Fluorescent Probes Based on Nucleophilic Substitution-Cyclization for Hydrogen Sulfide Detection and Bioimaging

被引：198

作者：

Peng, Bo ^{[1
]}

Chen, Wei ^{[1
]}

Liu, Chunrong ^{[1
]}

Rosser, Ethan W. ^{[1
]}

Pacheco, Armando ^{[1
]}

Zhao, Yu ^{[1
]}

Aguilar, Hector C. ^{[2
]}

Xian, Ming ^{[1
]}

机构：

[1] Washington State Univ, Dept Chem, Pullman, WA 99164 USA

[2] Washington State Univ, Paul G Allen Sch Global Anim Hlth, Pullman, WA 99164 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 04期

关键词：

cell imaging; cyclization; fluorescence; fluorescent probes; hydrogen sulfide; OFF-ON PROBE; SENSITIVE DETECTION; SIGNALING MOLECULE; FAST-RESPONSE; H2S; SULFHYDRATION; BIOCHEMISTRY; CHEMISTRY; SULFUR; AGENTS;

D O I：

10.1002/chem.201303757

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The design, synthesis, properties, and cell imaging applications of a series of 2-pyridyl disulfide based fluorescent probes (WSP1, WSP2, WSP3, WSP4 and WSP5) for hydrogen sulfide detection are reported. The strategy is based on the dual-nucleophilicity of hydrogen sulfide. A hydrogen sulfide mediated tandem nucleophilic substitution-cyclization reaction is used to release the fluorophores and turn on the fluorescence. The probes showed high sensitivity and selectivity for hydrogen sulfide over other reactive sulfur species, including cysteine and glutathione.

引用

页码：1010 / 1016

页数：7

共 50 条

[1]

[Anonymous], 2012, ANGEW CHEM

[2]

Chan J, 2012, NAT CHEM, V4, P973, DOI [10.1038/NCHEM.1500, 10.1038/nchem.1500]

[3] New fluorescent probes for sulfane sulfurs and the application in bioimaging [J].

Chen, Wei ;

Liu, Chunrong ;

Peng, Bo ;

Zhao, Yu ;

Pacheco, Armando ;

Xian, Ming .

CHEMICAL SCIENCE, 2013, 4 (07) :2892-2896

[4] A new resorufin-based spectroscopic probe for simple and sensitive detection of benzoyl peroxide via deboronation [J].

Chen, Wei ;

Li, Zhao ;

Shi, Wen ;

Ma, Huimin .

CHEMICAL COMMUNICATIONS, 2012, 48 (22) :2809-2811

[5] Light-Induced Hydrogen Sulfide Release from "Caged" gem-Dithiols [J].

Devarie-Baez, Nelmi O. ;

Bagdon, Powell E. ;

Peng, Bo ;

Zhao, Yu ;

Park, Chung-Min ;

Xian, Ming .

ORGANIC LETTERS, 2013, 15 (11) :2786-2789

[6] The reaction of H2S with oxidized thiols: Generation of persulfides and implications to H2S biology [J].

Francoleon, Nestor E. ;

Carrington, Samantha J. ;

Fukuto, Jon M. .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2011, 516 (02) :146-153

[7] Small Molecule Signaling Agents: The Integrated Chemistry and Biochemistry of Nitrogen Oxides, Oxides of Carbon, Dioxygen, Hydrogen Sulfide, and Their Derived Species [J].

Fukuto, Jon M. ;

Carrington, Samantha J. ;

Tantillo, Dean J. ;

Harrison, Jason G. ;

Ignarro, Louis J. ;

Freeman, Bruce A. ;

Chen, Andrew ;

Wink, David A. .

CHEMICAL RESEARCH IN TOXICOLOGY, 2012, 25 (04) :769-793

[8] A Fast Response Highly Selective Probe for the Detection of Glutathione in Human Blood Plasma [J].

Guo, Yixing ;

Yang, Xiaofeng ;

Hakuna, Lovemore ;

Barve, Aabha ;

Escobedo, Jorge O. ;

Lowry, Mark ;

Strongin, Robert M. .

SENSORS, 2012, 12 (05) :5940-5950

[9] Perspective on Recent Developments on Sulfur-Containing Agents and Hydrogen Sulfide Signaling [J].

Jacob, Claus ;

Anwar, Awais ;

Burkholz, Torsten .

PLANTA MEDICA, 2008, 74 (13) :1580-1592

[10] Fluorescence Probe for Lysophospholipase C/NPP6 Activity and a Potent NPP6 Inhibitor [J].

Kawaguchi, Mitsuyasu ;

Okabe, Takayoshi ;

Okudaira, Shinichi ;

Hanaoka, Kenjiro ;

Fujikawa, Yuuta ;

Terai, Takuya ;

Komatsu, Toru ;

Kojima, Hirotatsu ;

Aoki, Junken ;

Nagano, Tetsuo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :12021-12030

← 1 2 3 4 5 →