Document Type

Journal Article

Department/Unit

Department of Biology

Title

Ratiometric fluorescent Zn2+ chemosensor constructed by appending a pair of carboxamidoquinoline on 1,2-diaminocyclohexane scaffold

Language

English

Abstract

By appending a pair of carboxamidoquinoline pendants onto 1,2-diaminocyclohexane scaffold via N-alkylation, multifunctionalized ACAQ was designed and synthesized as a water soluble fluorescent ratiometric chemosensor for Zn2+. In 50% aqueous methanol buffer pH 7.4 solution, upon excitation at 316 nm, ACAQ (5 μM) displayed a selective ratiometric fluorescence changes with a shift from 410 to 490 nm in response to the interaction with Zn2+. After binding with 1 equiv of Zn2+, ACAQ exhibited a 12-fold enhancement in I490/I410 characterized by a clear isoemissive point at 440 nm. The metal sensor binding mode was established by Job's plot and the combined fluorescence and 1H NMR spectroscopic method. The selectivity of the probe toward biological relevant cations and transition metal ions was proven to be good. In addition, the interference caused by Cu2+ and Cd2+ in the quantitation of Zn2+ can be completely eliminated by the use of diethyldithiocarbamate as the screening agent. Exploitation of ACAQ as the sensing probe, ratiometric determination of Zn2+ with the limit of detection (LOD) at 28.3 nm can be realized. In addition, the unique responsive properties of the probe toward Fe3+ and Zn2+ were used to construct a fluorescent switch. The membrane permeability of ACAQ to living cells and bio-imaging of Zn2+ were demonstrated. © 2011 Published by Elsevier Ltd.

Keywords

Cell imaging, Fluorescence, Molecular switch, Ratiometric, Zinc chemosensor

Publication Date

2011

Source Publication Title

Tetrahedron

Volume

67

Issue

19

Start Page

3412

End Page

3419

Publisher

Elsevier

DOI

10.1016/j.tet.2011.03.053

Link to Publisher's Edition

http://dx.doi.org/10.1016/j.tet.2011.03.053

ISSN (print)

00404020

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