分子印迹微流控手性分离研究
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摘要
手性化合物在生命体系中往往显示不同的生物活性,因而对手性化合物的拆分极为重要。研究与发展低成本、高效率的手性拆分技术的重要性日益凸现,给研究者带来了巨大的挑战和机遇,具有广阔的应用前景。近年来,微流控手性拆分的兴起使拆分平台芯片化,从而使拆分速度大大提高,试剂和样品用量减少至微升级,具有发展高通量和集成化的潜力。酶法拆分、色谱和电泳法手性分离均已在芯片上有所尝试,手性拆分方法在微流控芯片上的运用使拆分时间通常以秒甚至毫秒计算,体现了芯片手性拆分最为显著的优点,即拆分速度快。分子印迹技术(MIT)是一种新兴的人工抗体制备技术,制得的材料稳定性好、亲和能力强、对目标分子能进行特异性识别。以分子印迹聚合物(MIP)作为固定相用于色谱法手性分离,不仅可以完全分离对映体,还可以预测其洗脱顺序。迄今为止MIT在微流控手性分离的应用还是一个空白领域。本论文首次将MIT用于微流控手性分离,并围绕此课题展开了一系列工作,开拓了其在微流控手性分离中的应用,主要包括以下四个部分：
1.微通道内壁原位分子印迹用于手性分离和电化学检测
本文首次将MIT引入微流控分析领域,通过在微通道内原位印迹MIP实现快速手性分离。以丙烯酰胺为功能单体,乙二醇二甲基丙烯酸酯(EDMA)为交联剂,通过原位化学聚合法将MIP聚合在微通道壁上,并用扫描电子显微镜法、原子力显微镜法和红外光谱法进行表征。在优化条件(包括MIP制备条件、流动相的组成和pH值以及分离电压)下可在75 s内实现模型分子叔丁氧羰基-色氨酸(Boc-Trp)对映体的基线分离。用碳纤维微盘电极在电位为+1.2 V(vsAg/AgCl)下对Boc-Trp对映体进行安培法检测,线性范围和检测限分别为Boc-D-Trp:75-4000μM,20μM; Boc-L-Trp:4000μM,140μM。分子印迹微芯片电色谱法提供了一个Boc-Trp对映体快速手性分离和在线检测的新方法。本文提出的微通道内壁原位分子印迹的策略为手性化合物快速手性分离开辟了一条新途径。
2.一锅法印迹微流控通道用于微芯片毛细管电色谱同时多组分手性分离
本文通过一锅原位印迹法制备了多模板印迹的微通道,并以此发展了一个基于芯片的同时多组分手性分离的新方法。利用一锅印迹法可在毛细管内壁形成多模板印迹的多孔薄层(约2μm),印迹膜用扫描电子显微镜法、红外光谱法和固体紫外光谱法进行表征。将印迹的毛细管作为微通道集成在以载玻片为基底的聚二甲基硅氧烷基质中即可方便地组装成多组分分析微芯片。以L-酪氨酸(L-Tyr)和L-Trp作为模板分子,在优化的制备条件和分离条件下,在6 cm长的分离通道中,在120s内即可实现两对对映体的同时基线分离,具有良好的分离效果。用碳纤维微盘电极在+1.2V(vs Ag/AgCl)电位可对两对对映体进行安培法检测,消旋Tyr和Trp的线性范围均为20-500μM。本文提出的多模板印迹策略可扩展到更多对对映体的同时快速分离和在线检测,为手性化合物高通量筛选提供了新方法。
3.分子印迹磁性纳米颗粒在微流控通道内定位与手性分离
设计了一个在微通道内定位分子印迹磁性纳米颗粒(MIP-MNPs)作为可调控的固定相的微流控装置,通过毛细管电色谱法实现了氧氟沙星对映体的快速手性分离。MIP-MNPs是在模板分子S-氧氟沙星的存在下,由甲基丙烯酸和EDMA在3-甲基丙烯酸酯基三甲氧硅烷功能化的MNPs(直径25 nm)上经共聚作用合成,并用红外光谱法、热重法和透射电子显微镜法对其进行表征。在外磁场作用下,MIP-MNPs(直径200 nm)作为填充长度可调控的固定相定位于微流控装置的微通道中。对MIP-MNPs的制备条件、流动相的组成和pH值、以及分离电压进行优化后,可在195 s内实现氧氟沙星对映体的基线分离。另外,通过调节MIP-MNPs区带的填充长度能够方便的提高分离效果,这显示出其优于常规填充毛细管电色谱的一个特点。在电位+1.0V(vs Ag/AgCl)对氧氟沙星对映体进行安培法检测,线性范围和检测限分别为：R-氧氟沙星,1.0-500μM,0.4μM；S-氧氟沙星,5.0-500μM,2.0μM。磁调控的微流控装置有望扩展到定位多模板印迹的磁性纳米颗粒从而实现同时多组分手性分离。
4.超大孔整体印迹微流控通道用于微芯片手性分离
制备了超大孔整体印迹的微流控通道,发展了一个微芯片手性分离的新方法。键合在毛细管内壁的超大孔整体柱通过原位化学共聚作用制备而成,并通过扫描电子显微镜法、红外光谱法和固体紫外光谱法进行表征。印迹毛细管内的多孔网络结构可以产生大的比表面积、良好的渗透性和低的传质阻力,从而获得高的柱效。以5 cm长的印迹毛细管为分离通道,碳纤维微盘电极为工作电极,组装成可抛型杂化微芯片。在优化的制备条件和分离条件下,以L-Tyr作为模板分子,在55 s内即可实现Tyr对映体的基线分离和在线电化学检测,消旋Tyr的线性范围为20-2400μM。相比表面印迹法,超大孔整体法显示更好的手性分离效果和更高的柱容量。本文提出的超大孔整体印迹微通道的策略有望用于手性化合物高通量筛选。
Enantioseparation is of paramount importance since chiral compounds exhibit different properties in biochemical systems. Exploring new enantioseparation techniques with low cost and high efficiency is urgent, and provides huge challenge and opportunity to the researchers and market. Recently, the development of the microfluidic enantioseparation provides feasibility for the miniaturized enantioseparation with short analysis time and low consumption of reagent and sample, showing a promising avenue for high-through enantioscreening of chiral compound. Some microfluidic enantioseparation methods by using enzyme, chromatography and electrophoresis have been developed and showed fast analysis speed. However, molecular imprinting technique (MIT), a well-known means for the preparation of biomimetic recognition matrices using molecularly imprinted polymer (MIP) with good binding affinity, stability and specificity toward the target molecules, has not been used to combine with microfluidic technique yet, although one of the widest applications of MIP as chiral stationary phases for enantioseparation has been developed by coupling with high-performance liquid chromatography and capillary electrochromatography with the predetermined elution order. This dissertation first introduced MIT into microfluidic analysis for the enantioseparation of chiral compounds, and four methods were proposed for microfluidic enantioseparation:
1. Enantioseparation and amperometric detection of chiral compounds by in situ molecular imprinting on the microchannel wall
The MIT was first introduced into the microchannel of a microfluidic device (MD) to form in situ the imprinted polymer for fast enantioseparation of chiral compounds. The MIP was in situ chemically polymerized on the microchannel wall using acrylamide as the functional monomer and ethylene glycol dimethacrylate (EDMA) as the cross-linker, and characterized by scanning electron microscopy, atomic force microscopy, and infrared spectroscopy. Under the optimized conditions, such as optimal preparation of MIP, composition and pH of mobile phase, and separation voltage, the model enantiomers, tert-butoxycarbonyl-D-tryptophan (Boc-D-Trp) and Boc-L-Trp, could be baseline separated within 75 s. The linear ranges for amperometric detection of the enantiomers using carbon fiber microdisk electrode at +1.2 V (vs Ag/AgCl) were from 75 to 4000μM and 400 to 4000μM with the detection limits of 20 and 140μM, respectively. The MIP-microchip electrochromatography provided a powerful protocol for separation and detection of Boc-Trp enantiomers within a short analytical time. The molecular imprinting on microchannel wall opens a promising avenue for fast enantioscreening of chiral compounds.
2. Molecularly imprinted magnetic nanoparticles as tunable stationary phase located in microfluidic channel for enantioseparation
A MD integrated with molecularly imprinted magnetic nanoparticles (MIP-MNPs) as stationary phase was designed for rapid enantioseparation by capillary electrochromatography. The nanoparticles were synthesized by the co-polymerization of methacrylic acid and EDMA on 3-(methacryloyloxy)propyltrimethoxysilane-functionalized MNPs (25-nm diameter) in the presence of template molecule, and characterized with infrared spectroscopy, thermal gravimetric analysis, and transmission electron microscope. MIP-MNPs (200-nm diameter) could be localized as stationary phase in the microchannel of MD with the tunable packing length by the help of an external magnetic field. Using S-ofloxacin as the template molecule, the preparation of MIP-MNPs, the composition and pH of mobile phase, and the separation voltage were optimized to obtain baseline separation of ofloxacin enantiomers within 195 s. The analytical performance could be conveniently improved by varying the packing length of nanoparticles zone, showing an advantage over the conventional packed capillary electrochromatography. The linear ranges for amperometric detection of the enantiomers using carbon fiber microdisk electrode at +1.0V (vs Ag/AgCl) were from 1.0 to 500μM and 5.0 to 500μM with the detection limits of 0.4 and 2.0μM, respectively. The magnetically tunable MIP-MNPs-MD could be expanded to localize more than one kind of template-imprinted magnetic nanoparticles for realizing simultaneous analysis of different kinds of chiral compounds.
3. Simultaneous multiple enantioseparation with one-pot imprinted microfluidic channel by microchip capillary electrochromatography
A multi-template imprinted microchannel was prepared by a one-pot in situ imprinting process. The imprinted microchannel led to a novel chip-based strategy for simultaneous multiple enantioseparation. The one-pot imprinting process formed a multi-template imprinted porous thin layer (about 2μm) on the inner wall of capillary, which was characterized by scanning electron microscopy, infrared spectroscopy, and solid-state UV-vis spectroscopy. By fixing the imprinted capillary to a support substrate composed of poly(dimethylsiloxane) on a glass slide, a multi-analyte microchip was thus conveniently constructed. Using L-tyrosine (L-Tyr) and L-Trp as the template molecules, two pairs of enantiomers were simultaneously baseline separated in a 6-cm separation channel within 120 s under the optimized preparation and electrochromatographic conditions. The separation showed excellent efficiency. The linear ranges for amperometric detection of four analytes using carbon fiber microdisk electrode at+1.2 V (vs Ag/AgCl) were from 20 to 500μM for racemic Tyr and Trp. This multi-template imprinting strategy could be expanded for simultaneous separation and detection of more pairs of enantiomers within a short analytical time. It would open a promising avenue for high-throughput screening of chiral compounds.
4. Superporous monolithic imprinted microfluidic channel for chip-based enantioseparation
A method for chip-based enantioseparation by superporous monolithic imprinted microfluidic channel was successfully developed. The superporous monolith anchored onto the surface of the microchannel wall was prepared by in situ chemically copolymerized, and characterized by scanning electron microscopy, infrared spectroscopy, and solid-state UV-vis spectroscopy. The monolithic network with high porosity gave a large surface area, good permeability, low mass-transfer resistance, leading to a high efficiency. A portable microchip was conveniently constructed by integrating the imprinted capillary with 5-cm length as the separation channel and a carbon fiber microdisk working electrode for amperometric detection. Using L-Tyr as the template molecule, Tyr enantiomers were baseline separated within 55 s under the optimized preparation and separation conditions. The linear ranges for on-line amperometric detection of the enantiomers were from 20 to 2400μM for racemic Tyr. Compared with the surface imprinting methods, the superporous monolithic imprinting strategy exhibited a higher efficiency of enantioseparation and column capacity. It opens a promising avenue for high-throughput screening of chiral compounds.
1.微通道内壁原位分子印迹用于手性分离和电化学检测
本文首次将MIT引入微流控分析领域,通过在微通道内原位印迹MIP实现快速手性分离。以丙烯酰胺为功能单体,乙二醇二甲基丙烯酸酯(EDMA)为交联剂,通过原位化学聚合法将MIP聚合在微通道壁上,并用扫描电子显微镜法、原子力显微镜法和红外光谱法进行表征。在优化条件(包括MIP制备条件、流动相的组成和pH值以及分离电压)下可在75 s内实现模型分子叔丁氧羰基-色氨酸(Boc-Trp)对映体的基线分离。用碳纤维微盘电极在电位为+1.2 V(vsAg/AgCl)下对Boc-Trp对映体进行安培法检测,线性范围和检测限分别为Boc-D-Trp:75-4000μM,20μM; Boc-L-Trp:4000μM,140μM。分子印迹微芯片电色谱法提供了一个Boc-Trp对映体快速手性分离和在线检测的新方法。本文提出的微通道内壁原位分子印迹的策略为手性化合物快速手性分离开辟了一条新途径。
2.一锅法印迹微流控通道用于微芯片毛细管电色谱同时多组分手性分离
本文通过一锅原位印迹法制备了多模板印迹的微通道,并以此发展了一个基于芯片的同时多组分手性分离的新方法。利用一锅印迹法可在毛细管内壁形成多模板印迹的多孔薄层(约2μm),印迹膜用扫描电子显微镜法、红外光谱法和固体紫外光谱法进行表征。将印迹的毛细管作为微通道集成在以载玻片为基底的聚二甲基硅氧烷基质中即可方便地组装成多组分分析微芯片。以L-酪氨酸(L-Tyr)和L-Trp作为模板分子,在优化的制备条件和分离条件下,在6 cm长的分离通道中,在120s内即可实现两对对映体的同时基线分离,具有良好的分离效果。用碳纤维微盘电极在+1.2V(vs Ag/AgCl)电位可对两对对映体进行安培法检测,消旋Tyr和Trp的线性范围均为20-500μM。本文提出的多模板印迹策略可扩展到更多对对映体的同时快速分离和在线检测,为手性化合物高通量筛选提供了新方法。
3.分子印迹磁性纳米颗粒在微流控通道内定位与手性分离
设计了一个在微通道内定位分子印迹磁性纳米颗粒(MIP-MNPs)作为可调控的固定相的微流控装置,通过毛细管电色谱法实现了氧氟沙星对映体的快速手性分离。MIP-MNPs是在模板分子S-氧氟沙星的存在下,由甲基丙烯酸和EDMA在3-甲基丙烯酸酯基三甲氧硅烷功能化的MNPs(直径25 nm)上经共聚作用合成,并用红外光谱法、热重法和透射电子显微镜法对其进行表征。在外磁场作用下,MIP-MNPs(直径200 nm)作为填充长度可调控的固定相定位于微流控装置的微通道中。对MIP-MNPs的制备条件、流动相的组成和pH值、以及分离电压进行优化后,可在195 s内实现氧氟沙星对映体的基线分离。另外,通过调节MIP-MNPs区带的填充长度能够方便的提高分离效果,这显示出其优于常规填充毛细管电色谱的一个特点。在电位+1.0V(vs Ag/AgCl)对氧氟沙星对映体进行安培法检测,线性范围和检测限分别为：R-氧氟沙星,1.0-500μM,0.4μM；S-氧氟沙星,5.0-500μM,2.0μM。磁调控的微流控装置有望扩展到定位多模板印迹的磁性纳米颗粒从而实现同时多组分手性分离。
4.超大孔整体印迹微流控通道用于微芯片手性分离
制备了超大孔整体印迹的微流控通道,发展了一个微芯片手性分离的新方法。键合在毛细管内壁的超大孔整体柱通过原位化学共聚作用制备而成,并通过扫描电子显微镜法、红外光谱法和固体紫外光谱法进行表征。印迹毛细管内的多孔网络结构可以产生大的比表面积、良好的渗透性和低的传质阻力,从而获得高的柱效。以5 cm长的印迹毛细管为分离通道,碳纤维微盘电极为工作电极,组装成可抛型杂化微芯片。在优化的制备条件和分离条件下,以L-Tyr作为模板分子,在55 s内即可实现Tyr对映体的基线分离和在线电化学检测,消旋Tyr的线性范围为20-2400μM。相比表面印迹法,超大孔整体法显示更好的手性分离效果和更高的柱容量。本文提出的超大孔整体印迹微通道的策略有望用于手性化合物高通量筛选。
Enantioseparation is of paramount importance since chiral compounds exhibit different properties in biochemical systems. Exploring new enantioseparation techniques with low cost and high efficiency is urgent, and provides huge challenge and opportunity to the researchers and market. Recently, the development of the microfluidic enantioseparation provides feasibility for the miniaturized enantioseparation with short analysis time and low consumption of reagent and sample, showing a promising avenue for high-through enantioscreening of chiral compound. Some microfluidic enantioseparation methods by using enzyme, chromatography and electrophoresis have been developed and showed fast analysis speed. However, molecular imprinting technique (MIT), a well-known means for the preparation of biomimetic recognition matrices using molecularly imprinted polymer (MIP) with good binding affinity, stability and specificity toward the target molecules, has not been used to combine with microfluidic technique yet, although one of the widest applications of MIP as chiral stationary phases for enantioseparation has been developed by coupling with high-performance liquid chromatography and capillary electrochromatography with the predetermined elution order. This dissertation first introduced MIT into microfluidic analysis for the enantioseparation of chiral compounds, and four methods were proposed for microfluidic enantioseparation:
1. Enantioseparation and amperometric detection of chiral compounds by in situ molecular imprinting on the microchannel wall
The MIT was first introduced into the microchannel of a microfluidic device (MD) to form in situ the imprinted polymer for fast enantioseparation of chiral compounds. The MIP was in situ chemically polymerized on the microchannel wall using acrylamide as the functional monomer and ethylene glycol dimethacrylate (EDMA) as the cross-linker, and characterized by scanning electron microscopy, atomic force microscopy, and infrared spectroscopy. Under the optimized conditions, such as optimal preparation of MIP, composition and pH of mobile phase, and separation voltage, the model enantiomers, tert-butoxycarbonyl-D-tryptophan (Boc-D-Trp) and Boc-L-Trp, could be baseline separated within 75 s. The linear ranges for amperometric detection of the enantiomers using carbon fiber microdisk electrode at +1.2 V (vs Ag/AgCl) were from 75 to 4000μM and 400 to 4000μM with the detection limits of 20 and 140μM, respectively. The MIP-microchip electrochromatography provided a powerful protocol for separation and detection of Boc-Trp enantiomers within a short analytical time. The molecular imprinting on microchannel wall opens a promising avenue for fast enantioscreening of chiral compounds.
2. Molecularly imprinted magnetic nanoparticles as tunable stationary phase located in microfluidic channel for enantioseparation
A MD integrated with molecularly imprinted magnetic nanoparticles (MIP-MNPs) as stationary phase was designed for rapid enantioseparation by capillary electrochromatography. The nanoparticles were synthesized by the co-polymerization of methacrylic acid and EDMA on 3-(methacryloyloxy)propyltrimethoxysilane-functionalized MNPs (25-nm diameter) in the presence of template molecule, and characterized with infrared spectroscopy, thermal gravimetric analysis, and transmission electron microscope. MIP-MNPs (200-nm diameter) could be localized as stationary phase in the microchannel of MD with the tunable packing length by the help of an external magnetic field. Using S-ofloxacin as the template molecule, the preparation of MIP-MNPs, the composition and pH of mobile phase, and the separation voltage were optimized to obtain baseline separation of ofloxacin enantiomers within 195 s. The analytical performance could be conveniently improved by varying the packing length of nanoparticles zone, showing an advantage over the conventional packed capillary electrochromatography. The linear ranges for amperometric detection of the enantiomers using carbon fiber microdisk electrode at +1.0V (vs Ag/AgCl) were from 1.0 to 500μM and 5.0 to 500μM with the detection limits of 0.4 and 2.0μM, respectively. The magnetically tunable MIP-MNPs-MD could be expanded to localize more than one kind of template-imprinted magnetic nanoparticles for realizing simultaneous analysis of different kinds of chiral compounds.
3. Simultaneous multiple enantioseparation with one-pot imprinted microfluidic channel by microchip capillary electrochromatography
A multi-template imprinted microchannel was prepared by a one-pot in situ imprinting process. The imprinted microchannel led to a novel chip-based strategy for simultaneous multiple enantioseparation. The one-pot imprinting process formed a multi-template imprinted porous thin layer (about 2μm) on the inner wall of capillary, which was characterized by scanning electron microscopy, infrared spectroscopy, and solid-state UV-vis spectroscopy. By fixing the imprinted capillary to a support substrate composed of poly(dimethylsiloxane) on a glass slide, a multi-analyte microchip was thus conveniently constructed. Using L-tyrosine (L-Tyr) and L-Trp as the template molecules, two pairs of enantiomers were simultaneously baseline separated in a 6-cm separation channel within 120 s under the optimized preparation and electrochromatographic conditions. The separation showed excellent efficiency. The linear ranges for amperometric detection of four analytes using carbon fiber microdisk electrode at+1.2 V (vs Ag/AgCl) were from 20 to 500μM for racemic Tyr and Trp. This multi-template imprinting strategy could be expanded for simultaneous separation and detection of more pairs of enantiomers within a short analytical time. It would open a promising avenue for high-throughput screening of chiral compounds.
4. Superporous monolithic imprinted microfluidic channel for chip-based enantioseparation
A method for chip-based enantioseparation by superporous monolithic imprinted microfluidic channel was successfully developed. The superporous monolith anchored onto the surface of the microchannel wall was prepared by in situ chemically copolymerized, and characterized by scanning electron microscopy, infrared spectroscopy, and solid-state UV-vis spectroscopy. The monolithic network with high porosity gave a large surface area, good permeability, low mass-transfer resistance, leading to a high efficiency. A portable microchip was conveniently constructed by integrating the imprinted capillary with 5-cm length as the separation channel and a carbon fiber microdisk working electrode for amperometric detection. Using L-Tyr as the template molecule, Tyr enantiomers were baseline separated within 55 s under the optimized preparation and separation conditions. The linear ranges for on-line amperometric detection of the enantiomers were from 20 to 2400μM for racemic Tyr. Compared with the surface imprinting methods, the superporous monolithic imprinting strategy exhibited a higher efficiency of enantioseparation and column capacity. It opens a promising avenue for high-throughput screening of chiral compounds.
引文
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