Quinoline-Malononitrile-Based Aggregation-Induced Emission Probe for Monoamine Oxidase Detection in Living Cells

被引:6
作者
Duangkamol, Chuthamat [1 ,2 ]
Wangngae, Sirilak [1 ]
Wet-osot, Sirawit [3 ]
Khaikate, Onnicha [1 ]
Chansaenpak, Kantapat [4 ]
Lai, Rung-Yi [1 ]
Kamkaew, Anyanee [1 ]
机构
[1] Suranaree Univ Technol, Inst Sci, Sch Chem, Nakhon Ratchasima 30000, Thailand
[2] Pathumthani Univ, Fac Allied Hlth Sci, Div Basic & Med Sci, Pathum Thani 12000, Thailand
[3] Minist Publ Hlth, Dept Med Sci, Med Life Sci Inst, Nonthaburi 11000, Thailand
[4] Natl Nanotechnol Ctr, Natl Sci & Technol Dev Agcy, Thailand Sci Pk, Pathum Thani 12120, Thailand
关键词
AIE; activity-based fluorescence probe; MAO; enzymatic detection; AIEgen; MAO-A; CLORGYLINE; DESIGN;
D O I
10.3390/molecules28062655
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A quinoline-malononitrile (QM)-based aggregation-induced emission probe was developed to detect MAOs in cells through an enzymatic reaction followed by beta-elimination. After being incubated at 37 degrees C, QM-NH2 responded to the MAO enzymes with great specificity and within just 5 min. This 5 min responsive mechanism was fast, with the limit of detection (LOD) at 5.49 and 4.76 mu g mL(-1) for MAO-A and MAO-B, respectively. Moreover, QM-NH2 displayed high enzyme specificity even in the presence of high concentrations of biological interferences, such as oxidizing and reducing agents, biothiols, amino acids, and glucose. Furthermore, QM-NH2 demonstrated biocompatibility as the cells retained more than 70% viability when exposed to QM-NH2 at concentrations of up to 20 mu M. As a result, QM-NH2 was used to detect MAO-A and MAO-B in SH-SY5Y and HepG2 cells, respectively. After 1h incubation with QM-NH2, the cells exhibited enhanced fluorescence by about 20-fold. Moreover, the signal from cells was reduced when MAO inhibitors were applied prior to incubating with QM-NH2. Therefore, our research recommends using a QM probe as a generic method for producing recognition moieties for fluorogenic enzyme probes.
引用
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页数:14
相关论文
共 39 条
[11]   High-Performance Quinoline-Malononitrile Core as a Building Block for the Diversity-Oriented Synthesis of AIEgens [J].
Guo, Zhiqian ;
Yan, Chenxu ;
Zhu, Wei-Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (25) :9812-9825
[12]   Long wavelength AIEgen of quinoline-malononitrile [J].
Guo, Zhiqian ;
Shao, Andong ;
Zhu, Wei-Hong .
JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (14) :2640-2646
[13]   Dicyanomethylene-4H-pyran chromophores for OLED emitters, logic gates and optical chemosensors [J].
Guo, Zhiqian ;
Zhu, Weihong ;
Tian, He .
CHEMICAL COMMUNICATIONS, 2012, 48 (49) :6073-6084
[14]   A novel activatable AIEgen fluorescent probe for peroxynitrite detection and its application in EC1 cells [J].
Han, Xiaojing ;
Yang, Xiaopeng ;
Zhang, Yongru ;
Li, Zipeng ;
Cao, Wenbo ;
Zhang, Di ;
Ye, Yong .
SENSORS AND ACTUATORS B-CHEMICAL, 2020, 321
[15]   Reaction-based two-photon probes for in vitro analysis and cellular imaging of monoamine oxidase activity [J].
Kim, Dokyoung ;
Sambasivan, Sunderraman ;
Nam, Hyoseok ;
Kim, Ki Hean ;
Kim, Jin Yong ;
Joo, Taiha ;
Lee, Kyung-Ha ;
Kim, Kyong-Tai ;
Ahn, Kyo Han .
CHEMICAL COMMUNICATIONS, 2012, 48 (54) :6833-6835
[16]   A Small-Molecule Probe for Selective Profiling and Imaging of Monoamine OxidaseB Activities in Models of Parkinson's Disease [J].
Li, Lin ;
Zhang, Cheng-Wu ;
Ge, Jingyan ;
Qian, Linghui ;
Chai, Bing-Han ;
Zhu, Qing ;
Lee, Jun-Seok ;
Lim, Kah-Leong ;
Yao, Shao Q. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (37) :10821-10825
[17]   A sensitive two-photon probe to selectively detect monoamine oxidase B activity in Parkinson's disease models [J].
Li, Lin ;
Zhang, Cheng-Wu ;
Chen, Grace Y. J. ;
Zhu, Biwei ;
Chai, Chou ;
Xu, Qing-Hua ;
Tan, Eng-King ;
Zhu, Qing ;
Lim, Kah-Leong ;
Yao, Shao Q. .
NATURE COMMUNICATIONS, 2014, 5 :3276
[18]   Red emission fluorescent probes for visualization of monoamine oxidase in living cells [J].
Li, Ling-Ling ;
Li, Kun ;
Liu, Yan-Hong ;
Xu, Hao-Ran ;
Yu, Xiao-Qi .
SCIENTIFIC REPORTS, 2016, 6
[19]   A role for sorting nexin 27 in AMPA receptor trafficking [J].
Loo, Li Shen ;
Tang, Ning ;
Al-Haddawi, Muthafar ;
Dawe, Gavin Stewart ;
Hong, Wanjin .
NATURE COMMUNICATIONS, 2014, 5
[20]   Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole [J].
Luo, JD ;
Xie, ZL ;
Lam, JWY ;
Cheng, L ;
Chen, HY ;
Qiu, CF ;
Kwok, HS ;
Zhan, XW ;
Liu, YQ ;
Zhu, DB ;
Tang, BZ .
CHEMICAL COMMUNICATIONS, 2001, (18) :1740-1741