一种以2-羟基-N,N-二甲基苄胺为新识别基团的钯离子近红外荧光探针及其细胞成像
收稿日期: 2021-12-02
修回日期: 2022-01-08
网络出版日期: 2022-02-25
基金资助
湖南省教育厅优秀青年基金(19B390); 湖南省教育厅优秀青年基金(19C1254); 湖南省自然科学基金(2020JJ4445); 湖南省自然科学基金(2020JJ5390)
A Near-Infrared Fluorescent Probe with 2-Hydroxy-N,N-dimethyl- benzylamine as a New Recognition Fragment for Pd2+ Detection and Bioimaging
Received date: 2021-12-02
Revised date: 2022-01-08
Online published: 2022-02-25
Supported by
Scientific Research Foundation of Hunan Provincial Education Department(19B390); Scientific Research Foundation of Hunan Provincial Education Department(19C1254); Hunan Provincial Natural Science Foundation of China(2020JJ4445); Hunan Provincial Natural Science Foundation of China(2020JJ5390)
设计、合成了一种含有异佛尔酮骨架和2-羟基-N,N-二甲基苄胺的近红外荧光探针DHDM. 荧光探针DHDM可用于特异性地检测Pd2+, 具有良好的检测限(53 nmol/L)和斯托克斯位移(220 nm). 在0~70 μmol/L浓度范围内, 660 nm处的荧光发射强度与Pd2+呈现良好的线性关系. 根据高分辨质谱、红外光谱、对比实验以及DFT计算的结果, 提出了一种可能的识别机理. 最后, 成功地将荧光探针DHDM应用于细胞中Pd2+的荧光成像, 显示其在生物体系中潜在的应用. 这种以2-羟基-N,N-二甲基苄胺为识别基团的设计策略将为构建性能优异的其它荧光探针提供新思路.
张向阳 , 吴庆林 , 王菲菲 , 申有名 , 唐裕才 . 一种以2-羟基-N,N-二甲基苄胺为新识别基团的钯离子近红外荧光探针及其细胞成像[J]. 有机化学, 2022 , 42(6) : 1786 -1791 . DOI: 10.6023/cjoc202112004
A near-infrared fluorescent probe DHDM bearing isophorone skeleton and 2-hydroxy-N,N-dimethylbenzylamine has been rationally designed and synthesized. DHDM showed excellent Pd2+ specificity with a low detection limit of 53 nmol/L and a large Stokes shift (220 nm). The fluorescence intensity at 660 nm was linear to Pd2+ concentrations in a wide range (0~70 μmol/L). Additionally, a possible sensing mechanism was proposed based on the results of the mass spectroscopy, infrared spectrum, a comparative experiment and density functional theory (DFT) calculations. Finally, DHDM was further successfully used to image Pd2+ in live cells, suggesting its potential applications in biological systems. The design strategy based on 2-hydroxy-N,N-dimethylbenzylamine or one of its analogues as a new recognition fragment will inspire researchers to construct privileged fluorescence probes in the future.
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