基于嵌段共聚物的纳米荧光探针的制备及生物成像性能研究
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摘要
近年来,嵌段共聚物超分子自组装形成的纳米微观结构引起了广泛的关注。其中,具有球形形貌的两亲性嵌段共聚物胶束的粒子尺寸在几十到几百纳米之间,其特殊的纳米尺寸效应和稳定性被广泛地应用在化学、催化、光电学、生物医药等众多领域。
本论文从两亲性嵌段共聚物聚苯乙烯-b-聚丙烯酸(PS-b-PAA)的球形纳米胶束出发,利用有机硅烷偶联剂((3-巯基丙基)三甲氧基硅烷以及3-氨丙基三甲氧基硅氧烷)的水解缩聚性能,对多种具有不同分子结构的疏水性荧光有机小分子进行包裹,合成了一系列具有良好水溶性的硅交联外壳的纳米荧光复合颗粒；将具有靶向功能的生物活性分子对其表面进行修饰,构建出一类新型的纳米荧光成像材料,并在细胞水平上研究了该类材料的细胞成像能力。
1)利用两亲性嵌段共聚物PS-b-PAA疏水自组装原理,将疏水的萘酰亚胺绿色荧光分子(DPN)包裹进胶束核内,结合溶胶凝胶工艺制备出一类具有表面巯基功能化的硅交联外壳的纳米荧光复合颗粒(DPN@NHs)。该纳米复合颗粒的平均尺寸控制在50nm左右,尺寸分布狭窄,在水溶液中高度稳定分散。硅交联壳层不但没有影响胶束的发光效果,而且大大提高了复合颗粒的分散稳定性,荧光分子包埋量大且不易泄漏及良好的物理和化学稳定性。研究了荧光分子包裹量对纳米颗粒形貌及荧光特性的影响；荧光成像实验中材料对MCF-7细胞具有良好的荧光标识信号。
2)荧光分子不仅可以引入到纳米胶束的疏水内核,同时还可以引入富硅壳层的骨架中。本文利用氨基硅烷偶联剂的自缩聚作用以及在氨催化下与荧光分子(4-哌啶-1,8萘酐)间的键合作用,一步法制备出一类具有表面氨基功能化的绿色荧光硅交联外壳的纳米复合粒子NAPI-NHx-NPS。通过改变硅烷的交联量,不仅可以有效地对纳米复合粒子的粒径尺寸进行调控,而且能够有效提高荧光分子的荧光效率和荧光寿命。通过TEM及DLS的表征表明,该纳米复合粒子的平均尺寸可控制在50-80nm以内,具有尺寸分布狭窄,在水溶液中高度稳定分散的优良特性。与纯染料相比,在水溶液中其荧光效率可提高约25倍,并维持较长的荧光寿命。这一类荧光复合粒子在体外生物实验中无明显细胞毒性,激光共聚焦显微镜的观测表明,该材料在短时间内可以被细胞大量吞噬。此外,利用胶束内部特殊的空腔结构,还可以将疏水性的磁性四氧化三铁粒子包裹在NAPI-NHx-NPs的胶束疏水核内部,形成了一类具有磁性、荧光多功能的纳米粒子。
3)利用嵌段共聚物的球形胶束和荧光分子本身的识别或响应能力,合成出一类具有环境响应/识别能力的智能荧光纳米探针NDI@HNPs。通过对pH响应型荧光探针分子NDI的原位包埋,制备出一类具有薄交联壳层的小尺寸荧光纳米探针。所合成的纳米探针具有良好的球形形貌和均一的粒径(46nm),并保持对环境pH响应的能力,在pH值为4到6之间具有极高的响应灵敏度,响应时间短(5s),具有很好的抗疲劳能力。进一步的细胞成像实验表明,该材料可以被癌细胞MCF-7大量吞噬,并且成功地标记出细胞内酸性环境的分布区域。同时,首次利用流式细胞术对该材料的分时段pH响应信号进行了定量测试。
4)在前面工作的基础上,制备了一系列具有近红外发射波长的纳米荧光探针。所选用的三个近红外荧光有机分子均可被包裹在嵌段共聚物胶束的疏水核内部,从而成功地由憎水转变为亲水。该类近红外纳米荧光探针的动力学直径在35nm左右。光物理性能测试表明,三种纳米荧光探针在水溶液中的荧光效率较纯的荧光分子都有显著的提高,光漂泊性大幅降低,并且斯托克斯位移也有明显的增大。通过在荧光纳米探针表面嫁接具有靶向识别效果的靶向分子—叶酸或乳糖酸,合成了具有特定细胞靶向识别能力的近红外纳米探针。在体外细胞毒性的评估中,三种探针均未显示出明显的细胞毒性。在较短的时间内,这种功能化的纳米探针可以对特定的细胞有靶向识别效果。
综上,本文发展出了一种具有通用性和较强操作性的制备可用于生物化学研究以及癌症追踪诊断的高效新型成像剂的新方法。这种方法不仅是对传统纳米材料的拓展,而且对进一步的生物研究和医疗研究也有良好的推进作用。
In recent years, the synthesis and application of amphiphilic block copolymer supramolecular self-assembled nano-microstructure have attracted extensive attention. These block copolymer micelles are featured with spherical morphology of tens to hundreds of nanometers in particle diameter, various special nano-size effect and stability, and are therefore being widely used in chemical catalysis, optical, biological medicine and many other fields. In this thesis, we focused on following four aspects:
1) We employed the spherical micelles of amphiphilic block copolymer (PS-b-PAA) as a template to prepare a new kind of core-shell structured fluorescent nanospheres (DPN@NHs). The hydrophobic dyes were encapsulated into the core of the hybrid nanospheres based on the self-assembly of amphiphilic block copolymers followed by shell cross-linking using3-mercaptopropyltrimethoxy-silane (MPTMS) as a cross-linking agent. The as-synthesized DPN@NHs were very uniform in size (50nm) and spherical morphology, and could be highly monodispersed in water. The fluorescent performances of the as-synthesized water-soluble DPN@NHs were greatly enhanced. The nanospheres exhibited no cytotoxicity and negligible cell apoptosis. By co-cultivating with MCF-7cells, DPN@NHs showed the successful cell uptake in cytoplasm regions in a large quantity.
2) An organic-inorganic fluorescent nanohybrids with extraordinarily enhanced fluorescent performance was synthesized based on the self-assembly of amphiphilic block copolymers. The thiol-functional group and a fluorescent dye,4-piperidyl-l,8-naphthalic anhydride, could be introduced into the system by a one step method based on the hydrolysis of APTMS and the binding interaction between APTMS and naphthalic anhydride under the presence of NH3. By adjusting the consumption amount of MPTMS, the diameters of the nanohybrids could be easily tuned from50nm to80nm, while the fluorescent yields could be also enhanced. The as-synthesized fluorescent nanocomposites are water-soluble and well-monodispersed in aqueous solution with a remarkably enhanced quantum yield by25times. The in-vitro experiments demonstrated that the nanocomposites exhibited good biocompatibility, large quantity and quick cell uptake, and accurate cell labeling capability.
3)The super-hydrophobic pH-responsive fluorophores (NDI) were encapsulted into the self-assembled micelles of amphiphilic diblock copolymer PS-6-PAA for recognizing and mapping the route of cell phagocytosis. With the subsequent shell cross-linking with3-mercaptopropyltrimethoxy-silane (MPTMS),the as-synthesized NDI@HNPs showed a typical spherical morphology with an average diameter of46nm and excellent monodispersity in aqueous solution. The fluorescent quantum yield of NDI@HNPs in acidic medium (pH=4.4) is55times larger than that in neutral medium, showing a real-time pH-sensitive fluorescent indication feature with fast response and large stokes shift. The encapsulation of NDI leads to a large stokes shift of～60nm in aqueous solution, which enables the nanoprobes to be a high quality imaging contrast agent. Its characteristic fluorescence response to pH is beneficial to the intracellular cancer cell labeling and organelle targeting, and can be employed to reveal the processes of its effective entry into the cancer cells, and the subsequent accumulation into the endolysosome and the further escape. This smart high quality contrast agent offers an easy and direct protocol to response the micro-environmental pH change and traces the phagocytosis pathway of nano-objects.
4) To test the versatility of our synthetic process, we prepared a series of NIR (Near-Infrared) nanoprobes. Three representative NIR dyes could be successfully converted from hydrophobicity to hydrophilicity by entrapping them into the core region of the block copolymer micelles. All three samples showed small and uniform size distribution at35nm and good solubility in water. The fluorescent properties of the three fluorescent molecules in aqueous solution were therefore dramatically improved through the encapsulation, and their Stokes shifts were also enlarged. Finally, by grafting targeting molecules (Folic acid and Lactobionic acid) on the surface of the fluorescent nanoprobes, the NIR nanoprobes were synthesized with specific cell targeting capability. The in vitro cytotoxicity tests showed insignificant cytotoxicity, and in the functionalized nanoprobes were found capable of effectively targeting toward MCF-7and HepG2cells during a few hours as revealed by confocal laser scanning imaging.
The present approach presents a general synthetic strategy for obtaining fluorescent nanoparticles with high and stable fluorescent efficiency, and promising application potentials for future biomedical applications.
本论文从两亲性嵌段共聚物聚苯乙烯-b-聚丙烯酸(PS-b-PAA)的球形纳米胶束出发,利用有机硅烷偶联剂((3-巯基丙基)三甲氧基硅烷以及3-氨丙基三甲氧基硅氧烷)的水解缩聚性能,对多种具有不同分子结构的疏水性荧光有机小分子进行包裹,合成了一系列具有良好水溶性的硅交联外壳的纳米荧光复合颗粒；将具有靶向功能的生物活性分子对其表面进行修饰,构建出一类新型的纳米荧光成像材料,并在细胞水平上研究了该类材料的细胞成像能力。
1)利用两亲性嵌段共聚物PS-b-PAA疏水自组装原理,将疏水的萘酰亚胺绿色荧光分子(DPN)包裹进胶束核内,结合溶胶凝胶工艺制备出一类具有表面巯基功能化的硅交联外壳的纳米荧光复合颗粒(DPN@NHs)。该纳米复合颗粒的平均尺寸控制在50nm左右,尺寸分布狭窄,在水溶液中高度稳定分散。硅交联壳层不但没有影响胶束的发光效果,而且大大提高了复合颗粒的分散稳定性,荧光分子包埋量大且不易泄漏及良好的物理和化学稳定性。研究了荧光分子包裹量对纳米颗粒形貌及荧光特性的影响；荧光成像实验中材料对MCF-7细胞具有良好的荧光标识信号。
2)荧光分子不仅可以引入到纳米胶束的疏水内核,同时还可以引入富硅壳层的骨架中。本文利用氨基硅烷偶联剂的自缩聚作用以及在氨催化下与荧光分子(4-哌啶-1,8萘酐)间的键合作用,一步法制备出一类具有表面氨基功能化的绿色荧光硅交联外壳的纳米复合粒子NAPI-NHx-NPS。通过改变硅烷的交联量,不仅可以有效地对纳米复合粒子的粒径尺寸进行调控,而且能够有效提高荧光分子的荧光效率和荧光寿命。通过TEM及DLS的表征表明,该纳米复合粒子的平均尺寸可控制在50-80nm以内,具有尺寸分布狭窄,在水溶液中高度稳定分散的优良特性。与纯染料相比,在水溶液中其荧光效率可提高约25倍,并维持较长的荧光寿命。这一类荧光复合粒子在体外生物实验中无明显细胞毒性,激光共聚焦显微镜的观测表明,该材料在短时间内可以被细胞大量吞噬。此外,利用胶束内部特殊的空腔结构,还可以将疏水性的磁性四氧化三铁粒子包裹在NAPI-NHx-NPs的胶束疏水核内部,形成了一类具有磁性、荧光多功能的纳米粒子。
3)利用嵌段共聚物的球形胶束和荧光分子本身的识别或响应能力,合成出一类具有环境响应/识别能力的智能荧光纳米探针NDI@HNPs。通过对pH响应型荧光探针分子NDI的原位包埋,制备出一类具有薄交联壳层的小尺寸荧光纳米探针。所合成的纳米探针具有良好的球形形貌和均一的粒径(46nm),并保持对环境pH响应的能力,在pH值为4到6之间具有极高的响应灵敏度,响应时间短(5s),具有很好的抗疲劳能力。进一步的细胞成像实验表明,该材料可以被癌细胞MCF-7大量吞噬,并且成功地标记出细胞内酸性环境的分布区域。同时,首次利用流式细胞术对该材料的分时段pH响应信号进行了定量测试。
4)在前面工作的基础上,制备了一系列具有近红外发射波长的纳米荧光探针。所选用的三个近红外荧光有机分子均可被包裹在嵌段共聚物胶束的疏水核内部,从而成功地由憎水转变为亲水。该类近红外纳米荧光探针的动力学直径在35nm左右。光物理性能测试表明,三种纳米荧光探针在水溶液中的荧光效率较纯的荧光分子都有显著的提高,光漂泊性大幅降低,并且斯托克斯位移也有明显的增大。通过在荧光纳米探针表面嫁接具有靶向识别效果的靶向分子—叶酸或乳糖酸,合成了具有特定细胞靶向识别能力的近红外纳米探针。在体外细胞毒性的评估中,三种探针均未显示出明显的细胞毒性。在较短的时间内,这种功能化的纳米探针可以对特定的细胞有靶向识别效果。
综上,本文发展出了一种具有通用性和较强操作性的制备可用于生物化学研究以及癌症追踪诊断的高效新型成像剂的新方法。这种方法不仅是对传统纳米材料的拓展,而且对进一步的生物研究和医疗研究也有良好的推进作用。
In recent years, the synthesis and application of amphiphilic block copolymer supramolecular self-assembled nano-microstructure have attracted extensive attention. These block copolymer micelles are featured with spherical morphology of tens to hundreds of nanometers in particle diameter, various special nano-size effect and stability, and are therefore being widely used in chemical catalysis, optical, biological medicine and many other fields. In this thesis, we focused on following four aspects:
1) We employed the spherical micelles of amphiphilic block copolymer (PS-b-PAA) as a template to prepare a new kind of core-shell structured fluorescent nanospheres (DPN@NHs). The hydrophobic dyes were encapsulated into the core of the hybrid nanospheres based on the self-assembly of amphiphilic block copolymers followed by shell cross-linking using3-mercaptopropyltrimethoxy-silane (MPTMS) as a cross-linking agent. The as-synthesized DPN@NHs were very uniform in size (50nm) and spherical morphology, and could be highly monodispersed in water. The fluorescent performances of the as-synthesized water-soluble DPN@NHs were greatly enhanced. The nanospheres exhibited no cytotoxicity and negligible cell apoptosis. By co-cultivating with MCF-7cells, DPN@NHs showed the successful cell uptake in cytoplasm regions in a large quantity.
2) An organic-inorganic fluorescent nanohybrids with extraordinarily enhanced fluorescent performance was synthesized based on the self-assembly of amphiphilic block copolymers. The thiol-functional group and a fluorescent dye,4-piperidyl-l,8-naphthalic anhydride, could be introduced into the system by a one step method based on the hydrolysis of APTMS and the binding interaction between APTMS and naphthalic anhydride under the presence of NH3. By adjusting the consumption amount of MPTMS, the diameters of the nanohybrids could be easily tuned from50nm to80nm, while the fluorescent yields could be also enhanced. The as-synthesized fluorescent nanocomposites are water-soluble and well-monodispersed in aqueous solution with a remarkably enhanced quantum yield by25times. The in-vitro experiments demonstrated that the nanocomposites exhibited good biocompatibility, large quantity and quick cell uptake, and accurate cell labeling capability.
3)The super-hydrophobic pH-responsive fluorophores (NDI) were encapsulted into the self-assembled micelles of amphiphilic diblock copolymer PS-6-PAA for recognizing and mapping the route of cell phagocytosis. With the subsequent shell cross-linking with3-mercaptopropyltrimethoxy-silane (MPTMS),the as-synthesized NDI@HNPs showed a typical spherical morphology with an average diameter of46nm and excellent monodispersity in aqueous solution. The fluorescent quantum yield of NDI@HNPs in acidic medium (pH=4.4) is55times larger than that in neutral medium, showing a real-time pH-sensitive fluorescent indication feature with fast response and large stokes shift. The encapsulation of NDI leads to a large stokes shift of～60nm in aqueous solution, which enables the nanoprobes to be a high quality imaging contrast agent. Its characteristic fluorescence response to pH is beneficial to the intracellular cancer cell labeling and organelle targeting, and can be employed to reveal the processes of its effective entry into the cancer cells, and the subsequent accumulation into the endolysosome and the further escape. This smart high quality contrast agent offers an easy and direct protocol to response the micro-environmental pH change and traces the phagocytosis pathway of nano-objects.
4) To test the versatility of our synthetic process, we prepared a series of NIR (Near-Infrared) nanoprobes. Three representative NIR dyes could be successfully converted from hydrophobicity to hydrophilicity by entrapping them into the core region of the block copolymer micelles. All three samples showed small and uniform size distribution at35nm and good solubility in water. The fluorescent properties of the three fluorescent molecules in aqueous solution were therefore dramatically improved through the encapsulation, and their Stokes shifts were also enlarged. Finally, by grafting targeting molecules (Folic acid and Lactobionic acid) on the surface of the fluorescent nanoprobes, the NIR nanoprobes were synthesized with specific cell targeting capability. The in vitro cytotoxicity tests showed insignificant cytotoxicity, and in the functionalized nanoprobes were found capable of effectively targeting toward MCF-7and HepG2cells during a few hours as revealed by confocal laser scanning imaging.
The present approach presents a general synthetic strategy for obtaining fluorescent nanoparticles with high and stable fluorescent efficiency, and promising application potentials for future biomedical applications.
引文
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