been studied. The results showed that the high yield and purity of pentamer should be synthesized through step-by-step method. Chemical structure of aniline tetramer and pentamer was characterized by FT-IR,~1H-NMR, ~(13)C-NMR and UV-Vis. The electrochemical properties of the as-synthesized oligoaniline also were investigated by CV and Four-Point probe method. Reactive poly(dichlorophosphazene) was prepared from hexachlorocyclotriphosphazene by thermal initiated ring-open polymerization. Polymerization conditions were investigated, including polymerization temperature, polymerization time and water concentration in respect to the yield of poly(dichlorophosphazene).
Monosubstituted polyphosphazene of Poly[(glycine ethyl ester)phosphazene] (PGEE) and poly[(methylphenoxy) phosphazene] (PMPP) were prepared by grafting glycine ethyl ester and methoxyphenol on polyphosphazene respectively. Poly[(methylphenoxy)(aniline tetramer) phosphazene] (PMAP) and poly[(glycine ethyl ester)(aniline pentamer) phosphazene] (PGAP) were further synthesized by grafting oligoaniline and biodegradable groups on polyphosphazene as side groups. Some factors affecting yields of two mixed-substituent poly (organophosphazenes), such as reaction temperature and order of substitutional group added, were studied and discussed. FT-IR、~1H-NMR、UV-Vis> ~(31)P-NMR were used to characterize the chemical structure of as-synthesized polymers. The electrochemical properties of PGAP and PMAP were characterized by CV and Four-point probe method. The conductivity of PGAP and PMAP is 2x10~(-5)S/cm and 1.45x10(-6)S/cm respectively, which confirmed that the conductivity of PGAP is better than PMAP. In addition, the molecular weight of PGAP determinated by GPC is Mw= 2.1 x10~5, Mn=6.2x104, and the heterogeneity is d=3.42.
The pH value of degradation medium, and the variation of molecular weight were determinated and the variation of the morphology and microstructure of PGEE、PMPP、PGAP and PMAP was observed during the degradation in vitro. The results showed that the biodegradability of poly (organophosphazenes) is relevant to the properties of substituent groups. The pH value of degradation medium tended to rise but still in the range of neutral during the whole degradation time of PGAP and PGEE. The results also illustrated that PGAP and PGEE is biodegradable.
After cultivating RSC96 Schwann cells on the surface of PGAP and PMAP materials, Biological evaluation was carried out through cell proliferation, cytotoxicity, hemolysis test and SEM observation. The viability using MTT assay of RSC96 cells seeded on PGAP films showed that PGAP could promote cells adhesion and proliferation. Fluorescent probe technology indicated that cytotoxicity of PGAP is similar to PDLLA, which suggested PGAP is non-toxic. The results of hemolysis test showed PGAP meets the requirements of medical materials. The SEM results showed that PGAP has better cell affinity than PDLLA. All of the above results suggested that the PGAP copolymer was non-toxic and could support the cell attachment and proliferation.
A novel adjustable direct current regulated power supply was designed and prepared for stimulating cell growth. In order to elucidate the effect of electrical stimulation through PGAP on RSC96 cells proliferation, experiments were performed in which RSC96 cells grown on PGAP were subjected to a potential through the film, through the solution and not subjected to any stimulation, respectively. The effects of non-conducting material, such as PDLLA and PGEE, with or without electrical stimulation on RSC96 cell proliferation were also evaluated. Different constant potential and stimulation time on proliferation of RSC96 cells were also studied. The results showed that electrical stimulation through the PGAP films could accelerate cells proliferation. Cells grown on PGAP materials in which charge was passed through the solution possessed medican pseudopodium length similar to cells without an electrical stimulus. As for non-conducting materials, medican pseudopodium length is no significantly different between with or without electrical stimulation. In addition, the cell proliferation results using MTT assay showed that there is no significant difference when stimulation potential and time exceed to 100 mV and 72 h, respectively.
合成了两种苯胺低聚体：苯胺四聚体和苯胺五聚体。探讨了苯胺四聚体合成过程中的反应温度、氧化剂的用量、质子酸的种类和浓度等因素对产率的影响。对合成苯胺五聚体的双向增长和单向增长两种方法进行比较,单向增长法能制备产率和纯度均较高的苯胺五聚体。利用傅立叶红外光谱(FT-IR)、核磁共振(~1H-NMR、~(13)C-NMR)、紫外可见光谱(UV-Vis)表征了苯胺四聚体和五聚体结构,分别采用循环伏安法(CV)和四点探针法表征了电化学性能和电导率。以六氯环三膦腈为原料,通过热开环聚合方法,合成线性聚二氯膦腈,并研究了聚合过程中的温度、聚合时间等因素对产率的影响。
通过亲核取代反应,首先制备两种由可降解基团单取代的聚膦腈高分子材料：聚[双(甘氨酸乙酯)]膦腈(PGEE)和聚甲基苯氧基膦腈(PMPP)。在此基础上,将导电苯胺低聚物和可降解基团与聚二氯膦腈接枝,合成两种由导电基团和可降解基团混合取代的聚膦腈导电高分子材料：聚[(甘氨酸乙酯／苯胺五聚体)膦腈](PGAP)、聚[(对甲基苯氧基)／(苯胺四聚体)膦腈](PMAP)。研究了混合取代聚膦腈合成过程中取代基加入顺序、反应温度等对产率的影响。采用FT-IR、~1H-NMR、UV-Vis、~(31)P-NMR等分析方法表征合成聚合物的结构,利用CV、四点探针法对合成的导电聚合物的电化学性能进行测试和表征。结果表明：合成的导电聚膦腈高分子具有类似苯胺低聚体的化学氧化特征,并能进行质子酸的掺杂；四点探针法测得PGAP的电导率为2×10~(-5)S/cm,PMAP的电导率为1.45×10~(-6)S/cm。前者比后者具有更好的电化学性能,与生物电的电导率相近。采用凝胶渗透色谱法(GPC)测试PGAP的分子量：(?)w=2.1×10~5,(?)n=6.2×10~4,分子量分布d=3.42。
对合成的聚合物PGEE、PMPP、PGAP、PMAP进行体外降解研究。测定降解过程中降解介质pH值、失重率变化和采用扫描电子显微镜(SEM)观察材料微观结构变化表明：聚膦腈的降解性能与侧基的性质有密切的关系,PGAP、PGEE材料比PMAP和PMPP材料具有更好的降解性能。PGAP、PGEE材料在降解过程中溶液的pH值略呈上升的趋势,基本处于中性。
将RSC96细胞与PGAP、PMAP材料体外联合培养,通过细胞增殖、细胞毒性、溶血试验、SEM观察进行生物学评价。噻唑蓝(MTT)比色法表明PGAP材料能促进细胞的增殖；荧光探针技术测试细胞毒性表明导电材料PGAP与对照组PDLLA一致；溶血试验表明PGAP材料的溶血率符合医用材料的溶血要求；SEM观察表明两种材料都具有良好的神经细胞亲和性。
设计和制备了电刺激装置,通过设计的电刺激实验,研究PGAP材料在有无电刺激以及电刺激不同方式下,对RSC96细胞生长、增殖的影响。比较了不导电材料PDLLA、PGEE在有无电刺激的条件下对RSC96细胞生长情况。探讨了不同电压和时间的电刺激对细胞的增殖。结果表明：电极与导电材料PGAP接触,能促进细胞增殖和片状伪足的生长；当电极不接触材料,电流从培养液中通过时,与无电刺激相比,细胞伪足的平均长度无显著性差异；不导电材料有电刺激与无电刺激相比,细胞伪足平均长度无显著性差异；电压超过100 mV,电刺激时间超过72 h时,细胞的增殖不再具有显著性差异。
As a new kind of functional material, conducting polymers not only possess good biocompatiblity but also can modulate cellular activities, including cell adhesion, migration, DNA synthesis, and protein secretion, implying a promising application in biomedical field. In this dissertation, a novel electroactive, biocompatible and biodegradable polyphosphazenes were designed and synthesized for peripheral nerve regeneration. The structure and properties of the synthesized polymer were characterized by different methods. Biological evaluation and electrical activation of materials were carried out, via electrical stimulation, by cultivating RSC96 Schwann cells on the surface of the materials. The idea of tethering conducting polymer and biodegradable materials together to create a new kind of polymer explores a new way for regenerating nerve tissue engineering. The major work is summarized as the following:
Oligoaniline of aniline tetramer and pentamer were synthesized successfully in this part. The influences of reaction temperature, dosage of oxidant and concentration of different proton acid on yield of aniline tetramer were investigated. Two synthetic routes for the preparation of aniline pentamer had been studied. The results showed that the high yield and purity of pentamer should be synthesized through step-by-step method. Chemical structure of aniline tetramer and pentamer was characterized by FT-IR,~1H-NMR, ~(13)C-NMR and UV-Vis. The electrochemical properties of the as-synthesized oligoaniline also were investigated by CV and Four-Point probe method. Reactive poly(dichlorophosphazene) was prepared from hexachlorocyclotriphosphazene by thermal initiated ring-open polymerization. Polymerization conditions were investigated, including polymerization temperature, polymerization time and water concentration in respect to the yield of poly(dichlorophosphazene).
Monosubstituted polyphosphazene of Poly[(glycine ethyl ester)phosphazene] (PGEE) and poly[(methylphenoxy) phosphazene] (PMPP) were prepared by grafting glycine ethyl ester and methoxyphenol on polyphosphazene respectively. Poly[(methylphenoxy)(aniline tetramer) phosphazene] (PMAP) and poly[(glycine ethyl ester)(aniline pentamer) phosphazene] (PGAP) were further synthesized by grafting oligoaniline and biodegradable groups on polyphosphazene as side groups. Some factors affecting yields of two mixed-substituent poly (organophosphazenes), such as reaction temperature and order of substitutional group added, were studied and discussed. FT-IR、~1H-NMR、UV-Vis> ~(31)P-NMR were used to characterize the chemical structure of as-synthesized polymers. The electrochemical properties of PGAP and PMAP were characterized by CV and Four-point probe method. The conductivity of PGAP and PMAP is 2x10~(-5)S/cm and 1.45x10(-6)S/cm respectively, which confirmed that the conductivity of PGAP is better than PMAP. In addition, the molecular weight of PGAP determinated by GPC is Mw= 2.1 x10~5, Mn=6.2x104, and the heterogeneity is d=3.42.
The pH value of degradation medium, and the variation of molecular weight were determinated and the variation of the morphology and microstructure of PGEE、PMPP、PGAP and PMAP was observed during the degradation in vitro. The results showed that the biodegradability of poly (organophosphazenes) is relevant to the properties of substituent groups. The pH value of degradation medium tended to rise but still in the range of neutral during the whole degradation time of PGAP and PGEE. The results also illustrated that PGAP and PGEE is biodegradable.
After cultivating RSC96 Schwann cells on the surface of PGAP and PMAP materials, Biological evaluation was carried out through cell proliferation, cytotoxicity, hemolysis test and SEM observation. The viability using MTT assay of RSC96 cells seeded on PGAP films showed that PGAP could promote cells adhesion and proliferation. Fluorescent probe technology indicated that cytotoxicity of PGAP is similar to PDLLA, which suggested PGAP is non-toxic. The results of hemolysis test showed PGAP meets the requirements of medical materials. The SEM results showed that PGAP has better cell affinity than PDLLA. All of the above results suggested that the PGAP copolymer was non-toxic and could support the cell attachment and proliferation.
A novel adjustable direct current regulated power supply was designed and prepared for stimulating cell growth. In order to elucidate the effect of electrical stimulation through PGAP on RSC96 cells proliferation, experiments were performed in which RSC96 cells grown on PGAP were subjected to a potential through the film, through the solution and not subjected to any stimulation, respectively. The effects of non-conducting material, such as PDLLA and PGEE, with or without electrical stimulation on RSC96 cell proliferation were also evaluated. Different constant potential and stimulation time on proliferation of RSC96 cells were also studied. The results showed that electrical stimulation through the PGAP films could accelerate cells proliferation. Cells grown on PGAP materials in which charge was passed through the solution possessed medican pseudopodium length similar to cells without an electrical stimulus. As for non-conducting materials, medican pseudopodium length is no significantly different between with or without electrical stimulation. In addition, the cell proliferation results using MTT assay showed that there is no significant difference when stimulation potential and time exceed to 100 mV and 72 h, respectively.
引文
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