羧酸甜菜碱聚合物的药物载体和医用植入体材料研究
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摘要
蛋白质在表面的非特异性吸附是纳米药物载体和医用植入体材料所面临的一个重要问题。目前,能够在复杂生物环境中有效抵抗非特异性蛋白质吸附,并能在诸如药物载体、医用植入体等领域中实际应用的材料十分有限。近年来,聚两性离子材料已被证实具有优良的抗非特异性蛋白质吸附性能和生物相容性,如聚甲基丙烯酰氧基乙基磷酰胆碱(PMPC)、聚磺基甜菜碱甲基丙烯酸酯(PSBMA)和聚羧基甜菜碱甲基丙烯酸酯(PCBMA),这与其强烈的水合能力和优秀的仿生结构密不可分。因此,这些两性离子材料的生物医学应用成为研究热点之一。本论文围绕聚两性离子材料的优秀特性,考察了羧酸甜菜碱聚合物在复杂环境中的相容性,探索了可逆交联的羧酸甜菜碱聚合物胶束的血液稳定性,评估了靶向基团修饰的聚己内酯-b-聚羧基甜菜碱交联胶束在乳腺癌治疗中的疗效,并研究了羧酸甜菜碱酯在新型生物相容性硅橡胶中的应用。主要内容和结论包括以下四部分：
1、以β-CD为引发剂,利用原子转移自由基聚合(ATRP)制备了四种不同分子量的星状羧酸甜菜碱聚合物。体外实验表明,这类聚合物被巨噬细胞RAW264.7内吞不明显。体内循环实验发现,分子量为123KDa的星状聚合物在小鼠血液中的循环半衰期可延长至40小时。在多次尾静脉注射两性离子星状聚合物后,仍保持与首次相似的衰减过程,并且未发现主要组织器官有明显损伤或炎症,以及血液中抗体的增加。由此证明了羧酸甜菜碱聚合物具有细胞内吞慢、无免疫原性和长循环等性能,有望成为PEG的替代物。
2、研究了一种通过共聚物自组装得到的胶束,该共聚物以羧酸甜菜碱甲基丙烯酸酯(CBMA)作为亲水性单元,硫辛酸甲基丙烯酸羟乙酯(MAEL)作为疏水性和交联单元。该胶束可以很容易地包载抗肿瘤药物阿霉素(DOX),并可在模拟细胞内还原环境下快速释放DOX。这种可逆交联的生物相容的两性离子胶束具有在纤维蛋白原(1mg/mL)和50%胎牛血清(FBS)中优异的稳定性和细胞内环境下加速释放药物的优点。
3、研究了含交联基团的聚己内酯-b-聚羧基甜菜碱的阿霉素胶束载体,并在其表面修饰靶向基团精氨酸-甘氨酸-天冬氨酸-酪氨酸-赖氨酸环肽c(RGDyK),从而使其能主动靶向作用于肿瘤细胞。本交联载药胶束可延长阿霉素在血液中的循环时间,并在c(RGDyK)靶向识别引导下,增强了阿霉素的抗肿瘤效果,同时降低了由阿霉素引起的心肌和生物毒性。这些结果说明,经c(RGDyK)修饰的两性离子交联胶束是一种很有前途的药物载体。
4、利用光聚合技术制备了一种由羧基甜菜碱酯衍生物、3-甲基丙烯氧基丙基三(三甲基硅氧烷基)硅烷(TRIS)和有机硅大分子单体双-αω-(甲基丙烯酰氧基丙基)聚二甲基硅氧烷组成的新型硅橡胶。该材料可通过两性离子前体羧基甜菜碱酯衍生物的表面水解得到高亲水性两性离子材料覆盖的硅橡胶材料,并表现出优异的抗非特异性蛋白质吸附和细菌粘附能力。也因为疏水基体的保护使酯水解速率缓慢而可控,极大提高了材料抗非特异性蛋白质吸附性能的长效性。这种表面水解方式使该材料能够避免水中的溶胀,水解前后能保持一致的光学和机械性能。因此,这种长效抗非特异性蛋白质吸附材料在隐形眼镜和其他医疗设备等领域具有良好的应用前景。
The non-specific protein adsorption on surfaces is a challenging problem faced by nano drug carriers and medical implantable materials. At present, there are few materials that can effectively resist non-specific protein adsorption from complex media for practical applications, such as drug carriers and medical implants. Polyzwitterionic materials such as poly(2-methacryloyloxyethyl phosphorylcholine)(PMPC), poly(sulfobetaine methacylate)(PSBMA) and poly(carboxybetaine methacylate)(PCBMA) are believed as ideal candidate materials for those applications in recent years due to their excellent nonfouling and biocompatibility properties. Both excellent properties mainly originated from the high levels of hydration and biomimetic-like structures, respectively. In this dissertation, we systematically investigated the in vivo compatibility of carboxybetaine polymer, the blood stability of reversible cross-linked carboxybetaine polymer micelles, and the cancer therapeutic efficacy of targeted cross-linked micelles of doxorubicin-encapsulated polycaprolactone-b-polycarboxybetaine. In addition, we developed a new biocompatible silicone baesd on a carboxybetaine ester analogue. The main contents and conclusions of this dissertation include the following four parts:
1. Four star carboxybetaine polymers with different molecular weights via atom transfer radical polymerization (ATRP) from a β-CD initiator were prepared for investigating the in vivo compatibility of carboxybetaine polymer. Results show that the internalization of macrophage cell RAW264.7in vitro is dramatically reduced. The circulation half-life of the largest star polymer (123KDa) in mice is prolonged to40hours. Furthermore, the circulation time of repeated injections shows similar results to the first injection; no appreciable damage or inflammation was observed in major organ tissues, and no obvious increase of antibody occured in blood. These results suggest that the CBMA coatings for nanoparticles have advantages such as reducing cellular uptake, no immune response and long circulation time, which might be a good alternative of PEG.
2. The cross-linked micelles based on a copolymer composed of carboxybetaine methacrylate (CBMA) as hydrophilic and nonfouling segment,2-(methacryloyloxy)ethyl lipoate (MAEL) as hydrophobic and cross-linked segment were prepared for investigating the blood stability of the micelles with CBMA protection layer. The micelles can easily encapsulate the anticancer drug doxorubicin (DOX), and quickly release DOX in response to an intracellular reductive environment. With the advantages in excellent stability in fibrinogen (1mg/mL) PBS solution and50%fetal bovine serum (FBS), and accelerated intracellular drug release, the biocompatible zwitterionic micelle stabilized by reversible cross-linkage is a promising drug carrier candidate.
3. It has been demonstrated that the active targeting of doxorubicin-encapsulated polycaprolactone-b-polycarboxybetaine cross-linked micelles to the integrin on cancer cells can be realized by the conjugation of cyclic pentapeptide c(RGDyK) on CBMA shell. The doxorubicin encapsulated cross-linked micelles show a prolonged circulation time in plasma in respect of the modification of c(RGDyK). Under the guide of c(RGDyK), the antitumor effeciveness of doxorubicin was enhanced, while the cardiac toxicity and biotoxicity of doxorubicin reduced. These results indicate that the c(RGDyK)-modified zwitterionic cross-linked micelle is a promising drug carrier.
4. A new biocompatible silicone comprising a carboxybetaine (CB) ester analogue,3-methacryloxypropyltris-(trimethylsiloxy)silane (TRIS) and an organic silicone macromer bis-a,co-(methacryloxypropyl) polydimethylsiloxane using photo-polymerisation was developed. Following interfacial hydrolysis of the CB ester, the resulting zwitterionic material coated silicone became significantly more hydrophilic and exhibited high resistance to both non-specific protein adsorption and bacterial adhesion. Moreover, the stability of these nonfouling properties was dramatically improved by using a slow and controlled rate of ester hydrolysis of the original protective hydrophobic matrix. Meanwhile, the original optical and mechanical properties of the bare silicone remained unchanged after surface activation. These results indicate that this material is an ideal candidate for preparing contact lenses and other medical devices.
1、以β-CD为引发剂,利用原子转移自由基聚合(ATRP)制备了四种不同分子量的星状羧酸甜菜碱聚合物。体外实验表明,这类聚合物被巨噬细胞RAW264.7内吞不明显。体内循环实验发现,分子量为123KDa的星状聚合物在小鼠血液中的循环半衰期可延长至40小时。在多次尾静脉注射两性离子星状聚合物后,仍保持与首次相似的衰减过程,并且未发现主要组织器官有明显损伤或炎症,以及血液中抗体的增加。由此证明了羧酸甜菜碱聚合物具有细胞内吞慢、无免疫原性和长循环等性能,有望成为PEG的替代物。
2、研究了一种通过共聚物自组装得到的胶束,该共聚物以羧酸甜菜碱甲基丙烯酸酯(CBMA)作为亲水性单元,硫辛酸甲基丙烯酸羟乙酯(MAEL)作为疏水性和交联单元。该胶束可以很容易地包载抗肿瘤药物阿霉素(DOX),并可在模拟细胞内还原环境下快速释放DOX。这种可逆交联的生物相容的两性离子胶束具有在纤维蛋白原(1mg/mL)和50%胎牛血清(FBS)中优异的稳定性和细胞内环境下加速释放药物的优点。
3、研究了含交联基团的聚己内酯-b-聚羧基甜菜碱的阿霉素胶束载体,并在其表面修饰靶向基团精氨酸-甘氨酸-天冬氨酸-酪氨酸-赖氨酸环肽c(RGDyK),从而使其能主动靶向作用于肿瘤细胞。本交联载药胶束可延长阿霉素在血液中的循环时间,并在c(RGDyK)靶向识别引导下,增强了阿霉素的抗肿瘤效果,同时降低了由阿霉素引起的心肌和生物毒性。这些结果说明,经c(RGDyK)修饰的两性离子交联胶束是一种很有前途的药物载体。
4、利用光聚合技术制备了一种由羧基甜菜碱酯衍生物、3-甲基丙烯氧基丙基三(三甲基硅氧烷基)硅烷(TRIS)和有机硅大分子单体双-αω-(甲基丙烯酰氧基丙基)聚二甲基硅氧烷组成的新型硅橡胶。该材料可通过两性离子前体羧基甜菜碱酯衍生物的表面水解得到高亲水性两性离子材料覆盖的硅橡胶材料,并表现出优异的抗非特异性蛋白质吸附和细菌粘附能力。也因为疏水基体的保护使酯水解速率缓慢而可控,极大提高了材料抗非特异性蛋白质吸附性能的长效性。这种表面水解方式使该材料能够避免水中的溶胀,水解前后能保持一致的光学和机械性能。因此,这种长效抗非特异性蛋白质吸附材料在隐形眼镜和其他医疗设备等领域具有良好的应用前景。
The non-specific protein adsorption on surfaces is a challenging problem faced by nano drug carriers and medical implantable materials. At present, there are few materials that can effectively resist non-specific protein adsorption from complex media for practical applications, such as drug carriers and medical implants. Polyzwitterionic materials such as poly(2-methacryloyloxyethyl phosphorylcholine)(PMPC), poly(sulfobetaine methacylate)(PSBMA) and poly(carboxybetaine methacylate)(PCBMA) are believed as ideal candidate materials for those applications in recent years due to their excellent nonfouling and biocompatibility properties. Both excellent properties mainly originated from the high levels of hydration and biomimetic-like structures, respectively. In this dissertation, we systematically investigated the in vivo compatibility of carboxybetaine polymer, the blood stability of reversible cross-linked carboxybetaine polymer micelles, and the cancer therapeutic efficacy of targeted cross-linked micelles of doxorubicin-encapsulated polycaprolactone-b-polycarboxybetaine. In addition, we developed a new biocompatible silicone baesd on a carboxybetaine ester analogue. The main contents and conclusions of this dissertation include the following four parts:
1. Four star carboxybetaine polymers with different molecular weights via atom transfer radical polymerization (ATRP) from a β-CD initiator were prepared for investigating the in vivo compatibility of carboxybetaine polymer. Results show that the internalization of macrophage cell RAW264.7in vitro is dramatically reduced. The circulation half-life of the largest star polymer (123KDa) in mice is prolonged to40hours. Furthermore, the circulation time of repeated injections shows similar results to the first injection; no appreciable damage or inflammation was observed in major organ tissues, and no obvious increase of antibody occured in blood. These results suggest that the CBMA coatings for nanoparticles have advantages such as reducing cellular uptake, no immune response and long circulation time, which might be a good alternative of PEG.
2. The cross-linked micelles based on a copolymer composed of carboxybetaine methacrylate (CBMA) as hydrophilic and nonfouling segment,2-(methacryloyloxy)ethyl lipoate (MAEL) as hydrophobic and cross-linked segment were prepared for investigating the blood stability of the micelles with CBMA protection layer. The micelles can easily encapsulate the anticancer drug doxorubicin (DOX), and quickly release DOX in response to an intracellular reductive environment. With the advantages in excellent stability in fibrinogen (1mg/mL) PBS solution and50%fetal bovine serum (FBS), and accelerated intracellular drug release, the biocompatible zwitterionic micelle stabilized by reversible cross-linkage is a promising drug carrier candidate.
3. It has been demonstrated that the active targeting of doxorubicin-encapsulated polycaprolactone-b-polycarboxybetaine cross-linked micelles to the integrin on cancer cells can be realized by the conjugation of cyclic pentapeptide c(RGDyK) on CBMA shell. The doxorubicin encapsulated cross-linked micelles show a prolonged circulation time in plasma in respect of the modification of c(RGDyK). Under the guide of c(RGDyK), the antitumor effeciveness of doxorubicin was enhanced, while the cardiac toxicity and biotoxicity of doxorubicin reduced. These results indicate that the c(RGDyK)-modified zwitterionic cross-linked micelle is a promising drug carrier.
4. A new biocompatible silicone comprising a carboxybetaine (CB) ester analogue,3-methacryloxypropyltris-(trimethylsiloxy)silane (TRIS) and an organic silicone macromer bis-a,co-(methacryloxypropyl) polydimethylsiloxane using photo-polymerisation was developed. Following interfacial hydrolysis of the CB ester, the resulting zwitterionic material coated silicone became significantly more hydrophilic and exhibited high resistance to both non-specific protein adsorption and bacterial adhesion. Moreover, the stability of these nonfouling properties was dramatically improved by using a slow and controlled rate of ester hydrolysis of the original protective hydrophobic matrix. Meanwhile, the original optical and mechanical properties of the bare silicone remained unchanged after surface activation. These results indicate that this material is an ideal candidate for preparing contact lenses and other medical devices.
引文
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