A quaternary ammonium modified fluorescent probe for hydrogen sulfide detection in living cells

被引:10
作者
Liu, Zhengkun [1 ]
Wang, Qianqian [1 ]
Wang, Hao [1 ]
Lan, Yuheng [1 ]
Dong, Shouliang [1 ,2 ]
机构
[1] Lanzhou Univ, Inst Biochem & Mol Biol, Sch Life Sci, 222 Tianshui South Rd, Lanzhou 730000, Gansu, Peoples R China
[2] Lanzhou Univ, Key Lab Preclin Study New Drugs Gansu Prov, 222 Tianshui South Rd, Lanzhou 730000, Gansu, Peoples R China
关键词
Hydrogen sulfide; Fluorescent probe; Azide-reduction; Quaternary ammonium; Sequestration effect; SELECTIVE RECOGNITION; H2S; CHEMOSENSOR; SENSOR; RAT; ETHYLENEDIAMINE; HYPERTENSION; COMPLEX; ACETATE; AZIDE;
D O I
10.1016/j.jphotochem.2019.112213
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Azide-reduction based fluorescent probes are one of the most important methods for H2S detection. However, low water solubility and low sensitivity are common problems encountered by such probes. Herein, five azide-reduction based probes with corresponding hydrophilic moieties (hydroxyl, tertiary amine, and quaternary ammonium) attached were rationally designed and synthesized. After a comparative study of their spectral properties, we found that the quaternary ammonium modified probe H3 showed the total solubility in water and the best reactivity to H2S as well as the lowest detection limit, indicating that the quaternary ammonium moiety not only improved the solubility of the probe, but also had a significant sequestration effect for HS-. A further application of H3 in HeLa cells was also carried out and validated its potential for biological imaging.
引用
收藏
页数:6
相关论文
共 46 条
[41]   The possible role of hydrogen sulfide on the pathogenesis of spontaneous hypertension in rats [J].
Yan, H ;
Du, JB ;
Tang, CS .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2004, 313 (01) :22-27
[42]   H2S as a physiologic vasorelaxant:: Hypertension in mice with deletion of cystathionine γ-lyase [J].
Yang, Guangdong ;
Wu, Lingyun ;
Jiang, Bo ;
Yang, Wei ;
Qi, Jiansong ;
Cao, Kun ;
Meng, Qinghe ;
Mustafa, Asif K. ;
Mu, Weitong ;
Zhang, Shengming ;
Snyder, Solomon H. ;
Wang, Rui .
SCIENCE, 2008, 322 (5901) :587-590
[43]   Construction of a turn-on probe for fast detection of H2S in living cells based on a novel H2S trap group with an electron rich dye [J].
Yang, Qian ;
Zhan, Fuxu ;
Wang, Qiufen ;
Zhuang, Zhiyuan ;
Zhang, Guangyou ;
Zheng, Gengxiu .
RSC ADVANCES, 2015, 5 (128) :106156-106160
[44]   Activation of KATP channels by H2S in rat insulin-secreting cells and the underlying mechanisms [J].
Yang, W ;
Yang, GD ;
Jia, XM ;
Wu, LY ;
Wang, R .
JOURNAL OF PHYSIOLOGY-LONDON, 2005, 569 (02) :519-531
[45]   An Evaluation of Acute Hydrogen Sulfide Poisoning in Rats through Serum Metabolomics Based on Gas Chromatography-Mass Spectrometry [J].
Zhang, Meiling ;
Deng, Mingjie ;
Ma, Jianshe ;
Wang, Xianqin .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (06) :505-507
[46]   Excited state intramolecular proton transfer (ESIPT): from principal photophysics to the development of new chromophores and applications in fluorescent molecular probes and luminescent materials [J].
Zhao, Jianzhang ;
Ji, Shaomin ;
Chen, Yinghui ;
Guo, Huimin ;
Yang, Pei .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2012, 14 (25) :8803-8817