新型单克隆抗体荧光探针和pH值荧光探针的合成及免疫荧光组织化学应用
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摘要
荧光探针技术是一种借助荧光显微镜在分子水平上进行实时监测的重要技术手段。荧光探针技术灵敏度高、可视性强,并且对所研究的目标细胞或者生物大分子干扰小、无损伤,所以得到广泛的应用。荧光探针已经在分子生物学、微生物学、分析化学、生物化学、化工和医药工业等领域发挥着重要作用,并且应用越来越广泛。化学家和生物学家不断设计和合成各种新型的荧光探针染料来满足不同应用需求和更高的荧光性能要求。荧光探针染料的合成和应用研究已经成为一个化学和生命科学的交叉前沿热点研究领域。
在各种荧光探针染料中,荧光素类荧光探针染料应用最为普遍。荧光素由于它合成方便、容易分离提纯,具有高的荧光量子产率,没有毒性等优点,成为人们广泛关注的重要的探针染料。荧光素母体容易进行化学修饰,可以得到满足不同需求的荧光素衍生物。所以,荧光素类探针染料广泛应用于DNA测序和抗体蛋白标记等生物体系的研究领域。
本论文主要论述了新型荧光素类单克隆抗体荧光探针染料的设计、合成以及荧光素类荧光探针在免疫荧光组织化学方面的应用。同时,本论文还阐述了新型荧光素类pH值荧光探针的设计合成及光谱性质测定。主要内容有如下几个方面。
1.对合成荧光素母体的重要原料2,4-二氯间苯二酚的合成进行详细研究,提出简便的2,4-二氯间苯二酚一步合成方法,优化反应条件。对比了传统的合成方法和一步合成方法的优缺点。介绍了三氟乙酸N-琥珀酰亚胺酯的合成方法。
2.设计并合成了5(6)-羧基-4,7-二氯荧光素和5(6)-羧基-2’,4’,5’,7’,4,7-六氯荧光素,并表征了它们的结构。讨论了反应条件对产率的影响,提出最佳反应条件。详细研究了几种结构相似的含氯荧光素的荧光性质与氯原子个数的构效关系。成功分离出5(6)-羧基-4,7-二氯荧光素的6位异构体和5(6)-羧基-2’,4’,5’,7’,4,7-六氯荧光素的6位异构体,并且表征了它们的结构。
3.合成了1种未见文献报道的具有氨基醇连接链的荧光素基单克隆抗体DNA荧光探针,表征了化合物的结构,研究了光谱性质。该荧光探针主要应用在DNA测序。合成了10种未见文献报道的具有氨基酸链的新型荧光素基单克隆抗体蛋白标记荧光探针染料,并对其结构进行表征,详细研究了它们的光谱性质。
4.合成了10种未见文献报道含氯荧光素类荧光探针,并表征它们的结构。选取5(6)-酰氨己酸琥珀酰亚胺酯-2’,4’,5’,7’,4,7-六氯荧光素(化合物8dh)进行免疫荧光组织化学应用实验,用直接法标记了人体骨肉瘤上皮细胞,并且通过激光共聚焦显微镜获得标记细胞荧光图像。用直接法标记小鼠心肌组织,并用荧光显微镜获得组织荧光图片。免疫荧光组织化学应用表明新型单克隆抗体荧光素探针染料具有良好的荧光性能和生物学性能,是一类性能优良的单克隆荧光探针。
5.简要综述了pH值荧光探针的研究进展；设计合成了八种荧光素为母体的荧光素pH值探针染料,表征了它们的结构；详细研究了pH值荧光探针的荧光光谱和紫外光谱性质,实验发现,它们能够在酸性范围内指示pH值的变化。它们是性能优良的pH值荧光探针,将会在生物学中发挥重要作用。
Fluorescent probe is an important technical mean, which is used to monitor biomolecule real-time by a fluorescence microscope. Fluorescent probes are widely used because of high sensitivity, strong visibility, no damage and little interference on the target cells or biological macromolecules. Fluorescent probes have been widely used in molecular biology, microbiology, biochemistry, analytical chemistry, chemical engineering and medicine engineering. Chemists and biologists continue to design and synthesis of new types of fluorescent probe dye to meet different application requirements and higher fluorescence performance requirements. The synthesis and application research of fluorescent probe dyes become a hot point in interdisciplinary of life science and chemistry.
In a variety of fluorescent probe dye, fluorescein dyes are most widely used. Because of easy synthesis, easy isolation and purification, with high fluorescence quantum yield and non-toxic, fluorescein has become an important probe. Fluorescein derivatives are easily obtained by modifying fluorescein in order to meet different needs. Fluorescein dyes are widely used in DNA sequencing, antibody protein staining and other biological research.
Design, synthesis and application in immunofluorescence of monoclonal antibody fluorescent dye were discussed in this thesis. Design, synthesis and spectral properties of new pH probes were also discussed in this thesis. Summarized as follows:
1. Compound 2,4-dichloro-resorcinol which was an important material for synthesis of fluorescein was study in detail. A simple synthetic method of 2,4-dichloro-resorcinol was reported and reaction conditions was optimized. Compared with the traditional synthesis methods, the new synthesis method has many advantages. The synthesis of N-hydroxysuccinimidyl trifluoroacacetate (NHS-TFA) was reported in this thesis.
2. Two novel chlorinated fluoresceins 4,7-dichlorofluorescein and 2',4',5',7'-Tetrachloro-6-(5-carboxyl)-4,7-dichlorofluorescein were synthesized. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis. The effects of reaction conditions was discussed and reaction conditions was optimized. The relationship between fluorescence properties and the number of chlorine atoms was studied in detail.6-carboxyl-4,7-dichlorofluorescein and 2',4',5',7'-Tetrachloro-6-carboxyl-4, 7-dichlorofluorescein were isolated as their diisopropylamine salt, which can be converted to the free acid. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis.
3. One chlorofluorescein-based monoclonal antibody fluorescent probe dyeswith 6-amiohexanol linker was synthesized as dye-labeled primers in DNA sequence analysis. All of the dyes isomers were determined by 1HNMR, IR, elemental analysis and MS.
Ten chlorofluorescein-based monoclonal antibody fluorescent probe dyes with amino acid linker were synthesized as fluorescent probes for labeling proteins. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis. Spectral properties were studied in detail. All the probes for labeling proteins have not been reported in references.
4. One of the novel dyes (8dh) were investigated for application in immunofluorescence histochemistry. The compound 8dh was used to label fixed U2OS cell. Fluorescence images of U2OS cells in 96-well costar black plate were taken by fluorescence confocal microscopy. It was found that the novel dye (8dh) is excellent green fluorescent probe dyes that can be used to label a variety of monoclonal antibody and other biopolymers.
5. The research progress of pH value fluorescent probes was overviewed in this thesis. Eight chlorinated fluoresceins have been synthesized by the reaction of chlorinated resorcinols with 4,5,6,7-tetrachlorophthalic anhydride or 3,6-dichloro-4-carboxyphthalic anhydride in the presence of methanesulfonic acid. The spectral properties of the chlorinated fluoresceins were studied. It was found that they have absorption and emission maxima at long wavelengths and high fluorescence quantum yields. Emission spectra of chlorinated fluoresceins shifted towards long wavelength with increase of chlorine. pH-Dependent properties of chlorinated fluoresceins were studied in detail. These compounds showed strongly pH-sensitive range of 3.0～7.0. These chlorinated fluoresceins will be used as pH probes for pH measurement of the cell because of the high quantum yield and the strong pH-sensitivity.
在各种荧光探针染料中,荧光素类荧光探针染料应用最为普遍。荧光素由于它合成方便、容易分离提纯,具有高的荧光量子产率,没有毒性等优点,成为人们广泛关注的重要的探针染料。荧光素母体容易进行化学修饰,可以得到满足不同需求的荧光素衍生物。所以,荧光素类探针染料广泛应用于DNA测序和抗体蛋白标记等生物体系的研究领域。
本论文主要论述了新型荧光素类单克隆抗体荧光探针染料的设计、合成以及荧光素类荧光探针在免疫荧光组织化学方面的应用。同时,本论文还阐述了新型荧光素类pH值荧光探针的设计合成及光谱性质测定。主要内容有如下几个方面。
1.对合成荧光素母体的重要原料2,4-二氯间苯二酚的合成进行详细研究,提出简便的2,4-二氯间苯二酚一步合成方法,优化反应条件。对比了传统的合成方法和一步合成方法的优缺点。介绍了三氟乙酸N-琥珀酰亚胺酯的合成方法。
2.设计并合成了5(6)-羧基-4,7-二氯荧光素和5(6)-羧基-2’,4’,5’,7’,4,7-六氯荧光素,并表征了它们的结构。讨论了反应条件对产率的影响,提出最佳反应条件。详细研究了几种结构相似的含氯荧光素的荧光性质与氯原子个数的构效关系。成功分离出5(6)-羧基-4,7-二氯荧光素的6位异构体和5(6)-羧基-2’,4’,5’,7’,4,7-六氯荧光素的6位异构体,并且表征了它们的结构。
3.合成了1种未见文献报道的具有氨基醇连接链的荧光素基单克隆抗体DNA荧光探针,表征了化合物的结构,研究了光谱性质。该荧光探针主要应用在DNA测序。合成了10种未见文献报道的具有氨基酸链的新型荧光素基单克隆抗体蛋白标记荧光探针染料,并对其结构进行表征,详细研究了它们的光谱性质。
4.合成了10种未见文献报道含氯荧光素类荧光探针,并表征它们的结构。选取5(6)-酰氨己酸琥珀酰亚胺酯-2’,4’,5’,7’,4,7-六氯荧光素(化合物8dh)进行免疫荧光组织化学应用实验,用直接法标记了人体骨肉瘤上皮细胞,并且通过激光共聚焦显微镜获得标记细胞荧光图像。用直接法标记小鼠心肌组织,并用荧光显微镜获得组织荧光图片。免疫荧光组织化学应用表明新型单克隆抗体荧光素探针染料具有良好的荧光性能和生物学性能,是一类性能优良的单克隆荧光探针。
5.简要综述了pH值荧光探针的研究进展；设计合成了八种荧光素为母体的荧光素pH值探针染料,表征了它们的结构；详细研究了pH值荧光探针的荧光光谱和紫外光谱性质,实验发现,它们能够在酸性范围内指示pH值的变化。它们是性能优良的pH值荧光探针,将会在生物学中发挥重要作用。
Fluorescent probe is an important technical mean, which is used to monitor biomolecule real-time by a fluorescence microscope. Fluorescent probes are widely used because of high sensitivity, strong visibility, no damage and little interference on the target cells or biological macromolecules. Fluorescent probes have been widely used in molecular biology, microbiology, biochemistry, analytical chemistry, chemical engineering and medicine engineering. Chemists and biologists continue to design and synthesis of new types of fluorescent probe dye to meet different application requirements and higher fluorescence performance requirements. The synthesis and application research of fluorescent probe dyes become a hot point in interdisciplinary of life science and chemistry.
In a variety of fluorescent probe dye, fluorescein dyes are most widely used. Because of easy synthesis, easy isolation and purification, with high fluorescence quantum yield and non-toxic, fluorescein has become an important probe. Fluorescein derivatives are easily obtained by modifying fluorescein in order to meet different needs. Fluorescein dyes are widely used in DNA sequencing, antibody protein staining and other biological research.
Design, synthesis and application in immunofluorescence of monoclonal antibody fluorescent dye were discussed in this thesis. Design, synthesis and spectral properties of new pH probes were also discussed in this thesis. Summarized as follows:
1. Compound 2,4-dichloro-resorcinol which was an important material for synthesis of fluorescein was study in detail. A simple synthetic method of 2,4-dichloro-resorcinol was reported and reaction conditions was optimized. Compared with the traditional synthesis methods, the new synthesis method has many advantages. The synthesis of N-hydroxysuccinimidyl trifluoroacacetate (NHS-TFA) was reported in this thesis.
2. Two novel chlorinated fluoresceins 4,7-dichlorofluorescein and 2',4',5',7'-Tetrachloro-6-(5-carboxyl)-4,7-dichlorofluorescein were synthesized. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis. The effects of reaction conditions was discussed and reaction conditions was optimized. The relationship between fluorescence properties and the number of chlorine atoms was studied in detail.6-carboxyl-4,7-dichlorofluorescein and 2',4',5',7'-Tetrachloro-6-carboxyl-4, 7-dichlorofluorescein were isolated as their diisopropylamine salt, which can be converted to the free acid. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis.
3. One chlorofluorescein-based monoclonal antibody fluorescent probe dyeswith 6-amiohexanol linker was synthesized as dye-labeled primers in DNA sequence analysis. All of the dyes isomers were determined by 1HNMR, IR, elemental analysis and MS.
Ten chlorofluorescein-based monoclonal antibody fluorescent probe dyes with amino acid linker were synthesized as fluorescent probes for labeling proteins. Structures of target compounds and intermediates were determined via IR, MS,1H NMR and element analysis. Spectral properties were studied in detail. All the probes for labeling proteins have not been reported in references.
4. One of the novel dyes (8dh) were investigated for application in immunofluorescence histochemistry. The compound 8dh was used to label fixed U2OS cell. Fluorescence images of U2OS cells in 96-well costar black plate were taken by fluorescence confocal microscopy. It was found that the novel dye (8dh) is excellent green fluorescent probe dyes that can be used to label a variety of monoclonal antibody and other biopolymers.
5. The research progress of pH value fluorescent probes was overviewed in this thesis. Eight chlorinated fluoresceins have been synthesized by the reaction of chlorinated resorcinols with 4,5,6,7-tetrachlorophthalic anhydride or 3,6-dichloro-4-carboxyphthalic anhydride in the presence of methanesulfonic acid. The spectral properties of the chlorinated fluoresceins were studied. It was found that they have absorption and emission maxima at long wavelengths and high fluorescence quantum yields. Emission spectra of chlorinated fluoresceins shifted towards long wavelength with increase of chlorine. pH-Dependent properties of chlorinated fluoresceins were studied in detail. These compounds showed strongly pH-sensitive range of 3.0～7.0. These chlorinated fluoresceins will be used as pH probes for pH measurement of the cell because of the high quantum yield and the strong pH-sensitivity.
引文
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