树状大分子辅助的金属纳米颗粒的合成、功能化及其生物医学应用
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摘要
随着纳米技术的发展,越来越多的纳米颗粒显现潜在的生物医学应用前景。良好的稳定性和生物相容性是纳米颗粒是否可用于生物医学领域的重要指标。本课题旨在开发性能良好的纳米颗粒作为CT(computed tomography,计算机断层扫描)造影剂,探索其在癌症检测中的应用。以聚酰胺-胺树状大分子为载体,本文构建了多种树状大分子/金、银及其合金的有机/无机杂化纳米颗粒。利用树状大分子独特的三维结构和其表面的易修饰性,可以制备多功能化的纳米颗粒,以满足特定的应用需求。
在前期树状大分子/金、银纳米颗粒工作的基础上,本文探索了树状大分子/金-银合金纳米颗粒性质的可控性及其作为CT造影剂的可行性。在发现特定金/银摩尔比下可以得到纳米线结构后,本文进一步优化了纳米线的制备参数,并尝试制备功能化的纳米线结构。鉴于金纳米颗粒的优势,本文制备了多功能化的树状大分子/金纳米颗粒,用于体外和体内癌细胞靶向CT造影。为了降低造价,本文后期偏向于开发基于低代数树状大分子/金纳米颗粒的CT造影剂。本文的方法与结论如下所述：
1)以氨基末端第五代聚酰胺-胺树状大分子(G5.NH2)为模板或稳定剂,以硼氢化钠为还原剂,制备不同树状大分子/金/银摩尔比的金-银合金纳米颗粒。随后,对金-银合金纳米颗粒进行乙酰化处理,中和其表面电荷。产物合金纳米颗粒呈球形,具有可控的光学性质和尺寸。在恒定树状大分子/金属摩尔配比条件下,合金纳米颗粒的尺寸随着金含量的提高而降低。在同样金属组分条件下,乙酰化后合金纳米颗粒的尺寸略有增大。所得合金纳米颗粒显示良好的稳定性,并在乙酰化后表现出良好的细胞相容性。合金纳米颗粒的X-射线衰减系数依赖于其金属组分和表面修饰。随着组分中金含量的提高或是乙酰化的进行,合金纳米颗粒的X-射线衰减系数呈升高趋势。
2)以G5.NH2为稳定剂和还原剂,制备不同树状大分子/金/银摩尔比的金-银合金纳米颗粒。随着调控金/银投料比,纳米颗粒的形貌从球形进化为不规则多面体,进而为卷曲的线状。合金纳米颗粒的X-射线衰减系数依赖于其金属组分和表面修饰。随着组分中金含量的提高或是乙酰化的进行,其相应的X-射线衰减系数呈升高趋势。随后,系统研究各个实验参数,最终探索出制备形貌均一金纳米线(平均直径1.3nm,长度达微米级)的最优路线为：以第五代聚酰胺-胺树状大分子为稳定剂、树状大分子/金/银摩尔投料比1/15/5、反应温度40℃、反应时间48小时、反应体系为水相。这些参数会影响纳米线的横向生长和Ag+的还原速度。通过密度泛函理论计算和进一步的实验数据,本章提出了金纳米线的生长机理：Ag+的协同选择性吸附、还原和Au0的定向迁移。本章发展的制备方法对在水相中制备其它纳米线提供了一定的借鉴意义,并为功能化纳米线的制备奠定了坚实基础。
3)基于前一章的工作,本章期望制备具有靶向功能的纳米线结构。以G5.NH2为稳定剂,首先修饰靶向配体叶酸(folic acid,FA)或异硫氰酸酯荧光素(fluorescein isothiocyanate,FI),然后加入金盐、银盐,于恒温水浴中进行反应,最后进行乙酰化处理。令人惊奇的是,TEM结果显示制备得到的产物呈球形。所得合金纳米颗粒显示良好的稳定性,并在乙酰化后表现出良好的细胞相容性。研究发现,树状大分子的表面修饰会影响其在水相中的团聚状态,进而对合金纳米颗粒的形貌产生重要的影响。所得合金纳米颗粒表现出良好的体外癌细胞靶向吞噬能力和X-射线衰减性能,并且可作为探针,用于癌细胞的靶向CT造影。
4)为了制备具有肿瘤靶向CT造影功能的纳米探针,以G5.NH2为模板,通过表面修饰FI和乳糖酸(lactobionic acid,LA)-聚乙二醇(polyethylene glycol,PEG),然后包裹金纳米颗粒,最后乙酰化制备得到多功能化的靶向CT造影剂(LA-Au DENPs)。制备得到的LA-Au DENPs具有优良的稳定性、细胞相容性、体外肝癌细胞靶向性能。X-射线衰减测试表明,LA-Au DENPs具有明显高于临床用CT造影剂碘海醇的CT值。更为重要的是,LA-Au DENPs做为探针,可以有效地在体外和体内对肝癌细胞进行靶向CT造影。
5)鉴于高代数树状大分子造价较高,开发基于低代数树状大分子的CT造影剂具有更好的应用前景。以氨基末端第二代聚酰胺-胺树状大分子(G2.NH2)为稳定剂,通过水热法制备金纳米颗粒,随后可通过FA和乙酰化对纳米颗粒表面进行功能化。通过优化树状大分子／金的摩尔投料比、反应时间及温度、修饰方法等实验参数,可制备得到具有良好稳定性和细胞相容性的金纳米颗粒。未FA修饰的纳米颗粒表现出与临床用CT造影剂碘海醇相近的体外X-射线衰减系数。FA修饰后,其表现出优于碘海醇的X-射线衰减系数。体内实验表明,所得金纳米颗粒具有良好的器官造影性能,远优于碘海醇。更重要的是,所得叶酸修饰的纳米颗粒表现出良好的体外和体内癌细胞靶向CT造影性能。
6)最后,以G2.NH2为载体,表面进行PEG化,然后通过硼氢化钠还原法制备金纳米颗粒。通过实验手段优化树状大分子／金摩尔比和反应时间等制备参数。制备得到的聚乙二醇化金纳米颗粒在表现出良好的稳定性。由于PEG的修饰,产物金纳米颗粒不需要进行乙酰化处理便可表现出良好的细胞相容性,在浓度3000nM的范围内不表现出明显的细胞毒性。聚乙二醇化金纳米颗粒具有明显高于临床用CT造影剂碘海醇的X-射线衰减系数。重要的是,所得产物纳米颗粒可对小鼠心脏、膀胱和肿瘤模型进行CT造影。
With the development of nanotechnology, more and more nanoparticles (NPs) show their great potential in biomedical applications, in which desirable stability and biocompatibility are essential. The aim of this research is to develop dendrimer/metal NPs-based computed tomography (CT) contrast agents with desirable properities for CT imaging of cancer. We employed poly(amidoamine)(PAMAM) dendrimers as the platform to develop several kinds of gold, silver, and their alloy NPs-based CT contrast agents. Taking advantage of the modifiable dendrimer surface, multifunctional hybrid NPs can be formed, meeting certain requirements of applications.
Based on the previous work of dendrimer/gold and dendrimer/silver NPs, here firstly dendrimer/gold-silver alloy NPs were controllably synthesized and their abilities as contrast agents for CT imaging were investigated. After finding nanowires (NWs) formed in certain gold/silver molar ratios, the experimental parameters were optimized and their feasibility of functionalization was investigated. Considering the advantage of gold, multifunctional dendrimer/gold NPs were synthesized for in vitro and in vivo CT imaging of cancer cells. In order to reduce the cost, low generation dendrimers were employed to form gold NPs for CT imaging applications. The methods and results are as follows:
1) Using amine-terminated generation5PAMAM dendrimer (G5.NH2) as templates or stabilizers and NaBH4as reducing agent, Au-Ag alloy NPs with different components can be formed by simply regulating the molar ratio of dendrimer/gold atom/silver atom. Followed by an acetylation reaction to transform the dendrimer terminal amines to acetyl groups, the surface charge of the particles was changed toward neutral. UV-vis spectra indicate that the formed NPs are alloy with tunable optical properties. TEM studies reveal that the size of the alloy NPs is variable depending on both dendrimer/Au atom/Ag atom molar ratio and the acetylation modification. Under constant total dendrimer/metal atom molar ratio, the size of the alloy NPs decreases with gold composition. For particles with similar metal composition, the size of the particles becomes a little larger after acetylation. The formed Au-Ag alloy NPs are stable and cytocompatible. X-ray absorption coefficient measurements show that the attenuation of the alloy NPs is dependent on both gold content and the particle surface characteristics. With the Au content increasing and after acetylation, the corresponding CT value of the particles increases.
2) Using G5.NH2as stabilizers and reducing agents, Au-Ag alloy NPs with different components can be formed at room temperature. By regulating the Au/Ag feed molar ratio, the formed NPs experience a shape evolution from spherical particles and polyhedrons to curved NWs. The alloy NPs display desirable stability. X-ray absorption coefficient measurements show that the attenuation of the binary NPs is dependent on both gold content and the particle surface characteristics. With the Au content increasing and after acetylation, the corresponding CT value of the particles increases. After that, a wide range of synthetic parameters such as reaction time, temperature, solvent, and additive were systematically investigated to explore their effects on the morphology of the Au NWs. The optimized synthesis protocol is as follows:G5.NH2as stabilizers, dendrimer/Au/Ag molar ratio at1/15/5, reaction performed at40℃for48h in aqueous solution. Our data show that the selection of these parameters is essential to obtain relatively uniform Au NWs, which are associated with the transverse growth control of Au NWs and the proper reduction rate of Ag(I). A new growth mechanism involving a synergic facet-dependent deposition/reduction of Ag(I) and anisotropic migration of Au atoms is proposed, which is based on density functional theory calculations. This may provide guidance for synthesis of other kinds of NWs in aqueous solution and also make the formation of other functionalized NWs possible.
3) Based on the previous chapter, following a similar synthetic procedure, we were aiming to prepare NWs with functionalized surface. Using G5.NH2as stabilizers, which were pre-modified with folic acid (FA) or fluorescein isothiocyanate (FI), Au-Ag alloy NPs can be formed in the water bath following an acetylation reaction. To our surprise, spherical Au-Ag alloy NPs were formed. They display good water solubility and colloidal stability, and excellent cytocompatibility in a given concentration range. It can be concluded that modification of dendrimer surface may influence their cluster state in aqueous solution, which may further affect the shape of the alloy NPs. With the much better X-ray attenuation property than that of conventional iodine-based CT contrast agent Omnipaque and the ability to be specifically uptaken by cancer cells overexpressing high affinity FA receptor, the developed FA-targeted Au-Ag alloy NPs are able to be used as a nanoprobe for targeted CT imaging of cancer cells in vitro.
4) To generate tumor-targeting CT imaging nanoprobes, G5.NH2were firstly modified with FI and polyethylene glycol (PEG)-linked lactobionic acid (LA), which can be employed as templates to form dendrimer entrapped Au NPs (LA-Au DENPs). The formed LA-Au DENPs display good stability, desirable cytocompatibility in the given concentration range, and specifically targeting ability towards human hepatocellular carcinoma cells in vitro. X-ray attenuation measurements show that the LA-Au DENPs display much stronger attenuation intensity than Omnipaque at the same concentration of radiodense element (Au or iodine). Importantly, the LA-modified Au DENPs are able to be used as an efficient nanoprobe for targeted CT imaging of human hepatocellular carcinoma in vitro and xenografted tumor model in vivo via LA-mediated active targeting.
5) In consideration of the high cost of high generation dendrimer, development of low generation dendrimer based CT contrast agents may be more potential for practical applications. In this chapter, amine-terminated generation2PAMAM dendrimers (G2.NH2) were employed as stabilizers to form dendrimer-stabilized Au NPs (Au DSNPs) via a simple hydrothermal approach without addition of reducing agents, followed by surface modification of FA and acetyl groups. Au DSNPs with desirable stability and cytocompatibility can be prepared via optimizing the synthesis parameters. X-ray attenuation coefficient measurements show that nontargeted acetylated Au DSNPs display approximately similar X-ray attenuation property to that of Omnipaque. In contrast, FA-targeted Au DSNPs displayed better X-ray attenuation intensity than Omnipaque. The acetylated Au DSNPs show much better performance in CT imaging of the major organs of rats in vivo than Omnipaque. Importantly, the FA-modified Au DSNPs enable targeted CT imaging of cancer cells in vitro and xenograft tumor model in vivo via FA receptor-mediated active targeting pathway.
6) Lastly, we show that G2.NH2firstly modified with PEG chains can be employed as templates to form Au NPs via a chemical reduction protocol. The formed PEGylated Au DENPs are quite stable and show desirable cytocompatibility in the given concentration range. In addition, the PEGylated Au DENPs display much stronger X-ray attenuation intensity than Omnipaque at the same concentration of radiodense element (Au or iodine). The formed particles can be used for CT imaging of heart and bladder of mice and xenografted tumor model in vivo.
在前期树状大分子/金、银纳米颗粒工作的基础上,本文探索了树状大分子/金-银合金纳米颗粒性质的可控性及其作为CT造影剂的可行性。在发现特定金/银摩尔比下可以得到纳米线结构后,本文进一步优化了纳米线的制备参数,并尝试制备功能化的纳米线结构。鉴于金纳米颗粒的优势,本文制备了多功能化的树状大分子/金纳米颗粒,用于体外和体内癌细胞靶向CT造影。为了降低造价,本文后期偏向于开发基于低代数树状大分子/金纳米颗粒的CT造影剂。本文的方法与结论如下所述：
1)以氨基末端第五代聚酰胺-胺树状大分子(G5.NH2)为模板或稳定剂,以硼氢化钠为还原剂,制备不同树状大分子/金/银摩尔比的金-银合金纳米颗粒。随后,对金-银合金纳米颗粒进行乙酰化处理,中和其表面电荷。产物合金纳米颗粒呈球形,具有可控的光学性质和尺寸。在恒定树状大分子/金属摩尔配比条件下,合金纳米颗粒的尺寸随着金含量的提高而降低。在同样金属组分条件下,乙酰化后合金纳米颗粒的尺寸略有增大。所得合金纳米颗粒显示良好的稳定性,并在乙酰化后表现出良好的细胞相容性。合金纳米颗粒的X-射线衰减系数依赖于其金属组分和表面修饰。随着组分中金含量的提高或是乙酰化的进行,合金纳米颗粒的X-射线衰减系数呈升高趋势。
2)以G5.NH2为稳定剂和还原剂,制备不同树状大分子/金/银摩尔比的金-银合金纳米颗粒。随着调控金/银投料比,纳米颗粒的形貌从球形进化为不规则多面体,进而为卷曲的线状。合金纳米颗粒的X-射线衰减系数依赖于其金属组分和表面修饰。随着组分中金含量的提高或是乙酰化的进行,其相应的X-射线衰减系数呈升高趋势。随后,系统研究各个实验参数,最终探索出制备形貌均一金纳米线(平均直径1.3nm,长度达微米级)的最优路线为：以第五代聚酰胺-胺树状大分子为稳定剂、树状大分子/金/银摩尔投料比1/15/5、反应温度40℃、反应时间48小时、反应体系为水相。这些参数会影响纳米线的横向生长和Ag+的还原速度。通过密度泛函理论计算和进一步的实验数据,本章提出了金纳米线的生长机理：Ag+的协同选择性吸附、还原和Au0的定向迁移。本章发展的制备方法对在水相中制备其它纳米线提供了一定的借鉴意义,并为功能化纳米线的制备奠定了坚实基础。
3)基于前一章的工作,本章期望制备具有靶向功能的纳米线结构。以G5.NH2为稳定剂,首先修饰靶向配体叶酸(folic acid,FA)或异硫氰酸酯荧光素(fluorescein isothiocyanate,FI),然后加入金盐、银盐,于恒温水浴中进行反应,最后进行乙酰化处理。令人惊奇的是,TEM结果显示制备得到的产物呈球形。所得合金纳米颗粒显示良好的稳定性,并在乙酰化后表现出良好的细胞相容性。研究发现,树状大分子的表面修饰会影响其在水相中的团聚状态,进而对合金纳米颗粒的形貌产生重要的影响。所得合金纳米颗粒表现出良好的体外癌细胞靶向吞噬能力和X-射线衰减性能,并且可作为探针,用于癌细胞的靶向CT造影。
4)为了制备具有肿瘤靶向CT造影功能的纳米探针,以G5.NH2为模板,通过表面修饰FI和乳糖酸(lactobionic acid,LA)-聚乙二醇(polyethylene glycol,PEG),然后包裹金纳米颗粒,最后乙酰化制备得到多功能化的靶向CT造影剂(LA-Au DENPs)。制备得到的LA-Au DENPs具有优良的稳定性、细胞相容性、体外肝癌细胞靶向性能。X-射线衰减测试表明,LA-Au DENPs具有明显高于临床用CT造影剂碘海醇的CT值。更为重要的是,LA-Au DENPs做为探针,可以有效地在体外和体内对肝癌细胞进行靶向CT造影。
5)鉴于高代数树状大分子造价较高,开发基于低代数树状大分子的CT造影剂具有更好的应用前景。以氨基末端第二代聚酰胺-胺树状大分子(G2.NH2)为稳定剂,通过水热法制备金纳米颗粒,随后可通过FA和乙酰化对纳米颗粒表面进行功能化。通过优化树状大分子／金的摩尔投料比、反应时间及温度、修饰方法等实验参数,可制备得到具有良好稳定性和细胞相容性的金纳米颗粒。未FA修饰的纳米颗粒表现出与临床用CT造影剂碘海醇相近的体外X-射线衰减系数。FA修饰后,其表现出优于碘海醇的X-射线衰减系数。体内实验表明,所得金纳米颗粒具有良好的器官造影性能,远优于碘海醇。更重要的是,所得叶酸修饰的纳米颗粒表现出良好的体外和体内癌细胞靶向CT造影性能。
6)最后,以G2.NH2为载体,表面进行PEG化,然后通过硼氢化钠还原法制备金纳米颗粒。通过实验手段优化树状大分子／金摩尔比和反应时间等制备参数。制备得到的聚乙二醇化金纳米颗粒在表现出良好的稳定性。由于PEG的修饰,产物金纳米颗粒不需要进行乙酰化处理便可表现出良好的细胞相容性,在浓度3000nM的范围内不表现出明显的细胞毒性。聚乙二醇化金纳米颗粒具有明显高于临床用CT造影剂碘海醇的X-射线衰减系数。重要的是,所得产物纳米颗粒可对小鼠心脏、膀胱和肿瘤模型进行CT造影。
With the development of nanotechnology, more and more nanoparticles (NPs) show their great potential in biomedical applications, in which desirable stability and biocompatibility are essential. The aim of this research is to develop dendrimer/metal NPs-based computed tomography (CT) contrast agents with desirable properities for CT imaging of cancer. We employed poly(amidoamine)(PAMAM) dendrimers as the platform to develop several kinds of gold, silver, and their alloy NPs-based CT contrast agents. Taking advantage of the modifiable dendrimer surface, multifunctional hybrid NPs can be formed, meeting certain requirements of applications.
Based on the previous work of dendrimer/gold and dendrimer/silver NPs, here firstly dendrimer/gold-silver alloy NPs were controllably synthesized and their abilities as contrast agents for CT imaging were investigated. After finding nanowires (NWs) formed in certain gold/silver molar ratios, the experimental parameters were optimized and their feasibility of functionalization was investigated. Considering the advantage of gold, multifunctional dendrimer/gold NPs were synthesized for in vitro and in vivo CT imaging of cancer cells. In order to reduce the cost, low generation dendrimers were employed to form gold NPs for CT imaging applications. The methods and results are as follows:
1) Using amine-terminated generation5PAMAM dendrimer (G5.NH2) as templates or stabilizers and NaBH4as reducing agent, Au-Ag alloy NPs with different components can be formed by simply regulating the molar ratio of dendrimer/gold atom/silver atom. Followed by an acetylation reaction to transform the dendrimer terminal amines to acetyl groups, the surface charge of the particles was changed toward neutral. UV-vis spectra indicate that the formed NPs are alloy with tunable optical properties. TEM studies reveal that the size of the alloy NPs is variable depending on both dendrimer/Au atom/Ag atom molar ratio and the acetylation modification. Under constant total dendrimer/metal atom molar ratio, the size of the alloy NPs decreases with gold composition. For particles with similar metal composition, the size of the particles becomes a little larger after acetylation. The formed Au-Ag alloy NPs are stable and cytocompatible. X-ray absorption coefficient measurements show that the attenuation of the alloy NPs is dependent on both gold content and the particle surface characteristics. With the Au content increasing and after acetylation, the corresponding CT value of the particles increases.
2) Using G5.NH2as stabilizers and reducing agents, Au-Ag alloy NPs with different components can be formed at room temperature. By regulating the Au/Ag feed molar ratio, the formed NPs experience a shape evolution from spherical particles and polyhedrons to curved NWs. The alloy NPs display desirable stability. X-ray absorption coefficient measurements show that the attenuation of the binary NPs is dependent on both gold content and the particle surface characteristics. With the Au content increasing and after acetylation, the corresponding CT value of the particles increases. After that, a wide range of synthetic parameters such as reaction time, temperature, solvent, and additive were systematically investigated to explore their effects on the morphology of the Au NWs. The optimized synthesis protocol is as follows:G5.NH2as stabilizers, dendrimer/Au/Ag molar ratio at1/15/5, reaction performed at40℃for48h in aqueous solution. Our data show that the selection of these parameters is essential to obtain relatively uniform Au NWs, which are associated with the transverse growth control of Au NWs and the proper reduction rate of Ag(I). A new growth mechanism involving a synergic facet-dependent deposition/reduction of Ag(I) and anisotropic migration of Au atoms is proposed, which is based on density functional theory calculations. This may provide guidance for synthesis of other kinds of NWs in aqueous solution and also make the formation of other functionalized NWs possible.
3) Based on the previous chapter, following a similar synthetic procedure, we were aiming to prepare NWs with functionalized surface. Using G5.NH2as stabilizers, which were pre-modified with folic acid (FA) or fluorescein isothiocyanate (FI), Au-Ag alloy NPs can be formed in the water bath following an acetylation reaction. To our surprise, spherical Au-Ag alloy NPs were formed. They display good water solubility and colloidal stability, and excellent cytocompatibility in a given concentration range. It can be concluded that modification of dendrimer surface may influence their cluster state in aqueous solution, which may further affect the shape of the alloy NPs. With the much better X-ray attenuation property than that of conventional iodine-based CT contrast agent Omnipaque and the ability to be specifically uptaken by cancer cells overexpressing high affinity FA receptor, the developed FA-targeted Au-Ag alloy NPs are able to be used as a nanoprobe for targeted CT imaging of cancer cells in vitro.
4) To generate tumor-targeting CT imaging nanoprobes, G5.NH2were firstly modified with FI and polyethylene glycol (PEG)-linked lactobionic acid (LA), which can be employed as templates to form dendrimer entrapped Au NPs (LA-Au DENPs). The formed LA-Au DENPs display good stability, desirable cytocompatibility in the given concentration range, and specifically targeting ability towards human hepatocellular carcinoma cells in vitro. X-ray attenuation measurements show that the LA-Au DENPs display much stronger attenuation intensity than Omnipaque at the same concentration of radiodense element (Au or iodine). Importantly, the LA-modified Au DENPs are able to be used as an efficient nanoprobe for targeted CT imaging of human hepatocellular carcinoma in vitro and xenografted tumor model in vivo via LA-mediated active targeting.
5) In consideration of the high cost of high generation dendrimer, development of low generation dendrimer based CT contrast agents may be more potential for practical applications. In this chapter, amine-terminated generation2PAMAM dendrimers (G2.NH2) were employed as stabilizers to form dendrimer-stabilized Au NPs (Au DSNPs) via a simple hydrothermal approach without addition of reducing agents, followed by surface modification of FA and acetyl groups. Au DSNPs with desirable stability and cytocompatibility can be prepared via optimizing the synthesis parameters. X-ray attenuation coefficient measurements show that nontargeted acetylated Au DSNPs display approximately similar X-ray attenuation property to that of Omnipaque. In contrast, FA-targeted Au DSNPs displayed better X-ray attenuation intensity than Omnipaque. The acetylated Au DSNPs show much better performance in CT imaging of the major organs of rats in vivo than Omnipaque. Importantly, the FA-modified Au DSNPs enable targeted CT imaging of cancer cells in vitro and xenograft tumor model in vivo via FA receptor-mediated active targeting pathway.
6) Lastly, we show that G2.NH2firstly modified with PEG chains can be employed as templates to form Au NPs via a chemical reduction protocol. The formed PEGylated Au DENPs are quite stable and show desirable cytocompatibility in the given concentration range. In addition, the PEGylated Au DENPs display much stronger X-ray attenuation intensity than Omnipaque at the same concentration of radiodense element (Au or iodine). The formed particles can be used for CT imaging of heart and bladder of mice and xenografted tumor model in vivo.
引文
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