新型DNA电致化学发光探针及其在DNA分析中的应用研究
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摘要
脱氧核糖核酸(DNA)被称为生命体内的遗传物质，研究发现人类的许多遗传疾病都与DNA分子中碱基序列的变异有关。检测与疾病有关的变异对基因筛选、遗传疾病的早期诊断和治疗具有十分深远的意义。
DNA杂交分析技术是目前生物化学和分子生物学研究中应用最广泛的技术之一，是定性或定量检测特异DNA序列片段的有力工具。目前，它已广泛应用在生命科学，尤其是医学的各个领域。传统的DNA分子杂交采用的是放射性标记的检测方法，这种方法虽然灵敏度高，但存在放射性物质对人体及环境的危害。自20世纪80年代以来，各种非同位素如酶、荧光素、生物素、地高辛标记的化学发光法和荧光分析法以及以电活性物质做标记的电化学方法相继问世，这些方法虽然在一定程度上克服了同位素标记的缺陷，但由于存在灵敏度不够高或检测系统庞杂或仪器价格昂贵或标记物不稳定等缺陷，还不能完全取代传统方法。因此寻求简单、灵敏、可靠、价廉的非放射性标记的DNA检测方法具有十分重要的现实意义。
电致化学发光(ECL)分析是一种通过电极反应而产生化学发光的微量分析方法。它将电化学技术与化学发光检测结合起来，弥补了电化学方法和化学发光方法的不足，具有灵敏度高、选择性好、动力学范围宽、检测快速方便、仪器价格便宜等优点，近几年来在分析化学，尤其在生物分析领域引起了人们的极大关注。本论文通过研究了多种ECL活性物质的发光性能，并以这些物质为标记物制备了多种高灵敏度的DNA-ECL探针，结合DNA杂交技术和DNA固定化技术，将高灵敏度的ECL检测手段应用于生命物质DNA的序列识别及含量测定，为DNA传感器的研究和基因芯片的开发提供了新的思路和方法。
摘要
论文主要研究内容如下:
第一章绪论
简单介绍了ECL分析方法的概念、原理和特点，重点介绍了各种ECL反应
类型及其在分析化学中的应用，系统总结了各种ECL传感器，展望了ECL分析
的未来发展方向。介绍了DNA传感器的构造和各种DNA传感器的原理、特点
及分析应用。最后阐述了本论文的目的和意义，指出论文的创新之处及主要研究
内容。
第二章ECL活性标记物的性能研究及其ECL分析体系的建立
研究了环酞麟类物质N一(4一氨基丁基)一乙基异鲁米诺(ABEI)和鲁米诺
(Luminol)、叮淀酷类物质醛基叮淀酷和竣基叮睫酷、抗癌药物道诺霉素(DNR)
的ECL行为，建立了这几种物质的ECL分析体系，并结合电化学、紫外一可见
光谱、荧光光谱等手段讨论了它们的ECL反应机理，为DNA的ECL分析奠定
了方法基础。
1 ABEI的ECL性能研究及其ECL分析体系的建立
ABEI是一种环酞麟类衍生物，其分子结构上含有一个特殊的长臂功能团一氨
基，可直接用来标记生物大分子。本文研究了ABEI的ECL性能，发现在碱性
溶液中，施加+l .ov(vsA留AgCI)的电压时，ABEI可在Pt电极上产生很强的
ECL信号，适量HZO:的加入可催化这一发光反应。考察了各种影响因素，建立
了ABEI的ECL分析方法.方法测定ABEI的线性响应范围为1 .3 x 10石一6.5x
10·’Zmol/L，检出限可以达到9.6xz0·’3mo比。
2 FCA催化Luminol一HZO:ECL反应的研究及其ECL分析体系的建立
Luminol是最早被发现的ECL物质，也是目前为止发光效率最高的物质之一，
但由于其分子结构上缺乏合适的标识基团而使其难以直接标记生物大分子。梭基
二茂铁(FCA)是一种电化学活性物质，其分子结构上的梭基能够和生物大分子
摘要
作用，可用于标记生物大分子。本文研究了FCA对Luminol一HZOZ的ECL催化作用，
发现在低电位下，FCA可极大地催化Luminol和HZOZ的ECL反应，而且催化信号
与FCA的浓度在5.0、10一9一2.0x10礴moFL的范围内呈良好的线性关系，检出限可
以达到1.5、10一gmol几。以FCA作为DNA标记物，方法可用于DNA的ECL检测。
3叮睫酷类化合物的ECL性能研究及其ECL分析体系的建立
叮咙醋是一类较好的化学发光(CL)物质，而且其分子结构上含有特殊的
功能团，可用来标记生物大分子，实现生物物质的CL分析。但有关其ECL性
能的研究却较少。本文研究了碘化10一乙梭基叮咙一9一梭酸苯醋(C AcPEI)和对甲
酞基苯基一10一甲基叮咤一9一梭酸酷氟磺酸盐(MFPA)的ECL行为，发现在中性
KNO3介质中，这两种叮咙醋都能在一定的电位下产生很强的ECL信号，考察
了各种影响因素，确定了发光的最佳条件，探讨了可能的发光机理。在最佳条件
下EeL信号与eAePEx及MF琳的浓度分别在5.oxlo.，o一l.Zxlo一79/ml和
2.4xl0‘’0一9.6xlo一8留ml范围内呈良好的线性关系。检出限可分别达到2.4只10一’“
g加l和l.6xlo一’“g/ml。比eL法的灵敏度高1000倍。
4道诺霉素的
道诺霉素
ECL性能研究及其ECL分析体系的建立
(DNR)是一种葱环类抗生素，
上得到广泛的应用
可选择性地嵌入到
。与DNA作用机理研究表明
具有广谱的抗肿瘤作用，在临床
，DNR以其特殊的葱环平面结构
DNA
研究了DNR的ECL行为
的双链结构区。因此可作为DNA的杂交指示剂。本文
，发现在
Deoxyribonucleic Acid (DNA) is known as inherited substance in life body. With the increasing of knowledge about human beings diseases it is found that the mutations of base sequence in DNA are responsible for numerous inherited human disorders. In order to make early diagnosis and cure for disease, much effort is needed to detect the specific DNA sequences related to diseases, which is also helpful for the selection of genes and the development of drugs.
Most of the conventional methods for the analysis of specific DNA sequences are based on the nucleic acid hybridization. Single-stranded ss- DNA probe binds to its complementary strand (target sequence) to form a double-stranded (ds) DNA with high efficiency. The signal provided by the probe is a measure of the degree of hybridization.
Traditional DNA probes are labeled with radioisotopes i.e. 32P, I25I, 3H or 35S. Although this method gives high sensitivity, the radioactive labels present many problems such as a potential hazard to analyst and environment, which limited its application in DNA diagnostic laboratories. In order to overcome these problems a serious of non-radioactive DNA probes such as fluorescent, chemiluminescent and electrochemical probes have been developed. Although these new methods display many advantages, they have not been used to take place completely the traditional method because of low sensitivity or complex equipment or other shortcomings. So it is necessary to develop other rapid and sensitive methods for the detection of specific DNA sequences, which can also be used easily in non-specialized laboratories. Electrochemiluminescence (ECL) is a technique that combines chemiluminescence
(CL) and electrochemistry (EC). The CL reaction was initiated by an electrochemical reaction at electrode surface. Such an electro-initiation reaction introduces a large number of additional advantages, such as high sensitivity and selectivity, rapid and convenient operation and relatively simple instrumentation system. Due to these inherent advantages, ECL method has attracted much attention from all analytical fields, especially from biochemical analysis. In this dissertation we focused on the preparation of a new type of DNA probes which were labeled with ECL activated substances. Based on coupling with the DNA hybridization and immobilization techniques, we have developed new ECL methods for the determination of special DNA sequence. Compared with other methods the new methods are simple, rapid as well as sensitive and selective. The dissertation is composed of four chapters as folio wings:
Chapter 1: Introduced the ECL and its application in analytical chemistry field, paid more attention to the types of ECL reaction and ECL sensors. Reviewed the DNA sensors, including their principles, advantage and disadvantage. At last pointed out the purpose of the dissertation.
Chapter 2: Study on the ECL behaviors of several substances and establishment of ECL analytical systems
1 The ECL behavior of N-(4-aminobutyl)-N-ethylisoluminol (ABEI) was studied and found ABEI could produce emission light when oxidized at a +1.0 V (vs Ag/AgCl) potential in alkaline solution. The addition of H_(2)O_(2) markedly improved the ECL sensitivity. The effected factors on the ECL were examined. Under optimal conditions, ABEI took a linear response to ECL intensity in the range of 1.3x10-6 ~ 6.5 xl0-12 mol/L. The detection limit is 2.2 xl0-12 mol/L at a signal to noise ratio of 3.
2 The catalytic reaction of ferrocenecarboxylic acid (FCA) to Luminol and hydrogen peroxide was investigated. It was found the Chemiluminescent intensity of
Luminol with hydrogen peroxide can be greatly enhanced by electrochemically oxidizing of FCA at low potential in Tris buffer solution. Under optimal conditions the ECL intensity exhibits a good linear response with the concentration of FCA in the range of 5.0x10~(-9).~2.0xl0-4 mol/L. The detection limit is 1.5xl0-9mol/L.
3 A study on the ECL of acridinum esters
DNA杂交分析技术是目前生物化学和分子生物学研究中应用最广泛的技术之一，是定性或定量检测特异DNA序列片段的有力工具。目前，它已广泛应用在生命科学，尤其是医学的各个领域。传统的DNA分子杂交采用的是放射性标记的检测方法，这种方法虽然灵敏度高，但存在放射性物质对人体及环境的危害。自20世纪80年代以来，各种非同位素如酶、荧光素、生物素、地高辛标记的化学发光法和荧光分析法以及以电活性物质做标记的电化学方法相继问世，这些方法虽然在一定程度上克服了同位素标记的缺陷，但由于存在灵敏度不够高或检测系统庞杂或仪器价格昂贵或标记物不稳定等缺陷，还不能完全取代传统方法。因此寻求简单、灵敏、可靠、价廉的非放射性标记的DNA检测方法具有十分重要的现实意义。
电致化学发光(ECL)分析是一种通过电极反应而产生化学发光的微量分析方法。它将电化学技术与化学发光检测结合起来，弥补了电化学方法和化学发光方法的不足，具有灵敏度高、选择性好、动力学范围宽、检测快速方便、仪器价格便宜等优点，近几年来在分析化学，尤其在生物分析领域引起了人们的极大关注。本论文通过研究了多种ECL活性物质的发光性能，并以这些物质为标记物制备了多种高灵敏度的DNA-ECL探针，结合DNA杂交技术和DNA固定化技术，将高灵敏度的ECL检测手段应用于生命物质DNA的序列识别及含量测定，为DNA传感器的研究和基因芯片的开发提供了新的思路和方法。
摘要
论文主要研究内容如下:
第一章绪论
简单介绍了ECL分析方法的概念、原理和特点，重点介绍了各种ECL反应
类型及其在分析化学中的应用，系统总结了各种ECL传感器，展望了ECL分析
的未来发展方向。介绍了DNA传感器的构造和各种DNA传感器的原理、特点
及分析应用。最后阐述了本论文的目的和意义，指出论文的创新之处及主要研究
内容。
第二章ECL活性标记物的性能研究及其ECL分析体系的建立
研究了环酞麟类物质N一(4一氨基丁基)一乙基异鲁米诺(ABEI)和鲁米诺
(Luminol)、叮淀酷类物质醛基叮淀酷和竣基叮睫酷、抗癌药物道诺霉素(DNR)
的ECL行为，建立了这几种物质的ECL分析体系，并结合电化学、紫外一可见
光谱、荧光光谱等手段讨论了它们的ECL反应机理，为DNA的ECL分析奠定
了方法基础。
1 ABEI的ECL性能研究及其ECL分析体系的建立
ABEI是一种环酞麟类衍生物，其分子结构上含有一个特殊的长臂功能团一氨
基，可直接用来标记生物大分子。本文研究了ABEI的ECL性能，发现在碱性
溶液中，施加+l .ov(vsA留AgCI)的电压时，ABEI可在Pt电极上产生很强的
ECL信号，适量HZO:的加入可催化这一发光反应。考察了各种影响因素，建立
了ABEI的ECL分析方法.方法测定ABEI的线性响应范围为1 .3 x 10石一6.5x
10·’Zmol/L，检出限可以达到9.6xz0·’3mo比。
2 FCA催化Luminol一HZO:ECL反应的研究及其ECL分析体系的建立
Luminol是最早被发现的ECL物质，也是目前为止发光效率最高的物质之一，
但由于其分子结构上缺乏合适的标识基团而使其难以直接标记生物大分子。梭基
二茂铁(FCA)是一种电化学活性物质，其分子结构上的梭基能够和生物大分子
摘要
作用，可用于标记生物大分子。本文研究了FCA对Luminol一HZOZ的ECL催化作用，
发现在低电位下，FCA可极大地催化Luminol和HZOZ的ECL反应，而且催化信号
与FCA的浓度在5.0、10一9一2.0x10礴moFL的范围内呈良好的线性关系，检出限可
以达到1.5、10一gmol几。以FCA作为DNA标记物，方法可用于DNA的ECL检测。
3叮睫酷类化合物的ECL性能研究及其ECL分析体系的建立
叮咙醋是一类较好的化学发光(CL)物质，而且其分子结构上含有特殊的
功能团，可用来标记生物大分子，实现生物物质的CL分析。但有关其ECL性
能的研究却较少。本文研究了碘化10一乙梭基叮咙一9一梭酸苯醋(C AcPEI)和对甲
酞基苯基一10一甲基叮咤一9一梭酸酷氟磺酸盐(MFPA)的ECL行为，发现在中性
KNO3介质中，这两种叮咙醋都能在一定的电位下产生很强的ECL信号，考察
了各种影响因素，确定了发光的最佳条件，探讨了可能的发光机理。在最佳条件
下EeL信号与eAePEx及MF琳的浓度分别在5.oxlo.，o一l.Zxlo一79/ml和
2.4xl0‘’0一9.6xlo一8留ml范围内呈良好的线性关系。检出限可分别达到2.4只10一’“
g加l和l.6xlo一’“g/ml。比eL法的灵敏度高1000倍。
4道诺霉素的
道诺霉素
ECL性能研究及其ECL分析体系的建立
(DNR)是一种葱环类抗生素，
上得到广泛的应用
可选择性地嵌入到
。与DNA作用机理研究表明
具有广谱的抗肿瘤作用，在临床
，DNR以其特殊的葱环平面结构
DNA
研究了DNR的ECL行为
的双链结构区。因此可作为DNA的杂交指示剂。本文
，发现在
Deoxyribonucleic Acid (DNA) is known as inherited substance in life body. With the increasing of knowledge about human beings diseases it is found that the mutations of base sequence in DNA are responsible for numerous inherited human disorders. In order to make early diagnosis and cure for disease, much effort is needed to detect the specific DNA sequences related to diseases, which is also helpful for the selection of genes and the development of drugs.
Most of the conventional methods for the analysis of specific DNA sequences are based on the nucleic acid hybridization. Single-stranded ss- DNA probe binds to its complementary strand (target sequence) to form a double-stranded (ds) DNA with high efficiency. The signal provided by the probe is a measure of the degree of hybridization.
Traditional DNA probes are labeled with radioisotopes i.e. 32P, I25I, 3H or 35S. Although this method gives high sensitivity, the radioactive labels present many problems such as a potential hazard to analyst and environment, which limited its application in DNA diagnostic laboratories. In order to overcome these problems a serious of non-radioactive DNA probes such as fluorescent, chemiluminescent and electrochemical probes have been developed. Although these new methods display many advantages, they have not been used to take place completely the traditional method because of low sensitivity or complex equipment or other shortcomings. So it is necessary to develop other rapid and sensitive methods for the detection of specific DNA sequences, which can also be used easily in non-specialized laboratories. Electrochemiluminescence (ECL) is a technique that combines chemiluminescence
(CL) and electrochemistry (EC). The CL reaction was initiated by an electrochemical reaction at electrode surface. Such an electro-initiation reaction introduces a large number of additional advantages, such as high sensitivity and selectivity, rapid and convenient operation and relatively simple instrumentation system. Due to these inherent advantages, ECL method has attracted much attention from all analytical fields, especially from biochemical analysis. In this dissertation we focused on the preparation of a new type of DNA probes which were labeled with ECL activated substances. Based on coupling with the DNA hybridization and immobilization techniques, we have developed new ECL methods for the determination of special DNA sequence. Compared with other methods the new methods are simple, rapid as well as sensitive and selective. The dissertation is composed of four chapters as folio wings:
Chapter 1: Introduced the ECL and its application in analytical chemistry field, paid more attention to the types of ECL reaction and ECL sensors. Reviewed the DNA sensors, including their principles, advantage and disadvantage. At last pointed out the purpose of the dissertation.
Chapter 2: Study on the ECL behaviors of several substances and establishment of ECL analytical systems
1 The ECL behavior of N-(4-aminobutyl)-N-ethylisoluminol (ABEI) was studied and found ABEI could produce emission light when oxidized at a +1.0 V (vs Ag/AgCl) potential in alkaline solution. The addition of H_(2)O_(2) markedly improved the ECL sensitivity. The effected factors on the ECL were examined. Under optimal conditions, ABEI took a linear response to ECL intensity in the range of 1.3x10-6 ~ 6.5 xl0-12 mol/L. The detection limit is 2.2 xl0-12 mol/L at a signal to noise ratio of 3.
2 The catalytic reaction of ferrocenecarboxylic acid (FCA) to Luminol and hydrogen peroxide was investigated. It was found the Chemiluminescent intensity of
Luminol with hydrogen peroxide can be greatly enhanced by electrochemically oxidizing of FCA at low potential in Tris buffer solution. Under optimal conditions the ECL intensity exhibits a good linear response with the concentration of FCA in the range of 5.0x10~(-9).~2.0xl0-4 mol/L. The detection limit is 1.5xl0-9mol/L.
3 A study on the ECL of acridinum esters
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