时间分辨荧光分析用新型稀土荧光探针研究
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摘要
稀土配合物荧光探针因具有荧光寿命长、Stokes位移大及发光峰尖锐等特殊的荧光性质在高灵敏度时间分辨荧光分析、临床检测与生物技术等领域得到了广泛的应用。在本学位论文研究中,分别设计合成了稀土离子与几种功能性多羧酸联三吡啶配位体的配合物,在充分考察其荧光性质的基础上,建立了这些配合物在时间分辨荧光分析中的应用方法。
设计合成了一种新型的以硼酸基为识别基团的联三吡啶多羧酸配体的铕配合物荧光探针(4’-硼酸基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸)-Eu3+(BTTA-Eu3+)以用于过氧化氢的特异性识别与荧光测定。BTTA-Eu3+本身具有很强的荧光,与过氧化氢反应生成其脱硼酸化衍生物(4’-羟基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸)-Eu3+(HTTA-Eu3+)后荧光可被强烈淬灭。由于作为硼酸化试剂BTTA可与溴苯进行Suzuki偶联反应生成4’-苯基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸(PTTA),而PTTA-Eu3+的荧光不受H202影响,利用H2O2-BTTA-Eu3+体系成功地建立了该偶联反应动力学的时间分辨荧光监测新方法。
设计合成了一种新型的铕-铽混合配合物比率型pH荧光探针4’-羟基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸-Eu3+/Tb3+(HTTA-Eu3+/Tb3+)以用于pH值的比率型时间分辨荧光测定。研究发现配合物HTTA-Eu3+的荧光强度在pH值4.8-7.5之间随pH值的增加显著减弱,而配合物HTTA-Tb3+的荧光强度则不随pH值的变化而变化,因此可利用混合配合物HTTA-Eu3+/Tb3+的1540nm/1610nm荧光强度比值作为信号进行pH值的比率型荧光测定。为考察新型探针在细胞成像中的应用价值,分别制备了HTTA-Eu3+及HTTA-Tb3+标记的HeLa细胞,并对标记细胞进行了荧光成像及时间分辨荧光成像测定,所得结果表明探针可作为一种有用的工具用于测定细胞内的pH值。
设计合成了一种基于铕配合物的具有更宽pH适用范围的新型NO荧光探针4’-(3-甲氨基-4氨基苯基)-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸-Eu3+(MATTA-Eu3+)以用于NO的时间分辨荧光测定。在系统表征了该探针对NO荧光响应的基础上,制备出了MATTA-Eu3+标记的PC12神经细胞,并通过时间分辨荧光成像模式成功地对谷氨酸诱导下PC12细胞内NO的产生进行了荧光成像测定。
Lanthanide complex-based fluorescence probes have shown great utilities in the fields of highly sensitive time-resolved fluorescence analysis, clinical diagnostics and biotechnology owing to their unique fluorescence properties including long fluorescence lifetimes, large Stokes shifts and sharp emission peaks. In this doctoral dissertation, several new lanthanide complexes with functional terpyridine polyacid ligands were designed and synthesized. After the detailed fluorescence characterizations of the complexes, the application methods of the complexes for the time-resolved fluorescence detections were established.
A new europium(III) complex with a borono-substituted terpyridine polyacid ligand,(4'-borono-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+(BTTA-Eu3+), was designed and synthesized as a probe for the-time-resolved luminescence detection of hydrogen peroxide (H2O2). The complex BTTA-Eu3+is highly luminescent in aqueous media, upon reaction with H2O2to form its deboronation derivative (4'-hydroxy-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+(HTTA-Eu3+), the luminescence can be remarkably weakened in neutral and basic buffers. Because the pyridine-4-boronic acid structure of BTTA allows it to be a useful reagent for the Suzuki cross-coupling reaction with bromobenzene to synthesize (4'-phenyl-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetic acid)(PTTA), the luminescence of BTTA-Eu3+can be quenched by H2O2, while that of PTTA-Eu3+is not affected by H2O2, a new time-resolved luminescence method for tracking the kinetics of the Suzuki cross-coupling reaction between BTTA-Eu3+and bromobenzene was developed by using the H2O2-BTTA-Eu3+system to monitor the PTTA formation.
A new lanthanide complex mixture-based ratiometric luminescence probe,(4'-hydroxy-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+/Tb3+(HTTA-Eu3+/Tb3+), was designed and synthesized for the pH detection. The luminescence characterization results reveal that the luminescence intensity of HTTA-Eu3+is strongly dependent on the pH value in the pH range of4.8-7.5, while that of HTTA-Tb3+is pH-independent. This unique luminescence response allows the mixture of HTTA-Eu3+and HTTA-Tb3+(the HTTA-Eu3+/Tb3+mixture) to be used as a ratiometric luminescence probe for the time-resolved luminescence detection of pH with the intensity ratio of Tb3+emission at540nm to Eu3+emission at610nm, I540nm/l610nm, as a signal. For investigating the utility of the new probe for cell imaging, the HTTA-Eu3+-loaded and HTTA-Tb3+-loaded HeLa cells were prepared, and used for the luminescence imaging measurements, respectively. The results suggest that the new probe could be a useful tool for the intercellular pH detection.
A new europium(Ⅲ) complex-based luminescence probe having wider pH available range,[4'-(3-methylamino-4-aminophenoxy)-2,2':6',2"-terpyridine-6,6"-diyl] bis(methyle-nenitrilo) tetrakis(acetate)-Eu3+(MATTA-Eu3+), was designed and synthesized for the time-resolved luminescence detection of NO. After systemic characterizations of the luminescence response of the probe to NO, the MATTA-Eu3+-loaded PCl2cells were prepared, and the glutamate-induced NO production in the cells was successfully imaged with time-resolved luminescence imaging mode.
设计合成了一种新型的以硼酸基为识别基团的联三吡啶多羧酸配体的铕配合物荧光探针(4’-硼酸基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸)-Eu3+(BTTA-Eu3+)以用于过氧化氢的特异性识别与荧光测定。BTTA-Eu3+本身具有很强的荧光,与过氧化氢反应生成其脱硼酸化衍生物(4’-羟基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸)-Eu3+(HTTA-Eu3+)后荧光可被强烈淬灭。由于作为硼酸化试剂BTTA可与溴苯进行Suzuki偶联反应生成4’-苯基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸(PTTA),而PTTA-Eu3+的荧光不受H202影响,利用H2O2-BTTA-Eu3+体系成功地建立了该偶联反应动力学的时间分辨荧光监测新方法。
设计合成了一种新型的铕-铽混合配合物比率型pH荧光探针4’-羟基-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸-Eu3+/Tb3+(HTTA-Eu3+/Tb3+)以用于pH值的比率型时间分辨荧光测定。研究发现配合物HTTA-Eu3+的荧光强度在pH值4.8-7.5之间随pH值的增加显著减弱,而配合物HTTA-Tb3+的荧光强度则不随pH值的变化而变化,因此可利用混合配合物HTTA-Eu3+/Tb3+的1540nm/1610nm荧光强度比值作为信号进行pH值的比率型荧光测定。为考察新型探针在细胞成像中的应用价值,分别制备了HTTA-Eu3+及HTTA-Tb3+标记的HeLa细胞,并对标记细胞进行了荧光成像及时间分辨荧光成像测定,所得结果表明探针可作为一种有用的工具用于测定细胞内的pH值。
设计合成了一种基于铕配合物的具有更宽pH适用范围的新型NO荧光探针4’-(3-甲氨基-4氨基苯基)-2,2’：6’,2”-联三吡啶-6,6”-二甲胺四乙酸-Eu3+(MATTA-Eu3+)以用于NO的时间分辨荧光测定。在系统表征了该探针对NO荧光响应的基础上,制备出了MATTA-Eu3+标记的PC12神经细胞,并通过时间分辨荧光成像模式成功地对谷氨酸诱导下PC12细胞内NO的产生进行了荧光成像测定。
Lanthanide complex-based fluorescence probes have shown great utilities in the fields of highly sensitive time-resolved fluorescence analysis, clinical diagnostics and biotechnology owing to their unique fluorescence properties including long fluorescence lifetimes, large Stokes shifts and sharp emission peaks. In this doctoral dissertation, several new lanthanide complexes with functional terpyridine polyacid ligands were designed and synthesized. After the detailed fluorescence characterizations of the complexes, the application methods of the complexes for the time-resolved fluorescence detections were established.
A new europium(III) complex with a borono-substituted terpyridine polyacid ligand,(4'-borono-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+(BTTA-Eu3+), was designed and synthesized as a probe for the-time-resolved luminescence detection of hydrogen peroxide (H2O2). The complex BTTA-Eu3+is highly luminescent in aqueous media, upon reaction with H2O2to form its deboronation derivative (4'-hydroxy-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+(HTTA-Eu3+), the luminescence can be remarkably weakened in neutral and basic buffers. Because the pyridine-4-boronic acid structure of BTTA allows it to be a useful reagent for the Suzuki cross-coupling reaction with bromobenzene to synthesize (4'-phenyl-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetic acid)(PTTA), the luminescence of BTTA-Eu3+can be quenched by H2O2, while that of PTTA-Eu3+is not affected by H2O2, a new time-resolved luminescence method for tracking the kinetics of the Suzuki cross-coupling reaction between BTTA-Eu3+and bromobenzene was developed by using the H2O2-BTTA-Eu3+system to monitor the PTTA formation.
A new lanthanide complex mixture-based ratiometric luminescence probe,(4'-hydroxy-2,2':6',2"-terpyridine-6,6"-diyl) bis(methylenenitrilo) tetrakis(acetate)-Eu3+/Tb3+(HTTA-Eu3+/Tb3+), was designed and synthesized for the pH detection. The luminescence characterization results reveal that the luminescence intensity of HTTA-Eu3+is strongly dependent on the pH value in the pH range of4.8-7.5, while that of HTTA-Tb3+is pH-independent. This unique luminescence response allows the mixture of HTTA-Eu3+and HTTA-Tb3+(the HTTA-Eu3+/Tb3+mixture) to be used as a ratiometric luminescence probe for the time-resolved luminescence detection of pH with the intensity ratio of Tb3+emission at540nm to Eu3+emission at610nm, I540nm/l610nm, as a signal. For investigating the utility of the new probe for cell imaging, the HTTA-Eu3+-loaded and HTTA-Tb3+-loaded HeLa cells were prepared, and used for the luminescence imaging measurements, respectively. The results suggest that the new probe could be a useful tool for the intercellular pH detection.
A new europium(Ⅲ) complex-based luminescence probe having wider pH available range,[4'-(3-methylamino-4-aminophenoxy)-2,2':6',2"-terpyridine-6,6"-diyl] bis(methyle-nenitrilo) tetrakis(acetate)-Eu3+(MATTA-Eu3+), was designed and synthesized for the time-resolved luminescence detection of NO. After systemic characterizations of the luminescence response of the probe to NO, the MATTA-Eu3+-loaded PCl2cells were prepared, and the glutamate-induced NO production in the cells was successfully imaged with time-resolved luminescence imaging mode.
引文
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