N-（4-氨基丁基）-乙基异鲁米诺功能化纳米材料的合成、发光性质及分析应用研究
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摘要
论文首先综述了化学发光、化学发光功能化纳米材料的研究现状及其在生物分析中的最新应用进展。近年来,发光试剂功能化的纳米材料的研究得到了人们的广泛关注,以发光试剂功能化纳米材料为分析探针和纳米界面的分析方法得到了迅速发展,在临床诊断、食品安全检测、环境监测等领域显示了重要的应用前景。但目前所制备的发光功能化纳米材料发光效率有限,对于一些生物体系中超低含量物质的测定仍存在挑战。本论文针对发展高效的发光功能化纳米材料,围绕着特殊形貌发光试剂功能化纳米材料及发光试剂功能化金纳米材料／碳纳米管复合材料的制备及无标记化学发光生物分析新方法这一研究主题,展开了一系列研究工作。成功合成了N-(4-氨丁基)-N-乙基异鲁米诺(ABEI)功能化爆米花状金纳米粒子和ABEI功能化金纳米点/壳聚糖/多壁碳纳米管复合材料,研究了其化学发光和电致化学发光性质。基于上述发光功能化纳米复合材料,发展了一系列无标记电致化学发光生物分析新方法,实现了对金属离子和抗原分子的超灵敏测定。此外,基于ABEI良好的荧光性能,进一步探讨了ABEI功能化金纳米颗粒的荧光特性及在荧光共振能量转移中的应用。主要研究内容如下：
1.在室温乙醇溶液中,采用种晶生长法,利用ABEI还原硫辛酸和氯金酸,发展了一种制备高发光效率的爆米花状发光试剂功能化金纳米材料的简单合成方法。借助透射电子显微镜等仪器分析手段对合成的金纳米材料的形貌进行了表征,结果显示该方法成功制备了爆米花状、准球形、不规则多面体等形貌金纳米材料。进一步,通过X射线电子能谱等仪器手段对产物的表面化学组成进行了表征。结果表明,ABEI、ABEI的氧化产物通过Au-N键连接于金纳米表面,硫辛酸的还原产物通过Au-S键连接于金纳米表面。对于所合成的爆米花状金纳米粒子,其表面密布的不规则凸起使其具有更大的比较面积,在化学发光性能上明显优于前期合成的球形ABEI功能化金纳米材料。尤为重要的是,爆米花状金纳米材料可以标记生物分子如蛋白质和DNA,制备的生物探针仍具有良好的化学发光活性。这种化学发光功能化的生物探针能够被用于生物测定和临床诊断中,对公共健康、食品安全及环境监测等均具有重要意义。
2.采用一步合成法成功制备了高密度ABEI功能化金纳米点功能化的碳纳米管。实验中先将壳聚糖吸附于羧基化碳纳米管,分离纯化后与氯金酸溶液混合均匀,而后加入ABEI溶液还原氯金酸,ABEI与碳管表面壳聚糖同时作为保护试剂连接于金纳米点表面,制备了ABEI功能化纳米点/壳聚糖/碳纳米管复合材料。借助透射电子显微镜、高角环形暗场扫描透射原子成像技术、X射线能谱仪、X射线光电子能谱和拉曼光谱等仪器手段对所合成复合材料形貌及表面特性进行了表征。分析结果表明ABEI功能化的金纳米点高密度、均匀的分布于碳纳米管表面。进一步我们研究了ABEI功能化纳米点/壳聚糖/碳纳米管复合材料的化学发光性能,结果表明该复合材料具有良好的化学发光和电致化学发光特性。基于ABEI高效的化学发光特性、壳聚糖良好的成膜特性和碳纳米管良好的导电性能,利用合成的ABEI功能化纳米点/壳聚糖/碳纳米管复合材料构建了一种新型无标记适配体传感器,并成功实现了对水体样本中的汞离子的高灵敏、特异性的测定,线性范围为1.0×10～1.0×10-8mol/L,检测限为3.2x10-9mol/L。
3.基于前一章工作所合成的ABEI功能化金纳米点-壳聚糖-多壁碳纳米管复合材料,我们构建了电致化学发光活性传感平台,发展一种无标记免疫分析新方法用于测定氨基末端脑钠肽前体(NT-proBNP).基于氧化铟锡(Indium tin oxide, ITO)玻片电极,通过简单的滴加将经过纯化处理的复合材料滴涂于ITO电极表面,复合材料中的壳聚糖具有很好的成膜性,能够将材料稳定的固载于电极表面,同时复合材料具有优良的电致化学发光特性,作为电化学发光活性基底。而后利用戊二醛作为连接分子将人NT-proBNP单克隆抗体修饰于复合材料表面,并用牛血清蛋白对上述界面未反应的活性位点进行封闭,该修饰电极即可作为一种无标记电致化学发光免疫传感器,用于检测NT-proBNP。实验中通过监测电致化学行为对传感器的构建过程进行了表征。结果表明,该复合材料功能化的纳米界面具有良好的电致化学发光性质和电子传导能力。该传感器用于检测目标抗原NT-proBNP时展现了较宽的线性范围1.0×10-10g/mL-1.0×10-14g/mL和较低的检测限3.86×10-15g/mL。此外,研究表明该传感器具有良好的精确度、稳定性和重现性。本研究为蛋白质的检测提供了一种简单、快速、灵敏的检测方法,为无标记免疫传感器开辟了新的途径。
4.研究了ABEI功能化金纳米粒子的荧光特性。研究结果表明ABEI功能化金纳米粒子作为纳米光学探针具有以下重要优点。第一,1.23×10-9mol/L的ABEI功能化金纳米粒子具有与7.8×10-7mol/L ABEI纯溶液可比拟的荧光发射强度。虽然功能化金纳米粒子之间存在粒子间淬灭效应、金纳米核对其表面的ABEI分子存在粒子内淬灭效应,但一个功能化金纳米粒子的荧光强度仍比单个ABEI分子强634倍。此外,纳米金具有良好的标记性能,这对将ABEI功能化金纳米粒子用作荧光探针具有重要的意义。第二,ABEI功能化金纳米粒子表现了良好的抗光漂白特性,性能优于实验室前期合成的鲁米诺功能化金纳米粒子。在激发光源持续照射45分钟后,ABEI功能化金纳米粒子仍保留70%的荧光发射强度。此外,我们将ABEI功能化金纳米作为能量给体,将吖啶黄作为能量受体,开发了一种新颖的荧光共振能量转移体系。研究表明,在不需要额外添加连接分子的情况下,二者在水溶液中就能发生有效的荧光共振能量转移。本章工作首次提出将发光试剂功能化金属纳米材料用作共振能量转移的能量给体。基于金纳米材料优良的标记特性,ABEI功能化金纳米材料-吖啶黄共振能量转移对有望应用于荧光相关的生物分析测定中。
In this dissertation, the state of arts in the field of chemiluminescence (CL), chemiluminescent functionalized nanomaterials (CF-NMs) and their applications in bioassays were reviewed. Recently, much attention has been paid to CF-NMs and a series of CF-NMs have been synthesized. The analytical method based on CL-NMs as analytical probes and analytical interface is developed rapidly, showing promising application potential in clinical diagnosis, food safety, environmental monitoring etc. However, the CL efficiency of CF-NMs is limited and it remains great challenge for the detection of trace substance in the biological systems. The aim of this dissertation is to explore the synthesis of CF-NMs with high CL yield and their applications in label-free bioassays. N-(aminobytyl)-N-(ethylisoluminol)(ABEI) functionalized gold nanopopcorns and ABEI functionalized gold nanodots onto chitosan-grafted multi-walled carbon nanotubes (ABEI-AuNDs-cs-MWCNTs) were successfully synthesized. These nanocomposites exhibited excellent CL and electrochemiluminescence (ECL) properties. Based on the as-prepared CF-NMs, novel label-free ECL biosensors for highly sensitive and selective detection of mercury and N-terminal of the prohormone brain natriuretic peptide (NT-proBNP) were developed based on the target-induced directed ECL signal change. Besides, the fluorescence property of ABEI functionalized gold nanoparticles (ABEI-AuNPs) and applications of ABEI-AuNPs in fluorescence resonance energy transfer were studied. The main results are as follows:
1. A facile method for the synthesis of popcorn-shaped gold nanomaterials (GNMs) with high CL yield and good monodispersity by reducing LA and HAuCl4with ABEI in ethyl alcohol solution at room temperature through a seed growth method was reproted. The morphologies of GNMs were characterized by transmission electron microscopy, scanning electron microscopy and energy dispersive spectroscopy. The results showed that various morphologies of GNMs from gold nanopopcorns (AuNPCs), quasi-spherical to irregular GNMs could be obtained. The surface composition of AuNPCs was studied and the results strongly supported that ABEI, the oxidation product of ABEI and reduction product of LA were attached to a gold core by covalent bonds. A possible mechanism of shape evolution is proposed. The special morphology of AuNPCs maintains the large specific surface area and provides excellent catalytic property when involved in the CL reaction. Thus the CL functionalized AuNPCs exhibited good CL property (two orders of magnitude higher than that of ABEI functionalized gold nanoparticles in our previous work). Furthermore, DNA and protein labeled with AuNPCs showed excellent CL activity, which implies their application potential as bio-probes for immunoassay and DNA assay.
2. A one-step strategy for high-density assembly of ABEI functionalized gold nanodots onto the sidewalls of chitosan-grafted multi-walled carbon nanotubes (ABEI-AuNDs-cs-MWCNTs) via the reduction of HAuCl4with ABEI in the presence of cs-MWCNTs. During the synthesis process, a great number of ABEI molecules as stabilizers were directly coated on the surface of ABEI-AuNDs-cs-MWCNTs. The morphology and surface composition of ABEI-AuNDs-cs-MWCNTs were studied by transmission electron microscopy, energy dispersive spectroscopy, X-ray photoelectron spectroscopy and Raman spectra. The results showed that ABEI-AuNDs uniformly distributed on the surface of composites. Furthermore, the CL and ECL properties of ABEI-AuNDs-cs-MWCNTs were studied and ABEI-AuNDs-cs-MWCNTs exhibited excellent CL and ECL properties. Based on the excellent ECL activity of ABEI-AuNDs-cs-MWCNTs and the good electro-transfer property of MWCNTs and film-forming property of chitosan, a novel label-free ECL biosensor was developed and has an extremely sensitive response to mercury ions in a liner range of1.0×10-6mol/～1.0×10-8mol/L, and the detection limit was3.2×10-9mol/L.
3. A novel lable-free immunoassay for NT-proBNP was developed based on the ABEI-AuNDs-cs-MWCNTs as ECL sensing platform. ITO-coated glass slides were used as an assembly electrode owing to their stability, easy miniaturization and compatibility with microfabrication. After a centrifugation-ultrasonic dispersion process, ABEI-AuNDs-cs-MWCNTs were dripped onto the surface of ITO glass and ABEI-AuNDs-cs-MWCNTs functionalized ITO electrode was obtained. Glutaraldehyde molecules were used as bridge molecules for anti-NT-proBNP coated on the surface of ITO electrode. After blocking with bovine serum albumin, the electrode could be used as a label-free ECL immunosensor for the detection of NT-proBNP. ECL behavior of the modified electrode was studied by a homemade ECL system. It demonstrated that the ABEI-AuNDs-cs-MWCNTs constructed nano-interface showed high ECL intensity. The as-prepared label-free ECL immunosensor has an extremely sensitive response to NT-proBNP in a liner range of1.0×10-10g/mL-1.0×10-14g/mL with the detection limit of3.86×10-15g/mL. It also shows good precision, acceptable stability and reproducibility. This work provides a promising technique for protein detection, which may open up a new avenue for the ultrasensitive label-free immunoassays.
4. The FL properties of as-prepared ABEI-AuNPs were studied in this work. It was observed that as-prepared ABEI-AuNPs with a concentration of1.23×10-9mol/L displayed comparable FL emission to that of the7.8×10-7mol/L ABEI solution. Although86%of the FL emission of ABEI molecules on the surface of ABEI-AuNPs was inhibited by gold cores through intra-and inter-particle quenching effects, the FL intensity of a gold nanoparticle was still-634times brighter than that of a single ABEI molecule. The as-prepared ABEI-AuNPs also exhibited much better photostability than luminol-AuNPs reported by our previous work.96%FL intensity of as-prepared ABEI-AuNPs solution remained after5min continuous excitation and only80%FL intensity of luminol-AuNPs would be kept in our previous work. Furthermore, almost70%FL intensity of ABEI-AuNPs still remained after45min. Moreover, ABEI-AuNPs and acriflavine were successfully used as energy donor and energy acceptor, respectively, to construct a novel FRET system. And an efficient energy transfer from ABEI-AuNPs to acriflavine in the solution was observed. This work demonstrates for the first time that ABEI functionalized gold nanomaterials could be used as energy donor. Taking advantage of excellent labeling property of gold nanomaterials, the FRET property between ABEI-AuNPs and acriflavine may find future applications in bioassays with FL detection.
1.在室温乙醇溶液中,采用种晶生长法,利用ABEI还原硫辛酸和氯金酸,发展了一种制备高发光效率的爆米花状发光试剂功能化金纳米材料的简单合成方法。借助透射电子显微镜等仪器分析手段对合成的金纳米材料的形貌进行了表征,结果显示该方法成功制备了爆米花状、准球形、不规则多面体等形貌金纳米材料。进一步,通过X射线电子能谱等仪器手段对产物的表面化学组成进行了表征。结果表明,ABEI、ABEI的氧化产物通过Au-N键连接于金纳米表面,硫辛酸的还原产物通过Au-S键连接于金纳米表面。对于所合成的爆米花状金纳米粒子,其表面密布的不规则凸起使其具有更大的比较面积,在化学发光性能上明显优于前期合成的球形ABEI功能化金纳米材料。尤为重要的是,爆米花状金纳米材料可以标记生物分子如蛋白质和DNA,制备的生物探针仍具有良好的化学发光活性。这种化学发光功能化的生物探针能够被用于生物测定和临床诊断中,对公共健康、食品安全及环境监测等均具有重要意义。
2.采用一步合成法成功制备了高密度ABEI功能化金纳米点功能化的碳纳米管。实验中先将壳聚糖吸附于羧基化碳纳米管,分离纯化后与氯金酸溶液混合均匀,而后加入ABEI溶液还原氯金酸,ABEI与碳管表面壳聚糖同时作为保护试剂连接于金纳米点表面,制备了ABEI功能化纳米点/壳聚糖/碳纳米管复合材料。借助透射电子显微镜、高角环形暗场扫描透射原子成像技术、X射线能谱仪、X射线光电子能谱和拉曼光谱等仪器手段对所合成复合材料形貌及表面特性进行了表征。分析结果表明ABEI功能化的金纳米点高密度、均匀的分布于碳纳米管表面。进一步我们研究了ABEI功能化纳米点/壳聚糖/碳纳米管复合材料的化学发光性能,结果表明该复合材料具有良好的化学发光和电致化学发光特性。基于ABEI高效的化学发光特性、壳聚糖良好的成膜特性和碳纳米管良好的导电性能,利用合成的ABEI功能化纳米点/壳聚糖/碳纳米管复合材料构建了一种新型无标记适配体传感器,并成功实现了对水体样本中的汞离子的高灵敏、特异性的测定,线性范围为1.0×10～1.0×10-8mol/L,检测限为3.2x10-9mol/L。
3.基于前一章工作所合成的ABEI功能化金纳米点-壳聚糖-多壁碳纳米管复合材料,我们构建了电致化学发光活性传感平台,发展一种无标记免疫分析新方法用于测定氨基末端脑钠肽前体(NT-proBNP).基于氧化铟锡(Indium tin oxide, ITO)玻片电极,通过简单的滴加将经过纯化处理的复合材料滴涂于ITO电极表面,复合材料中的壳聚糖具有很好的成膜性,能够将材料稳定的固载于电极表面,同时复合材料具有优良的电致化学发光特性,作为电化学发光活性基底。而后利用戊二醛作为连接分子将人NT-proBNP单克隆抗体修饰于复合材料表面,并用牛血清蛋白对上述界面未反应的活性位点进行封闭,该修饰电极即可作为一种无标记电致化学发光免疫传感器,用于检测NT-proBNP。实验中通过监测电致化学行为对传感器的构建过程进行了表征。结果表明,该复合材料功能化的纳米界面具有良好的电致化学发光性质和电子传导能力。该传感器用于检测目标抗原NT-proBNP时展现了较宽的线性范围1.0×10-10g/mL-1.0×10-14g/mL和较低的检测限3.86×10-15g/mL。此外,研究表明该传感器具有良好的精确度、稳定性和重现性。本研究为蛋白质的检测提供了一种简单、快速、灵敏的检测方法,为无标记免疫传感器开辟了新的途径。
4.研究了ABEI功能化金纳米粒子的荧光特性。研究结果表明ABEI功能化金纳米粒子作为纳米光学探针具有以下重要优点。第一,1.23×10-9mol/L的ABEI功能化金纳米粒子具有与7.8×10-7mol/L ABEI纯溶液可比拟的荧光发射强度。虽然功能化金纳米粒子之间存在粒子间淬灭效应、金纳米核对其表面的ABEI分子存在粒子内淬灭效应,但一个功能化金纳米粒子的荧光强度仍比单个ABEI分子强634倍。此外,纳米金具有良好的标记性能,这对将ABEI功能化金纳米粒子用作荧光探针具有重要的意义。第二,ABEI功能化金纳米粒子表现了良好的抗光漂白特性,性能优于实验室前期合成的鲁米诺功能化金纳米粒子。在激发光源持续照射45分钟后,ABEI功能化金纳米粒子仍保留70%的荧光发射强度。此外,我们将ABEI功能化金纳米作为能量给体,将吖啶黄作为能量受体,开发了一种新颖的荧光共振能量转移体系。研究表明,在不需要额外添加连接分子的情况下,二者在水溶液中就能发生有效的荧光共振能量转移。本章工作首次提出将发光试剂功能化金属纳米材料用作共振能量转移的能量给体。基于金纳米材料优良的标记特性,ABEI功能化金纳米材料-吖啶黄共振能量转移对有望应用于荧光相关的生物分析测定中。
In this dissertation, the state of arts in the field of chemiluminescence (CL), chemiluminescent functionalized nanomaterials (CF-NMs) and their applications in bioassays were reviewed. Recently, much attention has been paid to CF-NMs and a series of CF-NMs have been synthesized. The analytical method based on CL-NMs as analytical probes and analytical interface is developed rapidly, showing promising application potential in clinical diagnosis, food safety, environmental monitoring etc. However, the CL efficiency of CF-NMs is limited and it remains great challenge for the detection of trace substance in the biological systems. The aim of this dissertation is to explore the synthesis of CF-NMs with high CL yield and their applications in label-free bioassays. N-(aminobytyl)-N-(ethylisoluminol)(ABEI) functionalized gold nanopopcorns and ABEI functionalized gold nanodots onto chitosan-grafted multi-walled carbon nanotubes (ABEI-AuNDs-cs-MWCNTs) were successfully synthesized. These nanocomposites exhibited excellent CL and electrochemiluminescence (ECL) properties. Based on the as-prepared CF-NMs, novel label-free ECL biosensors for highly sensitive and selective detection of mercury and N-terminal of the prohormone brain natriuretic peptide (NT-proBNP) were developed based on the target-induced directed ECL signal change. Besides, the fluorescence property of ABEI functionalized gold nanoparticles (ABEI-AuNPs) and applications of ABEI-AuNPs in fluorescence resonance energy transfer were studied. The main results are as follows:
1. A facile method for the synthesis of popcorn-shaped gold nanomaterials (GNMs) with high CL yield and good monodispersity by reducing LA and HAuCl4with ABEI in ethyl alcohol solution at room temperature through a seed growth method was reproted. The morphologies of GNMs were characterized by transmission electron microscopy, scanning electron microscopy and energy dispersive spectroscopy. The results showed that various morphologies of GNMs from gold nanopopcorns (AuNPCs), quasi-spherical to irregular GNMs could be obtained. The surface composition of AuNPCs was studied and the results strongly supported that ABEI, the oxidation product of ABEI and reduction product of LA were attached to a gold core by covalent bonds. A possible mechanism of shape evolution is proposed. The special morphology of AuNPCs maintains the large specific surface area and provides excellent catalytic property when involved in the CL reaction. Thus the CL functionalized AuNPCs exhibited good CL property (two orders of magnitude higher than that of ABEI functionalized gold nanoparticles in our previous work). Furthermore, DNA and protein labeled with AuNPCs showed excellent CL activity, which implies their application potential as bio-probes for immunoassay and DNA assay.
2. A one-step strategy for high-density assembly of ABEI functionalized gold nanodots onto the sidewalls of chitosan-grafted multi-walled carbon nanotubes (ABEI-AuNDs-cs-MWCNTs) via the reduction of HAuCl4with ABEI in the presence of cs-MWCNTs. During the synthesis process, a great number of ABEI molecules as stabilizers were directly coated on the surface of ABEI-AuNDs-cs-MWCNTs. The morphology and surface composition of ABEI-AuNDs-cs-MWCNTs were studied by transmission electron microscopy, energy dispersive spectroscopy, X-ray photoelectron spectroscopy and Raman spectra. The results showed that ABEI-AuNDs uniformly distributed on the surface of composites. Furthermore, the CL and ECL properties of ABEI-AuNDs-cs-MWCNTs were studied and ABEI-AuNDs-cs-MWCNTs exhibited excellent CL and ECL properties. Based on the excellent ECL activity of ABEI-AuNDs-cs-MWCNTs and the good electro-transfer property of MWCNTs and film-forming property of chitosan, a novel label-free ECL biosensor was developed and has an extremely sensitive response to mercury ions in a liner range of1.0×10-6mol/～1.0×10-8mol/L, and the detection limit was3.2×10-9mol/L.
3. A novel lable-free immunoassay for NT-proBNP was developed based on the ABEI-AuNDs-cs-MWCNTs as ECL sensing platform. ITO-coated glass slides were used as an assembly electrode owing to their stability, easy miniaturization and compatibility with microfabrication. After a centrifugation-ultrasonic dispersion process, ABEI-AuNDs-cs-MWCNTs were dripped onto the surface of ITO glass and ABEI-AuNDs-cs-MWCNTs functionalized ITO electrode was obtained. Glutaraldehyde molecules were used as bridge molecules for anti-NT-proBNP coated on the surface of ITO electrode. After blocking with bovine serum albumin, the electrode could be used as a label-free ECL immunosensor for the detection of NT-proBNP. ECL behavior of the modified electrode was studied by a homemade ECL system. It demonstrated that the ABEI-AuNDs-cs-MWCNTs constructed nano-interface showed high ECL intensity. The as-prepared label-free ECL immunosensor has an extremely sensitive response to NT-proBNP in a liner range of1.0×10-10g/mL-1.0×10-14g/mL with the detection limit of3.86×10-15g/mL. It also shows good precision, acceptable stability and reproducibility. This work provides a promising technique for protein detection, which may open up a new avenue for the ultrasensitive label-free immunoassays.
4. The FL properties of as-prepared ABEI-AuNPs were studied in this work. It was observed that as-prepared ABEI-AuNPs with a concentration of1.23×10-9mol/L displayed comparable FL emission to that of the7.8×10-7mol/L ABEI solution. Although86%of the FL emission of ABEI molecules on the surface of ABEI-AuNPs was inhibited by gold cores through intra-and inter-particle quenching effects, the FL intensity of a gold nanoparticle was still-634times brighter than that of a single ABEI molecule. The as-prepared ABEI-AuNPs also exhibited much better photostability than luminol-AuNPs reported by our previous work.96%FL intensity of as-prepared ABEI-AuNPs solution remained after5min continuous excitation and only80%FL intensity of luminol-AuNPs would be kept in our previous work. Furthermore, almost70%FL intensity of ABEI-AuNPs still remained after45min. Moreover, ABEI-AuNPs and acriflavine were successfully used as energy donor and energy acceptor, respectively, to construct a novel FRET system. And an efficient energy transfer from ABEI-AuNPs to acriflavine in the solution was observed. This work demonstrates for the first time that ABEI functionalized gold nanomaterials could be used as energy donor. Taking advantage of excellent labeling property of gold nanomaterials, the FRET property between ABEI-AuNPs and acriflavine may find future applications in bioassays with FL detection.
引文
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