两亲无规药物聚合物合成及其靶向胶束组装研究
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摘要
聚合物-药物偶合物(以下简称药物聚合物)以及基于药物聚合物的胶束或纳米粒子具有优于传统小分子药物的可控缓释、靶向等很多优势,因此它们的合成和构筑已经成为一个热门的研究领域。论文发展了一种化学-酶促法制备药物聚合物的合成策略,并利用这些两亲无规药物聚合物的自组装构筑了一系列药物聚合物胶束型组装体,考察了它们的体外缓释行为和HepG2肝肿瘤细胞靶向能力。
论文发展了多官能团药物可聚合单体及光学活性药物可聚合单体的酶促选择性合成方法。以多官能团药物阿昔洛韦、利巴韦林、氮杂胞苷为底物,具有不同链长的脂肪二酸二乙烯酯为酰化试剂,分别利用有机介质中酶促高化学选择性和区域选择性酯交换反应,合成了一系列具有不同链长的药物可聚合单体；以外消旋酮洛芬药物为底物,醋酸乙烯酯为酰化试剂,化学法合成酮洛芬乙烯酯后对其进行酶促立体选择性水解拆分得到光学活性酮洛芬可聚合单体；考察了酶源、反应介质、溶剂含水量等因素对酶促反应的选择性和产率等的影响。
论文发展了一种酶促选择性合成与自由基聚合反应相结合制备药物聚合物的合成策略。利用酶促选择性酯交换反应得到的药物(阿昔洛韦、利巴韦林、氮杂胞苷)可聚合单体的自由基均聚反应制备了一系列高载药量的药物聚合物；利用这些药物可聚合单体与肝靶向糖(半乳糖、乳糖)可聚合单体的自由基共聚反应,制备了一系列具有潜在肝靶向的两亲无规药物聚合物；合成了两种具有不同聚乙二醇(PEG)分子量(PEG350、PEG1000)的甲基丙烯酸单甲氧基PEG酯可聚合单体,并利用其与光学活性酮洛芬可聚合单体的自由基共聚反应,制备了一系列具有不同酮洛芬含量、不同PEG链段长度的光学活性两亲无规药物聚合物。
论文实现了两亲无规药物聚合物水相中的自组装,并构筑了一系列药物聚合物胶束型组装体。利用合成的含利巴韦林和半乳糖及含利巴韦林和乳糖的两亲无规药物聚合物的自组装分别构筑了直径为208 nm和135 nm的药物聚合物胶束,并研究了这类两亲无规药物聚合物在水相中的自组装能力,考察了聚合物结构及组装条件对其自组装行为的影响；利用合成的含氮杂胞苷和半乳糖的两亲无规药物聚合物的自组装构筑了半径为250-500 nm,厚度约为16 nm的药物聚合物微圆盘结构,并考察了这种药物聚合物在水相中的自组装能力,探讨了其自组装机理；利用含酮洛芬和PEG链段的两亲无规药物聚合物的自组装构筑了一系列半径为70 nm-1.1μm尺寸可控的药物聚合物微纳米球,并考察了聚合物的结构包括酮洛芬的含量及PEG的链长对于组装体尺寸的影响。
论文考察了制备的一系列含糖药物聚合物或药物聚合物胶束的体外缓释行为和靶向能力。研究表明：这些小分子药物可以从药物聚合物或药物聚合物胶束中缓慢释放出来,其释放速率与培养介质的pH值、连接药物到聚合物主链中的连接臂的相对长度以及聚合物的组成结构等有关；含半乳糖或乳糖的药物聚合物或药物聚合物胶束均具有明显的HepG2肝癌细胞靶向性,可以通过半乳糖或乳糖介导的胞吞作用实现药物的细胞内在化。
Synthesis of polymer-drug conjugates and fabrication of conjugate-based micelles or nanoparticles have been an intense field of research, since these systems offer numerous advantages compared to conventional low-molecular-weight drugs including controlled drug release and improved targeting ability. In this thesis, a chemo-enzymatic synthetic strategy was employed to prepare polymer-drug conjugates. Moreover, the resulting amphiphilic random polymer-drug conjugates were successfully self-assembled to fabricate a series of micelle-type assemblies. Their in vitro release behaviors and targeting abilities to HepG2 liver carcinoma cell were further investigated.
The enzymatic selective synthesis of polymerizable drug monomers including multifunctional drug and optically active drug monomers was studied. Three multifunctional drugs including acyclovir, ribavirin and azacitidine were chosen as substrates, and divinyl dicarboxylates with different chain lengths were used as acylating agents. By enzymatic chemoselective or regioselective transesterification in organic medium, a series of polymerizable drug monomers with different chain lengths were prepared. Choosing racemic ketoprofen as substrate and vinyl acetate as acylating agent, optically active ketoprofen polymerizable monomer was obtained by enzymatic stereoselective hydrolysis resolution of ketoprofen vinyl ester prepared using chemical method. Moreover, such influence factors of enzymatic synthesis as enzyme sources, reaction media, water content and so on were investigated.
A strategy combining enzymatic selective synthesis with radical polymerization was developed to fabricate polymer-drug conjugates. Radical homopolymerization of the drug (acyclovir, ribavirin, azacitidine) polymerizable monomers prepared by enzymatic selective transesterification offered a series of polymer-drug conjugates with high drug content. By radical copolymerization of these drug polymerizable monomers with liver-targeting sugar (galactose, lactose) polymerizable monomers, a series of amphiphilic random polymer-drug conjugates with potential liver-targeting function were prepared. Besides sugar vinyl esters, two monomethoxyl PEG methylacrylate with different PEG molecular weight (PEG350, PEG1000) were synthesized and chosen as comonomers. A series of amphiphilic random polymer-drug conjugates with different ketoprofen contents and PEG chain lengths were obtained by copolymerization of optically active ketoprofen vinyl ester with the PEG comonomers.
Self-assembly of the resulting amphiphilic random polymer-drug conjugates in aqueous phase was successfully achieved to fabricate a series of conjugate-based micelle-type assemblies. Polymeric micelles with diameter of 208 nm or 135 nm were respectively prepared by self-assembly of the amphiphilic random polymer-ribavirn conjugates containing galactose or lactose. Assembly abilities of these conjugates were studied, and influence of conjugate structure and assembly conditions on their self-assembly behaviors was investigated. By self-assembly of the amphiphilic random polymer-azacitidine conjugate containing galactose, microdisk-type assemblies with radium from 250 nm to 500 nm and thickness of 16 nm were obtained. Assembly ability of the conjugate was investigated, and assembly mechanism was preliminary discussed. A series of size-controllable spheric micro- or nano-particles with radii from 70 nm to 1.1μm were fabricated by self-assembly of the amphiphilic random polymer-ketoprofen conjugates containing PEG, and influence of conjugate structure including ketoprofen content and PEG chain length on size of the assemblies was investigated.
In vitro release behaviors and targeting abilities of the polymer-drug conjugates or conjugate-based micelles containing sugar were studied. The results showed that the small molecular drugs could be slowed released, and the release rate was relative to the pH value of incubation medium, relative length of the linker binding drug to polymer main chain and conjugate composition. The polymer-drug conjugates and conjugate-based micelles containing glactose or lactose showed evident targeting function to HepG2 liver carcinoma cell, and cellar internalization of the drugs could be achieved by galactose- or lactose-mediated endocytosis process.
论文发展了多官能团药物可聚合单体及光学活性药物可聚合单体的酶促选择性合成方法。以多官能团药物阿昔洛韦、利巴韦林、氮杂胞苷为底物,具有不同链长的脂肪二酸二乙烯酯为酰化试剂,分别利用有机介质中酶促高化学选择性和区域选择性酯交换反应,合成了一系列具有不同链长的药物可聚合单体；以外消旋酮洛芬药物为底物,醋酸乙烯酯为酰化试剂,化学法合成酮洛芬乙烯酯后对其进行酶促立体选择性水解拆分得到光学活性酮洛芬可聚合单体；考察了酶源、反应介质、溶剂含水量等因素对酶促反应的选择性和产率等的影响。
论文发展了一种酶促选择性合成与自由基聚合反应相结合制备药物聚合物的合成策略。利用酶促选择性酯交换反应得到的药物(阿昔洛韦、利巴韦林、氮杂胞苷)可聚合单体的自由基均聚反应制备了一系列高载药量的药物聚合物；利用这些药物可聚合单体与肝靶向糖(半乳糖、乳糖)可聚合单体的自由基共聚反应,制备了一系列具有潜在肝靶向的两亲无规药物聚合物；合成了两种具有不同聚乙二醇(PEG)分子量(PEG350、PEG1000)的甲基丙烯酸单甲氧基PEG酯可聚合单体,并利用其与光学活性酮洛芬可聚合单体的自由基共聚反应,制备了一系列具有不同酮洛芬含量、不同PEG链段长度的光学活性两亲无规药物聚合物。
论文实现了两亲无规药物聚合物水相中的自组装,并构筑了一系列药物聚合物胶束型组装体。利用合成的含利巴韦林和半乳糖及含利巴韦林和乳糖的两亲无规药物聚合物的自组装分别构筑了直径为208 nm和135 nm的药物聚合物胶束,并研究了这类两亲无规药物聚合物在水相中的自组装能力,考察了聚合物结构及组装条件对其自组装行为的影响；利用合成的含氮杂胞苷和半乳糖的两亲无规药物聚合物的自组装构筑了半径为250-500 nm,厚度约为16 nm的药物聚合物微圆盘结构,并考察了这种药物聚合物在水相中的自组装能力,探讨了其自组装机理；利用含酮洛芬和PEG链段的两亲无规药物聚合物的自组装构筑了一系列半径为70 nm-1.1μm尺寸可控的药物聚合物微纳米球,并考察了聚合物的结构包括酮洛芬的含量及PEG的链长对于组装体尺寸的影响。
论文考察了制备的一系列含糖药物聚合物或药物聚合物胶束的体外缓释行为和靶向能力。研究表明：这些小分子药物可以从药物聚合物或药物聚合物胶束中缓慢释放出来,其释放速率与培养介质的pH值、连接药物到聚合物主链中的连接臂的相对长度以及聚合物的组成结构等有关；含半乳糖或乳糖的药物聚合物或药物聚合物胶束均具有明显的HepG2肝癌细胞靶向性,可以通过半乳糖或乳糖介导的胞吞作用实现药物的细胞内在化。
Synthesis of polymer-drug conjugates and fabrication of conjugate-based micelles or nanoparticles have been an intense field of research, since these systems offer numerous advantages compared to conventional low-molecular-weight drugs including controlled drug release and improved targeting ability. In this thesis, a chemo-enzymatic synthetic strategy was employed to prepare polymer-drug conjugates. Moreover, the resulting amphiphilic random polymer-drug conjugates were successfully self-assembled to fabricate a series of micelle-type assemblies. Their in vitro release behaviors and targeting abilities to HepG2 liver carcinoma cell were further investigated.
The enzymatic selective synthesis of polymerizable drug monomers including multifunctional drug and optically active drug monomers was studied. Three multifunctional drugs including acyclovir, ribavirin and azacitidine were chosen as substrates, and divinyl dicarboxylates with different chain lengths were used as acylating agents. By enzymatic chemoselective or regioselective transesterification in organic medium, a series of polymerizable drug monomers with different chain lengths were prepared. Choosing racemic ketoprofen as substrate and vinyl acetate as acylating agent, optically active ketoprofen polymerizable monomer was obtained by enzymatic stereoselective hydrolysis resolution of ketoprofen vinyl ester prepared using chemical method. Moreover, such influence factors of enzymatic synthesis as enzyme sources, reaction media, water content and so on were investigated.
A strategy combining enzymatic selective synthesis with radical polymerization was developed to fabricate polymer-drug conjugates. Radical homopolymerization of the drug (acyclovir, ribavirin, azacitidine) polymerizable monomers prepared by enzymatic selective transesterification offered a series of polymer-drug conjugates with high drug content. By radical copolymerization of these drug polymerizable monomers with liver-targeting sugar (galactose, lactose) polymerizable monomers, a series of amphiphilic random polymer-drug conjugates with potential liver-targeting function were prepared. Besides sugar vinyl esters, two monomethoxyl PEG methylacrylate with different PEG molecular weight (PEG350, PEG1000) were synthesized and chosen as comonomers. A series of amphiphilic random polymer-drug conjugates with different ketoprofen contents and PEG chain lengths were obtained by copolymerization of optically active ketoprofen vinyl ester with the PEG comonomers.
Self-assembly of the resulting amphiphilic random polymer-drug conjugates in aqueous phase was successfully achieved to fabricate a series of conjugate-based micelle-type assemblies. Polymeric micelles with diameter of 208 nm or 135 nm were respectively prepared by self-assembly of the amphiphilic random polymer-ribavirn conjugates containing galactose or lactose. Assembly abilities of these conjugates were studied, and influence of conjugate structure and assembly conditions on their self-assembly behaviors was investigated. By self-assembly of the amphiphilic random polymer-azacitidine conjugate containing galactose, microdisk-type assemblies with radium from 250 nm to 500 nm and thickness of 16 nm were obtained. Assembly ability of the conjugate was investigated, and assembly mechanism was preliminary discussed. A series of size-controllable spheric micro- or nano-particles with radii from 70 nm to 1.1μm were fabricated by self-assembly of the amphiphilic random polymer-ketoprofen conjugates containing PEG, and influence of conjugate structure including ketoprofen content and PEG chain length on size of the assemblies was investigated.
In vitro release behaviors and targeting abilities of the polymer-drug conjugates or conjugate-based micelles containing sugar were studied. The results showed that the small molecular drugs could be slowed released, and the release rate was relative to the pH value of incubation medium, relative length of the linker binding drug to polymer main chain and conjugate composition. The polymer-drug conjugates and conjugate-based micelles containing glactose or lactose showed evident targeting function to HepG2 liver carcinoma cell, and cellar internalization of the drugs could be achieved by galactose- or lactose-mediated endocytosis process.
引文
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