生物可吸收聚酯—聚碳酸酯共聚物的合成及其结构性能研究
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摘要
本论文首先制备了丙交酯、乙交酯、三亚甲基碳酸酯等环状单体,然后采用乳酸锌或辛酸亚锡作为催化剂制备了一系列均聚物如聚乳酸(PLLA或PDLLA)、聚羟基乙酸(PGA)、聚三亚甲基碳酸酯(PTMC)、聚己内酯(PCL),和共聚物如聚(乳酸-co-三亚甲基碳酸酯)(PTLLA和PTDLA)、聚(三亚甲基碳酸酯-co-羟基乙酸)(PTGA)、聚(三亚甲基碳酸酯-co-己内酯)(PTCA)、聚乙二醇-b-聚(乳酸-co-三亚甲基碳酸酯)(PTDLA-b-PEG),然后采用DSC、NMR、SEC、ESEM、DMA、Instron拉伸仪和Kr(u|¨)ss表面张力仪等研究了它们的热性能、水降解和酶降解性能、力学性能和形变记忆行为,并通过溶血实验、血小板吸附、MTT法和细胞培养等方法评价了它们的生物相容性。
乳酸锌合成的PTDLA共聚物为无定形态,玻璃化温度(Tg)随着LA含量的增加而增加。它们不仅能够被水解,而且能够被蛋白酶K所降解,在水解53周后失重率均达到了50%左右,而在酶降解过程中,PTDLA的失重率随着LA含量的增加而逐渐增加,LA单元含量为82%的共聚物PTDLA在酶降解264小时后,失重率达到了91%。同时,共聚物的分子量在水解的初始阶段即迅速降低。LA含量越高,分子量降低越快;在降解后期,分子量下降速度减慢,且趋于一致。酶降解的初始阶段,PTDLA共聚物的分子量也有所降低,而后基本不变。酶降解过程中,共聚物组成基本保持不变;而在水解过程中,LA含量有所降低,这是由于LA单元优先降解所致。LA含量较高的共聚物在酶降解过程中则出现了非均相的孔洞结构,并且随着降解时间的延长,聚合物表面被逐渐溶蚀,孔洞也逐渐深入到聚合物本体。降解过程的研究表明,共聚物的水解是本体溶蚀的过程,而酶解是表面逐步溶蚀的过程。对于相同LA和TMC单元含量的PTDLA共聚物则具有高弹性和形变回复性能,在50%应变的初次拉伸循环后,其残余应变仅为4%,拉伸循环20次后其仍然具有80%以上的应变,形状回复比为83%,起始回复温度在其玻璃化转变湍度Tg附近。Tg充当形变记忆的转变温度,在Tg之上获得临时形状,然后在Tg之下形状被固定,再次在人体温度附近其能够回复到固有形状。
PTMC均聚物基本不能被水解,也不能够被蛋白酶K降解,其失重率、数均分子量以及表面形貌基本保持不变。但它能够被脂肪酶CA和HP降解,其中在脂肪酶CA中降解最快,在216h后其失重率达到98%,基本上是完全降解的,而在脂肪酶HP中降解较慢,在216h后失重率为22%。分子量均显著降低,分子量分布也变宽,并且在降解过程中出现双峰分布现象。但是,PTGA共聚物在两种脂肪酶中的降解则与PTMC均聚物显著不同,脂肪酶CA几乎不能降解PTGA,216h后失重仅5.8%,分子量及其分布也基本不变。而在脂肪酶HP中降解明显,216h后失重达到了58%,分子量也显著降低,分子量分布显著变宽,并且也出现分子量分布的双峰现象,但共聚物组成却保持不变。ESEM和接触角测试表明,酶首先吸附于聚合物表面,然后使聚合物表面溶蚀而发生降解。
采用辛酸亚锡催化合成的PTDLA-b-PEG嵌段共聚物,随着EG含量的增加,其玻璃化温度降低,而EG含量较高共聚物能够结晶PTDLA-b-PEG嵌段共聚物的蛋白酶K降解依据不同的LA和EG含量而不同,随着LA含量的降低和EG含量的增加,共聚物的接触角降低、亲水性增强,共聚物变得不容易被降解。Ptd12e12k在200h后的失重率仅为5.6%,分子量及其分布和ESEM观察表明,其在150h的酶降解过程中仅出现了表面低分子量齐聚物的溶蚀。而PLA含量较高的聚合物能够在不同降解时间内达到20%以上,分子量降低但共聚物组成却不变,降解由聚合物表面的溶蚀开始。
PLLA、PTMC、PCL、PTLLA、PTDLA、PTCA聚合物的溶血率都很小、其中又以PCL和PTCA的溶血率最低,分别为1.5%和1.4%。PLLA、PCL、PTLLA、PTDLA的血小板激活程度比较高,PTMC次之,PTCA的血小板粘附最少、变形最小、血小板激活程度最低,具有很强的抗血小板黏附能力。同时,这些聚合物对ECV304细胞的毒性很低,它能在所有聚合物表面黏附、生长和繁殖,并在5天之内形成一个细胞层,聚合物表面上的细胞形态没有明显变化,但是细胞繁殖速度略低于对照组,而其中又以PTMC和PTDLA为最低,分别为对照组的68%和71%。
因此,聚酯-聚碳酸酯共聚物,尤其是DLLA和TMC含量相当的聚(乳酸-co-三亚甲基碳酸酯)共聚物,在组织工程支架、体内支架涂层等智能生物材料方面具有良好的应用前景。
Cyclic monomers such as lactide,glycolide and trimethylene carbonate were prepared by polycondensation followed by cyclization.A series of homopolymers such as poly(lactide)(PLLA or PDLLA),poly(glycolide)(PGA),poly(trimethylene carbonate)(PTMC),poly(ε-caprolactone)(PCL) and copolymers such as poly(trimethylene carbonate-co-lactide)(PTLLA and PTDLA),poly(trimethylene carbonate-co-glycolide)(PTGA),poly(trimethylene carbonate-co-caprolactone) (PTCA),poly(ethylene glycol)-b-poly(trimethylene carbonate-co-lactide)(PTDLA-b-PEG) were then synthesized by ring opening polymerization(ROP) of appropriate monomer feeds using zinc lactate or stannous octoate as catalyst.The thermal properties,hydrolytic degradation,enzymatic degradation,mechanical properties and shape memory behavior were investigated by using DSC,NMR,SEC,ESEM,DMA and Instron tensile instrument.The biocompatibility was evaluated from haemolysis experiments,platelet adhesion,MTT assay and cell culture.
PTDLA copolymers are all amorphous.The glass transition temperature(Tg) increases with increasing LA content.PTDLA copolymers can be degraded not only by pure hydrolysis,but also by proteinase K.The mass loss reaches about 50%after 53 weeks' hydrolytic degradation,while during enzymatic degradation,the mass loss increases with increasing LA content.In particular,PTDLA copolymer containing 82mol.%LA units lost 91%of its initial mass after 264 h in the presence of proteinase K.The molecular weight of PTDLA copolymers rapidly decreases in the initial stage of hydrolytic degradation,followed by slower decrease.The LA content also decreases during hydrolytic degradation.In the case of enzymatic degradation,the molecular weight decreases at the initial stage,and then remains unchanged.The composition also remains unchanged during enzymatic degradation.Heterogeneous cavities are observed on the surface of PTDLA copolymers with high LA contents (＞50%),and gradually reach the polymer bulk.It can be concluded that the PTDLA copolymers are degraded through surface erosion during enzymatic degradation.
The PTDLA copolymer composed of the same TMC and LA contents is highly elastic.The residual strain is approximately 4%after the first cycle at a strain of 50%, and ca.80%recovery even after 20 cycles.The shape recovery ratio is up to 83%. Moreover,the initial recovery temperature is close to the glass transition temperature (Tg).Tg acts as the switch temperature between temporary shape and permanent shape.The temporary shape of the copolymer is formed above the T_g,and fixed below the T_g.The permanent shape can be recovered above the Tg(near body temperature).
PTMC homopolymer cannot be degraded by pure hydrolysis,or by proteinase K. The mass,molecular weight and surface morphology of PTMC remain pratically unchanged during degradation.In contrast,PTMC can be degraded by lipase CA and lipase HP.Lipase CA is most efficient.The mass loss of PTMC reaches 98%after 216h in lipase CA solution,and 22%lipase HP solution.During enzymatic degradation,the molecular weight significantly decreases and the molecular weight distribution becomes larger.Bimodal molecular weight distributions are observed. The enzymatic degradation of PTGA copolymer with 10%GA units is significantly different from that of PTMC homopolymer.PTGA cannot be degraded by lipase CA. Only 5.8%of mass loss is detetced after 216h,and the molecular weight and its distribution keep constant.In the lipase HP solution,however,the mass loss of PTGA reaches 58%after 216h.Meanwhile,the molecular weight decreases and its distribution becomes broader.Bimodal molecular weight distributions are also obtained.The composition of the PTGA copolymer remains constant.ESEM and contact angle measurements show that the polymers are homogeneously eroded from the surface during enzymatic degradation.
PTDLA-b-PEG triblock copolymers were synthesized using stannous octoate as catalyst.The glass transition temperature of the copolymers decrease with increasing EG content,while copolymers with high EG contents are crystallizable.During degradation by proteinase K,copolymers with higher EG content or lower LA content degrade at slower rate.In fact,proteinae K can only degrade the PLA component.On the other hand,high EG content leads to increase of the hydrophilicity of the polymer surface as shown by contact angle measurements.During degradation,the molecular weight slightly decreases and the composition remains constant.Changes in surface morphology are observed,in agreement with surface erosion process.
The haemolysis rate of the PLLA,PTMC,PCL,PTLLA,PTDLA and PTCA polymers is very small,especially that of PCL and PTCA,respectively 1.5%and 1.4%.Adhesion and activation of platelets are observed on the surface of PLLA,PCL, PTLLA,PTDLA films,while less platelets and lower activation are found on PTMC. The most interesting results were obtained with PTCA which exhibited the lowest degree of activation with few adhered platelets,in agreement with its outstanding anti-coagulant properties.Both indirect and direct cytocompatibility studies were performed on the polymers.The relative growth ratio data obtained from the liquid extracts during the 6-day cell culture period indicate that all the polymers present very low cytotoxicity.Microscopic observations demonstrate adhesion,spreading and proliferation of human umbilical vein endothelial cells ECV304 cells.
Therefore,copolyester-carbonates,and especially PTDLA,are promising candidate for applications in minimally invasive surgery such as bioresorbable stents or stent coating.
乳酸锌合成的PTDLA共聚物为无定形态,玻璃化温度(Tg)随着LA含量的增加而增加。它们不仅能够被水解,而且能够被蛋白酶K所降解,在水解53周后失重率均达到了50%左右,而在酶降解过程中,PTDLA的失重率随着LA含量的增加而逐渐增加,LA单元含量为82%的共聚物PTDLA在酶降解264小时后,失重率达到了91%。同时,共聚物的分子量在水解的初始阶段即迅速降低。LA含量越高,分子量降低越快;在降解后期,分子量下降速度减慢,且趋于一致。酶降解的初始阶段,PTDLA共聚物的分子量也有所降低,而后基本不变。酶降解过程中,共聚物组成基本保持不变;而在水解过程中,LA含量有所降低,这是由于LA单元优先降解所致。LA含量较高的共聚物在酶降解过程中则出现了非均相的孔洞结构,并且随着降解时间的延长,聚合物表面被逐渐溶蚀,孔洞也逐渐深入到聚合物本体。降解过程的研究表明,共聚物的水解是本体溶蚀的过程,而酶解是表面逐步溶蚀的过程。对于相同LA和TMC单元含量的PTDLA共聚物则具有高弹性和形变回复性能,在50%应变的初次拉伸循环后,其残余应变仅为4%,拉伸循环20次后其仍然具有80%以上的应变,形状回复比为83%,起始回复温度在其玻璃化转变湍度Tg附近。Tg充当形变记忆的转变温度,在Tg之上获得临时形状,然后在Tg之下形状被固定,再次在人体温度附近其能够回复到固有形状。
PTMC均聚物基本不能被水解,也不能够被蛋白酶K降解,其失重率、数均分子量以及表面形貌基本保持不变。但它能够被脂肪酶CA和HP降解,其中在脂肪酶CA中降解最快,在216h后其失重率达到98%,基本上是完全降解的,而在脂肪酶HP中降解较慢,在216h后失重率为22%。分子量均显著降低,分子量分布也变宽,并且在降解过程中出现双峰分布现象。但是,PTGA共聚物在两种脂肪酶中的降解则与PTMC均聚物显著不同,脂肪酶CA几乎不能降解PTGA,216h后失重仅5.8%,分子量及其分布也基本不变。而在脂肪酶HP中降解明显,216h后失重达到了58%,分子量也显著降低,分子量分布显著变宽,并且也出现分子量分布的双峰现象,但共聚物组成却保持不变。ESEM和接触角测试表明,酶首先吸附于聚合物表面,然后使聚合物表面溶蚀而发生降解。
采用辛酸亚锡催化合成的PTDLA-b-PEG嵌段共聚物,随着EG含量的增加,其玻璃化温度降低,而EG含量较高共聚物能够结晶PTDLA-b-PEG嵌段共聚物的蛋白酶K降解依据不同的LA和EG含量而不同,随着LA含量的降低和EG含量的增加,共聚物的接触角降低、亲水性增强,共聚物变得不容易被降解。Ptd12e12k在200h后的失重率仅为5.6%,分子量及其分布和ESEM观察表明,其在150h的酶降解过程中仅出现了表面低分子量齐聚物的溶蚀。而PLA含量较高的聚合物能够在不同降解时间内达到20%以上,分子量降低但共聚物组成却不变,降解由聚合物表面的溶蚀开始。
PLLA、PTMC、PCL、PTLLA、PTDLA、PTCA聚合物的溶血率都很小、其中又以PCL和PTCA的溶血率最低,分别为1.5%和1.4%。PLLA、PCL、PTLLA、PTDLA的血小板激活程度比较高,PTMC次之,PTCA的血小板粘附最少、变形最小、血小板激活程度最低,具有很强的抗血小板黏附能力。同时,这些聚合物对ECV304细胞的毒性很低,它能在所有聚合物表面黏附、生长和繁殖,并在5天之内形成一个细胞层,聚合物表面上的细胞形态没有明显变化,但是细胞繁殖速度略低于对照组,而其中又以PTMC和PTDLA为最低,分别为对照组的68%和71%。
因此,聚酯-聚碳酸酯共聚物,尤其是DLLA和TMC含量相当的聚(乳酸-co-三亚甲基碳酸酯)共聚物,在组织工程支架、体内支架涂层等智能生物材料方面具有良好的应用前景。
Cyclic monomers such as lactide,glycolide and trimethylene carbonate were prepared by polycondensation followed by cyclization.A series of homopolymers such as poly(lactide)(PLLA or PDLLA),poly(glycolide)(PGA),poly(trimethylene carbonate)(PTMC),poly(ε-caprolactone)(PCL) and copolymers such as poly(trimethylene carbonate-co-lactide)(PTLLA and PTDLA),poly(trimethylene carbonate-co-glycolide)(PTGA),poly(trimethylene carbonate-co-caprolactone) (PTCA),poly(ethylene glycol)-b-poly(trimethylene carbonate-co-lactide)(PTDLA-b-PEG) were then synthesized by ring opening polymerization(ROP) of appropriate monomer feeds using zinc lactate or stannous octoate as catalyst.The thermal properties,hydrolytic degradation,enzymatic degradation,mechanical properties and shape memory behavior were investigated by using DSC,NMR,SEC,ESEM,DMA and Instron tensile instrument.The biocompatibility was evaluated from haemolysis experiments,platelet adhesion,MTT assay and cell culture.
PTDLA copolymers are all amorphous.The glass transition temperature(Tg) increases with increasing LA content.PTDLA copolymers can be degraded not only by pure hydrolysis,but also by proteinase K.The mass loss reaches about 50%after 53 weeks' hydrolytic degradation,while during enzymatic degradation,the mass loss increases with increasing LA content.In particular,PTDLA copolymer containing 82mol.%LA units lost 91%of its initial mass after 264 h in the presence of proteinase K.The molecular weight of PTDLA copolymers rapidly decreases in the initial stage of hydrolytic degradation,followed by slower decrease.The LA content also decreases during hydrolytic degradation.In the case of enzymatic degradation,the molecular weight decreases at the initial stage,and then remains unchanged.The composition also remains unchanged during enzymatic degradation.Heterogeneous cavities are observed on the surface of PTDLA copolymers with high LA contents (＞50%),and gradually reach the polymer bulk.It can be concluded that the PTDLA copolymers are degraded through surface erosion during enzymatic degradation.
The PTDLA copolymer composed of the same TMC and LA contents is highly elastic.The residual strain is approximately 4%after the first cycle at a strain of 50%, and ca.80%recovery even after 20 cycles.The shape recovery ratio is up to 83%. Moreover,the initial recovery temperature is close to the glass transition temperature (Tg).Tg acts as the switch temperature between temporary shape and permanent shape.The temporary shape of the copolymer is formed above the T_g,and fixed below the T_g.The permanent shape can be recovered above the Tg(near body temperature).
PTMC homopolymer cannot be degraded by pure hydrolysis,or by proteinase K. The mass,molecular weight and surface morphology of PTMC remain pratically unchanged during degradation.In contrast,PTMC can be degraded by lipase CA and lipase HP.Lipase CA is most efficient.The mass loss of PTMC reaches 98%after 216h in lipase CA solution,and 22%lipase HP solution.During enzymatic degradation,the molecular weight significantly decreases and the molecular weight distribution becomes larger.Bimodal molecular weight distributions are observed. The enzymatic degradation of PTGA copolymer with 10%GA units is significantly different from that of PTMC homopolymer.PTGA cannot be degraded by lipase CA. Only 5.8%of mass loss is detetced after 216h,and the molecular weight and its distribution keep constant.In the lipase HP solution,however,the mass loss of PTGA reaches 58%after 216h.Meanwhile,the molecular weight decreases and its distribution becomes broader.Bimodal molecular weight distributions are also obtained.The composition of the PTGA copolymer remains constant.ESEM and contact angle measurements show that the polymers are homogeneously eroded from the surface during enzymatic degradation.
PTDLA-b-PEG triblock copolymers were synthesized using stannous octoate as catalyst.The glass transition temperature of the copolymers decrease with increasing EG content,while copolymers with high EG contents are crystallizable.During degradation by proteinase K,copolymers with higher EG content or lower LA content degrade at slower rate.In fact,proteinae K can only degrade the PLA component.On the other hand,high EG content leads to increase of the hydrophilicity of the polymer surface as shown by contact angle measurements.During degradation,the molecular weight slightly decreases and the composition remains constant.Changes in surface morphology are observed,in agreement with surface erosion process.
The haemolysis rate of the PLLA,PTMC,PCL,PTLLA,PTDLA and PTCA polymers is very small,especially that of PCL and PTCA,respectively 1.5%and 1.4%.Adhesion and activation of platelets are observed on the surface of PLLA,PCL, PTLLA,PTDLA films,while less platelets and lower activation are found on PTMC. The most interesting results were obtained with PTCA which exhibited the lowest degree of activation with few adhered platelets,in agreement with its outstanding anti-coagulant properties.Both indirect and direct cytocompatibility studies were performed on the polymers.The relative growth ratio data obtained from the liquid extracts during the 6-day cell culture period indicate that all the polymers present very low cytotoxicity.Microscopic observations demonstrate adhesion,spreading and proliferation of human umbilical vein endothelial cells ECV304 cells.
Therefore,copolyester-carbonates,and especially PTDLA,are promising candidate for applications in minimally invasive surgery such as bioresorbable stents or stent coating.
引文
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