作者：韩琪, 吴楠, 程思宇, 杨想, 包尚哲, 陈颂
作者单位：齐齐哈尔医学院药学院, 黑龙江 齐齐哈尔 161006
关键词：荧光探针;水合肼;分子内电荷转移;细胞成像
摘要：
该文以氰基联苯酚为荧光载体，乙酰基为识别基团，基于水合肼引发的脱保护反应和分子内电荷转移机制（ICT），研发一种能快速识别N2H4的开关型荧光探针。在pH=7.4（含1 mmol/L CTAB）的PBS缓冲溶液中，相对于其他测试的分子或离子，探针化合物对N2H4表现出良好的选择性和灵敏度，能在5 min内快速检测识别到N2H4。当探针浓度为10.0 μmol/L时，探针化合物对N2H4的检出限为0.08 μmol/L，这个限度符合美国环保局定义的N2H4浓度水平。在生理条件下，探针识别N2H4可以呈现显著的荧光开启信号。同时，细胞成像实验表明探针可以透过细胞膜与N2H4作用，为在线监测提供有效的工具分子。
Research on the synthesis and cell imaging of fast identifiable hydrazine fluorescent probe
HAN Qi, WU Nan, CHENG Siyu, YANG Xiang, BAO Shangzhe, CHEN Song
College of Pharmacy, Qiqihar Medical University, Qiqihar 161006, China
Abstract: Based on the deprotection reaction initiated by hydrazine and the mechanism of intramolecular charge transfer (ICT), a switch type fluorescent probe was developed to recognize N2H4 rapidly. Compared with other tested molecules and ions, the probe showed good selectivity and sensitivity to N2H4 in pH=7.4 PBS buffer solution containing 1 mmol/L CTAB, and it could detect N2H4 quickly within 5 min. When the concentration of the probe was 10.0 μmol/L, the detection limit of the probe to N2H4 was 0.08 μmol/L, which conforms to the concentration level of N2H4 defined by the U.S. Environmental Protection Agency. Under physiological conditions, the probe recognition of N2H4 showed a significant fluorescence signal. At the same time, the cell imaging experiments exhibited that the probe could react with N2H4 through the cell membrane, providing an effective tool molecule for on-line monitoring.
Keywords: fluorescent probe;hydrazine;intramolecular charge transfer;cell imaging
2020, 46(6):56-60 收稿日期: 2020-02-18;收到修改稿日期: 2020-03-21
基金项目: 黑龙江省大学生创新创业训练计划项目（201911230021）
作者简介: 韩琪(1997-),女,黑龙江大庆市人,专业方向为荧光探针的合成与生物学应用
参考文献
[1] DING Y U, ZHAO S, WANG Q Q, et al. Construction of a coumarin based sensing platform for palladium and hydrazine detection[J]. Sensors and Actuators B-Chemical, 2018, 256: 1107-1113
[2] CHEN Z, ZHONG X X, QU W B, et al. A highly selective HBT-based “turn-on” fluorescent probe for hydrazine detection and its application[J]. Tetrahedron Letters, 2017, 58: 2596-2601
[3] MA J H, FAN J L, LI H D, et al. Probing hydrazine with a near-infrared fluorescent chemodosimeter[J]. Dyes and Pigments, 2017, 138: 39-46
[4] HAO Y Q, ZHANG Y T, RUAN K H, et al. A highly selective long-wavelength fluorescent probe for hydrazine and its application in living cell imaging[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, 184: 355-360
[5] 侯鹏, 董玉晶, 李爽, 等. 反应型香豆素N2H4荧光探针的生物成像研究[J]. 中国测试, 2017, 226(5): 53-57
[6] 陈颂, 王静, 侯鹏, 等. 用于检测生物硫醇的新型萘酰亚胺荧光探针的合成与应用[J]. 中国测试, 2016, 217(8): 64-67
[7] LEE S Y, LI J, ZHOU X, et al. Recent progress on the development of glutathione (GSH) selective fluorescent and colorimetric probes[J]. Coordination Chemistry Reviews, 2018, 366: 29-68
[8] WANG Z L, ZHANG Y, SONG J, et al. A novel isolongifolanone based fluorescent pochlorite and its application in bio-imaging[J]. Analytica Chimica Acta, 2019, 1051: 169-178
[9] CHOI M G, HWANG J, MOON J O, et al. Hydrazine-selective chromogenic and fluorogenic probe based on levulinated coumarin[J]. Organic Letters, 2011, 13: 5260-5263
[10] RAMAKRISHNAMRAJU M V, PRAKASH E C, CHANG H, et al. A facile ratiometric drazine based on Ing-Manske hydrazinolysis and its application in living cells[J]. Dyes and Pigments, 2014, 103: 9-20
[11] ZHOU J, SHIR Y, LIU J X, et al. An ESIPT-based fluorescent probe for sensitive detection of hydrazine in aqueous solution[J]. Organic and Biomolecular Chemistry, 2015, 13: 5344-5348
[12] CHEN S, HOU P, WANG J, et al. A simple but effective fluorescent probe with large stokes shift for specific detection of cysteine in living cells[J]. Journal of Photochemistry and Photobiology A-Chemistry, 2018, 363: 7-12
[13] CHEN S, HOU P, WANG J, et al. A simple but effective probe with large stokes shift for the detection of hydrogen sulfide[J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 203: 258-262
[14] XIA X T, ZENG F, ZHANG P S, et al. An ICT-based iometric fluorescent probe for hydrazine detection and its application in living cells and in vivo[J]. Sensors and Actuators B-Chemical, 2016, 227: 411-418
[15] RAN Y Z, XU H R, LI K, et al. Developmet of mitochondria-targeted fluorescent probe for hydrazine monitoring in living cells[J]. RSC Advance, 2016, 6: 111016-111019
