Rational design of novel near-infrared fluorescent DCM derivatives and their application in bioimaging

被引:40
作者
Wang, Xiaohang [1 ,2 ]
Guo, Zhiqian [1 ,2 ,4 ]
Zhu, Shiqin [1 ,2 ]
Liu, Yajing [3 ]
Shi, Ping [3 ]
Tian, He [1 ,2 ]
Zhu, Wei-Hong [1 ,2 ]
机构
[1] East China Univ Sci & Technol, Sch Chem & Mol Engn, Collaborat Innovat Ctr Coal Based Energy i CCE, Inst Fine Chem,Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] East China Univ Sci & Technol, Sch Chem & Mol Engn, Collaborat Innovat Ctr Coal Based Energy i CCE, Shanghai Key Lab Funct Mat Chem,Inst Fine Chem, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China
[4] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116024, Peoples R China
关键词
INTRAMOLECULAR CHARGE-TRANSFER; AGGREGATION-INDUCED EMISSION; IN-VIVO; HIGHLY FLUORESCENT; SELECTIVE DETECTION; HYDROGEN-SULFIDE; SQUARAINE DYES; LIVING CELLS; PROBES; FLUOROPHORE;
D O I
10.1039/c6tb01096b
中图分类号
TB3 [工程材料学]; R318.08 [生物材料学];
学科分类号
0805 ; 080501 ; 080502 ;
摘要
The development of innovative strategies for high-performance near-infrared (NIR) fluorescent materials is in urgent demand for bioimaging. By replacing the stronger electron-withdrawing groups or extending the p-conjugated system, novel NIR fluorescent materials of DCM analogues have been developed, along with several striking characteristics: bright NIR fluorescence over 700 nm, large Stokes shift and good photo-stability. It is demonstrated that introducing a stronger electron-withdrawing unit to the acceptor moiety of DCM analogues is a favourably efficient strategy to tune and prolong the emission wavelength into the NIR region with a large Stokes shift. In comparison with the commercial NIR dye ICG, S-DCM-N and S-DCM-P display excellent photostability and low photobleaching. The large Stokes Shift and NIR fluorescence channel of S-DCM-N and S-DCM-P are very favourable for fluorescence labelling with a high signal-to-noise ratio in living species.
引用
收藏
页码:4683 / 4689
页数:7
相关论文
共 69 条
[1]   Chemistry of squaraine-derived materials: Near-IR dyes, low band gap systems, and cation sensors [J].
Ajayaghosh, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (06) :449-459
[2]  
An ZF, 2015, NAT MATER, V14, P685, DOI [10.1038/nmat4259, 10.1038/NMAT4259]
[3]   New one- and two-dimensional 4H-pyranylidene NLO-phores [J].
Andreu, Raquel ;
Carrasquer, Laura ;
Garin, Javier ;
Jesus Modrego, Maria ;
Orduna, Jesus ;
Alicante, Raquel ;
Villacampa, Belen ;
Allain, Magali .
TETRAHEDRON LETTERS, 2009, 50 (24) :2920-2924
[4]   Effect of Extended π Conjugation on the Spectroscopic and Electrochemical Properties of Boron Difluoride Formazanate Complexes [J].
Barbon, Stephanie M. ;
Staroverov, Viktor N. ;
Gilroy, Joe B. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10) :5226-5235
[5]   Solvent and pH dependent fluorescent properties of a dimethylaminostyryl borondipyrromethene dye in solution [J].
Baruah, Mukulesh ;
Qin, Wenwu ;
Flors, Cristina ;
Hofkens, Johan ;
Valle, Renaud A. L. ;
Beljonne, David ;
Van der Auweraer, Mark ;
De Borggraeve, Wim M. ;
Boens, Noel .
JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (18) :5998-6009
[6]   Near-Infrared Phosphorus-Substituted Rhodamine with Emission Wavelength above 700 nm for Bioimaging [J].
Chai, Xiaoyun ;
Cui, Xiaoyan ;
Wang, Baogang ;
Yang, Fan ;
Cai, Yi ;
Wu, Qiuye ;
Wang, Ting .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) :16754-16758
[7]   Sensor targets [J].
Chang, Christopher J. ;
Gunnlaugsson, Thorfinnur ;
James, Tony D. .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (13) :4176-4178
[8]   A Series of Squaraine Dyes: Effects of Side Chain and the Number of Hydroxyl Groups on Material Properties and Photovoltaic Performance [J].
Chen, Guo ;
Sasabe, Hisahiro ;
Sasaki, Yusuke ;
Katagiri, Hiroshi ;
Wang, Xiao-Feng ;
Sano, Takeshi ;
Hong, Ziruo ;
Yang, Yang ;
Kido, Junji .
CHEMISTRY OF MATERIALS, 2014, 26 (03) :1356-1364
[9]   Fluorescent and colorimetric probes for detection of thiols [J].
Chen, Xiaoqiang ;
Zhou, Ying ;
Peng, Xiaojun ;
Yoon, Juyoung .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2120-2135
[10]   A naphthalimide-based fluorescent sensor for halogenated solvents [J].
Dai, Li ;
Wu, Di ;
Qiao, Qinglong ;
Yin, Wenting ;
Yin, Jun ;
Xu, Zhaochao .
CHEMICAL COMMUNICATIONS, 2016, 52 (10) :2095-2098