Fluorogen-Peptide Conjugates with Tunable Aggregation-Induced Emission Characteristics for Bioprobe Design

被引:45
作者
Zhang, Ruoyu [1 ]
Yuan, Youyong [1 ]
Liang, Jing [1 ]
Kwok, Ryan T. K. [2 ]
Zhu, Qing [3 ]
Feng, Guangxue [1 ]
Geng, Junlong [1 ]
Tang, Ben Zhong [2 ,4 ]
Liu, Bin [1 ,5 ]
机构
[1] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
[2] Hong Kong Univ Sci & Technol, Div Biomed Engn, Dept Chem, Kowloon, Hong Kong, Peoples R China
[3] Zhejiang Univ Technol, Inst Bioengn, Hangzhou 310014, Zhejiang, Peoples R China
[4] S China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangdong Innovat Res Team, SCUT HKUST Joint Res Lab, Guangzhou 510640, Guangdong, Peoples R China
[5] Inst Mat Res Engn, Singapore 117602, Singapore
基金
新加坡国家研究基金会;
关键词
light-up probe; aggregation-induced emission; fluorescent probes; thiol detection; tetraphenylethene; TURN-ON DETECTION; WATER PARTITION-COEFFICIENT; LIGHT-UP BIOPROBE; FLUORESCENT-PROBES; CHEMICAL SENSORS; CELL APOPTOSIS; ACTIVITY ASSAY; CANCER-CELLS; GLUTATHIONE; CYSTEINE;
D O I
10.1021/am5036048
中图分类号
TB3 [工程材料学];
学科分类号
0805 ; 080502 ;
摘要
Fluorogens with aggregation-induced emission (AIE) characteristics are attracting intense research interest, and an AIE-peptide conjugate strategy has been reported for developing turn-on probes based on hydrophilic peptide ligands. To build a model also suitable for hydrophobic ligands, we propose to fine-tune the AIE characteristics for probe design. In this work, an iconic AIE fluorogen tetraphenylethene (TPE) was designed to conjugate with peptide fragments containing different numbers of aspartic acid (D) units. Relationships between the numbers of D and the hydrophilicity, optical properties, and aggregate sizes and the ATE characteristics of TPE-peptide conjugates were investigated carefully. Five carboxyl groups were found to be the threshold to "turn off" the fluorescence of TPE. As a proof-of-concept, TPE-SS-D-5 containing a cleavable disulfide bond was synthesized for thiol turn-on detection. The validated tunable AIE characteristic offers new opportunities to design fluorescence turn-on probes based on hydrophobic recognition elements and AIE fluorogens.
引用
收藏
页码:14302 / 14310
页数:9
相关论文
共 54 条
[1]  
[Anonymous], [No title captured], DOI DOI 10.1063/1.555755
[2]   Luminescent sensors and switches in the early 21st century [J].
Callan, JF ;
de Silva, AP ;
Magri, DC .
TETRAHEDRON, 2005, 61 (36) :8551-8588
[3]   Genetically encoded FRET-based biosensors for multiparameter fluorescence imaging [J].
Carlson, Haley J. ;
Campbell, Robert E. .
CURRENT OPINION IN BIOTECHNOLOGY, 2009, 20 (01) :19-27
[4]   Real-Time Fluorescence Turn-On Detection of Alkaline Phosphatase Activity with a Novel Perylene Probe [J].
Chen, Jian ;
Jiao, Huping ;
Li, Wenying ;
Liao, Dongli ;
Zhou, Huipeng ;
Yu, Cong .
CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (01) :276-281
[5]   Fluorescence turn-on detection of protamine based on aggregation-induced emission enhancement characteristics of 4-(6′-carboxyl)hexyloxysalicylaldehyde azine [J].
Chen, Xiao-tong ;
Xiang, Yu ;
Li, Na ;
Song, Pan-Shu ;
Tong, Ai-jun .
ANALYST, 2010, 135 (05) :1098-1105
[6]   Recent advances in organic mechanofluorochromic materials [J].
Chi, Zhenguo ;
Zhang, Xiqi ;
Xu, Bingjia ;
Zhou, Xie ;
Ma, Chunping ;
Zhang, Yi ;
Liu, Siwei ;
Xu, Jiarui .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (10) :3878-3896
[7]   Light-up bioprobe with aggregation-induced emission characteristics for real-time apoptosis imaging in target cancer cells [J].
Ding, Dan ;
Liang, Jing ;
Shi, Haibin ;
Kwok, Ryan T. K. ;
Gao, Meng ;
Feng, Guangxue ;
Yuan, Youyong ;
Tang, Ben Zhong ;
Liu, Bin .
JOURNAL OF MATERIALS CHEMISTRY B, 2014, 2 (02) :231-238
[8]   Bioprobes Based on AIE Fluorogens [J].
Ding, Dan ;
Li, Kai ;
Liu, Bin ;
Tang, Ben Zhong .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (11) :2441-2453
[9]   A New Highly Selective, Ratiometric and Colorimetric Fluorescence Sensor for Cu2+ with a Remarkable Red Shift in Absorption and Emission Spectra Based on Internal Charge Transfer [J].
Goswami, Shyamaprosad ;
Sen, Debabrata ;
Das, Nirmal Kumar .
ORGANIC LETTERS, 2010, 12 (04) :856-859
[10]   Highly selective fluorescent OFF-ON thiol probes based on dyads of BODIPY and potent intramolecular electron sink 2,4-dinitrobenzenesulfonyl subunits [J].
Guo, Huimin ;
Jing, Yingying ;
Yuan, Xiaolin ;
Ji, Shaomin ;
Zhao, Jianzhang ;
Li, Xiaohuan ;
Kan, Yanyan .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (10) :3844-3853