Mitochondria-Targeted Reaction-Based Fluorescent Probe for Hydrogen Sulfide

被引:230
作者
Pak, Yen Leng [1 ]
Li, Jun [1 ]
Ko, Kyoung Chul [2 ]
Kim, Gyoungmi [1 ]
Lee, Jin Yong [2 ]
Yoon, Juyoung [1 ]
机构
[1] Ewha Womans Univ, Dept Chem & Nano Sci, Seoul 120750, South Korea
[2] Sungkyunkwan Univ, Dept Chem, Suwon 16419, South Korea
基金
新加坡国家研究基金会;
关键词
TURN-ON PROBE; SELECTIVE DETECTION; RAPID DETECTION; 2-PHOTON PROBE; FAST-RESPONSE; LIVING CELLS; IN-VIVO; H2S; GASOTRANSMITTER; CHEMOSENSOR;
D O I
10.1021/acs.analchem.6b00956
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
In this study, we developed a turn-on mitochondria-targeting hydrogen sulfide, "probe 1", based on the selective thiolysis of 7-nitro-1,2,3-benzoxadiazole amine moiety attached to the piperazine-based naphthalimide scaffold. Probe 1 exhibited excellent properties with 68-fold fluorescence enhancement, a low detection limit (2.46 mu M), a low cytotoxicity, and a good selectivity toward hydrogen sulfide. The success of intracellular imaging indicated that probe 1 could be used in further applications for the investigation of biological functions and pathological roles of H2S in living systems.
引用
收藏
页码:5476 / 5481
页数:6
相关论文
共 84 条
[1]   A highly selective and fast-response fluorescent probe for visualization of enzymatic H2S production in vitro and in living cells [J].
不详 .
CHEMICAL COMMUNICATIONS, 2015, 51 (52) :10463-10466
[2]   A Ratiometric Two-Photon Fluorescent Probe Reveals Reduction in Mitochondrial H2S Production in Parkinson's Disease Gene Knockout Astrocytes [J].
Bae, Sung Keun ;
Heo, Cheol Ho ;
Choi, Dong Joo ;
Sen, Debabrata ;
Joe, Eun-Hye ;
Cho, Bong Rae ;
Kim, Hwan Myung .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (26) :9915-9923
[3]   A near-infrared fluorescent turn-on probe for fluorescence imaging of hydrogen sulfide in living cells based on thiolysis of dinitrophenyl ether [J].
Cao, Xiaowei ;
Lin, Weiying ;
Zheng, Kaibo ;
He, Longwei .
CHEMICAL COMMUNICATIONS, 2012, 48 (85) :10529-10531
[4]   Fluorescent probe for highly selective and sensitive detection of hydrogen sulfide in living cells and cardiac tissues [J].
Chen, Bifeng ;
Li, Wei ;
Lv, Cong ;
Zhao, Manman ;
Jin, Hongwei ;
Jin, Hongfang ;
Du, Junbao ;
Zhang, Liangren ;
Tang, Xinjing .
ANALYST, 2013, 138 (03) :946-951
[5]   Endogenous hydrogen sulfide in patients with COPD [J].
Chen, YH ;
Yao, WZ ;
Geng, B ;
Ding, YL ;
Lu, M ;
Zhao, MW ;
Tang, CS .
CHEST, 2005, 128 (05) :3205-3211
[6]   A Ratiometric Fluorescent Probe for Rapid Detection of Hydrogen Sulfide in Mitochondria [J].
Chen, Yuncong ;
Zhu, Chengcheng ;
Yang, Zhenghao ;
Chen, Junjie ;
He, Yafeng ;
Jiao, Yang ;
He, Weijiang ;
Qiu, Lin ;
Cen, Jiajie ;
Guo, Zijian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) :1688-1691
[7]   H2S Biogenesis by Human Cystathionine γ-Lyase Leads to the Novel Sulfur Metabolites Lanthionine and Homolanthionine and Is Responsive to the Grade of Hyperhomocysteinemia [J].
Chiku, Taurai ;
Padovani, Dominique ;
Zhu, Weidong ;
Singh, Sangita ;
Vitvitsky, Victor ;
Banerjee, Ruma .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2009, 284 (17) :11601-11612
[8]   Fluorimetric optode membrane for sulfide detection [J].
Choi, MMF .
ANALYST, 1998, 123 (07) :1631-1634
[9]   Sulfide-selective chemosignaling by a Cu2+ complex of dipicolylamine appended fluorescein [J].
Choi, Myung Gil ;
Cha, Sunyoung ;
Lee, Haekyung ;
Jeon, Hye Lim ;
Chang, Suk-Kyu .
CHEMICAL COMMUNICATIONS, 2009, (47) :7390-7392
[10]   NO NEWS IS GOOD-NEWS [J].
CULOTTA, E ;
KOSHLAND, DE .
SCIENCE, 1992, 258 (5090) :1862-1865