A Fast-Response Red Shifted Fluorescent Probe for Detection of H2S in Living Cells

被引:24
作者
Ismail, Ismail [1 ,2 ]
Chen, Zhuoyue [3 ,4 ]
Ji, Xiuru [5 ]
Sun, Lu [5 ]
Yi, Long [3 ,4 ,6 ]
Xi, Zhen [1 ,2 ,6 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Natl Engn Res Ctr Pesticide Tianjin, Tianjin 300071, Peoples R China
[2] Nankai Univ, Dept Chem Biol, Natl Engn Res Ctr Pesticide Tianjin, Coll Chem, Tianjin 300071, Peoples R China
[3] Beijing Univ Chem Technol, Beijing Key Lab Bioproc, 15 Beisanhuan East Rd, Beijing 100029, Peoples R China
[4] Beijing Univ Chem Technol, Coll Chem Engn, 15 Beisanhuan East Rd, Beijing 100029, Peoples R China
[5] Tianjin Med Univ, Sch Pharm, Tianjin Key Lab Technol Enabling Dev Clin Therape, Tianjin 300070, Peoples R China
[6] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
关键词
fluorescent probe; red shifted; H2S; bioimaging; HYDROGEN-SULFIDE; FAR-RED; DESIGN STRATEGIES; UNIQUE APPROACH; CANCER-CELLS; RHODAMINE; DYES; SULFUR; PEROXYNITRITE; CHEMISTRY;
D O I
10.3390/molecules25030437
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Near-infrared (NIR) fluorescent probes are attractive tools for bioimaging applications because of their low auto-fluorescence interference, minimal damage to living samples, and deep tissue penetration. H2S is a gaseous signaling molecule that is involved in redox homeostasis and numerous biological processes in vivo. To this end, we have developed a new red shifted fluorescent probe 1 to detect physiological H2S in live cells. The probe 1 is based on a rhodamine derivative as the red shifted fluorophore and the thiolysis of 7-nitro 1,2,3-benzoxadiazole (NBD) amine as the H2S receptor. The probe 1 displays fast fluorescent enhancement at 660 nm (about 10-fold turn-ons, k(2) = 29.8 M(-1)s(-1)) after reacting with H2S in buffer (pH 7.4), and the fluorescence quantum yield of the activated red shifted product can reach 0.29. The probe 1 also exhibits high selectivity and sensitivity towards H2S. Moreover, 1 is cell-membrane-permeable and mitochondria-targeting, and can be used for imaging of endogenous H2S in living cells. We believe that this red shifted fluorescent probe can be a useful tool for studies of H2S biology.
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页数:13
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共 77 条
[1]   Synthesis and applications of Rhodamine derivatives as fluorescent probes [J].
Beija, Mariana ;
Afonso, Carlos A. M. ;
Martinho, Jose M. G. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2410-2433
[2]   Hydrogen sulfide in plants: From dissipation of excess sulfur to signaling molecule [J].
Calderwood, Alexander ;
Kopriva, Stanislav .
NITRIC OXIDE-BIOLOGY AND CHEMISTRY, 2014, 41 :72-78
[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]   Dithioesters: simple, tunable, cysteine-selective H2S donors [J].
Cerda, Matthew M. ;
Newton, Turner D. ;
Zhao, Yu ;
Collins, Brylee K. ;
Hendon, Christopher H. ;
Pluth, Michael D. .
CHEMICAL SCIENCE, 2019, 10 (06) :1773-1779
[5]   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
[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]   Straightforward Access to Water-Soluble Unsymmetrical Sulfoxanthene Dyes: Application to the Preparation of Far-Red Fluorescent Dyes with Large Stokes' Shifts [J].
Chevalier, Arnaud ;
Renard, Pierre-Yves ;
Romieu, Anthony .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (27) :8330-8337
[8]   Regulation of Vascular Tone, Angiogenesis and Cellular Bioenergetics by the 3-Mercaptopyruvate Sulfurtransferase/H2S Pathway: Functional Impairment by Hyperglycemia and Restoration by DL-α-Lipoic Acid [J].
Coletta, Ciro ;
Modis, Katalin ;
Szczesny, Bartosz ;
Brunyanszki, Attila ;
Olah, Gabor ;
Rios, Ester C. S. ;
Yanagi, Kazunori ;
Ahmad, Akbar ;
Papapetropoulos, Andreas ;
Szabo, Csaba .
MOLECULAR MEDICINE, 2015, 21 :1-14
[9]   A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water [J].
Dujols, V ;
Ford, F ;
Czarnik, AW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (31) :7386-7387
[10]   Development of a Far-Red to Near-Infrared Fluorescence Probe for Calcium Ion and its Application to Multicolor Neuronal Imaging [J].
Egawa, Takahiro ;
Hanaoka, Kenjiro ;
Koide, Yuichiro ;
Ujita, Sakiko ;
Takahashi, Naoya ;
Ikegaya, Yuji ;
Matsuki, Norio ;
Terai, Takuya ;
Ueno, Tasuku ;
Komatsu, Toru ;
Nagano, Tetsuo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) :14157-14159