A near-infrared fluorescent probe for monitoring and imaging of β-galactosidase in living cells

被引：29

作者：

Wu, Cuiyan ^{[1
]}

Ni, Ziqi ^{[1
]}

Li, Peijuan ^{[1
]}

Li, Yaqian ^{[1
]}

Pang, Xiao ^{[1
]}

Xie, Ruihua ^{[1
]}

Zhou, Zile ^{[1
]}

Li, Haitao ^{[1
]}

Zhang, Youyu ^{[1
]}

机构：

[1] Hunan Normal Univ, Key Lab Chem Biol & Tradit Chinese Med Res, Minist Educ, Coll Chem & Chem Engn, Changsha 410081, Peoples R China

来源：

TALANTA | 2020年 / 219卷

基金：

中国国家自然科学基金;

关键词：

Fluorescence imaging; NIR; Off-on probe; beta-Galactosidase; Biomarker; Tumor; Living ovarian cells; TURN-ON FLUORESCENT; LARGE STOKES SHIFT; ENZYME-ACTIVITY; SELECTIVE DETECTION; TRACKING; VISUALIZATION; SERUM; AIE;

D O I：

10.1016/j.talanta.2020.121307

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

beta-Galactosidase (beta-gal) which is overexpressed in primary ovarian cancer can be employed as a valuable biomarker for ovarian cancer. Thus, monitoring and imaging endogenous beta-gal in living cells is of great importance. Herein, a dicyanoisophorone-based near-infrared (NIR) fluorescent probe 2-(5,5-dimethyl-3-((E)-4-(((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)styryl)cyclohex-2-en-1-ylidene)malononitrile named DP-beta gal, was rationally designed and synthesized for the monitoring of beta-gal activity in living cells. In the presence of beta-gal, with the breaking of the glycosidic bond, the NIR fluorescence of the dicyanoisophorone derivative gradually recovered, enabling the fluorescence "off-on" quantitative determination of beta-gal activity. DP-beta gal has the advantages of good selectivity and high sensitivity for the detection of beta-gal, with the limit of detection (LOD) of 3.2 x 10(-3) U. Furthermore, based on its advantages of long-wavelength emission and excellent biocompatibility, the practical applications of DP-beta gal in NIR imaging of beta-gal in living ovarian cancer cells (SKOV-3) were demonstrated.

引用

页数：8

共 37 条

[1] A "turn-on" fluorescent and colorimetric sensor for selective detection of Cu2+ in aqueous media and living cells [J].

An, Ruibing ;

Zhang, Datong ;

Chen, Yan ;

Cui, Yue-zhi .

SENSORS AND ACTUATORS B-CHEMICAL, 2016, 222 :48-54

[2] Sensitive β-galactosidase-targeting fluorescence probe for visualizing small peritoneal metastatic tumours in vivo [J].

Asanuma, Daisuke ;

Sakabe, Masayo ;

Kamiya, Mako ;

Yamamoto, Kyoko ;

Hiratake, Jun ;

Ogawa, Mikako ;

Kosaka, Nobuyuki ;

Choyke, Peter L. ;

Nagano, Tetsuo ;

Kobayashi, Hisataka ;

Urano, Yasuteru .

NATURE COMMUNICATIONS, 2015, 6

[3] Novel fluorescent probe for rapid and ratiometric detection of β-galactosidase and live cell imaging [J].

Chen, Xiangzhu ;

Zhang, Xueyan ;

Ma, Xiaodong ;

Zhang, Yuanyuan ;

Gao, Gui ;

Liu, Jingling ;

Hou, Shicong .

TALANTA, 2019, 192 :308-313

[4] ortho-Chlorination of phenoxy 1,2-dioxetane yields superior chemiluminescent probes for in vitro and in vivo imaging [J].

Eilon-Shaffer, Tal ;

Roth-Konforti, Michal ;

Eldar-Boock, Anat ;

Satchi-Fainaro, Ronit ;

Shabat, Doron .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) :1708-1712

[5] Determination of human serum semicarbazide-sensitive amine oxidase activity via flow injection analysis with fluorescence detection after online derivatization of the enzymatically produced benzaldehyde with 1,2-diaminoanthraquinone [J].

El-Maghrabey, Mahmoud H. ;

Kishikawa, Naoya ;

Ohyama, Kaname ;

Imazato, Takahiro ;

Ueki, Yukitaka ;

Kuroda, Naotaka .

ANALYTICA CHIMICA ACTA, 2015, 881 :139-147

[6] In vivo near-infrared fluorescence imaging [J].

Frangioni, JV .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2003, 7 (05) :626-634

[7] An enzyme-activatable probe liberating AIEgens: on-site sensing and long-term tracking of -galactosidase in ovarian cancer cells [J].

Gu, Kaizhi ;

Qiu, Wanshan ;

Guo, Zhiqian ;

Yan, Chenxu ;

Zhu, Shiqin ;

Yao, Defan ;

Shi, Ping ;

Tian, He ;

Zhu, Wei-Hong .

CHEMICAL SCIENCE, 2019, 10 (02) :398-405

[8] Real-Time Tracking and In Vivo Visualization of β-Galactosidase Activity in Colorectal Tumor with a Ratiometric Near-Infrared Fluorescent Probe [J].

Gu, Kaizhi ;

Xu, Yisheng ;

Li, Hui ;

Guo, Zhiqian ;

Zhu, Shaojia ;

Zhu, Shiqin ;

Shi, Ping ;

James, Tony D. ;

Tian, He ;

Zhu, Wei-Hong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (16) :5334-5340

[9] A novel fluorescent probe with a large stokes shift for cysteine based on dicyanoisophorone [J].

Hou, Jiaqi ;

Cai, Pengfei ;

Wang, Chengyun ;

Shen, Yongjia .

TETRAHEDRON LETTERS, 2018, 59 (26) :2581-2585

[10] A lysosome-targetable and two-photon fluorescent probe for imaging endogenous β-galactosidase in living ovarian cancer cells [J].

Huang, Jinxin ;

Li, Nan ;

Wang, Qianqian ;

Gu, Yueqing ;

Wang, Peng .

SENSORS AND ACTUATORS B-CHEMICAL, 2017, 246 :833-839

← 1 2 3 4 →