鲁米诺及衍生物功能化的金纳米材料及其在化学发光生物分析中的应用
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摘要
论文首先综述了各种化学发光体系、多种功能化纳米材料合成及性质以及纳米材料参与的化学发光生物分析的研究现状。目前,带有化学发光的功能化纳米金材料的研究受到了人们的关注,但关于其合成的则鲜有报道。目前,构建化学发光功能化金纳米材料的方法是将化学发光分子直接通过桥联分子嫁接到金纳米材料的表面。这些化学发光分子包括钌的配合物和鲁米诺。尽管这些方法对于生物分析有很高的灵敏度,但是仍存在一些缺点。例如,操作过程需要多步反应、沉淀洗涤、减压蒸馏、过滤、分散等多个步骤才能完成,非常麻烦、耗时。这些缺点限制了这些方法的实际可应用性。基于此,本论文以化学发光功能化纳米金材料的合成及其在生物传感器中应用为研究对象。利用化学发光试剂同时作为还原和保护试剂,发展了两种常温下合成发光功能化纳米金材料的方法,制备出既具有金纳米粒子特性又能保持发光试剂发光活性的功能化纳米金材料,并以发光功能化纳米金为基元构建了免疫和DNA生物分析探针,探讨了其在化学发光和电致化学发光生物分析中的应用;分别以发光试剂和发光功能化纳米金为标记物,发展了两种基于纳米金放大技术的超灵敏电致化学发光免疫传感器。主要研究内容如下:
1.基于N-(4-氨基丁基)-N-乙基异鲁米诺为发光标记物和纳米金放大技术,构建了一种新型的电致化学发光免疫传感器测定人免疫球蛋白G(IgG)。首先一抗可以有效的被直接固载到纳米金修饰电极上,然后通过双抗夹心的模式将被测物抗原和ABEI标记的二抗固载到修饰电极上,形成电致化学发光免疫传感器。在双阶脉冲的电化学方式下,对人IgG的检测浓度范围为5 ? 100 ng/mL,以三倍信噪比(S/N = 3)计算,其检测限为1.68 ng/mL。通过平行测定9次浓度为60 ng/mL的人IgG对该免疫传感器重现性进行评价,测定的相对标准偏差为3.79 %。该传感器的使用十分简单,灵敏度高,已被成功用于实际人血清样品中IgG的检测。
2.建立了一种基于鲁米诺功能化纳米金同时作为标记物和发光物以及纳米金和生物素与链酶亲和素体共同放大作用的新型超灵敏电致化学发光免疫传感器。生物素化的一抗可以有效的被固载到连有链酶亲和素的纳米金修饰电极上,抗原和鲁米诺功能化纳米金标记的二抗随后通过双抗夹心的模式被进一步的固载到修饰电极上,从而得到电致化学发光免疫传感器。在双阶脉冲电压的电化学方式下,在含有1 mmol/L过氧化氢的0.02 mol/L pH=9.8碳酸盐缓冲为工作液中,该免疫传感器表现出极好的电致化学发光信号响应。利用电致化学发光强度,测定人IgG的线性范围为7.5 ? 100 pg/mL,以三倍信噪比(S/N = 3)计算,检测限为1.0 pg/mL。通过平行测定9次浓度分别为30、50、70 pg/mL的人IgG对该免疫传感器重现性进行评价,所得到的相对标准偏差的结果分别为4.4%、2.1%、2.6%,证实此电致化学发光免疫传感器的重现性较好,该免疫传感器还被成功用于对实际人血清样品中IgG的检测。与分子、酶、量子点和其它纳米金为标记的化学发光免疫分析方法相比,鲁米诺功能化纳米金用于标记时,标记过程十分简单、快速且廉价。在原理上,该传感器可以被应用到其它基于抗原与抗体的生物分子的测定。
3.发现化学发光试剂N-(4-氨基丁基)-N-乙基异鲁米诺能够在水相室温下,通过种子生长法直接还原HAuCl4制备出不同形态的化学发光功能化纳米金材料。这种合成方法非常简单,不需要加入其它的稳定剂和还原试剂。利用紫外-可见吸收光谱、X射线光电子能谱、透射电子显微镜和X射线粉末衍射等分析手段对所合成的金纳米粒子的形貌和表面化学组成进行仔细研究。结果表明随着ABEI的量的增加可得到从球状、球状金纳米颗粒组装的链状、球状金纳米颗粒组装的准网状到球状金纳米颗粒组装的网状的不同形态的金纳米材料。在金与氮之间的弱共价作用下,N-(4-氨基丁基)-N-乙基异鲁米诺及其氧化产物被连接在金纳米颗粒的表面。同时,对所制得具有不同形态的金纳米材料的组装机理也进行了探讨。进一步的研究所合成出的纳米金材料具有优良的化学发光活性,可用于标记生物分子如蛋白质和DNA,制备生物探针,在生物分析中具有广阔的应用前景。
4.在水相常温环境下,以发光试剂异鲁米诺作为还原剂,通过种子诱导生长法还原HAuCl4制备具有特殊形貌(蝌蚪状)的化学发光功能化的金纳米材料。我们通过透射电子显微镜和紫外-可见吸收光谱等分析手段表征和研究了所合成的蝌蚪状金纳米粒子的形貌及状态。实验发现,种子溶液和硝酸银的用量、异鲁米诺及十六烷基三甲基溴化铵的浓度对所合成的蝌蚪状金纳米材料有重要的影响。随后,对所得蝌蚪状化学发光功能化的金纳米材料生长机机理进行了详细的探讨研究。通过紫外-可见吸收光谱和荧光光谱研究了本工作所合成的金纳米材料的表面化学成分,结果发现蝌蚪状金纳米粒子表面存在发光试剂异鲁米诺及其氧化产物。同时,所合成出的蝌蚪状纳米金材料也展现出优良的化学发光活性。
In this dissertation, vatious chemiluminescence systems, the synthesis and properties of chemiluminescent functionalized gold nanomaterials (CF-AuNMs) and their applications in bioassays were reviewed. Recently, CF-AuNMs have been used for various types of biolabeling and life-related molecular diagnostics due to their unique optical, catalytic, and biocompatible properties. However, limited CF-AuNMs have been reported. Currently, the fabrication protocol of CF-GNMs is to graft the CL reagent indirect on the surface of GNMs by virtue of bridge molecules. The used CL reagents include Ru-complex and luminol. Although the protocols can achieve very high sensitivity for bioassays, there are some drawbacks. For example, indirect synthesis process needs several reaction and purification steps, thus is complicated and time-consuming. These problems limit the practical applications of these protocols. Therefore, it is highly desired to exploit the new synthesis strategy for the preparation of new CF-GNMs with high CL efficiency, stability and biocompatibility, which is of great value in the fields such as public health, food safety, and environmental science and so on. In this work, direct synthesis of CF-AuNMs using luminol and its derivatives as reductant and stabilizing reagent and their applications in CL bioassays was explored.The main results are as follows:
1. A novel electrochemiluminescence (ECL) sandwich-type immunosensor for human immunoglobulin G (hIgG) on a gold nanoparticle modified electrode was developed by using N-(aminobutyl)-N-ethylisoluminol (ABEI) labeling. The first goat-anti-human IgG antibody was immobilized on a gold nanoparticle modified electrode, then human IgG and the ABEI-labeled second goat-anti-human IgG antibody was conjugated successively to form a sandwich-type immunocomplex. ECL was carried out with a double-step potential in carbonate buffer solution (CBS) containing 1.5 mM H2O2. The ECL intensity increased linearly with the concentration of hIgG over the range 5.0– 100 ng/mL. The limit of detection was 1.68 ng/mL (S/N = 3). The relative standard deviation was 3.79% at 60 ng/mL (n = 9). The present immunosensor is simple and sensitive. It has been successfully applied to the detection of hIgG in human serums.
2. An ultrasensitive electrochemiluminescence (ECL) immunosensor based on luminol functionalized gold nanoparticle (AuNP) labeling was developed by using human immunoglobulin G (hIgG) as a model analyte. The primary antibody biotin-conjugated goat-anti-human IgG was first immobilized on a streptavidin-coated AuNP modified electrode, then the antigen (human IgG) and the luminol functionalized AuNP-labeled second antibody was conjugated successively to form a sandwich-type immunocomplex, i.e. immunosensor. ECL was carried out with a double-step potential in carbonate buffer solution containing 1.0 mmol/L H2O2. Since thousand of luminol molecules were coated on the surface of AuNPs to realize labeling of multiple molecules with CL activity at a single antibody and the amplification of AuNPs and biotin-streptavidin system were utilized, luminol ECL signal could be enhanced greatly, finally resulting in extremely high sensitivity. The ECL method shows a detection limit of 1.0 pg/mL (S/N = 3) for hIgG, which is superior to all previously reported methods for the determination of hIgG. Moreover, the proposed method is also simple, stable, specific, and time-saving, avoiding the complicated stripping procedure during CL detection and the uncontrollable synthesis of irregular nanoparticles compared with other chemiluminescence immunoassay based on AuNP labeling. Additionally, the labeling procedure is also superior to that of other reported multilabeling strategies, such as Ru complex-encapsulated polymer microspheres, and most of Ru complex-encapsulated liposomes in simplicity, stability, labeling property and practical applicability. Finally, hIgG in human serums was successfully detected by this ECL immunosensor.
3. It was found that the CF-AuNMs could be prepared by reducing HAuCl4 with N-(aminobutyl)-N-ethylisoluminol (ABEI) in aqueous solution at room temperature through a seed growth method. Transmission electron microscopy, UV-visible spectroscopy, X-ray photoelectron spectroscopy, and powder X-ray diffraction analysis were used to characterize the morphology and surface component of the CF-AuNMs. The results indicated that various morphologies (mono-disperse sphericity, assembled chain of sphere AuNPs, assembled qusi-network of sphere AuNPs, assembled network of sphere AuNPs) of CF-AuNMs could be obtained. Moreover, ABEI and N-(aminobutyl)-N-(ethylphthalate) (ABEI’s oxidation product ) were bounded on the surface of the AuNPs through weak Au-N covalent bond. The assembling mechanism of the various morphologies of CF-AuNMs was discussed by theoretical calculation and UV-visible spectroscopy. Finally, the CF-AuNMs exhibited good CL activity in alkaline solution and were successfully applied in bio-probe for bioassays.
4. Iso-luminol functionalized gold nanomaterials (AuNPs) were synthesized in high yield by a simple seeding approach using chemiluminescent (CL) reagent iso-luminol as reductant in the presence of HAuCl4, AgNO3 and cetyltrimethylammonium bromide (CTAB). The morphology characterization of iso-luminol functionalized AuNPs was performed by UV-visible spectroscopy and transmission electron microscopy, showing that tadpole-shaped gold nanoparticles (AuNTps) were obtained. Subsequent experiments reveal that the amounts of added seed colloids, added AgNO3, the concentrations of iso-luminol and CTAB in the growth solution play critical roles in the formation of well shaped AuNTps. The surface state of AuNTps was characterized by UV-visible spectroscopy and fluorescence spectroscopy, indicating that iso-luminol and 4-aminophthalate (iso-luminol’s oxidation product) were bounded on the surface of AuNTps. The CL behavior was studied by static injection CL experiments, demonstrating that AuNTps were of CL activity. Finally, the growth mechanism of AuNTps was also discussed.
1.基于N-(4-氨基丁基)-N-乙基异鲁米诺为发光标记物和纳米金放大技术,构建了一种新型的电致化学发光免疫传感器测定人免疫球蛋白G(IgG)。首先一抗可以有效的被直接固载到纳米金修饰电极上,然后通过双抗夹心的模式将被测物抗原和ABEI标记的二抗固载到修饰电极上,形成电致化学发光免疫传感器。在双阶脉冲的电化学方式下,对人IgG的检测浓度范围为5 ? 100 ng/mL,以三倍信噪比(S/N = 3)计算,其检测限为1.68 ng/mL。通过平行测定9次浓度为60 ng/mL的人IgG对该免疫传感器重现性进行评价,测定的相对标准偏差为3.79 %。该传感器的使用十分简单,灵敏度高,已被成功用于实际人血清样品中IgG的检测。
2.建立了一种基于鲁米诺功能化纳米金同时作为标记物和发光物以及纳米金和生物素与链酶亲和素体共同放大作用的新型超灵敏电致化学发光免疫传感器。生物素化的一抗可以有效的被固载到连有链酶亲和素的纳米金修饰电极上,抗原和鲁米诺功能化纳米金标记的二抗随后通过双抗夹心的模式被进一步的固载到修饰电极上,从而得到电致化学发光免疫传感器。在双阶脉冲电压的电化学方式下,在含有1 mmol/L过氧化氢的0.02 mol/L pH=9.8碳酸盐缓冲为工作液中,该免疫传感器表现出极好的电致化学发光信号响应。利用电致化学发光强度,测定人IgG的线性范围为7.5 ? 100 pg/mL,以三倍信噪比(S/N = 3)计算,检测限为1.0 pg/mL。通过平行测定9次浓度分别为30、50、70 pg/mL的人IgG对该免疫传感器重现性进行评价,所得到的相对标准偏差的结果分别为4.4%、2.1%、2.6%,证实此电致化学发光免疫传感器的重现性较好,该免疫传感器还被成功用于对实际人血清样品中IgG的检测。与分子、酶、量子点和其它纳米金为标记的化学发光免疫分析方法相比,鲁米诺功能化纳米金用于标记时,标记过程十分简单、快速且廉价。在原理上,该传感器可以被应用到其它基于抗原与抗体的生物分子的测定。
3.发现化学发光试剂N-(4-氨基丁基)-N-乙基异鲁米诺能够在水相室温下,通过种子生长法直接还原HAuCl4制备出不同形态的化学发光功能化纳米金材料。这种合成方法非常简单,不需要加入其它的稳定剂和还原试剂。利用紫外-可见吸收光谱、X射线光电子能谱、透射电子显微镜和X射线粉末衍射等分析手段对所合成的金纳米粒子的形貌和表面化学组成进行仔细研究。结果表明随着ABEI的量的增加可得到从球状、球状金纳米颗粒组装的链状、球状金纳米颗粒组装的准网状到球状金纳米颗粒组装的网状的不同形态的金纳米材料。在金与氮之间的弱共价作用下,N-(4-氨基丁基)-N-乙基异鲁米诺及其氧化产物被连接在金纳米颗粒的表面。同时,对所制得具有不同形态的金纳米材料的组装机理也进行了探讨。进一步的研究所合成出的纳米金材料具有优良的化学发光活性,可用于标记生物分子如蛋白质和DNA,制备生物探针,在生物分析中具有广阔的应用前景。
4.在水相常温环境下,以发光试剂异鲁米诺作为还原剂,通过种子诱导生长法还原HAuCl4制备具有特殊形貌(蝌蚪状)的化学发光功能化的金纳米材料。我们通过透射电子显微镜和紫外-可见吸收光谱等分析手段表征和研究了所合成的蝌蚪状金纳米粒子的形貌及状态。实验发现,种子溶液和硝酸银的用量、异鲁米诺及十六烷基三甲基溴化铵的浓度对所合成的蝌蚪状金纳米材料有重要的影响。随后,对所得蝌蚪状化学发光功能化的金纳米材料生长机机理进行了详细的探讨研究。通过紫外-可见吸收光谱和荧光光谱研究了本工作所合成的金纳米材料的表面化学成分,结果发现蝌蚪状金纳米粒子表面存在发光试剂异鲁米诺及其氧化产物。同时,所合成出的蝌蚪状纳米金材料也展现出优良的化学发光活性。
In this dissertation, vatious chemiluminescence systems, the synthesis and properties of chemiluminescent functionalized gold nanomaterials (CF-AuNMs) and their applications in bioassays were reviewed. Recently, CF-AuNMs have been used for various types of biolabeling and life-related molecular diagnostics due to their unique optical, catalytic, and biocompatible properties. However, limited CF-AuNMs have been reported. Currently, the fabrication protocol of CF-GNMs is to graft the CL reagent indirect on the surface of GNMs by virtue of bridge molecules. The used CL reagents include Ru-complex and luminol. Although the protocols can achieve very high sensitivity for bioassays, there are some drawbacks. For example, indirect synthesis process needs several reaction and purification steps, thus is complicated and time-consuming. These problems limit the practical applications of these protocols. Therefore, it is highly desired to exploit the new synthesis strategy for the preparation of new CF-GNMs with high CL efficiency, stability and biocompatibility, which is of great value in the fields such as public health, food safety, and environmental science and so on. In this work, direct synthesis of CF-AuNMs using luminol and its derivatives as reductant and stabilizing reagent and their applications in CL bioassays was explored.The main results are as follows:
1. A novel electrochemiluminescence (ECL) sandwich-type immunosensor for human immunoglobulin G (hIgG) on a gold nanoparticle modified electrode was developed by using N-(aminobutyl)-N-ethylisoluminol (ABEI) labeling. The first goat-anti-human IgG antibody was immobilized on a gold nanoparticle modified electrode, then human IgG and the ABEI-labeled second goat-anti-human IgG antibody was conjugated successively to form a sandwich-type immunocomplex. ECL was carried out with a double-step potential in carbonate buffer solution (CBS) containing 1.5 mM H2O2. The ECL intensity increased linearly with the concentration of hIgG over the range 5.0– 100 ng/mL. The limit of detection was 1.68 ng/mL (S/N = 3). The relative standard deviation was 3.79% at 60 ng/mL (n = 9). The present immunosensor is simple and sensitive. It has been successfully applied to the detection of hIgG in human serums.
2. An ultrasensitive electrochemiluminescence (ECL) immunosensor based on luminol functionalized gold nanoparticle (AuNP) labeling was developed by using human immunoglobulin G (hIgG) as a model analyte. The primary antibody biotin-conjugated goat-anti-human IgG was first immobilized on a streptavidin-coated AuNP modified electrode, then the antigen (human IgG) and the luminol functionalized AuNP-labeled second antibody was conjugated successively to form a sandwich-type immunocomplex, i.e. immunosensor. ECL was carried out with a double-step potential in carbonate buffer solution containing 1.0 mmol/L H2O2. Since thousand of luminol molecules were coated on the surface of AuNPs to realize labeling of multiple molecules with CL activity at a single antibody and the amplification of AuNPs and biotin-streptavidin system were utilized, luminol ECL signal could be enhanced greatly, finally resulting in extremely high sensitivity. The ECL method shows a detection limit of 1.0 pg/mL (S/N = 3) for hIgG, which is superior to all previously reported methods for the determination of hIgG. Moreover, the proposed method is also simple, stable, specific, and time-saving, avoiding the complicated stripping procedure during CL detection and the uncontrollable synthesis of irregular nanoparticles compared with other chemiluminescence immunoassay based on AuNP labeling. Additionally, the labeling procedure is also superior to that of other reported multilabeling strategies, such as Ru complex-encapsulated polymer microspheres, and most of Ru complex-encapsulated liposomes in simplicity, stability, labeling property and practical applicability. Finally, hIgG in human serums was successfully detected by this ECL immunosensor.
3. It was found that the CF-AuNMs could be prepared by reducing HAuCl4 with N-(aminobutyl)-N-ethylisoluminol (ABEI) in aqueous solution at room temperature through a seed growth method. Transmission electron microscopy, UV-visible spectroscopy, X-ray photoelectron spectroscopy, and powder X-ray diffraction analysis were used to characterize the morphology and surface component of the CF-AuNMs. The results indicated that various morphologies (mono-disperse sphericity, assembled chain of sphere AuNPs, assembled qusi-network of sphere AuNPs, assembled network of sphere AuNPs) of CF-AuNMs could be obtained. Moreover, ABEI and N-(aminobutyl)-N-(ethylphthalate) (ABEI’s oxidation product ) were bounded on the surface of the AuNPs through weak Au-N covalent bond. The assembling mechanism of the various morphologies of CF-AuNMs was discussed by theoretical calculation and UV-visible spectroscopy. Finally, the CF-AuNMs exhibited good CL activity in alkaline solution and were successfully applied in bio-probe for bioassays.
4. Iso-luminol functionalized gold nanomaterials (AuNPs) were synthesized in high yield by a simple seeding approach using chemiluminescent (CL) reagent iso-luminol as reductant in the presence of HAuCl4, AgNO3 and cetyltrimethylammonium bromide (CTAB). The morphology characterization of iso-luminol functionalized AuNPs was performed by UV-visible spectroscopy and transmission electron microscopy, showing that tadpole-shaped gold nanoparticles (AuNTps) were obtained. Subsequent experiments reveal that the amounts of added seed colloids, added AgNO3, the concentrations of iso-luminol and CTAB in the growth solution play critical roles in the formation of well shaped AuNTps. The surface state of AuNTps was characterized by UV-visible spectroscopy and fluorescence spectroscopy, indicating that iso-luminol and 4-aminophthalate (iso-luminol’s oxidation product) were bounded on the surface of AuNTps. The CL behavior was studied by static injection CL experiments, demonstrating that AuNTps were of CL activity. Finally, the growth mechanism of AuNTps was also discussed.
引文
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