Highly Selective and Sensitive One- and Two-Photon Ratiometric Fluorescent Probe for Intracellular Hydrogen Polysulfide Sensing

被引:97
作者
Han, Qingxin
Mou, Zuolin
Wang, Haihong
Tang, Xiaoliang
Dong, Zhe
Wang, Li
Dong, Xue
Liu, Weisheng [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Nonferrous Met Chem & Resources Utilizat, Lanzhou 730000, Peoples R China
关键词
S-SULFHYDRATION; LIVING CELLS; SULFIDE; SULFUR; CYSTEINE; CONSTRUCTION; BIOCHEMISTRY; PERSULFIDE; MOLECULES; CHEMISTRY;
D O I
10.1021/acs.analchem.6b01391
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Hydrogen polysulfide (H2Sn) has attracted increasing attention due to the fact that it is actually the key signaling molecule rather than hydrogen sulfide (H2Sn). Therefore, developing a sensitive and accurate assay to investigate the biosynthetic pathways of H2Sn is of physiological and pathological significance. In this work, based on the commonly used two-photon fluorophore, 1,8-naphthalimide, a new probe, NRT-HP, has been designed and synthesized that displayed both one- and two-photon ratiometric fluorescence changes toward H2Sn via H2Sn-mediated benzodithiolone formation. NRT-HP exhibits excellent pH stability, high selectivity and low detection limit (0.1 mu M) in aqueous media. Furthermore, two-photon fluorescence microscopy experiments have demonstrated that NRT-HP could be used for the H2Sn detection in live cells as well as tissue slices.
引用
收藏
页码:7206 / 7212
页数:7
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[1]   Design of organic molecules with large two-photon absorption cross sections [J].
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Beljonne, D ;
Brédas, JL ;
Ehrlich, JE ;
Fu, JY ;
Heikal, AA ;
Hess, SE ;
Kogej, T ;
Levin, MD ;
Marder, SR ;
McCord-Maughon, D ;
Perry, JW ;
Röckel, H ;
Rumi, M ;
Subramaniam, C ;
Webb, WW ;
Wu, XL ;
Xu, C .
SCIENCE, 1998, 281 (5383) :1653-1656
[2]   Generation of reactive oxygen species by a persultide (BnSSH) [J].
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[7]   Small Molecule Signaling Agents: The Integrated Chemistry and Biochemistry of Nitrogen Oxides, Oxides of Carbon, Dioxygen, Hydrogen Sulfide, and Their Derived Species [J].
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