腙类衍生物金属离子荧光探针及单核苷酸多态性荧光检测
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摘要
首先,本文设计合成了新型腙类衍生物金属离子荧光探针,实现了对溶液中铜离子、锌离子和镁离子的荧光增强型或双波长比率型检测。根据荧光探针与金属离子的结合方式不同本文研究了两类不同类别的金属离子荧光探针,即:金属离子诱导的反应型荧光探针和络合型荧光探针。7-二乙胺基香豆素-3-(2-羟基苯胺)希弗碱是本论文设计合成的一种新型高效的反应型铜离子荧光探针,其香豆素内酯结构在铜离子的诱导下能够发生水解反应,生成荧光产物。基于此原理,该探针能够在水溶液中对铜离子进行荧光增强型检测,其检测限可达20 nM。由于只有铜离子能够诱导水解反应的发生,所以该探针对铜离子具有很高的选择性,其它金属离子均不干扰测定。本文进而设计合成了两种针对锌离子的络合型荧光探针1-芘基丁酰基水杨醛腙和罗丹明B酰4-N,N-二乙胺基水杨醛腙,它们均可对锌离子产生双波长比率型的荧光响应。其中1-芘基丁酰基水杨醛腙至少可以在0～5μM锌离子浓度范围内对其进行检测,检测限为80 nM锌;罗丹明B酰4-N,N-二乙胺基水杨醛腙至少可以在0～10μM锌离子浓度范围内对其进行检测,检测限为50 nM锌。由于该探针与锌离子络合前后溶液的荧光颜色由蓝绿色到黄绿色产生明显的变化,因此可以实现紫外灯下锌离子的裸眼检测。这两种锌离子荧光探针均已用于实际水样中锌离子浓度的测定。本文还合成了镁离子的络合型荧光探针α-(喹啉-8-氧基)-乙酰水杨醛腙,探针在与镁离子络合前后显示显著的吸收光谱和荧光光谱变化。
其次,本文设计了检测单核苷酸多态性的新方法——双探针法和突起法。与传统的荧光团或有机小分子共价标记DNA链的检测方法不同,双探针法和突起法采用了不加任何标记的DNA链,通过将对不同碱基具有选择性识别作用的荧光探针引入互补DNA双链提供的疏水性微环境中产生的荧光淬灭作用,实现了中性水溶液中单核苷酸多态性的荧光检测,并且成功用于实际基因序列中的C碱基突变检测。双探针法和突起法的优点是方法简单,成本低廉,在高通量单核苷酸多态性检测领域具有潜在的应用价值。
A series of hydrazone derivatives were synthesized and their potential application as fluorescent probes for Cu~(2+), Zn~(2+) and Mg~(2+) was investigated in this dissertation. The interaction between these fluorescent probes and metal ions could be divided into two different mechanisms, i.e., metal ion-induced reaction and metal ion-ligand chelation. In the former case, 7-diethylamino-3-[(2-hydroxy-phenylimino) -methyl]-coumarin was designed and synthesized as a fluorescence“turn-on”probe for Cu~(2+) via Cu~(2+)-promoted hydrolysis of the lactone moiety in coumarin. The probe showed high sensitivity to Cu~(2+) in water solution with a detection limit of 20 nM. Fluorescence response of the probe to Cu~(2+) was also highly selective, because other metal ions could neither promote nor interfere the hydrolysis reaction. In the latter case, novel fluorescence probes salicylaldehyde 4-pyren-1-yl-butyric hydrazone and 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone for Zn~(2+) were developed. They exhibited selective and ratiometric fluorescent response toward Zn~(2+) over other metal ions in aqueous ethanol. Salicylaldehyde 4-pyren-1-yl-butyric hydrazone exhibited a linear range of 0~5.0μM and detection limit of 80 nM for Zn~(2+) in optimal condition. 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone exhibited a linear range of 0~10.0μM and the detection limit was found to be 50 nM for Zn~(2+). When 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone was used, fluorescence emission color changed from dark cyan to green yellow by formation of a 1:1 metal-to-ligand complex and the color change could be easily recognized by naked eye. Detection of Zn~(2+) in real water samples using the two probes was successfully carried out. In addition,α-(quinlin-8-yloxy)-acetyl salicyl hydrazone was proposed as a fluorescent probe for Mg~(2+). Significant absorption spectra changes and fluorescence enhancement were observed upon chelation of the probe with Mg~(2+).
In this dissertation, a double-probe method and a bulge form method were also proposed for the detection of single-nucleotide polymorphisms (SNPs) by coupling with a small fluorescent dye 2-amino-5, 7-dimethyl-1, 8-naphthyridine (ADMND). Since the methods required no labeling of DNA strands and thus simple, economic and cost-effective SNPs detection was realized. Using the double-probe method and bulge form method, ADMND was successfully applied to the detection of C/G and C/A mutations in the estrogen receptor 2 gene and the progesterone receptor genes.
其次,本文设计了检测单核苷酸多态性的新方法——双探针法和突起法。与传统的荧光团或有机小分子共价标记DNA链的检测方法不同,双探针法和突起法采用了不加任何标记的DNA链,通过将对不同碱基具有选择性识别作用的荧光探针引入互补DNA双链提供的疏水性微环境中产生的荧光淬灭作用,实现了中性水溶液中单核苷酸多态性的荧光检测,并且成功用于实际基因序列中的C碱基突变检测。双探针法和突起法的优点是方法简单,成本低廉,在高通量单核苷酸多态性检测领域具有潜在的应用价值。
A series of hydrazone derivatives were synthesized and their potential application as fluorescent probes for Cu~(2+), Zn~(2+) and Mg~(2+) was investigated in this dissertation. The interaction between these fluorescent probes and metal ions could be divided into two different mechanisms, i.e., metal ion-induced reaction and metal ion-ligand chelation. In the former case, 7-diethylamino-3-[(2-hydroxy-phenylimino) -methyl]-coumarin was designed and synthesized as a fluorescence“turn-on”probe for Cu~(2+) via Cu~(2+)-promoted hydrolysis of the lactone moiety in coumarin. The probe showed high sensitivity to Cu~(2+) in water solution with a detection limit of 20 nM. Fluorescence response of the probe to Cu~(2+) was also highly selective, because other metal ions could neither promote nor interfere the hydrolysis reaction. In the latter case, novel fluorescence probes salicylaldehyde 4-pyren-1-yl-butyric hydrazone and 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone for Zn~(2+) were developed. They exhibited selective and ratiometric fluorescent response toward Zn~(2+) over other metal ions in aqueous ethanol. Salicylaldehyde 4-pyren-1-yl-butyric hydrazone exhibited a linear range of 0~5.0μM and detection limit of 80 nM for Zn~(2+) in optimal condition. 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone exhibited a linear range of 0~10.0μM and the detection limit was found to be 50 nM for Zn~(2+). When 4-N,N-diethylamino-salicylaldehyde rhodamine B hydrazone was used, fluorescence emission color changed from dark cyan to green yellow by formation of a 1:1 metal-to-ligand complex and the color change could be easily recognized by naked eye. Detection of Zn~(2+) in real water samples using the two probes was successfully carried out. In addition,α-(quinlin-8-yloxy)-acetyl salicyl hydrazone was proposed as a fluorescent probe for Mg~(2+). Significant absorption spectra changes and fluorescence enhancement were observed upon chelation of the probe with Mg~(2+).
In this dissertation, a double-probe method and a bulge form method were also proposed for the detection of single-nucleotide polymorphisms (SNPs) by coupling with a small fluorescent dye 2-amino-5, 7-dimethyl-1, 8-naphthyridine (ADMND). Since the methods required no labeling of DNA strands and thus simple, economic and cost-effective SNPs detection was realized. Using the double-probe method and bulge form method, ADMND was successfully applied to the detection of C/G and C/A mutations in the estrogen receptor 2 gene and the progesterone receptor genes.
引文
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