新型铕、铽配合物荧光探针的合成及应用研究
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摘要
稀土配合物荧光探针与普通有机荧光探针相比具有水溶性好,Stokes位移大,发光寿命长等优点,在应用于生理分子或离子的时间分辨荧光检测时可以有效地消除复杂环境背景荧光的干扰,进而极大地提高检测的特异性与灵敏度。本学位论文在系统查阅文献的基础上,选取可与稀土离子形成稳定性强、发光量子产率高、水溶性好的联三吡啶衍生物2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸(TTA)作为稀土离子的发光天线基团,通过进行结构改进引入不同的识别基团,设计合成了如下几种对一些生理活性分子及离子具有特异性识别与传感功能的稀土配合物荧光探针,并考察了这些探针在时间分辨荧光生化分析中的应用性能。
设计合成了一种可用于高活性氧组分(hROS,包括羟基自由基及次氯酸)比率型荧光传感测定的基于Eu3+和Tb3+双发射的时间分辨荧光探针AMTTA-Eu3+/Tb3+,并将其用于hROS的比率型时间分辨荧光测定。研究发现,两种稀土配合物AMTTA-Eu3+与AMTTA-Tb3+的混合物与hROS作用时,其荧光强度比值I540／I610与hROS的浓度呈现剂量依赖性增加,而且不受pH值和金属移位等的影响,为复杂生物样品中hROS的测定提供了一种兼具比率型及时间分辨功能的荧光测定新方法。
利用分子内光诱导电子转移作用(PeT),通过在联三吡啶配位体中以醚键的方式引入3-硝基-4-氨基苯基基团的方法,设计合成了两种对次氯酸具有高度特异性识别与高灵敏度响应的时间分辨荧光探针ANMTTA-Eu3+和ANMTTA-Tb3+。通过考察探针用于水溶液及活细胞中次氯酸的荧光测定,证明了两种探针在用于次氯酸荧光检测时均具有稳定性及水溶性好、选择性及灵敏度高、响应迅速、pH适用范围宽等优点,可用于活细胞中外源性及内源性次氯酸的时间分辨荧光成像测定,为复杂生物样品中次氯酸的荧光检测提供了一种有实用价值的新方法。
设计合成了一种对锌离子具有特异性识别与响应的时间分辨荧光探针PAMTTA-Tb3+,与已报道的基于稀土配合物的锌离子荧光探针相比,该探针独特的分子构型设计使其对锌离子响应的特异性显著提高。该探针除了具有水溶性好、选择性及灵敏度高、响应迅速等优点外,还可实现对锌离子的可逆响应及活细胞内锌离子的时间分辨荧光成像测定。
Compared with ordinary organic luminescent probes, the lanthanide complex-based luminescent probes have some advantages, such as high solubility and stability, large Stokes shift and long luminescence life time, which enable these complexes to be easily used for the time-resolved luminescence measurement to eliminate the interferences from auto-fluorescence and scattering lights. On the basis of results reported in previous literature, this doctoral dissertation chose (2,2':6',2"-terpyridine-6,6"-diyl)bis(methylenenitrilo)-tetrakis(acetic acid)(TTA) as a luminous antenna owing to the high luminescence quantum yield, stability, and water-solubility of its lanthanide complexes, and several lanthanide complex-based luminescent probes and chemosensors for specific detection of bioactive molecules have been designed and synthesized by introducing different recognizers to TTA ligand. The applicability of these probes for time-resolved luminescence bioassays were investigated.
A unique ratiometric luminescent probe, AMTTA-Eu3+/Tb3+, has been designed and synthesized for highly sensitive detection of hROS (highly reactive oxygen species,·OH and HOC1). The ratio of the probe is based on the different variations of Tb3+emission at540nm and Eu3+emission at610nm. When the ratiometric probe was reacted with hROS, the dose-dependent increase of the ratio, I540/I610, displayed a double exponential correlation to the concentration of hROS. This unique luminescence response is pH-independent and does not affected by other ions and ROS/RNS, which provides a useful tool that can be used for luminescence detection of hROS with both time-resolved mode and ratiometric mode.
Based on the photo-induced electron transfer (PeT), two novel lanthanide complex-based luminescent probes, ANMTTA-Eu3+and ANMTTA-Tb3+, have been designed and synthesized for the highly sensitive and selective time-resolved luminescence detection of hypochlorous acid (HOCl) in aqueous media. The luminescence of the probes increased remarkably after reaction with HOCl due to the elimination of the PeT process. The dose-dependent luminescence enhancements show good linearity to the concentration of HOCl. The luminescence responses of ANMTTA-Eu3+and ANMTTA-Tb3+to HOCl are pH-independent with excellent selectivity to other reactive oxygen/nitrogen species (ROS/RNS). In combination with a time-resolved luminescence microscope, the exogenous and endogenous HOCl in HeLa cells and RAW264.7macrophage cells were successfully monitored, respectively, which provides a new and valuable method for detection of HOCl in complicated biological samples.
A new terbium complex-based luminescent probe, PAMTTA-Tb3+, has been designed and synthesized for the highly sensitive and selective detection of Zn2+ions. Compared with reported lanthanide complex-based luminescent probes for Zn2+ions, the selectivity of such "OFF-ON-OFF" time-resolved luminescent probe has been improved remarkably due to the unique probe design. The response of PAMTTA-Tb3+to Zn2+is reversible and can be used as an excellent time-resolved luminescent probe for the detection of intracellular Zn2+ions in HeLa cells.
设计合成了一种可用于高活性氧组分(hROS,包括羟基自由基及次氯酸)比率型荧光传感测定的基于Eu3+和Tb3+双发射的时间分辨荧光探针AMTTA-Eu3+/Tb3+,并将其用于hROS的比率型时间分辨荧光测定。研究发现,两种稀土配合物AMTTA-Eu3+与AMTTA-Tb3+的混合物与hROS作用时,其荧光强度比值I540／I610与hROS的浓度呈现剂量依赖性增加,而且不受pH值和金属移位等的影响,为复杂生物样品中hROS的测定提供了一种兼具比率型及时间分辨功能的荧光测定新方法。
利用分子内光诱导电子转移作用(PeT),通过在联三吡啶配位体中以醚键的方式引入3-硝基-4-氨基苯基基团的方法,设计合成了两种对次氯酸具有高度特异性识别与高灵敏度响应的时间分辨荧光探针ANMTTA-Eu3+和ANMTTA-Tb3+。通过考察探针用于水溶液及活细胞中次氯酸的荧光测定,证明了两种探针在用于次氯酸荧光检测时均具有稳定性及水溶性好、选择性及灵敏度高、响应迅速、pH适用范围宽等优点,可用于活细胞中外源性及内源性次氯酸的时间分辨荧光成像测定,为复杂生物样品中次氯酸的荧光检测提供了一种有实用价值的新方法。
设计合成了一种对锌离子具有特异性识别与响应的时间分辨荧光探针PAMTTA-Tb3+,与已报道的基于稀土配合物的锌离子荧光探针相比,该探针独特的分子构型设计使其对锌离子响应的特异性显著提高。该探针除了具有水溶性好、选择性及灵敏度高、响应迅速等优点外,还可实现对锌离子的可逆响应及活细胞内锌离子的时间分辨荧光成像测定。
Compared with ordinary organic luminescent probes, the lanthanide complex-based luminescent probes have some advantages, such as high solubility and stability, large Stokes shift and long luminescence life time, which enable these complexes to be easily used for the time-resolved luminescence measurement to eliminate the interferences from auto-fluorescence and scattering lights. On the basis of results reported in previous literature, this doctoral dissertation chose (2,2':6',2"-terpyridine-6,6"-diyl)bis(methylenenitrilo)-tetrakis(acetic acid)(TTA) as a luminous antenna owing to the high luminescence quantum yield, stability, and water-solubility of its lanthanide complexes, and several lanthanide complex-based luminescent probes and chemosensors for specific detection of bioactive molecules have been designed and synthesized by introducing different recognizers to TTA ligand. The applicability of these probes for time-resolved luminescence bioassays were investigated.
A unique ratiometric luminescent probe, AMTTA-Eu3+/Tb3+, has been designed and synthesized for highly sensitive detection of hROS (highly reactive oxygen species,·OH and HOC1). The ratio of the probe is based on the different variations of Tb3+emission at540nm and Eu3+emission at610nm. When the ratiometric probe was reacted with hROS, the dose-dependent increase of the ratio, I540/I610, displayed a double exponential correlation to the concentration of hROS. This unique luminescence response is pH-independent and does not affected by other ions and ROS/RNS, which provides a useful tool that can be used for luminescence detection of hROS with both time-resolved mode and ratiometric mode.
Based on the photo-induced electron transfer (PeT), two novel lanthanide complex-based luminescent probes, ANMTTA-Eu3+and ANMTTA-Tb3+, have been designed and synthesized for the highly sensitive and selective time-resolved luminescence detection of hypochlorous acid (HOCl) in aqueous media. The luminescence of the probes increased remarkably after reaction with HOCl due to the elimination of the PeT process. The dose-dependent luminescence enhancements show good linearity to the concentration of HOCl. The luminescence responses of ANMTTA-Eu3+and ANMTTA-Tb3+to HOCl are pH-independent with excellent selectivity to other reactive oxygen/nitrogen species (ROS/RNS). In combination with a time-resolved luminescence microscope, the exogenous and endogenous HOCl in HeLa cells and RAW264.7macrophage cells were successfully monitored, respectively, which provides a new and valuable method for detection of HOCl in complicated biological samples.
A new terbium complex-based luminescent probe, PAMTTA-Tb3+, has been designed and synthesized for the highly sensitive and selective detection of Zn2+ions. Compared with reported lanthanide complex-based luminescent probes for Zn2+ions, the selectivity of such "OFF-ON-OFF" time-resolved luminescent probe has been improved remarkably due to the unique probe design. The response of PAMTTA-Tb3+to Zn2+is reversible and can be used as an excellent time-resolved luminescent probe for the detection of intracellular Zn2+ions in HeLa cells.
引文
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