One Stone, Three Birds: pH Triggered Transformation of Aminopyronine and Iminopyronine Based Lysosome Targeting Viscosity Probe for Cancer Visualization

被引:99
作者
Song, Yan [1 ]
Zhang, Hongxing [2 ]
Wang, Xia [3 ]
Geng, Xin [1 ]
Sun, Yuanqiang [1 ]
Liu, Jing [2 ]
Li, Zhaohui [1 ]
机构
[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Henan Joint Int Res Lab Green Construct Funct Mol, Zhengzhou 450001, Peoples R China
[2] Shanxi Univ, Sch Chem & Chem Engn, Taiyuan 030006, Peoples R China
[3] Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
FLUORESCENT-PROBE; DESIGN; SENSOR; DYES;
D O I
10.1021/acs.analchem.0c04644
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
The lysosomes of cancer cells have lower pH and higher viscosity than those of normal cells. These features can be used as sensitive and selective markers for cancer diagnosis. In this work, a pH and viscosity dual responsive lysosome targeting fluorescent probe 1 was designed based on the transformation of amino- and imino- forms of pyronine and the twisted intramolecular charge shuttle (TICS) sensing mechanism. Live cancer cells and tumors were effectively distinguished from normal cells and organs through fluorescence imaging of probe 1, which indicated that probe 1 could serve as an effective tool for visualization of tumors at organ level with high selectivity.
引用
收藏
页码:1786 / 1791
页数:6
相关论文
共 37 条
[1]   Cell-Permeant Large Stokes Shift Dyes for Transfection-Free Multicolor Nanoscopy [J].
Butkevich, Alexey N. ;
Lukinavicius, Graivydas ;
D'Este, Elisa ;
Hell, Stefan W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) :12378-12381
[2]   An acidic pH independent piperazine-TPE AIEgen as a unique bioprobe for lysosome tracing [J].
Cai, Yuanjing ;
Gui, Chen ;
Samedov, Kerim ;
Su, Huifang ;
Gu, Xinggui ;
Li, Shiwu ;
Luo, Wenwen ;
Sung, Herman H. Y. ;
Lam, Jacky W. Y. ;
Kwok, Ryan T. K. ;
Williams, Ian D. ;
Qin, Anjun ;
Tang, Ben Zhong .
CHEMICAL SCIENCE, 2017, 8 (11) :7593-7603
[3]   Engineering Organelle-Specific Molecular Viscosimeters Using Aggregation-Induced Emission Luminogens for Live Cell Imaging [J].
Chen, Wen ;
Gao, Cai ;
Liu, Xianjun ;
Liu, Feng ;
Wang, Fenglin ;
Tang, Li-Juan ;
Jiang, Jian-Hui .
ANALYTICAL CHEMISTRY, 2018, 90 (15) :8736-8741
[4]   A Photoexcitation-Induced Twisted Intramolecular Charge Shuttle [J].
Chi, Weijie ;
Qiao, Qinglong ;
Lee, Richmond ;
Liu, Wenjuan ;
Teo, Yock Siong ;
Gu, Danning ;
Lang, Matthew John ;
Chang, Young-Tae ;
Xu, Zhaochao ;
Liu, Xiaogang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) :7073-7077
[5]   Excited State Proton Transfer in the Lysosome of Live Lung Cells: Normal and Cancer Cells [J].
Chowdhury, Rajdeep ;
Saha, Abhijit ;
Mandal, Amit Kumar ;
Jana, Batakrishna ;
Ghosh, Surajit ;
Bhattacharyya, Kankan .
JOURNAL OF PHYSICAL CHEMISTRY B, 2015, 119 (06) :2149-2156
[6]   A lysosome-targeting and polarity-specific fluorescent probe for cancer diagnosis [J].
Fan, Li ;
Wang, Xiaodong ;
Ge, Jinyin ;
Li, Feng ;
Wang, Xiao ;
Wang, Juanjuan ;
Shuang, Shaomin ;
Dong, Chuan .
CHEMICAL COMMUNICATIONS, 2019, 55 (32) :4703-4706
[7]   Fluorescent pH Indicators for Neutral to Near-Alkaline Conditions Based on 9-Iminopyronin Derivatives [J].
Horvath, Peter ;
Sebej, Peter ;
Kovar, David ;
Damborsky, Jiri ;
Prokop, Zbynek ;
Klan, Petr .
ACS OMEGA, 2019, 4 (03) :5479-5485
[8]   Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags [J].
Horvath, Peter ;
Sebej, Peter ;
Solomek, Tomas ;
Klan, Petr .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03) :1299-1311
[9]  
Huang Tianzhi, 2018, Critical Reviews in Oncogenesis, V23, P247, DOI 10.1615/CritRevOncog.2018027913
[10]  
Jemal A, 2010, CA-CANCER J CLIN, V60, P277, DOI [10.3322/caac.20073, 10.3322/caac.21254]