Hydrogen sulfide mediated cascade reaction forming an iminocoumarin: applications in fluorescent probe development and live-cell imaging

被引:36
作者
Mishra, Pratryush Kumar [1 ]
Saha, Tanmoy [1 ]
Talukdar, Pinaki [1 ]
机构
[1] Indian Inst Sci Educ & Res Pune, Dept Chem, Pune, Maharashtra, India
关键词
LIVING CELLS; H2S; ACTIVATION; KETONES;
D O I
10.1039/c5ob00785b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The study on a fluorescent probe that undergoes a H2S mediated cascade reaction to form an imino-coumarin fluorophore is reported. The probe features better water solubility and fast sensing time (t(1/2) = 6.1 min and response time = 24 min) as key advances compared to the reported probe that works on a similar mechanism. The sensing mechanism of the probe was demonstrated by mass spectrometric, HPLC titration and FT-IR titration methods. H2S sensing by the probe was characterized by a 31-fold fluorescence enhancement and alimit of detection of 169 nM. Application of the probe was demonstrated by imaging of H2S in live cells.
引用
收藏
页码:7430 / 7436
页数:7
相关论文
共 47 条
[1]  
Abe K, 1996, J NEUROSCI, V16, P1066
[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]   SYNTHETIC METHODS .14. FACILE CONVERSION OF VINYL AZIDES TO KETONES OR ALDEHYDES [J].
BELINKA, BA ;
HASSNER, A .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25) :4712-4713
[4]   Organocatalytic Synthesis of 1,2,3-Triazoles from Unactivated Ketones and Arylazides [J].
Belkheira, Mokhtaria ;
El Abed, Douniazad ;
Pons, Jean-Marc ;
Bressy, Cyril .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (46) :12917-12921
[5]   Novel neural modulators [J].
Boehning, D ;
Snyder, SH .
ANNUAL REVIEW OF NEUROSCIENCE, 2003, 26 :105-131
[6]   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
[7]   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
[8]   Reaction-Based Genetically Encoded Fluorescent Hydrogen Sulfide Sensors [J].
Chen, Si ;
Chen, Zhi-jie ;
Ren, Wei ;
Ai, Hui-wang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (23) :9589-9592
[9]   A small molecule two-photon probe for hydrogen sulfide in live tissues [J].
Das, Sajal Kumar ;
Lim, Chang Su ;
Yang, Sun Young ;
Han, Ji Hee ;
Cho, Bong Rae .
CHEMICAL COMMUNICATIONS, 2012, 48 (67) :8395-8397
[10]   Polarographic measurement of hydrogen sulfide production and consumption by mammalian tissues [J].
Doeller, JE ;
Isbell, TS ;
Benavides, G ;
Koenitzer, J ;
Patel, H ;
Patel, RP ;
Lancaster, JR ;
Darley-Usmar, VM ;
Kraus, DW .
ANALYTICAL BIOCHEMISTRY, 2005, 341 (01) :40-51