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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 10期

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

页码：2916 / 2919

页数：4

共 37 条

[1] A phenanthrene based highly selective fluorogenic and visual sensor for Cu2+ ion with nanomolar detection limit and its application in live cell imaging [J].

Anbu, Sellamuthu ;

Shanmugaraju, Sankarasekaran ;

Ravishankaran, Rajendran ;

Karande, Anjali A. ;

Mukherjee, Partha Sarathi .

INORGANIC CHEMISTRY COMMUNICATIONS, 2012, 25 :26-29

[2] Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives [J].

Chen, Xiaoqiang ;

Pradhan, Tuhin ;

Wang, Fang ;

Kim, Jong Seung ;

Yoon, Juyoung .

CHEMICAL REVIEWS, 2012, 112 (03) :1910-1956

[3] Fluorescent and colorimetric probes for detection of thiols [J].

Chen, Xiaoqiang ;

Zhou, Ying ;

Peng, Xiaojun ;

Yoon, Juyoung .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135

[4] Selective Removal of Copper(II) from Natural Waters by Nanoporous Sorbents Functionalized with Chelating Diamines [J].

Chouyyok, Wilaiwan ;

Shin, Yongsoon ;

Davidson, Joseph ;

Samuels, William D. ;

Lafemina, Nikki H. ;

Rutledge, Ryan D. ;

Fryxell, Glen E. ;

Sangvanich, Thanapon ;

Yantasee, Wassana .

ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2010, 44 (16) :6390-6395

[5] Rhodamine and BODIPY chemodosimeters and chemosensors for the detection of Hg2+, based on fluorescence enhancement effects [J].

Culzoni, M. J. ;

Munoz de la Pena, A. ;

Machuca, A. ;

Goicoechea, H. C. ;

Babiano, R. .

ANALYTICAL METHODS, 2013, 5 (01) :30-49

[6] Signaling recognition events with fluorescent sensors and switches [J].

de Silva, AP ;

Gunaratne, HQN ;

Gunnlaugsson, T ;

Huxley, AJM ;

McCoy, CP ;

Rademacher, JT ;

Rice, TE .

CHEMICAL REVIEWS, 1997, 97 (05) :1515-1566

[7] A Targetable Fluorescent Sensor Reveals That Copper-Deficient SCO1 and SCO2 Patient Cells Prioritize Mitochondrial Copper Homeostasis [J].

Dodani, Sheel C. ;

Leary, Scot C. ;

Cobine, Paul A. ;

Winge, Dennis R. ;

Chang, Christopher J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (22) :8606-8616

[8] Fluorescent chemodosimeters using "mild" chemical events for the detection of small anions and cations in biological and environmental media [J].

Du, Jianjun ;

Hu, Mingming ;

Fan, Jiangli ;

Peng, Xiaojun .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (12) :4511-4535

[9] A Highly Selective Turn-On Colorimetric, Red Fluorescent Sensor for Detecting Mobile Zinc in Living Cells [J].

Du, Pingwu ;

Lippard, Stephen J. .

INORGANIC CHEMISTRY, 2010, 49 (23) :10753-10755

[10] Development of an oxidative dehydrogenation-based fluorescent probe for Cu2+ and its biological imaging in living cells [J].

Fan, Jiangli ;

Liu, Xiaojian ;

Hu, Mingming ;

Zhu, Hao ;

Song, Fengling ;

Peng, Xiaojun .

ANALYTICA CHIMICA ACTA, 2012, 735 :107-113

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