电致化学发光及其在DNA序列分析中的应用研究
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摘要
电致化学发光(Electrochemiluminescence)简称ECL，是由电极反应而引发的一种化学发光(Chemiluminescence,CL)现象。它是通过电极对含有CL物质的体系施加一定的电压或通过一定的电流，电极产物之间或电极产物与体系中某种物质之间发生化学反应而产生CL，或发光物质直接在电极上发生氧化还原反应后生成某种不稳定的中间态物质分解而发光。通过光电倍增管或其他光学仪器测量发光强度，从而对物质进行定性和定量分析，即为ECL分析。
脱氧核糖核酸(DNA)是遗传信息的承担者，被称为生命体内的遗传物质。具有存储和传递信息的功能，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片段的有力工具。目前，它已被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。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，但所需仪器昂贵，且难以实现自动化。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)分析是利用电解技术在电极表面产生某些氧化还原物质而导致的化学发光，较一般的化学发光方法相比具有装置简单、仪器价格便宜、重现性好、可进行原位发光等特点，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。本论文研究了电致化学发光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
本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活性物质发光性能的研究
1 FCA催化Lumino1EcL反应的研究及其ECL分析体系的建立
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
物大分子作用，因而可用于标记生物大分子。本文研究发现在低电位下，FCA可
极大地催化Lumin。1和HZoZ的EcL反应，而且催化信号与FcA的浓度在5.0只10一9-
2.0又10‘4m。1/L的范围内呈现良好的线性关系，检出限可以达到1.5又10一”mol/L。
2齐敦果酸的ECL行为
齐敦果酸是一种五环三菇类药物，是治疗急性黄胆型肝炎和慢性病毒性肝炎
比较理想的药物，但有关其ECL性能的研究较少。本论文详细研究了齐墩果酸的
电致化学发光性能，确定了发光的最佳条件，探讨了可能的发光机理。发现在最
佳条件下，ECL信号与齐敦果酸的浓度在4.38义10一7一4.38又10一，mol/L范围内呈良
好的线性关系，检出限可达到2.oxlo一7 mol/L。为测定药物中齐敦果酸的含量提
供了一种可靠的方法。
第三章DNA一ECL探针的制备及其在DNA分析中的应用
采用直接标记法和纳米颗粒间接标记法制备了不同的SSDNA一ECL探针，与
固定在电极上的目标SSDNA进行杂交反应，通过ECL检测实现对目标DNA的序列
识别及含量测定，获得满意结果。
FCA一DNA探针的制备及应用
在EDAC的活化下，FCA分子结构上的梭基与NHZ一ssDNA上的氨基作用，将
摘要
FCA直接标记在NHZ一ssDNA上，制备成FCA一SSDNA探针。分别用ECL法、紫外-
可见光谱法和电化学法对其进行表征。然后与固定在电极上的SSDNA进行杂交反
应，用ECL法测定杂交信号，根据发光信号的大小对目标DNA进行识别及定量。
实验结果证明，该探针能准确识别出三碱基错配序列，对互补序列的响应可以达
到5x10一“mol/L。
2 Luminol一5102纳米颗粒标记SSDNA探针的制备及应用
纳米技术以其独特的优势引起了人们的极大关注。纳米颗粒标记是DNA分析
中的一个崭新课题。本文首次以Luminol为核材料，利用反相微乳液技术，制备
了掺杂有Lumin。1的5102纳米颗粒，并在纳米颗粒表面修饰一层壳聚糖，使其
能与DNA结合，从而制备成Luminol一510:纳米颗粒标记的SSDNA探针。结合DNA
杂交技术及高灵敏度的Luminol ECL检测方法对不同序列的目标DNA进行识别及
定量。实验结果证明，这种探针对DNA的序列特征具有更强的识别能力，对互补
序列的响应具有更高的灵敏度。检出限可以达到2x10一’“mol/L。
Electrogenerated chemiluminescence (ECL), know as electrochemilumicescence, which combines chemiluminescence (CL) and electrochemistry. 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. So ECL is becoming more and more important in many fields.
Deoxyribonucleic Acid (DNA) is known as inherited substance in life body. The analysis of DNA sequence and DNA mutant detection play fundamental roles in the rapid development of molecular diagnostics and in the anticancer drug screening.
Therefor many detection techniques of DNA sequence have been developed in recent years. These techniques mainly depend on the nucleic acid hybridization and their sensitivities are related to the specific activity of the label linked to the DNA probe. The degree of hybridization of probe to its complementary DNA sequence in sample is translated into a useful electric signal, which is a measurement of the amount of that specific sequence in the sample.
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 three chapters as followings:
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 two substances and establish their ECL analytical system.
1 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 5.0 10-9~2.0 10-4mol/L. The detection limit is 1.5 10-9mol/L.
2 The electrogenerated chemiluminescence (ECL) behavior of oleanlic acid(OA) in neutral solution was studied. It has been found that oleanlic acid gives ECL emission at Pt electrode when the applied potentials were over 0.8 V (vs. Ag/AgCl). The ECL intensity was greatly influenced by the electrochemical parameters. The strongest ECL signal was observed in 1.0 mol/L KCL solution, whose pH is 7.0. And adding H2O2 could catalyze its signal. Under optimum conditions the ECL intensity has a linear relationship with the concentration of oleanlic acid in the range of 4.38xlO-7 ~ 4.38x10-5mol/L . The detection limit was 2.0xlO-7 mol L-1. The proposed ECL mechanism was discussed.
Chapter 3: Preparation of new DNA-ECL probes and their applications to DNA assay
1 FCA-DNA probe. This probe was made by convalent bound between carboxyl group of FCA and 5'-amino of oligonucleotide in the presence of a water-soluble carbodiimide. The hybridization reaction was conducted by immersing the ssDNA-immobilized electrode in FCA-DNA probe solution. The hybridization events were estimated by the ECL signals from FCA. The results showed that the FCA-DNA probe was able to recognize three-base mismatch sequence and formed dsDNA only with complementary sequence. The linear response to the complementary sequence is of 2 10-10~5 10-8 mol/L and the detection limit is 5.0 10-11 mol/L .
2 Luminol-SiO2-DNA probe. Luminol-SiO2 nanoparticles were first synthesized by hydrolysis of tetraethoxysilane (TEOS) within a reverse microemulsion system. Particles in the size range 55 ~70
脱氧核糖核酸(DNA)是遗传信息的承担者，被称为生命体内的遗传物质。具有存储和传递信息的功能，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片段的有力工具。目前，它已被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。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，但所需仪器昂贵，且难以实现自动化。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)分析是利用电解技术在电极表面产生某些氧化还原物质而导致的化学发光，较一般的化学发光方法相比具有装置简单、仪器价格便宜、重现性好、可进行原位发光等特点，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。本论文研究了电致化学发光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
本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活性物质发光性能的研究
1 FCA催化Lumino1EcL反应的研究及其ECL分析体系的建立
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
物大分子作用，因而可用于标记生物大分子。本文研究发现在低电位下，FCA可
极大地催化Lumin。1和HZoZ的EcL反应，而且催化信号与FcA的浓度在5.0只10一9-
2.0又10‘4m。1/L的范围内呈现良好的线性关系，检出限可以达到1.5又10一”mol/L。
2齐敦果酸的ECL行为
齐敦果酸是一种五环三菇类药物，是治疗急性黄胆型肝炎和慢性病毒性肝炎
比较理想的药物，但有关其ECL性能的研究较少。本论文详细研究了齐墩果酸的
电致化学发光性能，确定了发光的最佳条件，探讨了可能的发光机理。发现在最
佳条件下，ECL信号与齐敦果酸的浓度在4.38义10一7一4.38又10一，mol/L范围内呈良
好的线性关系，检出限可达到2.oxlo一7 mol/L。为测定药物中齐敦果酸的含量提
供了一种可靠的方法。
第三章DNA一ECL探针的制备及其在DNA分析中的应用
采用直接标记法和纳米颗粒间接标记法制备了不同的SSDNA一ECL探针，与
固定在电极上的目标SSDNA进行杂交反应，通过ECL检测实现对目标DNA的序列
识别及含量测定，获得满意结果。
FCA一DNA探针的制备及应用
在EDAC的活化下，FCA分子结构上的梭基与NHZ一ssDNA上的氨基作用，将
摘要
FCA直接标记在NHZ一ssDNA上，制备成FCA一SSDNA探针。分别用ECL法、紫外-
可见光谱法和电化学法对其进行表征。然后与固定在电极上的SSDNA进行杂交反
应，用ECL法测定杂交信号，根据发光信号的大小对目标DNA进行识别及定量。
实验结果证明，该探针能准确识别出三碱基错配序列，对互补序列的响应可以达
到5x10一“mol/L。
2 Luminol一5102纳米颗粒标记SSDNA探针的制备及应用
纳米技术以其独特的优势引起了人们的极大关注。纳米颗粒标记是DNA分析
中的一个崭新课题。本文首次以Luminol为核材料，利用反相微乳液技术，制备
了掺杂有Lumin。1的5102纳米颗粒，并在纳米颗粒表面修饰一层壳聚糖，使其
能与DNA结合，从而制备成Luminol一510:纳米颗粒标记的SSDNA探针。结合DNA
杂交技术及高灵敏度的Luminol ECL检测方法对不同序列的目标DNA进行识别及
定量。实验结果证明，这种探针对DNA的序列特征具有更强的识别能力，对互补
序列的响应具有更高的灵敏度。检出限可以达到2x10一’“mol/L。
Electrogenerated chemiluminescence (ECL), know as electrochemilumicescence, which combines chemiluminescence (CL) and electrochemistry. 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. So ECL is becoming more and more important in many fields.
Deoxyribonucleic Acid (DNA) is known as inherited substance in life body. The analysis of DNA sequence and DNA mutant detection play fundamental roles in the rapid development of molecular diagnostics and in the anticancer drug screening.
Therefor many detection techniques of DNA sequence have been developed in recent years. These techniques mainly depend on the nucleic acid hybridization and their sensitivities are related to the specific activity of the label linked to the DNA probe. The degree of hybridization of probe to its complementary DNA sequence in sample is translated into a useful electric signal, which is a measurement of the amount of that specific sequence in the sample.
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 three chapters as followings:
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 two substances and establish their ECL analytical system.
1 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 5.0 10-9~2.0 10-4mol/L. The detection limit is 1.5 10-9mol/L.
2 The electrogenerated chemiluminescence (ECL) behavior of oleanlic acid(OA) in neutral solution was studied. It has been found that oleanlic acid gives ECL emission at Pt electrode when the applied potentials were over 0.8 V (vs. Ag/AgCl). The ECL intensity was greatly influenced by the electrochemical parameters. The strongest ECL signal was observed in 1.0 mol/L KCL solution, whose pH is 7.0. And adding H2O2 could catalyze its signal. Under optimum conditions the ECL intensity has a linear relationship with the concentration of oleanlic acid in the range of 4.38xlO-7 ~ 4.38x10-5mol/L . The detection limit was 2.0xlO-7 mol L-1. The proposed ECL mechanism was discussed.
Chapter 3: Preparation of new DNA-ECL probes and their applications to DNA assay
1 FCA-DNA probe. This probe was made by convalent bound between carboxyl group of FCA and 5'-amino of oligonucleotide in the presence of a water-soluble carbodiimide. The hybridization reaction was conducted by immersing the ssDNA-immobilized electrode in FCA-DNA probe solution. The hybridization events were estimated by the ECL signals from FCA. The results showed that the FCA-DNA probe was able to recognize three-base mismatch sequence and formed dsDNA only with complementary sequence. The linear response to the complementary sequence is of 2 10-10~5 10-8 mol/L and the detection limit is 5.0 10-11 mol/L .
2 Luminol-SiO2-DNA probe. Luminol-SiO2 nanoparticles were first synthesized by hydrolysis of tetraethoxysilane (TEOS) within a reverse microemulsion system. Particles in the size range 55 ~70
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