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

LI Jian-ling; DING Guo-hua; LIU Yan-ping; FENG Hua-jie; NIU Yan-yan; HE Meng-xiong; SHI Za

doi:10.3788/fgxb20194008.0969

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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

Synthesis and Properties of Materials | 更新时间：2020-08-12

- 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
- Chinese Journal of Luminescence Vol. 40, Issue 8, Pages: 969-978(2019)
- 作者机构：
  
  1. 海南师范大学化学与化工学院,海南海口,571158
  2. 热带药用资源化学教育部重点实验室,海南海口,571158
  3. 海南省水环境污染治理与资源化重点实验室,海南海口,571158
- 作者简介：
- 基金信息：
- DOI：10.3788/fgxb20194008.0969
  CLC： O657
- Received：07 September 2018，
  
  Revised：04 November 2018，
  
  Published Online：28 November 2018，
  
  Published：05 August 2019
- 稿件说明：
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李建玲, 丁国华, 刘艳萍等. 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): 969-978

LI Jian-ling, DING Guo-hua, LIU Yan-ping etc. 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): 969-978
李建玲, 丁国华, 刘艳萍等. 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): 969-978 DOI： 10.3788/fgxb20194008.0969.

LI Jian-ling, DING Guo-hua, LIU Yan-ping etc. 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): 969-978 DOI： 10.3788/fgxb20194008.0969.

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Hg

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Hg

的络合比为1:2，显色机理为Hg

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Hg

标记。

Abstract

Ethyl 2-(4-methoxyphenyl)-5-phenyl-2H-1

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 Hg

ions could induce a significantly fluorescent enhancement and an intensive absorption of REMPC with a rapid chemical reaction in N

N-dimethylformamide(DMF)-H

O (

V:V

=1:1

pH=7.4). Meanwhile the triazole appended colorless chemosensor turns to pink upon complex formation only with Hg

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 Hg

inducing the ring-opened rhodamine B moiety were proposed. The fluorescence imaging experiments of Hg

in HeLa cell demonstrated that the probe was successfully labeled and it could be used in biological systems.

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references

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