基于核酸修饰电极的新型电化学生物传感器
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摘要
快速、廉价、高灵敏度和高选择性检测生命活动相关的蛋白质与小分子、疾病相关的特征DNA序列以及环境毒性污染物是现代生物化学分析的重要课题,这一多学科的共性目标促使了生物传感器的出现和发展。电化学核酸传感器是一类以核酸分子作为识别元素,以电极作为信号转换器的生物传感器。核酸分子探针具有结构简单、特异性强、靶物质分子广泛和易于大量商业化合成的优点。电化学核酸传感器结合了核酸探针的优异性能和电化学检测方法的高灵敏度特性,在现代生物传感器研究领域中处于主体地位。核酸探针在电极表面的稳定固定、探针与目标分子间的有效识别以及识别事件的灵敏电化学信号转换,是构建高性能电化学核酸传感器的三个关键问题。此外,发掘核酸修饰电极的新性能、设计与制备新型核酸探针,对于扩大电化学核酸传感器的应用范围和开发新型高效传感系统具有重要的意义。本论文围绕这些电化学核酸传感器研究中的共性问题,在核酸修饰电极的新用途、核酸探针固定新方法和高灵敏度信号转换方法以及新型核酸探针设计等方面开展了一系列的研究工作,主要内容如下：
(1)多巴胺在电沉积DNA修饰电极表面的电催化氧化检测双链DNA是一种具有规则双螺旋结构的阴离子聚合物,广泛用作合成导电聚合物和金属纳米材料的分子模板。第2章的研究工作采用一步电沉积的方法将小牛胸腺DNA沉积于玻碳电极表面制成表面负电性的DNA修饰电极。修饰电极表面的负电性DNA分子层对中性pH值溶液中正电性的多巴胺分子表现出明显的静电吸附富集作用,可显著增强多巴胺分子的直接电化学氧化电流；同时该电沉积DNA修饰电极可以有效地分离多巴胺与电活性干扰组分抗坏血酸和尿酸的电化学氧化峰。基于电沉积DNA修饰电极这种选择性电催化氧化多巴胺分子的性质,发展了一种简单、快速、高灵敏度和高选择性的多巴胺电化学检测方法,有效地拓展了核酸修饰电极的应用范围。
(2)基于T-Hg(Ⅱ)-T络合与酶催化信号放大的电化学汞离子传感器酶催化信号放大是生物传感器系统中常用的一种高灵敏度信号转换手段,现己广泛应用于免疫传感和核酸分析。第3章的研究工作将酶催化信号放大引入基于汞离子特异核酸修饰电极的电化学传感体系中,根据碱基互补配对原则和T-Hg(Ⅱ)-T络合原理设计了两条汞离子特异的核酸探针,包括巯基固定基团标记的捕获核酸探针和生物素分子标记的信号核酸探针。利用T-Hg(Ⅱ)-T络合调节的核酸探针杂交和生物素-亲核素结合系统将链酶亲和素标记的辣根过氧化酶(streptavidin-horseradish peroxidase,S-HRP)固定于电极表面,固定化的S-HRP催化过氧化氢将对苯酚氧化为对苯醌,氧化性的酶催化产物对苯醌进一步在基底电极表面被电化学还原,提供用于Hg2+定量分析的放大电流信号。该酶催化信号放大电化学传感器对汞离子的检测表现出很高的灵敏度和选择性,汞离子浓度检测线性范围为0.5nM～1μM,检测限可低至0.3nM。
(3)基于乌嘌呤四股螺旋-血红素络合物电化学催化信号放大的汞离子传感器分子内包含重复鸟嘌呤碱基(guanine,G)单元的核酸链可与血红素分子(hemin)形成具有类似于辣根过氧化酶催化活性的鸟嘌呤四股螺旋-血红素络合物(G4-Hemin).在第4章,研究了通过核酸杂交固定于金电极表面的G4-Hemin络合物的电化学性质,发现G4-Hemin络合物在金电极表面表现出直接的电化学行为,并且可以显著催化过氧化氢的电化学还原。基于G4-Hemin络合物的电化学催化性质,设计了一条同时包含Hg2+特异碱基序列和G4序列的信号核酸探针,该信号核酸探针可以选择性识别Hg2+,同时可结合Hemin形成电化学催化信号标记。基于该新型核酸探针,成功地构建了一个无需共价修饰信号标记、电化学催化信号放大的高灵敏度和高选择性电化学汞离子传感器。
(4)基于分子识别调节碳纳米管隧道电流效应的电化学传感平台经由疏水作用吸附于烷基硫醇白组装层上的碳纳米管可以恢复电活性探针铁氰化钾被烷基硫醇绝缘单分子层抑制的氧化还原电流,表现出碳纳米管的“隧道电流效应”；单链核酸可通过分子内碱基与碳纳米管管壁间的π-π共轭作用稳定地结合于碳纳米管表而。第5章的研究工作发现烷基硫醇自组装层上碳纳米管吸附层的“隧道电流效应”可通过碳纳米管表面结合的单链核酸探针与目标分予间的识别反应进行灵活的调节,即核酸探针与目标分子之间的结合可调控铁氰化钾在碳纳米管吸附层上的隧道电流响应。利用这一独特的性质,开发了一种基于新的核酸探针固定方法和信号转换方法的电化学传感系统,并实现了重金属离子银离子的高灵敏度和高选择性电化学检测。
(5)基于发夹探针与酶催化信号放大的核酸扫描电化学显微镜研究第6章的研究工作针对传统三电极DNA电化学传感体系中工作电极(即DNA修饰电极)表面电化学惰性常常造成电化学响应信号灵敏度损失的缺点,尝试将四电极体系的扫描电化学显微镜(scanning electrochemical microscopy,SECM)引入DNA电化学传感器的设计与制备。在该SECM核酸传感体系中,末端分别标记巯基基团和生物素分子的发夹DNA探针通过自组装的方法固定于金电极表面,目标DNA与发夹探针的杂交导致发夹探针末端的生物素分子暴露于电极表面,进一步通过生物素-亲和素结合系统将链酶亲和素标记的辣根过氧化酶(streptavidin-horseradish peroxidase,S-HRP)固定,电极表面固定化的S-HRP催化过氧化氢氧化对苯二酚生成大量电化学氧化活性的对苯醌,然后采用SECM的“基底产生-探针收集”工作模式监测酶催化产物对苯醌的还原电流并以此实现对目标DNA的定量分析和电化学扫描成像。该SECM传感体系对目标DNA的检测限可低至17pM,并且对碱基错配具有良好的区分能力。
The quick, low-cost, highly sensitive and selective detection of biologically active proteins and small molecules, pathogenically associated sequence-specific nucleic acids and highly toxic heavy metal ions is one of the most important and attractive topics in modern biochemical analysis, which has activated the development of biosensors. An electrochemical nucleic acid-based biosensor is a biosensor that integrates an nucleic acid as the biological recognition element and an electrode as the physicochemical transducer. Electrochemical nucleic acid-based biosensor combines the high specificity of nucleic acid probes and the excellent sensitivity of electrochemical detection techniques; it has become the most important branch of biosensors. Typically, the design of an electrochemical nucleic acid-based biosensor includes three key steps:immobilization of the nucleic acid probe, interaction with the target molecule and electrochemical signal transduction of the molecular recognition event. Optimization of each step is required to improve the overall performance of the devices. For the development of novel electrochemical nucleic acid-based biosensors that meet the challenges of modern biochemical analysis, it is essential to explore new properties and application of the nucleic acid-modified electrodes, to construct simple and effective methods for immobilizing of the nucleic acid probes and highly sensitive signal transduction of the molecular recognition event. Focused on these basic items in the development of high-performance electrochemical nucleic acid-based biosensors, the extending application of nucleic acid-modified electrodes to new bioanalysis, the design of novel nucleic acid probes and the novel strategies for immobilizing nucleic acid probes and amplifying sensing signals have been investigated in the present dissertation and described as follows:
In chapter2, A DNA-modified glass carbon electrode (DNA-GCE) obtained by one-step electrodeposition was developed for electrochemical detection of dopamine (DA). The negatively charged DNA film electrodeposited on the GCE could electrostatically attract the positively charged DA in neutral buffer solution (pH:7.0), which greatly increased the electrochemical oxidation current of DA. The common overlapped oxidation peaks of DA and ascorbic acid were separated completely on the DNA-GCE. Based on this selective electrocatalysis of the DNA-GCE toward the oxidation of DA, a highly sensitive and selective electrochemical platform has been successfully established for DA detection.
In chapter3, a novel electrochemical sensor for Hg2+detection was developed using two mercury-specific oligonucleotide probes and streptavidin-horseradish peroxidase (HRP) enzymatic signal amplification. The two mercury-specific oligonucleotide probes comprised a thiolated capture probe and a biotinated signal probe. The thiolated capture probe was immobilized on a gold electrode. In the presence of Hg2+, the thymine-Hg2+-thymine (T-Hg2+-T) interaction between the mismatched T-T base pairs directed the biotinated signal probe hybridizing to the capture probe and yielded a biotin-functioned electrode surface. HRP was then immobilized on the biotin-modified substrate via biotin-streptavidin interaction. The immobilized HRP catalyzed the oxidation of hydroquinone (H2Q) to benzoquinone (BQ) by hydrogen peroxide and the generated BQ was further electrochemically reduced at the modified gold electrode, producing a readout signal for quantitative detection of Hg2+. The results showed that the enzyme-amplified electrochemical sensor system was highly sensitive to Hg2+in the concentration of0.5nM to1μM with a detection limit of0.3nM, and it also demonstrated excellent selectivity against other interferential metal ions.
In chapter4, a novel electrochemical catalytic biosensor for sensitive and selective detecting of Hg2+was developed. To construct the electrochemical catalytic Hg2+sensing system, a thiolated, mercury-specific oligonucleotide capture probe was first immobilized on gold electrode surface. In the presence of Hg2+, a oligonucleotide signal probe integrating a mercury-specific oligonucleotide sequence and a G-quadruplex (G4) sequence was then captured on the gold electrode surface through the thymine-mercury(Ⅱ)-thymine interaction-mediated surface hybridization. The further interaction of the immobilized G4sequence with hemin generated a G4-Hemin complex monolayer. The G4-Hemin units exhibited good electrochemical catalytic activity toward the electrochemical reduction of hydrogen peroxide, producing amplified readout signals for Hg2+sensing events. The electrochemical catalytic Hg2+sensor system was highly sensitive and selective to Hg2+in the concentration of1.0nM to1μM with a detection limit of0.5nM. This simple and effective electrochemical catalytic sensor system provides a potential alternative for Hg2+assay.
In chapter5, the electrochemical redox behavior of ferricyanide at the dodecanethiol modified electrode (H25C12S-Au), the single-walled carbon nanotube-dodecanethiol modified electrode (SWCNT-H25C12S-Au) and the single-stranded DNA-single-walled carbon nanotube-dodecanethiol modified electrode (ssDNA-SWCNT-H25C12S-Au) was thoroughly investigated. The results showed that SWCNT adsorbed on the surface of the H25C12S-Au could restore the restrained redox current of ferricyanide on the H25C12S-Au modified electrode, and this so-called "tunneling current effect" could be flexibly mediated by C-Ag+-C interaction between Ag+and the Ag+-specific oligonucleotide probe adsorbed on the sidewall of SWCNT. Based on this unique phenomenon, a sensitive, selective and simple electrochemical platform for Ag+detection was successfully developed.
In chapter6, a novel scheme for scanning electrochemical microscopy (SECM) assay of DNA based on molecular beacon (MB) and enzymatic amplification biosensor was described. In this method, streptavidin-horseradish peroxidase (HRP) was captured by double-stranded DNA (ds-DNA) modified gold substrate via biotin-streptavidin interaction after hybridization of target DNA to the immobilized MB probe functioned with a biotin at its3'-end. In the presence of H2O2, hydroquinone (H2Q) was oxidized to benzoquinone (BQ) at the modified substrate surface through the HRP catalytic reaction, and then the generated BQ corresponding to the amount of target DNA was electrochemically reduced by a SECM tip. The resulting reduction current allowed sensitive concentration determination of target DNA and SECM imaging of hybridization between the target DNA and the immobilized MB probe. The detection limit of this method was as low as17pM for the complementary target DNA and it has good selectivity to discriminate between the complementary target and the sequence containing mismatched bases.
(1)多巴胺在电沉积DNA修饰电极表面的电催化氧化检测双链DNA是一种具有规则双螺旋结构的阴离子聚合物,广泛用作合成导电聚合物和金属纳米材料的分子模板。第2章的研究工作采用一步电沉积的方法将小牛胸腺DNA沉积于玻碳电极表面制成表面负电性的DNA修饰电极。修饰电极表面的负电性DNA分子层对中性pH值溶液中正电性的多巴胺分子表现出明显的静电吸附富集作用,可显著增强多巴胺分子的直接电化学氧化电流；同时该电沉积DNA修饰电极可以有效地分离多巴胺与电活性干扰组分抗坏血酸和尿酸的电化学氧化峰。基于电沉积DNA修饰电极这种选择性电催化氧化多巴胺分子的性质,发展了一种简单、快速、高灵敏度和高选择性的多巴胺电化学检测方法,有效地拓展了核酸修饰电极的应用范围。
(2)基于T-Hg(Ⅱ)-T络合与酶催化信号放大的电化学汞离子传感器酶催化信号放大是生物传感器系统中常用的一种高灵敏度信号转换手段,现己广泛应用于免疫传感和核酸分析。第3章的研究工作将酶催化信号放大引入基于汞离子特异核酸修饰电极的电化学传感体系中,根据碱基互补配对原则和T-Hg(Ⅱ)-T络合原理设计了两条汞离子特异的核酸探针,包括巯基固定基团标记的捕获核酸探针和生物素分子标记的信号核酸探针。利用T-Hg(Ⅱ)-T络合调节的核酸探针杂交和生物素-亲核素结合系统将链酶亲和素标记的辣根过氧化酶(streptavidin-horseradish peroxidase,S-HRP)固定于电极表面,固定化的S-HRP催化过氧化氢将对苯酚氧化为对苯醌,氧化性的酶催化产物对苯醌进一步在基底电极表面被电化学还原,提供用于Hg2+定量分析的放大电流信号。该酶催化信号放大电化学传感器对汞离子的检测表现出很高的灵敏度和选择性,汞离子浓度检测线性范围为0.5nM～1μM,检测限可低至0.3nM。
(3)基于乌嘌呤四股螺旋-血红素络合物电化学催化信号放大的汞离子传感器分子内包含重复鸟嘌呤碱基(guanine,G)单元的核酸链可与血红素分子(hemin)形成具有类似于辣根过氧化酶催化活性的鸟嘌呤四股螺旋-血红素络合物(G4-Hemin).在第4章,研究了通过核酸杂交固定于金电极表面的G4-Hemin络合物的电化学性质,发现G4-Hemin络合物在金电极表面表现出直接的电化学行为,并且可以显著催化过氧化氢的电化学还原。基于G4-Hemin络合物的电化学催化性质,设计了一条同时包含Hg2+特异碱基序列和G4序列的信号核酸探针,该信号核酸探针可以选择性识别Hg2+,同时可结合Hemin形成电化学催化信号标记。基于该新型核酸探针,成功地构建了一个无需共价修饰信号标记、电化学催化信号放大的高灵敏度和高选择性电化学汞离子传感器。
(4)基于分子识别调节碳纳米管隧道电流效应的电化学传感平台经由疏水作用吸附于烷基硫醇白组装层上的碳纳米管可以恢复电活性探针铁氰化钾被烷基硫醇绝缘单分子层抑制的氧化还原电流,表现出碳纳米管的“隧道电流效应”；单链核酸可通过分子内碱基与碳纳米管管壁间的π-π共轭作用稳定地结合于碳纳米管表而。第5章的研究工作发现烷基硫醇自组装层上碳纳米管吸附层的“隧道电流效应”可通过碳纳米管表面结合的单链核酸探针与目标分予间的识别反应进行灵活的调节,即核酸探针与目标分子之间的结合可调控铁氰化钾在碳纳米管吸附层上的隧道电流响应。利用这一独特的性质,开发了一种基于新的核酸探针固定方法和信号转换方法的电化学传感系统,并实现了重金属离子银离子的高灵敏度和高选择性电化学检测。
(5)基于发夹探针与酶催化信号放大的核酸扫描电化学显微镜研究第6章的研究工作针对传统三电极DNA电化学传感体系中工作电极(即DNA修饰电极)表面电化学惰性常常造成电化学响应信号灵敏度损失的缺点,尝试将四电极体系的扫描电化学显微镜(scanning electrochemical microscopy,SECM)引入DNA电化学传感器的设计与制备。在该SECM核酸传感体系中,末端分别标记巯基基团和生物素分子的发夹DNA探针通过自组装的方法固定于金电极表面,目标DNA与发夹探针的杂交导致发夹探针末端的生物素分子暴露于电极表面,进一步通过生物素-亲和素结合系统将链酶亲和素标记的辣根过氧化酶(streptavidin-horseradish peroxidase,S-HRP)固定,电极表面固定化的S-HRP催化过氧化氢氧化对苯二酚生成大量电化学氧化活性的对苯醌,然后采用SECM的“基底产生-探针收集”工作模式监测酶催化产物对苯醌的还原电流并以此实现对目标DNA的定量分析和电化学扫描成像。该SECM传感体系对目标DNA的检测限可低至17pM,并且对碱基错配具有良好的区分能力。
The quick, low-cost, highly sensitive and selective detection of biologically active proteins and small molecules, pathogenically associated sequence-specific nucleic acids and highly toxic heavy metal ions is one of the most important and attractive topics in modern biochemical analysis, which has activated the development of biosensors. An electrochemical nucleic acid-based biosensor is a biosensor that integrates an nucleic acid as the biological recognition element and an electrode as the physicochemical transducer. Electrochemical nucleic acid-based biosensor combines the high specificity of nucleic acid probes and the excellent sensitivity of electrochemical detection techniques; it has become the most important branch of biosensors. Typically, the design of an electrochemical nucleic acid-based biosensor includes three key steps:immobilization of the nucleic acid probe, interaction with the target molecule and electrochemical signal transduction of the molecular recognition event. Optimization of each step is required to improve the overall performance of the devices. For the development of novel electrochemical nucleic acid-based biosensors that meet the challenges of modern biochemical analysis, it is essential to explore new properties and application of the nucleic acid-modified electrodes, to construct simple and effective methods for immobilizing of the nucleic acid probes and highly sensitive signal transduction of the molecular recognition event. Focused on these basic items in the development of high-performance electrochemical nucleic acid-based biosensors, the extending application of nucleic acid-modified electrodes to new bioanalysis, the design of novel nucleic acid probes and the novel strategies for immobilizing nucleic acid probes and amplifying sensing signals have been investigated in the present dissertation and described as follows:
In chapter2, A DNA-modified glass carbon electrode (DNA-GCE) obtained by one-step electrodeposition was developed for electrochemical detection of dopamine (DA). The negatively charged DNA film electrodeposited on the GCE could electrostatically attract the positively charged DA in neutral buffer solution (pH:7.0), which greatly increased the electrochemical oxidation current of DA. The common overlapped oxidation peaks of DA and ascorbic acid were separated completely on the DNA-GCE. Based on this selective electrocatalysis of the DNA-GCE toward the oxidation of DA, a highly sensitive and selective electrochemical platform has been successfully established for DA detection.
In chapter3, a novel electrochemical sensor for Hg2+detection was developed using two mercury-specific oligonucleotide probes and streptavidin-horseradish peroxidase (HRP) enzymatic signal amplification. The two mercury-specific oligonucleotide probes comprised a thiolated capture probe and a biotinated signal probe. The thiolated capture probe was immobilized on a gold electrode. In the presence of Hg2+, the thymine-Hg2+-thymine (T-Hg2+-T) interaction between the mismatched T-T base pairs directed the biotinated signal probe hybridizing to the capture probe and yielded a biotin-functioned electrode surface. HRP was then immobilized on the biotin-modified substrate via biotin-streptavidin interaction. The immobilized HRP catalyzed the oxidation of hydroquinone (H2Q) to benzoquinone (BQ) by hydrogen peroxide and the generated BQ was further electrochemically reduced at the modified gold electrode, producing a readout signal for quantitative detection of Hg2+. The results showed that the enzyme-amplified electrochemical sensor system was highly sensitive to Hg2+in the concentration of0.5nM to1μM with a detection limit of0.3nM, and it also demonstrated excellent selectivity against other interferential metal ions.
In chapter4, a novel electrochemical catalytic biosensor for sensitive and selective detecting of Hg2+was developed. To construct the electrochemical catalytic Hg2+sensing system, a thiolated, mercury-specific oligonucleotide capture probe was first immobilized on gold electrode surface. In the presence of Hg2+, a oligonucleotide signal probe integrating a mercury-specific oligonucleotide sequence and a G-quadruplex (G4) sequence was then captured on the gold electrode surface through the thymine-mercury(Ⅱ)-thymine interaction-mediated surface hybridization. The further interaction of the immobilized G4sequence with hemin generated a G4-Hemin complex monolayer. The G4-Hemin units exhibited good electrochemical catalytic activity toward the electrochemical reduction of hydrogen peroxide, producing amplified readout signals for Hg2+sensing events. The electrochemical catalytic Hg2+sensor system was highly sensitive and selective to Hg2+in the concentration of1.0nM to1μM with a detection limit of0.5nM. This simple and effective electrochemical catalytic sensor system provides a potential alternative for Hg2+assay.
In chapter5, the electrochemical redox behavior of ferricyanide at the dodecanethiol modified electrode (H25C12S-Au), the single-walled carbon nanotube-dodecanethiol modified electrode (SWCNT-H25C12S-Au) and the single-stranded DNA-single-walled carbon nanotube-dodecanethiol modified electrode (ssDNA-SWCNT-H25C12S-Au) was thoroughly investigated. The results showed that SWCNT adsorbed on the surface of the H25C12S-Au could restore the restrained redox current of ferricyanide on the H25C12S-Au modified electrode, and this so-called "tunneling current effect" could be flexibly mediated by C-Ag+-C interaction between Ag+and the Ag+-specific oligonucleotide probe adsorbed on the sidewall of SWCNT. Based on this unique phenomenon, a sensitive, selective and simple electrochemical platform for Ag+detection was successfully developed.
In chapter6, a novel scheme for scanning electrochemical microscopy (SECM) assay of DNA based on molecular beacon (MB) and enzymatic amplification biosensor was described. In this method, streptavidin-horseradish peroxidase (HRP) was captured by double-stranded DNA (ds-DNA) modified gold substrate via biotin-streptavidin interaction after hybridization of target DNA to the immobilized MB probe functioned with a biotin at its3'-end. In the presence of H2O2, hydroquinone (H2Q) was oxidized to benzoquinone (BQ) at the modified substrate surface through the HRP catalytic reaction, and then the generated BQ corresponding to the amount of target DNA was electrochemically reduced by a SECM tip. The resulting reduction current allowed sensitive concentration determination of target DNA and SECM imaging of hybridization between the target DNA and the immobilized MB probe. The detection limit of this method was as low as17pM for the complementary target DNA and it has good selectivity to discriminate between the complementary target and the sequence containing mismatched bases.
引文
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