Dual-signaling fluorescent chemosensor based on bisthiazole derivatives

被引:61
作者
Helal, Aasif [1 ]
Lee, Sang Hoon [1 ]
Kim, Sung Hong [2 ]
Kim, Hong-Seok [1 ]
机构
[1] Kyungpook Natl Univ, Dept Appl Chem, Taegu 702701, South Korea
[2] Korea Basic Sci Inst, Daegu Ctr, Anal Res Div, Taegu 702701, South Korea
关键词
Bisthiazole; Fluorescence; ESIPT; Ratiometric sensing; Quenching; INTRAMOLECULAR PROTON-TRANSFER; EXCITED-STATE; SENSING PROPERTIES; CROWN-ETHERS; ZINC; SENSOR; THIAZOLE; COPPER; COMPLEXES; BINDING;
D O I
10.1016/j.tetlet.2010.04.126
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new bisthiazole chemosensor (3) with phenolic substituents at the position 2 of the thiazole rings was prepared. The chemosensor 3 acts as a potential dual-function fluorescence chemosensor with Cu2+ and Zn2+ ions causing complete quenching and ratiometric change of fluorescence, respectively. The mechanism of fluorescence was based on the cation-induced inhibition of excited-state intramolecular proton transfer (ESIPT). (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3531 / 3535
页数:5
相关论文
共 75 条
[1]  
Amendola V, 1999, COORDIN CHEM REV, V190, P649
[2]  
[Anonymous], ZINC LEWIS ACID CATA
[3]   Copper [J].
Barceloux, DG .
JOURNAL OF TOXICOLOGY-CLINICAL TOXICOLOGY, 1999, 37 (02) :217-230
[4]   Functions of zinc in signaling, proliferation and differentiation of mammalian cells [J].
Beyersmann, D ;
Haase, H .
BIOMETALS, 2001, 14 (3-4) :331-341
[5]   Measuring picomolar intracellular exchangeable zinc in PC-12 cells using a ratiometric fluorescence biosensor [J].
Bozym, Rebecca A. ;
Thompson, Richard B. ;
Stoddard, Andrea K. ;
Fierke, Carol A. .
ACS CHEMICAL BIOLOGY, 2006, 1 (02) :103-111
[6]   Salicylaldehyde fluorescein hydrazone: A colorimetric logic chemosensor for pH and Cu(II) [J].
Chen, Xiaotong ;
Li, Zifan ;
Xiang, Yu ;
Tong, Aijun .
TETRAHEDRON LETTERS, 2008, 49 (32) :4697-4700
[7]   MLCT and LMCT transitions in acetylide complexes.: Structural, spectroscopic, and redox properties of ruthenium(II) and -(III) bis(σ-arylacetylide) complexes supported by a tetradentate macrocyclic tertiary amine ligand [J].
Choi, MY ;
Chan, MCW ;
Zhang, SB ;
Cheung, KK ;
Che, CM ;
Wong, KY .
ORGANOMETALLICS, 1999, 18 (11) :2074-2080
[8]   Bis(isoquinoline N-oxide) pincers as a new type of metal cation dual channel fluorosensor [J].
Collado, D ;
Perez-Inestrosa, E ;
Suau, R ;
Desvergne, JP ;
Bouas-Laurent, H .
ORGANIC LETTERS, 2002, 4 (05) :855-858
[9]   Zinc and Alzheimer's disease: Is there a direct link? [J].
Cuajungco, MP ;
Lees, GJ .
BRAIN RESEARCH REVIEWS, 1997, 23 (03) :219-236
[10]   EXCITED-STATE INTRAMOLECULAR PROTON-TRANSFER AND ROTAMERISM OF 2-(2'-HYDROXYPHENYL) BENZIMIDAZOLE [J].
DAS, K ;
SARKAR, N ;
MAJUMDAR, D ;
BHATTACHARYYA, K .
CHEMICAL PHYSICS LETTERS, 1992, 198 (05) :443-448