发光学报, 2019, 40 (8): 969, 网络出版: 2019-09-02
5-苯基-2-(4-甲氧基)-2H-1,2,3-三氮唑-4-羧酸乙酯的光谱性质及其罗丹明衍生物对Hg2+的显色机理和细胞成像
Spectral Properties of Ethyl 2-(4-methoxyphenyl)-5-phenyl-2H-1,2,3-triazole-4-carboxylate and Chromogenic Mechanism of Its Rhodamine B Derivatives to Hg2+ Ions and Application in Cell Imaging
5-苯基-2-(4-甲氧基)-2H-1,2,3-三氮唑-4-羧酸乙酯 光谱性质 罗丹明B 显色机理 Hg2+离子 Ethyl 2-(4 -methoxyphenyl)-5-phenyl-2H-1,2,3-triaz spectral properties rhodamine B chromogenic mechanism Hg2+ ion
摘要
对5-苯基-2-(4-甲氧基)-2H-1,2,3-三氮唑-4-羧酸乙酯(Ethyl 2-(4-methoxyphenyl)-5-phenyl-2H-1,2,3-triazole-4-carboxylate, 简称EMPC)进行了理论光谱及结构计算, 并与实验光谱作对比。设计合成了其罗丹明B衍生物REMPC, 用荧光和紫外吸收光谱法研究了REMPC与15种金属离子的作用, 在DMF(N, N-二甲基甲酰胺)-水溶液 (pH=7.4, 体积比1∶1)中, 肉眼可观察到REMPC仅对Hg2+有粉红色的快速显色反应, 使其在相应波长处的荧光强度及紫外吸收增强, REMPC与Hg2+的络合比为1∶2, 显色机理为Hg2+诱导REMPC中的罗丹明螺环开环。在HeLa细胞中的荧光成像实验表明: REMPC探针可成功用于生物体内的Hg2+标记。
Abstract
Ethyl 2-(4-methoxyphenyl)-5-phenyl-2H-1,2,3-triazole-4-carboxylate(EMPC) is a newly synthesized compound and used to investigate its theoretical spectrum and structural properties by quantum chemistry methods. Then EMPC was designed and synthesized to a novel rhodamine B derivative REMPC. The interactions of REMPC with 15 kinds of metal ions were investigated by fluorescence spectra and UV absorption spectra. The presence of Hg2+ ions could induce a significantly fluorescent enhancement and an intensive absorption of REMPC with a rapid chemical reaction in N, N-dimethylformamide(DMF)-H2O (V∶V=1∶1, pH=7.4). Meanwhile the triazole appended colorless chemosensor turns to pink upon complex formation only with Hg2+ ions and enables naked-eye detection. The equimolar continuous change method and structural computation were employed to measure the composition formed the new complex as 1∶2 molar ratio. The corresponding off-on fluorescence mechanisms which were ascribed to Hg2+ inducing the ring-opened rhodamine B moiety were proposed. The fluorescence imaging experiments of Hg2+ in HeLa cell demonstrated that the probe was successfully labeled and it could be used in biological systems.
李建玲, 丁国华, 刘艳萍, 冯华杰, 牛燕燕, 何猛雄, 史载锋, 何文英. 5-苯基-2-(4-甲氧基)-2H-1,2,3-三氮唑-4-羧酸乙酯的光谱性质及其罗丹明衍生物对Hg2+的显色机理和细胞成像[J]. 发光学报, 2019, 40(8): 969. LI Jian-ling, DING Guo-hua, LIU Yan-ping, FENG Hua-jie, NIU Yan-yan, HE Meng-xiong, SHI Zai-feng, HE Wen-ying. Spectral Properties of Ethyl 2-(4-methoxyphenyl)-5-phenyl-2H-1,2,3-triazole-4-carboxylate and Chromogenic Mechanism of Its Rhodamine B Derivatives to Hg2+ Ions and Application in Cell Imaging[J]. Chinese Journal of Luminescence, 2019, 40(8): 969.