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Issue 18, 2013
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Design and synthesis of an on–off “click” fluorophore that executes a logic operation and detects heavy and transition metal ions in water and living cells

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Abstract

We have designed and synthesized a novel fluorescent molecular probe using the Cu(I)-catalyzed Huisgen cycloaddition of 1,3-diethynyl-6-fluoroisoquinoline with 1-(2-azidoethyl)pyrrolidine. This water soluble “click” fluorescent chemosensor displays good sensitivity towards heavy and transition metal ions. It shows pronounced fluorescence enhancement and high selectivity for Zn2+ over other biologically relevant metal ions in water at pH 7.0. The fluorescence response of the bis-triazole derivative in the presence of Zn2+ is switchable and reversible as a function of pH. The chemosensor also exhibits fluorescence quenching with Fe2+ and Cu2+ in water at pH 7.0. A modified YES logic gate property has been proposed using the “turn-on” and “turn-off” behavior of the bis-triazole with Zn2+ and Fe2+. The sensor is cell membrane permeable and applicable for intracellular Zn2+ imaging.

Graphical abstract: Design and synthesis of an on–off “click” fluorophore that executes a logic operation and detects heavy and transition metal ions in water and living cells

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Publication details

The article was received on 14 Jan 2013, accepted on 05 Mar 2013 and first published on 05 Mar 2013


Article type: Paper
DOI: 10.1039/C3OB40075A
Citation: Org. Biomol. Chem., 2013,11, 3057-3063
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    Design and synthesis of an on–off “click” fluorophore that executes a logic operation and detects heavy and transition metal ions in water and living cells

    G. C. Midya, S. Paladhi, S. Bhowmik, S. Saha and J. Dash, Org. Biomol. Chem., 2013, 11, 3057
    DOI: 10.1039/C3OB40075A

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