A Phenylbenzothiazole Derived Fluorescent Sensor for Zn(II) Recognition in Aqueous Solution Through "Turn-On" Excited-State Intramolecular Proton Transfer Emission

被引：25
作者：
Tang, Lijun [1 ]
Dai, Xin [1 ]
Zhong, Keli [1 ]
Wen, Xin [1 ]
Wu, Di [1 ]
机构：
[1] Bohai Univ, Dept Chem, Liaoning Prov Key Lab Synth & Applicat Funct Cpds, Jinzhou 121013, Peoples R China
来源：
JOURNAL OF FLUORESCENCE | 2014年 / 24卷 / 05期
关键词：
Zinc recognition; Benzothiazole; Chemosensor; ESIPT; ENDOGENOUS ZINC; ZN2+; CHEMOSENSOR; PROBE; DERIVATIVES; RECEPTOR; LINKAGE; CU2+; IONS; CD2+;
D O I：
10.1007/s10895-014-1434-8
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
A highly selective and sensitive fluorescent Zn2+ sensor N-(2-(benzo[d]thiazol-2-yl)phenyl)-2-((pyridin-2-ylmethyl)amino)acetamide (1) that derived from 2-(2'-aminophenyl)benzothiazole has been developed. In aqueous solution (HEPES/CH3CN=4/6, v/v, HEPES 20 mM, pH = 7.4), sensor 1 displays highly selective recognition to Zn2+ over other metal ions with a distinct longer-wavelength emission enhancement. Sensor 1 binds Zn2+ through its amide form with a 1:1 binding stoichiometry, which switched on the excited-state intramolecular proton transfer (ESIPT).
引用
收藏
页码：1487 / 1493
页数：7
相关论文
共 49 条
[1]  
[Anonymous], 1987, BINDING CONSTANTS ME
[2]   Design of fluorescent materials for chemical sensing [J].
Basabe-Desmonts, Lourdes ;
Reinhoudt, David N. ;
Crego-Calama, Mercedes .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :993-1017
[3]  
BUSH AI, 1994, J BIOL CHEM, V269, P12152
[4]   A quinoline based fluorescent probe that can distinguish zinc(II) from cadmium(II) in water [J].
Cai, Yulei ;
Meng, Xiangming ;
Wang, Shuxin ;
Zhu, Manzhou ;
Pan, Zhongwen ;
Guo, QingXiang .
TETRAHEDRON LETTERS, 2013, 54 (09) :1125-1128
[5]   An 2-(2′-aminophenyl)benzoxazole-based OFF-ON fluorescent chemosensor for Zn2+ in aqueous solution [J].
Chen, Maliang ;
Lv, Xin ;
Liu, Yunlong ;
Zhao, Yun ;
Liu, Jing ;
Wang, Pi ;
Guo, Wei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (07) :2345-2349
[6]   Fluorescent gold nanoparticles-based fluorescence sensor for Cu2+ ions [J].
Chen, Wenbin ;
Tu, Xijuan ;
Guo, Xiangqun .
CHEMICAL COMMUNICATIONS, 2009, (13) :1736-1738
[7]   Simple pyrazoline and pyrazole "turn on" fluorescent sensors selective for Cd2+ and Zn2+ in MeCN [J].
Ciupa, Alexander ;
Mahon, Mary F. ;
De Bank, Paul A. ;
Caggiano, Lorenzo .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (44) :8753-8757
[8]   Zinc metabolism in the brain: Relevance to human neurodegenerative disorders [J].
Cuajungco, MP ;
Lees, GJ .
NEUROBIOLOGY OF DISEASE, 1997, 4 (3-4) :137-169
[9]   Reaction of isatoic anhydride with bifunctional reagents: Synthesis of some new quinazolone fused heterocycles, 2-substituted anilinoheterocyclic derivatives and other related compounds [J].
Fadda, AA ;
Refat, HM ;
Zaki, MEA ;
Monir, E .
SYNTHETIC COMMUNICATIONS, 2001, 31 (22) :3537-3545
[10]   A cyanine-based fluorescent sensor for detecting endogenous zinc ions in live cells and organisms [J].
Guo, Zhiqian ;
Kim, Gun-Hee ;
Shin, Injae ;
Yoon, Juyoung .
BIOMATERIALS, 2012, 33 (31) :7818-7827
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