Triazole-linked-thiophene conjugate of calix[4]arene: its selective recognition of Zn2+ and as Biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein

Pathak, Rakesh Kumar ; Hinge, Vijaya Kumar ; Mondal, Milon ; Rao, Chebrolu Pulla (2011) Triazole-linked-thiophene conjugate of calix[4]arene: its selective recognition of Zn2+ and as Biomimetic model in supporting the events of the metal detoxification and oxidative stress involving metallothionein Journal of Organic Chemistry, 76 (24). pp. 10039-10049. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo201865x

Related URL: http://dx.doi.org/10.1021/jo201865x

Abstract

Supramolecular calix[4]arene conjugate (L) has been developed as a sensitive and selective sensor for Zn2+ 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 Zn2+ from [ZnL] and forming {Cys/DTT·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. Cd2+ and Hg2+), as in the metal detoxification process or by ROS (such as H2O2) 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 [ZnL], which in turn mimics the zinc sensing element (MTF) in biology.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:79213
Deposited On:24 Jan 2012 15:35
Last Modified:19 Apr 2012 06:46

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