Rhodamine-based 'turn-on' fluorescent probe for Cu(II) and its fluorescence imaging in living cells

被引:46
作者
Tian, Mao-Zhong [1 ,2 ]
Hu, Ming-Ming [1 ]
Fan, Jiang-Li [1 ]
Peng, Xiao-Jun [1 ]
Wang, Jing-Yun [1 ]
Sun, Shi-Guo [1 ]
Zhang, Rong [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Shanxi Datong Univ, Coll Chem & Chem Engn, Datong 037009, Peoples R China
关键词
Fluorescence; Probe; Cu2+; Rhodamine; Cell imaging; NANOMOLAR DETECTION; AQUEOUS-SOLUTION; SENSOR; CU2+; COPPER(II); CHEMOSENSOR; CHEMODOSIMETERS; SENSITIVITY; SELECTIVITY; WATER;
D O I
10.1016/j.bmcl.2013.03.052
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel rhodamine spirolactam derivative 3',6'-Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[iso-indoline-1,9'-xanthen]-3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and H-1 NMR and C-13 NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu2+ over other metal ions with a detection limit of 0.56 ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu2+ induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu2+ changes by live cell imaging. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2916 / 2919
页数:4
相关论文
共 37 条
[11]   Multisignall chemosensor for Cr3+ and its application in bioimaging [J].
Huang, Kewei ;
Yang, Hong ;
Zhou, Zhiguo ;
Yu, Mengxiao ;
Li, Fuyou ;
Gao, Xia ;
Yi, Tao ;
Huang, Chunhui .
ORGANIC LETTERS, 2008, 10 (12) :2557-2560
[12]   Reactivity-Based Detection of Copper(II) Ion in Water: Oxidative Cyclization of Azoaromatics as Fluorescence Turn-On Signaling Mechanism [J].
Jo, Junyong ;
Lee, Ho Yong ;
Liu, Wenjun ;
Olasz, Andras ;
Chen, Chun-Hsing ;
Lee, Dongwhan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (38) :16000-16007
[13]  
Jung H.S., 2008, J AM CHEM SOC, V2009, P131
[14]   Rhodamine-Based "Turn-On" Fluorescent Chemodosimeter for Cu(II) on Ultrathin Platinum Films as Molecular Switches [J].
Kim, Yang-Rae ;
Kim, Hyun Jung ;
Kim, Jong Seung ;
Kim, Hasuck .
ADVANCED MATERIALS, 2008, 20 (23) :4428-4432
[15]   Highly Selective Fluorescence Turn-on Chemodosimeter Based on Rhodamine for Nanomolar Detection of Copper Ions [J].
Kumar, Manoj ;
Kumar, Naresh ;
Bhalla, Vandana ;
Sharma, Parduman Raj ;
Kaur, Tandeep .
ORGANIC LETTERS, 2012, 14 (01) :406-409
[16]   A fluorescent and colorimetric probe specific for palladium detection [J].
Li, Honglin ;
Fan, Jiangli ;
Du, Jianjun ;
Guo, Kexin ;
Sun, Shiguo ;
Liu, Xiaojian ;
Peng, Xiaojun .
CHEMICAL COMMUNICATIONS, 2010, 46 (07) :1079-1081
[17]   1,8-Naphthyridine-Derived Ni2+/Cu2+-Selective Fluorescent Chemosensor with Different Charge Transfer Processses [J].
Li, Zhanxian ;
Zhao, Wanying ;
Li, Xiaoya ;
Zhu, Yanyan ;
Liu, Chunmei ;
Wang, Lina ;
Yu, Mingming ;
Wei, Liuhe ;
Tang, Mingsheng ;
Zhang, Hongyan .
INORGANIC CHEMISTRY, 2012, 51 (22) :12444-12449
[18]   Ratiometric Detection of Cr3+ and Hg2+ by a Naphthalimide-Rhodamine Based Fluorescent Probe [J].
Mahato, Prasenjit ;
Saha, Sukdeb ;
Suresh, E. ;
Di Liddo, Rosa ;
Parnigotto, Pier Paolo ;
Conconi, Maria Teresa ;
Kesharwani, Manoj K. ;
Ganguly, Bishwajit ;
Das, Amitava .
INORGANIC CHEMISTRY, 2012, 51 (03) :1769-1777
[19]   Visible-Near-Infrared and Fluorescent Copper Sensors Based on Julolidine Conjugates: Selective Detection and Fluorescence Imaging in Living Cells [J].
Maity, Debabrata ;
Manna, Arun K. ;
Karthigeyan, D. ;
Kundu, Tapas K. ;
Pati, Swapan K. ;
Govindaraju, T. .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (40) :11152-11161
[20]   In Situ Imaging of Metals in Cells and Tissues [J].
McRae, Reagan ;
Bagchi, Pritha ;
Sumalekshmy, S. ;
Fahrni, Christoph J. .
CHEMICAL REVIEWS, 2009, 109 (10) :4780-4827