A TICT based two-photon fluorescent probe for cysteine and homocysteine in living cells

被引:44
作者
Wei, Xinjie [1 ]
Yang, Xiuli [2 ]
Feng, Yan [1 ]
Ning, Peng [1 ]
Yu, Haizhu [1 ]
Zhu, Manzhou [1 ]
Xi, Xinguo [2 ]
Guo, Qingxiang [1 ,3 ]
Meng, Xiangming [1 ]
机构
[1] Anhui Univ, Dept Chem, Hefei 230601, Peoples R China
[2] Yancheng Inst Technol, Jiangsu Collaborat Innovat Ctr Ecol Bldg Mat & En, Yancheng 224051, Peoples R China
[3] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
TICT; Two-photon; Fluorescent probe; Cysteine; Homocysteine; INTRAMOLECULAR CHARGE-TRANSFER; HIGH SELECTIVITY; GLUTATHIONE; CHEMOSENSOR; HYDRAZINE; MECHANISM; NEURONS; DESIGN; THIOLS; IONS;
D O I
10.1016/j.snb.2016.03.027
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
A two-photon fluorescent probe (NQ) for cysteine (Cys) and homocysteine (Hcy) was developed based on twisted-intramolecular-charge-transfer (TICT) mechanism. NQshowed excellent "OFF-ON" fluorescence (at 540 nm) detection signal on addition of Cys/Hcy with high selectivity. The detection mechanism was successfully proved by theoretical calculations, viscosity dependent fluorescence and time resolved fluorescence spectra. NQ exhibits large two-photon absorption (TPA) cross-section with Cys/Hcy (580 and 710 GM) at nearly 800 nm, respectively. Cell-culture results indicated that NQ was cell-permeable and could be used to detect Cys/Hcy with low cytotoxicity under two-photon excitation in living cells. To our best knowledge, NQ is the first TICT based two-photon fluorescent probe for Cys/Hcy. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:285 / 292
页数:8
相关论文
共 60 条
[1]   "Turn-on" fluorescence probe integrated polymer nanoparticles for sensing biological thiol molecules [J].
Ang, Chung Yen ;
Tan, Si Yu ;
Lu, Yunpeng ;
Bai, Linyi ;
Li, Menghuan ;
Li, Peizhou ;
Zhang, Quan ;
Selvan, Subramanian Tamil ;
Zhao, Yanli .
SCIENTIFIC REPORTS, 2014, 4
[2]  
[Anonymous], SENS ACTUATORS B
[3]  
[Anonymous], J PHYS CHEM A
[4]   Differences in heterocycle basicity distinguish homocysteine from cysteine using aldehyde-bearing fluorophores [J].
Barve, Aabha ;
Lowry, Mark ;
Escobedo, Jorge O. ;
Huynh, Katherine T. ;
Hakuna, Lovemore ;
Strongin, Robert M. .
CHEMICAL COMMUNICATIONS, 2014, 50 (60) :8219-8222
[5]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[6]   A highly selective fluorescent probe for thiol bioimaging [J].
Bouffard, Jean ;
Kim, Youngmi ;
Swager, Timothy M. ;
Weissleder, Ralph ;
Hilderbrand, Scott A. .
ORGANIC LETTERS, 2008, 10 (01) :37-40
[7]   TICT based fluorescence "turn-on" hydrazine probes [J].
Chen, Bin ;
Sun, Xi ;
Li, Xin ;
Agren, Hans ;
Xie, Yongshu .
SENSORS AND ACTUATORS B-CHEMICAL, 2014, 199 :93-100
[8]   Steric hindrance-enforced distortion as a general strategy for the design of fluorescence "turn-on" cyanide probes [J].
Chen, Bin ;
Ding, Yubin ;
Li, Xin ;
Zhu, Weihong ;
Hill, Jonathan P. ;
Ariga, Katsuhiko ;
Xie, Yongshu .
CHEMICAL COMMUNICATIONS, 2013, 49 (86) :10136-10138
[9]   A thiol-specific fluorescent probe and its application for bioimaging [J].
Chen, Xiaoqiang ;
Ko, Sung-Kyun ;
Kim, Min Jung ;
Shin, Injae ;
Yoon, Juyoung .
CHEMICAL COMMUNICATIONS, 2010, 46 (16) :2751-2753
[10]   7-(Dimethylamino)coumarin-3-carbaldehyde and Its Phenylsemicarbazone: TICT Excited State Modulation, Fluorescent H-Aggregates, and Preferential Solvation [J].
Cigan, Marek ;
Donovalova, Jana ;
Szoecs, Vojtech ;
Gaspar, Jan ;
Jakusova, Klaudia ;
Gaplovsky, Anton .
JOURNAL OF PHYSICAL CHEMISTRY A, 2013, 117 (23) :4870-4883