Ultra-pH-Sensitive Small Molecule Probe Showing a Ratiometric Fluorescence Color Change

被引:12
作者
Cui, Junjie [1 ]
Kim, Gayoung [2 ]
Kim, Sehoon [2 ]
Kwon, Ji Eon [1 ]
Park, Soo Young [1 ]
机构
[1] Seoul Natl Univ, Dept Mat Sci & Engn, Ctr Supramol Optoelect Mat, Res Inst Adv Mat, 1 Gwanak Ro, Seoul 08826, South Korea
[2] Korea Inst Sci & Technol, Ctr Theragnosis, 5 Hwarang Ro 14 Gil, Seoul 02792, South Korea
关键词
amphiphiles; bioimaging; fluorescence switching; pH responsiveness; self-assembly; supramolecular chemistry; INTRACELLULAR PH; RANGE; DESIGN; NANOFIBERS; VALUES; SENSOR; WATER;
D O I
10.1002/cptc.202000023
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We synthesized an amphiphilic small molecule 1 by attaching oligo(ethylene glycol) (OEG) and N,N-diethylamine (DEA) units to a fluorescent dicyanodistyrylbenzene (DCS) core. The molecule is fully soluble in aqueous solution at low pH (pH<4.3) by protonation of the DEA groups; but, above pH 4.3, it self-assembles to form nanoparticles due to increased hydrophobicity upon deprotonation, leading to a ratiometric fluorescence color change from green emission in the monomeric form (lambda(em,max)=538 nm) to red emission in the aggregated form (lambda(em,max)=646 nm). It should be noted that the ratio of emission intensities at 538 nm and 646 nm (R=I-538/I-646) changes drastically about 42-fold within a very narrow pH range of 4.3-4.6.
引用
收藏
页码:393 / 397
页数:5
相关论文
共 44 条
[1]   A protein-dye hybrid system as a narrow range tunable intracellular pH sensor [J].
Anees, Palapuravan ;
Sudheesh, Karivachery V. ;
Jayamurthy, Purushothaman ;
Chandrika, Arunkumar R. ;
Omkumar, Ramakrishnapillai V. ;
Ajayaghosh, Ayyappanpillai .
CHEMICAL SCIENCE, 2016, 7 (11) :6808-6814
[2]  
[Anonymous], ANGEW CHEM
[3]   Tunable Ratiometric Fluorescence Sensing of Intracellular pH by Aggregation-Induced Emission-Active Hyperbranched Polymer Nanoparticles [J].
Bao, Yinyin ;
De Keersmaecker, Herlinde ;
Corneillie, Stijn ;
Yu, Feng ;
Mizuno, Hideaki ;
Zhang, Guofeng ;
Hofkens, Johan ;
Mendrek, Barbara ;
Kowalczuk, Agnieszka ;
Smet, Mario .
CHEMISTRY OF MATERIALS, 2015, 27 (09) :3450-3455
[4]   In vivo observation of the pH alternation in mitochondria for various external stimuli [J].
Cao, Lixia ;
Zhao, Zhensheng ;
Zhang, Tao ;
Guo, Xudong ;
Wang, Shuangqing ;
Li, Shayu ;
Li, Yi ;
Yang, Guoqiang .
CHEMICAL COMMUNICATIONS, 2015, 51 (97) :17324-17327
[5]   Sensors and regulators of intracellular pH [J].
Casey, Joseph R. ;
Grinstein, Sergio ;
Orlowski, John .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2010, 11 (01) :50-61
[6]   A switchable peptide sensor for real-time lysosomal tracking [J].
Chen, Lei ;
Wu, Junchen ;
Schmuck, Carsten ;
Tian, He .
CHEMICAL COMMUNICATIONS, 2014, 50 (49) :6443-6446
[7]   Full-Range Intracellular pH Sensing by an Aggregation-Induced Emission-Active Two-Channel Ratiometric Fluorogen [J].
Chen, Sijie ;
Hong, Yuning ;
Liu, Yang ;
Liu, Jianzhao ;
Leung, Chris W. T. ;
Li, Min ;
Kwok, Ryan T. K. ;
Zhao, Engui ;
Lam, Jacky W. Y. ;
Yu, Yong ;
Tang, Ben Zhong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (13) :4926-4929
[8]  
Cornil J, 2001, ADV MATER, V13, P1053, DOI 10.1002/1521-4095(200107)13:14<1053::AID-ADMA1053>3.0.CO
[9]  
2-7
[10]   Smart Fluorescent Nanoparticles in Water Showing Temperature Dependent Ratiometric Fluorescence Color Change [J].
Cui, Junjie ;
Kwon, Ji Eon ;
Kim, Hyeong-Ju ;
Whang, Dong Ryeol ;
Park, Soo Young .
ACS APPLIED MATERIALS & INTERFACES, 2017, 9 (03) :2883-2890