烟酸衍生智能高分子的合成及其在药物控制释放中的应用
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摘要
高分子前药因其低毒、高效、缓释、长效等特点在现代医药发展中占据着越来越重要的地位。近些年来,pH响应智能高分子因为其便利的响应条件和潜在的应用价值而倍受研究者的关注。由于生物体特殊的体内酸碱环境,使得pH响应智能高分子在生物医药方面拥有广阔的应用前景。因此合成与研究具有pH响应行为的高分子前药载体具有极大的学术价值与应用前景。
本文以烟酸和甲基丙烯酸羟乙酯(HEMA)为原料合成烟酸衍生的甲基丙烯酰氧基乙基-3-吡啶甲酸酯(MAEPF)单体并对其进行表征。综合本课题组前期研究成果,采用CPFDB为链转移剂、TPO为光引发剂,研究MAEPF在柔和的可见光活化下的室温RAFT聚合规律,包括反应动力学行为和可控性特征。研究发现,在该条件下MAEPF单体聚合反应具有良好的活性和可控性。而且,提高单体的起始投料比,可显著提高聚合反应速率,并明显缩短聚合反应初期的引发期,这些效应对合成结构精确的高分子量的PMAEPF聚合物提供了极大的便利。在此基础上,本文以聚甲基丙烯酰氧基乙基-3-吡啶甲酸酯为大分子链转移剂,在柔和的可见光活化下通过室温RAFT共聚合反应,合成了多种不同结构且分子量分布较窄的嵌段共聚物。这些嵌段共聚物的精确合成为构筑具有特殊结构和性质(如两亲性、生物活性等)的烟酸衍生高分子药物载体提供了方法与前体。
本文还研究了不同聚合度的PMAEPF均聚物及其与小分子模型药物双嘧达莫(DIP)混合物的玻璃化转变温度。结果表明,在聚合度为24~81之间时PMAEPF均聚物的Tg在50oC左右。DIP的加入,显著降低PMAEPF的玻璃化转变温度。不同聚合度和嵌段长度比的PMAEPF-b-PPEGMA胶束化行为研究结果表明,亲疏水链长比直接影响胶束的稳定。在稳定的胶束中,因为胶束核为硬塑体,即使降低水溶液pH,胶束尺寸也不发生变化。以PMAEPF80-b-PPEGMA10胶束为载体,包覆小分子药物DIP,载药胶束在中性条件下其疏水胶束核的Tg在室温附近,有利于DIP向溶液中扩散。在偏酸性条件下,由于PMAEPF嵌段吡啶基团和DIP的季铵化,强化了两者的水合能力,驱动胶束核中的DIP向水溶液扩散,其释放速率明显快于中性条件。
Polymeric prodrugs are polymers that drugs are covalently bound to polymers. Because of low toxicity, high efficiency and controlled drug release, they become more and more important in biomedical field. In recent years, pH-responsive polymers have been extensively investigated. As a particular type of smart materials, they exhibited extensively potential applications. Clearly, developing a new type of pH-responsive polymeric prodrug is desirable from academic and industrial standpoints.
In this paper, a nicotinic-acid-based monomer, methacryloyloxylethyl 3-pyridylformate (MAEPF) was synthesized and characterized. A range of well-defined PMAEPF polymers were synthesized via highly efficient and well controlled 2-cyanoprop-2-yl(4-fluoro) dithiobenzoate or CPFDB-mediated RAFT polymerization of MAEPF monomer under an environmentally friendly visible light radiation at 30 oC, using (2,4,6-trimethylbenzoyl) diphenylphosphine oxide (TPO) as a photo-initiator. Kinetic studies indicated that this RAFT polymerization was well-controlled. A relatively low concentration of chain transfer agent (CTA) led to both effects of shortening initialization period of this RAFT process and accelerating the overall polymerization rate. Moreover, a variety of well-defined PMAEPF-based block copolymers with poly[poly(ethylene glycol) monomethacrylate] (PPEGMA) blocks, poly(N, N-dimethylaminoethyl methacrylate) (PDMAEMA) blocks and poly(glycidyl methacrylate) (PGMA) blocks were synthesized via ambient temperature RAFT polymerization under this mild visible light radiation at 30 oC, using above-synthesized PMAEPF polymers as macro-CTA.
The effect of molecular weights of PMAEPF and dipyridamole contents (DIP) on the glass transition temperature (Tg) of these polymers and blends were investigated. The results indicated that Tg of PMAEPF polymers were around 50 oC. On addition of DIP, the glass transition temperature of their blends was dramatically lowered to around room temperature. The molecular weight and structural unit ratio of PMAEPF to PPEGMA significantly affected the micellization of PMAEPF-b-PPEGMA copolymer in aqueous solution. The solution pH had negligible influence on the PMAEPF-b-PPEGMA copolymer micelles, due to the glass state of PMAEPF micellar cores at ambient temperature. However, blending DIP in PMAEPF micellar cores led to the dramatic decrease of Tg, thus facilitated the polymer chain diffusion between micelles, which caused narrow-size-distributed micelles. The drug release was remarkably accelerated on quarternization of pyridine groups and DIP in acidic solutions.
本文以烟酸和甲基丙烯酸羟乙酯(HEMA)为原料合成烟酸衍生的甲基丙烯酰氧基乙基-3-吡啶甲酸酯(MAEPF)单体并对其进行表征。综合本课题组前期研究成果,采用CPFDB为链转移剂、TPO为光引发剂,研究MAEPF在柔和的可见光活化下的室温RAFT聚合规律,包括反应动力学行为和可控性特征。研究发现,在该条件下MAEPF单体聚合反应具有良好的活性和可控性。而且,提高单体的起始投料比,可显著提高聚合反应速率,并明显缩短聚合反应初期的引发期,这些效应对合成结构精确的高分子量的PMAEPF聚合物提供了极大的便利。在此基础上,本文以聚甲基丙烯酰氧基乙基-3-吡啶甲酸酯为大分子链转移剂,在柔和的可见光活化下通过室温RAFT共聚合反应,合成了多种不同结构且分子量分布较窄的嵌段共聚物。这些嵌段共聚物的精确合成为构筑具有特殊结构和性质(如两亲性、生物活性等)的烟酸衍生高分子药物载体提供了方法与前体。
本文还研究了不同聚合度的PMAEPF均聚物及其与小分子模型药物双嘧达莫(DIP)混合物的玻璃化转变温度。结果表明,在聚合度为24~81之间时PMAEPF均聚物的Tg在50oC左右。DIP的加入,显著降低PMAEPF的玻璃化转变温度。不同聚合度和嵌段长度比的PMAEPF-b-PPEGMA胶束化行为研究结果表明,亲疏水链长比直接影响胶束的稳定。在稳定的胶束中,因为胶束核为硬塑体,即使降低水溶液pH,胶束尺寸也不发生变化。以PMAEPF80-b-PPEGMA10胶束为载体,包覆小分子药物DIP,载药胶束在中性条件下其疏水胶束核的Tg在室温附近,有利于DIP向溶液中扩散。在偏酸性条件下,由于PMAEPF嵌段吡啶基团和DIP的季铵化,强化了两者的水合能力,驱动胶束核中的DIP向水溶液扩散,其释放速率明显快于中性条件。
Polymeric prodrugs are polymers that drugs are covalently bound to polymers. Because of low toxicity, high efficiency and controlled drug release, they become more and more important in biomedical field. In recent years, pH-responsive polymers have been extensively investigated. As a particular type of smart materials, they exhibited extensively potential applications. Clearly, developing a new type of pH-responsive polymeric prodrug is desirable from academic and industrial standpoints.
In this paper, a nicotinic-acid-based monomer, methacryloyloxylethyl 3-pyridylformate (MAEPF) was synthesized and characterized. A range of well-defined PMAEPF polymers were synthesized via highly efficient and well controlled 2-cyanoprop-2-yl(4-fluoro) dithiobenzoate or CPFDB-mediated RAFT polymerization of MAEPF monomer under an environmentally friendly visible light radiation at 30 oC, using (2,4,6-trimethylbenzoyl) diphenylphosphine oxide (TPO) as a photo-initiator. Kinetic studies indicated that this RAFT polymerization was well-controlled. A relatively low concentration of chain transfer agent (CTA) led to both effects of shortening initialization period of this RAFT process and accelerating the overall polymerization rate. Moreover, a variety of well-defined PMAEPF-based block copolymers with poly[poly(ethylene glycol) monomethacrylate] (PPEGMA) blocks, poly(N, N-dimethylaminoethyl methacrylate) (PDMAEMA) blocks and poly(glycidyl methacrylate) (PGMA) blocks were synthesized via ambient temperature RAFT polymerization under this mild visible light radiation at 30 oC, using above-synthesized PMAEPF polymers as macro-CTA.
The effect of molecular weights of PMAEPF and dipyridamole contents (DIP) on the glass transition temperature (Tg) of these polymers and blends were investigated. The results indicated that Tg of PMAEPF polymers were around 50 oC. On addition of DIP, the glass transition temperature of their blends was dramatically lowered to around room temperature. The molecular weight and structural unit ratio of PMAEPF to PPEGMA significantly affected the micellization of PMAEPF-b-PPEGMA copolymer in aqueous solution. The solution pH had negligible influence on the PMAEPF-b-PPEGMA copolymer micelles, due to the glass state of PMAEPF micellar cores at ambient temperature. However, blending DIP in PMAEPF micellar cores led to the dramatic decrease of Tg, thus facilitated the polymer chain diffusion between micelles, which caused narrow-size-distributed micelles. The drug release was remarkably accelerated on quarternization of pyridine groups and DIP in acidic solutions.
引文
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