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Triazole-Linked-Thiophene Conjugate of Calix[4]arene: Its Selective Recognition of Zn(2+) and as Biomimetic Model in Supporting the Events of the Metal Detoxification and Oxidative Stress Involving Metallothionein

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Title Triazole-Linked-Thiophene Conjugate of Calix[4]arene: Its Selective Recognition of Zn(2+) and as Biomimetic Model in Supporting the Events of the Metal Detoxification and Oxidative Stress Involving Metallothionein
 
Creator PATHAK, RK
HINGE, VK
MONDAL, M
RAO, CP
 
Subject FLUORESCENT SENSOR
LOWER RIM
INTRACELLULAR ZINC
LIVING CELLS
COMPLEXES
BINDING
IONS
DERIVATIVES
LIGANDS
RECEPTORS
 
Description Supramolecular calix[4]arene conjugate (L) has been developed as a sensitive and selective sensor for Zn(2+) in HEPES buffer among the 12 metal ion by using fluorescence, absorption and ESI MS and also by visual fluorescent color. The structural, electronic, and emission properties of the calix[4]arene conjugates L and its zinc complex, [ZnL], have been demonstrated using ab initio density functional theory (DFT) combined with time-dependent density functional theory (TDDFT) calculations. The TDDFT calculations reveal the switch on fluorescence behavior of L is mainly due to the utilization of the lone pair of electrons on imine moiety by the Zn2+. The resultant fluorescent complex, [ZnL], has been used as a secondary sensing chemo-ensemble for the detection of -SH containing molecules by removing Zn(2+) from [ZnL] and forming {Cys/DTT center dot Zn} adducts as equivalent to those present in metallothioneins. The displacement followed by the release of the coordinated zinc from its Cys/DTT complex by heavy metal ion (viz. Cd(2+) and Hg(2+)), as in the metal detoxification process or by ROS (such as H(2)O(2)) as in the oxidative stress, has been well demonstrated using the conjugate L through the fluorescence intensity retrieval wherein the fluorescence intensity is the same as that observed with [ZriL], which in turn mimics the zinc sensing element (MTF) in biology.
 
Publisher AMER CHEMICAL SOC
 
Date 2012-06-26T09:00:46Z
2012-06-26T09:00:46Z
2011
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY,76(24)10039-10049
0022-3263
http://dx.doi.org/10.1021/jo201865x
http://dspace.library.iitb.ac.in/jspui/handle/100/14246
 
Language English