聚乳酸固载环糊精的制备及细胞相容性研究
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摘要
为了开发一种具有良好生物相容性和生物特异性的生物医用材料,本研究以D,L-乳酸为起始原料,在新型镧钛复合氧化物的的作用下催化乳酸脱水制备丙交酯。丙交酯在锌酸亚锡作用下开环聚合得到聚乳酸,在此基础上,通过一系列化学改性,将低聚糖环糊精共价接枝到聚乳酸分子骨架上,得到一种新型的糖伪饰聚乳酸基全降解生物材料。采用傅立叶红外光谱仪(FTIR)、核磁共振波谱仪(NMR)、GPC-十八角激光散射仪(MALLS)、差示扫描量热计(DSC)和一些常规化学分析方法对合成的材料进行测试与表征,并考察了材料的亲/疏水性、体外降解行为、生物相容性。主要研究内容和结论如下:
⑴反应性聚乳酸的制备
①首先以乳酸为原料,通过镧钛复合氧化物催化乳酸制备丙交酯(LA),镧钛复合氧化物的引入使乳酸低聚物的裂解温度整体下降,丙交酯的纯度得到提高,经DSC测定,丙交酯的熔点为126.4℃,X射线光电子能谱分析结果表明,丙交酯没有受到放射性元素镧的污染。
②丙交酯在锌酸亚锡作用下开环聚合得到聚乳酸,用多角度激光光散射仪测定实验所得PLA的分子量和分子量分布分别为:Mw=22480;Mn=19548;PD=1.15。
③通过马来酸酐单体在过氧化二苯甲酰引发下与聚乳酸发生自由基反应,向缺乏反应基团的聚乳酸分子提供高反应活性的酸酐键。FTIR和1HNMR分析结果表明,马来酸酐成功引入到聚乳酸分子骨架上。并确定了较佳的反应条件是:反应物重量比PLA:MAH=10:1,BPO用量4wt%(相对于MAH用量),反应时间10h、反应温度95℃。罗丹明比色法测定结果表明,在此条件下制备的MPLA中马来酸酐的接枝率为2.45%,MALLS检测表明MPLA的分子量和分子量分布分别为Mw=20473,Mn=16510,PD=1.24。
⑵合成了6-单-乙二胺-β-CD(β-CD-6-E)单体
①FTIR、1H NMR和DSC-TGA的分析结果表明,通过将对甲基苯磺酰氯配成乙腈溶液在10℃下滴加到β-环糊精(β-CD)的NaOH溶液中,β-CD转变成了6-单-对甲基苯磺酰β-环糊精酯(β-CD-6-OTs)中间体,且产物在181.7℃开始分解,187℃有一个强分解峰。考察了反应条件对产率的影响,得到最佳的反应工艺条件为:TsCl:β-CD的摩尔比为1.5,TsCl的乙腈液在10度下缓慢滴加,反应温度23~25℃,反应时间2h,最终产物pH值调整至7~8,这时产物产率可达到14%。
②红外光谱、核磁共振波谱仪以及元素分析仪(EA)分析的结果表明,β-CD-6-OTs与过量乙二胺在75~80℃反应4h能得到6-单-乙二胺-β-CD环糊精。
⑶通过MPLA分子中的酸酐键和β-CD-6-E分子中的胺基之间发生N-酰化反应合成环糊精改性的聚乳酸材料(PLA-β-CD)。FTIR、1H NMR的分析结果表明,在几乎不改变聚乳酸材料主链结构的前提下,通过N-酰化反应,能将环糊精固载到MPLA的分子骨架中;DSC分析显示合成得到的PLA-β-CD的玻璃化转变峰值温度为59.8℃,表明采用本研究的分离提纯技术可得到纯净的聚乳酸固载环糊精(PLA-β-CD)聚合物。较佳反应工艺条件是:反应物投料比为nβ-CD-6-E:nMPLA=1.2:1,反应温度:35~40℃,反应时间:2小时,PLA-β-CD产率可达到55%。苯酚-硫酸法测定结果表明,在此条件下制备的聚合物中环糊精的含量为12.7%。
⑷考察了PLA和PLA-β-CD的理化性能,包括材料的亲/疏水性能和降解性能。其中,亲/疏水性能的评价指标是静态水接触角和吸水率,降解性能的评价采用体外降解试验。
①静态水接触角和吸水率的测定结果表明:PLA-β-CD改性材料的静态水接触角与聚乳酸相比,静态水接触角由76.7o降低到72.1o。吸水率由单一聚乳酸的18.3%提高到23.9%。说明PLA-β-CD材料比PLA有更好的亲水性;
②PLA-β-CD材料在蒸馏水中降解时pH值的变化结果在5周以前,体系的pH值在相同时间点比PLA略高,5周以后在整个降解期间的pH值略低于相同时间点PLA的pH值,且陡降时间比纯PLA略提前一周;
③PLA-β-CD在PBS中降解失重率的测定结果表明:材料在PBS介质中降解经历阶段与聚乳酸材料的失重率变化趋势趋于一致,但降解速率有所提高;表明本研究得到的PLA-β-CD改性材料在亲水性改善的同时,并没有出现马来酸酐的引入导致聚乳酸材料酸性增强的现象。
⑸采用细胞形态学观察法和细胞增殖法,初步考察了材料与大鼠成骨细胞的细胞相容性。通过对基底材料上细胞形态、早期粘附和铺展的比较研究,结果表明PLA-β-CD上细胞不仅形态上优于其他组,而且在数量上也有优势;通过MTT法测定了成骨细胞在材料上培养2、4、6、8天的增殖活力。实验结果表明,成骨细胞在PLA-β-CD的增殖活力明显大于PLA上的增殖活力。这说明由环糊精改性聚乳酸比PLA表现出更好的细胞相容性。糖-蛋白质相互作用是信号传导、细胞黏附、增殖、分化和免疫应答等很多细胞识别过程的基础,无论是单糖还是多糖都对多肽、蛋白质都有较好的亲和性,对细胞也具有较好的亲和性。根据以上实验结果,预期PLA-β-CD可在生物医学领域尤其是组织工程领域和药物缓释载体中得到广泛的应用。
Aiming to develop a biomaterial with excellent biocompability and biospecificy and physiological functions, in this thesis, D,L-lactide was prepared from D,L-lactic acid by adopting a new lanthanum-titanium composite oxides as the catalyst. First, poly(D,L-lactic acid) (PLA) was prepared from D,L-lactide with the use of Sn(Oct)2, and then, with a series of chemical reactions in the bulk, it was modified by introducingβ-cyclodextrin(β-CD) oligosaccharide into PDLLA backbone, at last, a novel PLA was acquired, which was based on fully biodegradable matrix materials modified by polysaccharides. To explore the structures and properties of the obtained polymers, characterizations included multi-angle laser light scattering (MALLS), fourier transform infrared spectrometry (FTIR), nuclear magnetic resonance spectrometer (NMR), differential scanning calorimeter (DSC) and some classical chemical analysis methods, and then, surface wettability, biodegradation and biocompatibility of the synthetic materials were investigated, too. The main works and conclusions are listed as below:
⑴Synthesis of reactable poly(D,L-lactic acid).
①With D,L-lactic acid as raw material and lanthanum-titanium composite oxides as catalyst, the D,L-lactide was synthesized. The catalyst of lanthanum-titanium composite oxides is high efficient in decreasing the dehydrate temperature, pyrolysis temperature and viscosity of the reacting system, consequently the oligomer of lactic acid was kept in the reactor instead of escaping with lactide, which prevents the contamination of lactide by oligomer. Glass transition temperature of the D,L-lactide tested by DSC was 126.4℃, and analysis of X-ray photoelectron spectroscopy (XPS) indicated that the lactide was found to be hardly contaminated by La-radioactivity.
②Poly(D,L-lactic acid) was synthesized by melt ring-opening polymerization of D,L-lactide with Sn(Oct)2 as catalyst. Molecular weight (Mw=22480, Mn=19548), and polydispersity (PD=1.15) of PLA were detected by MALLS.
③To introduce highly reactive anhydride into backbone of PLA lacking of reaction group, free radical copolymerization happened between PLA and maleic anhydride(MAH) with the help of benzoyl peroxide (BPO) as an initiator. It is demonstrated by FTIR and 1HNMR that the MAH had been imported in PLA backbone successfully, and the relative optimum reactive conditions of MPLA were obtained: weight ratio of PLA to MAH was 10:1, weight ratio of BPO to MAH was 0.04, and reaction time was 10h, reaction temperature was 95℃. The results of rhodamine-carboxyl interaction method showed that under such conditions, the MAH grafting ratio in MPLA was 2.45%. Molecular weight and polydispersity of MPLA were detected by MALLS about Mw=20473, Mn=16510 and PD=1.24, respectively.
⑵Preparation of mono(6-(2-aminoethyl)-amino-6-deoxy)-β-cyclodextrin。
①It was indicated by FTIR, 1HNMR and DSC-TGA analysis that mono-6-O-6- tosyl-β-cyclo-dextrin(β-CD-6-OTs) had been successfully prepared by dropping p-TsCl acetonitrile solution intoβ-CD NaOH solution under 10℃, and then the reaction mixture was heated up to 25°C and lasted for 2h. Decomposition temperature ofβ-CD-6-OTs determined by DSC-TGA was 181.7℃and a strong decomposition peak was 187℃. The effect of reaction conditions on the yield ratio ofβ-CD-6-OTs was investigated, and the optimum conditions were: molar ratio of p–TsCl toβ-CD was 1.5, reaction time was 2h, reaction temperature was 23~25℃, the mixture was adjusted with 20%-hydrochloric acid solution to ca. pH7~8, theβ-CD-6-OTs yield could reach to 14%.
②It was shown by FTIR, 1HNMR and EA analysis thatβ-CD-6-E had been successfully prepared by the reaction ofβ-CD-6-OTs and excess ethylenediamine at 75℃for 4h.
⑶It was exhibited by FTIR, 1H NMR and DSC analysis that, by N-acylation reaction,β-CD was able to be introduced into the backbone of MPLA(maleic anhydride modified poly(d,l-lactic acid)) and the main chain structure of MPLA was maintained. And the glass transition temperature of PLA-β-CD acquired was 59.8℃by DSC analysis, the unique Tg of PLA-β-CD indicated that the purification method was efficient enough to produce pure PLA-β-CD. The optimum conditions were: molar ratio ofβ-CD-6-E to MPLA was 1.2, reaction temperature was 35~40℃, reaction time was 2h, the yield of PLA-β-CD was found to be 55%. It was indicated by Phenol-sulfuric Acid method that the content ofβ-CD was 12.7% under the above conditions.
⑷The properties of various poly(D,L-lactic acid) based substrate films were investigated, including surface wettability and biodegradation. The surface wettability evaluation was based on static water contact angle and water adsorption ratio, while the degradation experimentation in vitro was used to estimate the bio degradation behavior.
①The tests indicated that the static water contact angle of copolymer PLA-β-CD was decreased appreciably from 76.7o to 72.1o comparing with PLA, while the water absorption ratio was increased from 18.3% to 23.9%. The results revealed that hydrophilicity of PLA-β-CD was better than PLA.
②In the whole degradation period of PLA-β-CD materials in distilled water, the change rule of the pH value was: At first, the pH value of PLA-β-CD is slightly higher than that of PLA within the first 5 weeks, and then, the former is a little lower than the latter in all other degradation period after that time, and the rapid drop time of PLA-β-CD advanced 1 week comparing with PLA.
③Tests indicated that: the degradation stages of material PLA-β-CD in medium PBS tended to be accordance with the weight loss change trend of PLA, but the degradation rate improved to some extent. It demonstrated that the hydrophilicity of PLA-β-CD acquired by this research was improved, while the acidity of PLA had not enhanced by the introduction of MAH.
⑸Biocompatibility of PLA-β-CD and PLA with osteoblasts obtained from newborn Wistar calvaria was preliminarily investigated by means of cell morphology and cell proliferation. The morphology of the cells was observed by phase contrast microscope and cell proliferation determined by MTT assay. The morphology observations revealed that the osteoblasts cultured on PLA-β-CD spread was wider than PLA and the cell density on PLA-β-CD was higher than PLA. Cell proliferation was determined by MTT assay at 2、4、6、8d, The results showed that proliferation power of osteoblasts cultured on PLA-β-CD notablely stronger than PLA. The results revealed the much better biocompatibility of PLA-β-CD with osteoblasts than that of PLA. Carbohydrate-protein interactions are the fundamentals of many cellular processes, such as signal ransduction, cell adhesion, proliferation, differentiation and immune response. Saccharide show an affinity for peptide and protein, while show an affinity for cells. Therefore, PLA-β-CD was a promising biomedical material and hopeful to gain potentially wide application in biomedical fields, especially in tissue engineering and drug delivery system.
⑴反应性聚乳酸的制备
①首先以乳酸为原料,通过镧钛复合氧化物催化乳酸制备丙交酯(LA),镧钛复合氧化物的引入使乳酸低聚物的裂解温度整体下降,丙交酯的纯度得到提高,经DSC测定,丙交酯的熔点为126.4℃,X射线光电子能谱分析结果表明,丙交酯没有受到放射性元素镧的污染。
②丙交酯在锌酸亚锡作用下开环聚合得到聚乳酸,用多角度激光光散射仪测定实验所得PLA的分子量和分子量分布分别为:Mw=22480;Mn=19548;PD=1.15。
③通过马来酸酐单体在过氧化二苯甲酰引发下与聚乳酸发生自由基反应,向缺乏反应基团的聚乳酸分子提供高反应活性的酸酐键。FTIR和1HNMR分析结果表明,马来酸酐成功引入到聚乳酸分子骨架上。并确定了较佳的反应条件是:反应物重量比PLA:MAH=10:1,BPO用量4wt%(相对于MAH用量),反应时间10h、反应温度95℃。罗丹明比色法测定结果表明,在此条件下制备的MPLA中马来酸酐的接枝率为2.45%,MALLS检测表明MPLA的分子量和分子量分布分别为Mw=20473,Mn=16510,PD=1.24。
⑵合成了6-单-乙二胺-β-CD(β-CD-6-E)单体
①FTIR、1H NMR和DSC-TGA的分析结果表明,通过将对甲基苯磺酰氯配成乙腈溶液在10℃下滴加到β-环糊精(β-CD)的NaOH溶液中,β-CD转变成了6-单-对甲基苯磺酰β-环糊精酯(β-CD-6-OTs)中间体,且产物在181.7℃开始分解,187℃有一个强分解峰。考察了反应条件对产率的影响,得到最佳的反应工艺条件为:TsCl:β-CD的摩尔比为1.5,TsCl的乙腈液在10度下缓慢滴加,反应温度23~25℃,反应时间2h,最终产物pH值调整至7~8,这时产物产率可达到14%。
②红外光谱、核磁共振波谱仪以及元素分析仪(EA)分析的结果表明,β-CD-6-OTs与过量乙二胺在75~80℃反应4h能得到6-单-乙二胺-β-CD环糊精。
⑶通过MPLA分子中的酸酐键和β-CD-6-E分子中的胺基之间发生N-酰化反应合成环糊精改性的聚乳酸材料(PLA-β-CD)。FTIR、1H NMR的分析结果表明,在几乎不改变聚乳酸材料主链结构的前提下,通过N-酰化反应,能将环糊精固载到MPLA的分子骨架中;DSC分析显示合成得到的PLA-β-CD的玻璃化转变峰值温度为59.8℃,表明采用本研究的分离提纯技术可得到纯净的聚乳酸固载环糊精(PLA-β-CD)聚合物。较佳反应工艺条件是:反应物投料比为nβ-CD-6-E:nMPLA=1.2:1,反应温度:35~40℃,反应时间:2小时,PLA-β-CD产率可达到55%。苯酚-硫酸法测定结果表明,在此条件下制备的聚合物中环糊精的含量为12.7%。
⑷考察了PLA和PLA-β-CD的理化性能,包括材料的亲/疏水性能和降解性能。其中,亲/疏水性能的评价指标是静态水接触角和吸水率,降解性能的评价采用体外降解试验。
①静态水接触角和吸水率的测定结果表明:PLA-β-CD改性材料的静态水接触角与聚乳酸相比,静态水接触角由76.7o降低到72.1o。吸水率由单一聚乳酸的18.3%提高到23.9%。说明PLA-β-CD材料比PLA有更好的亲水性;
②PLA-β-CD材料在蒸馏水中降解时pH值的变化结果在5周以前,体系的pH值在相同时间点比PLA略高,5周以后在整个降解期间的pH值略低于相同时间点PLA的pH值,且陡降时间比纯PLA略提前一周;
③PLA-β-CD在PBS中降解失重率的测定结果表明:材料在PBS介质中降解经历阶段与聚乳酸材料的失重率变化趋势趋于一致,但降解速率有所提高;表明本研究得到的PLA-β-CD改性材料在亲水性改善的同时,并没有出现马来酸酐的引入导致聚乳酸材料酸性增强的现象。
⑸采用细胞形态学观察法和细胞增殖法,初步考察了材料与大鼠成骨细胞的细胞相容性。通过对基底材料上细胞形态、早期粘附和铺展的比较研究,结果表明PLA-β-CD上细胞不仅形态上优于其他组,而且在数量上也有优势;通过MTT法测定了成骨细胞在材料上培养2、4、6、8天的增殖活力。实验结果表明,成骨细胞在PLA-β-CD的增殖活力明显大于PLA上的增殖活力。这说明由环糊精改性聚乳酸比PLA表现出更好的细胞相容性。糖-蛋白质相互作用是信号传导、细胞黏附、增殖、分化和免疫应答等很多细胞识别过程的基础,无论是单糖还是多糖都对多肽、蛋白质都有较好的亲和性,对细胞也具有较好的亲和性。根据以上实验结果,预期PLA-β-CD可在生物医学领域尤其是组织工程领域和药物缓释载体中得到广泛的应用。
Aiming to develop a biomaterial with excellent biocompability and biospecificy and physiological functions, in this thesis, D,L-lactide was prepared from D,L-lactic acid by adopting a new lanthanum-titanium composite oxides as the catalyst. First, poly(D,L-lactic acid) (PLA) was prepared from D,L-lactide with the use of Sn(Oct)2, and then, with a series of chemical reactions in the bulk, it was modified by introducingβ-cyclodextrin(β-CD) oligosaccharide into PDLLA backbone, at last, a novel PLA was acquired, which was based on fully biodegradable matrix materials modified by polysaccharides. To explore the structures and properties of the obtained polymers, characterizations included multi-angle laser light scattering (MALLS), fourier transform infrared spectrometry (FTIR), nuclear magnetic resonance spectrometer (NMR), differential scanning calorimeter (DSC) and some classical chemical analysis methods, and then, surface wettability, biodegradation and biocompatibility of the synthetic materials were investigated, too. The main works and conclusions are listed as below:
⑴Synthesis of reactable poly(D,L-lactic acid).
①With D,L-lactic acid as raw material and lanthanum-titanium composite oxides as catalyst, the D,L-lactide was synthesized. The catalyst of lanthanum-titanium composite oxides is high efficient in decreasing the dehydrate temperature, pyrolysis temperature and viscosity of the reacting system, consequently the oligomer of lactic acid was kept in the reactor instead of escaping with lactide, which prevents the contamination of lactide by oligomer. Glass transition temperature of the D,L-lactide tested by DSC was 126.4℃, and analysis of X-ray photoelectron spectroscopy (XPS) indicated that the lactide was found to be hardly contaminated by La-radioactivity.
②Poly(D,L-lactic acid) was synthesized by melt ring-opening polymerization of D,L-lactide with Sn(Oct)2 as catalyst. Molecular weight (Mw=22480, Mn=19548), and polydispersity (PD=1.15) of PLA were detected by MALLS.
③To introduce highly reactive anhydride into backbone of PLA lacking of reaction group, free radical copolymerization happened between PLA and maleic anhydride(MAH) with the help of benzoyl peroxide (BPO) as an initiator. It is demonstrated by FTIR and 1HNMR that the MAH had been imported in PLA backbone successfully, and the relative optimum reactive conditions of MPLA were obtained: weight ratio of PLA to MAH was 10:1, weight ratio of BPO to MAH was 0.04, and reaction time was 10h, reaction temperature was 95℃. The results of rhodamine-carboxyl interaction method showed that under such conditions, the MAH grafting ratio in MPLA was 2.45%. Molecular weight and polydispersity of MPLA were detected by MALLS about Mw=20473, Mn=16510 and PD=1.24, respectively.
⑵Preparation of mono(6-(2-aminoethyl)-amino-6-deoxy)-β-cyclodextrin。
①It was indicated by FTIR, 1HNMR and DSC-TGA analysis that mono-6-O-6- tosyl-β-cyclo-dextrin(β-CD-6-OTs) had been successfully prepared by dropping p-TsCl acetonitrile solution intoβ-CD NaOH solution under 10℃, and then the reaction mixture was heated up to 25°C and lasted for 2h. Decomposition temperature ofβ-CD-6-OTs determined by DSC-TGA was 181.7℃and a strong decomposition peak was 187℃. The effect of reaction conditions on the yield ratio ofβ-CD-6-OTs was investigated, and the optimum conditions were: molar ratio of p–TsCl toβ-CD was 1.5, reaction time was 2h, reaction temperature was 23~25℃, the mixture was adjusted with 20%-hydrochloric acid solution to ca. pH7~8, theβ-CD-6-OTs yield could reach to 14%.
②It was shown by FTIR, 1HNMR and EA analysis thatβ-CD-6-E had been successfully prepared by the reaction ofβ-CD-6-OTs and excess ethylenediamine at 75℃for 4h.
⑶It was exhibited by FTIR, 1H NMR and DSC analysis that, by N-acylation reaction,β-CD was able to be introduced into the backbone of MPLA(maleic anhydride modified poly(d,l-lactic acid)) and the main chain structure of MPLA was maintained. And the glass transition temperature of PLA-β-CD acquired was 59.8℃by DSC analysis, the unique Tg of PLA-β-CD indicated that the purification method was efficient enough to produce pure PLA-β-CD. The optimum conditions were: molar ratio ofβ-CD-6-E to MPLA was 1.2, reaction temperature was 35~40℃, reaction time was 2h, the yield of PLA-β-CD was found to be 55%. It was indicated by Phenol-sulfuric Acid method that the content ofβ-CD was 12.7% under the above conditions.
⑷The properties of various poly(D,L-lactic acid) based substrate films were investigated, including surface wettability and biodegradation. The surface wettability evaluation was based on static water contact angle and water adsorption ratio, while the degradation experimentation in vitro was used to estimate the bio degradation behavior.
①The tests indicated that the static water contact angle of copolymer PLA-β-CD was decreased appreciably from 76.7o to 72.1o comparing with PLA, while the water absorption ratio was increased from 18.3% to 23.9%. The results revealed that hydrophilicity of PLA-β-CD was better than PLA.
②In the whole degradation period of PLA-β-CD materials in distilled water, the change rule of the pH value was: At first, the pH value of PLA-β-CD is slightly higher than that of PLA within the first 5 weeks, and then, the former is a little lower than the latter in all other degradation period after that time, and the rapid drop time of PLA-β-CD advanced 1 week comparing with PLA.
③Tests indicated that: the degradation stages of material PLA-β-CD in medium PBS tended to be accordance with the weight loss change trend of PLA, but the degradation rate improved to some extent. It demonstrated that the hydrophilicity of PLA-β-CD acquired by this research was improved, while the acidity of PLA had not enhanced by the introduction of MAH.
⑸Biocompatibility of PLA-β-CD and PLA with osteoblasts obtained from newborn Wistar calvaria was preliminarily investigated by means of cell morphology and cell proliferation. The morphology of the cells was observed by phase contrast microscope and cell proliferation determined by MTT assay. The morphology observations revealed that the osteoblasts cultured on PLA-β-CD spread was wider than PLA and the cell density on PLA-β-CD was higher than PLA. Cell proliferation was determined by MTT assay at 2、4、6、8d, The results showed that proliferation power of osteoblasts cultured on PLA-β-CD notablely stronger than PLA. The results revealed the much better biocompatibility of PLA-β-CD with osteoblasts than that of PLA. Carbohydrate-protein interactions are the fundamentals of many cellular processes, such as signal ransduction, cell adhesion, proliferation, differentiation and immune response. Saccharide show an affinity for peptide and protein, while show an affinity for cells. Therefore, PLA-β-CD was a promising biomedical material and hopeful to gain potentially wide application in biomedical fields, especially in tissue engineering and drug delivery system.
引文
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