A novel lysosome-targeted fluorogenic probe based on 5-triazole-quinoline for the rapid detection of hydrogen sulfide in living cells

被引:35
作者
Dou, Yandong [1 ,2 ]
Gu, Xiaoxu [2 ]
Ying, Shasha [2 ]
Zhu, Shen [2 ]
Yu, Shian [3 ]
Shen, Wei [3 ]
Zhu, Qing [1 ,2 ]
机构
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Biotechnol & Bioengn, Hangzhou 310014, Zhejiang, Peoples R China
[3] Jinhua Cent Hosp, Dept Gen Surg, Jinhua 321000, Peoples R China
基金
中国国家自然科学基金;
关键词
2-PHOTON FLUORESCENT-PROBE; LIVE CELLS; H2S; MITOCHONDRIA; DISEASE; SULFUR; BRAIN;
D O I
10.1039/c7ob02881d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A fluorogenic probe based on the novel fluorophore 5-triazolequinoline was developed for the detection of hydrogen sulfide, an endogenous signaling molecule associated with the development of various diseases. The lysosome-targeted probe Lyso-HS was synthesized via C-H direct azidation from 8-aminoquinoline; it was able to detect H2S in 1 min and exhibited excellent turn-on ability with 95-fold fluorescence enhancement based on a new fluorochrome. The high quenching efficiency was further verified using time-dependent density functional theory (TDDFT). The probe also exhibited high selectivity and a low detection limit (as low as 214.5 nM), which has practical applications for disease detection and monitoring.
引用
收藏
页码:712 / 716
页数:5
相关论文
共 34 条
  • [1] Understanding Hydrogen Sulfide Storage: Probing Conditions for Sulfide Release from Hydrodisulfides
    Bailey, T. Spencer
    Zalcharov, Lev N.
    Pluth, Michael D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (30) : 10573 - 10576
  • [2] Chemiluminescent Detection of Enzymatically Produced Hydrogen Sulfide: Substrate Hydrogen Bonding Influences Selectivity for H2S over Biological Thiols
    Bailey, T. Spencer
    Pluth, Michael D.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) : 16697 - 16704
  • [3] TDDFT Study of the Optical Properties of Cy5 and Its Derivatives
    Bamgbelu, Anu
    Wang, Jing
    Leszczynski, Jerzy
    [J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2010, 114 (10) : 3551 - 3555
  • [4] The Role of the Hydrogen Sulfide Pathway in Male and Female Urogenital System in Health and Disease
    Bianca, Roberta d'Emmanuele di Villa
    Fusco, Ferdinando
    Mirone, Vincenzo
    Cirino, Giuseppe
    Sorrentino, Raffaella
    [J]. ANTIOXIDANTS & REDOX SIGNALING, 2017, 27 (10) : 654 - 668
  • [5] Two-Input Fluorescent Probe for Thiols and Hydrogen Sulfide Chemosensing and Live Cell Imaging
    Dai, Chun-Guang
    Liu, Xiu-Ling
    Du, Xiao-Jiao
    Zhang, Yan
    Song, Qin-Hua
    [J]. ACS SENSORS, 2016, 1 (07): : 888 - 895
  • [6] New roles for cysteine and transsulfuration enzymes:: Production of H2S, a neuromodulator and smooth muscle relaxant
    Dominy, JE
    Stipanuk, MH
    [J]. NUTRITION REVIEWS, 2004, 62 (09) : 348 - 353
  • [7] Copper(II)-Catalyzed Direct Azidation of N-Acylated 8-Aminoquinolines by Remote C-H Activation
    Dou, Yandong
    Xie, Zhenda
    Sun, Zongguo
    Fang, Hongli
    Shen, Chao
    Zhang, Pengfei
    Zhu, Qing
    [J]. CHEMCATCHEM, 2016, 8 (23) : 3570 - 3574
  • [8] RETRACTED: Brain hydrogen sulfide is severely decreased in Alzheimer's disease (Retracted Article)
    Eto, K
    Asada, T
    Arima, K
    Makifuchi, T
    Kimura, H
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2002, 293 (05) : 1485 - 1488
  • [9] A Two-Photon Fluorescent Probe for Lysosomal Thiols in Live Cells and Tissues
    Fan, Jiangli
    Han, Zhichao
    Kang, Yao
    Peng, Xiaojun
    [J]. SCIENTIFIC REPORTS, 2016, 6
  • [10] The third gas:: H2S regulates perfusion pressure in both the isolated and perfused normal rat liver and in cirrhosis
    Fiorucci, S
    Antonelli, E
    Mencarelli, A
    Orlandi, S
    Renga, B
    Rizzo, G
    Distrutti, E
    Shah, V
    Morelli, A
    [J]. HEPATOLOGY, 2005, 42 (03) : 539 - 548