Issue 4, 2014

Phenanthroline bridged bis(β-cyclodextrin)s/adamantane-carboxylic acid supramolecular complex as an efficient fluorescence sensor to Zn2+

Abstract

A water-soluble fluorescent Zn2+ sensor, 1,10-phenanthroline bridged bis(β-cyclodextrin) (1), was synthesized by “click chemistry”, and its fluorescence sensing behavior toward Zn2+ against various metal ions was investigated under physiological conditions. Significantly, 1 showed high selectivity and sensitivity toward Zn2+ with a limit of detection (LOD) down to 10−7 M. Moreover, the spectrophotometric studies demonstrated that after complexation with 1-admantanecarboxylic acid sodium salt (AdCA), the 1/AdCA complex gave much stronger binding affinity and lower LOD value toward Zn2+ through a cyclodextrin/substrate/Zn2+ triple recognition mode. The fluorescence stopped-flow experiments also indicated that the association rate of complex 1/AdCA to Zn2+ was much faster than compound 1 to the same ion. Furthermore, the fluorescence intensity of 1 and 1/AdCA was greatly enhanced after binding Zn2+ in living cells, and thus 1 and complex 1/AdCA could be considered as a biosensor for Zn2+ at the cellular level.

Graphical abstract: Phenanthroline bridged bis(β-cyclodextrin)s/adamantane-carboxylic acid supramolecular complex as an efficient fluorescence sensor to Zn2+

Supplementary files

Article information

Article type
Research Article
Submitted
25 Nov 2013
Accepted
18 Feb 2014
First published
17 Mar 2014

Org. Chem. Front., 2014,1, 355-360

Phenanthroline bridged bis(β-cyclodextrin)s/adamantane-carboxylic acid supramolecular complex as an efficient fluorescence sensor to Zn2+

Y. Zhang, Y. Zhang, Y. Chen, Y. Yang and Y. Liu, Org. Chem. Front., 2014, 1, 355 DOI: 10.1039/C3QO00054K

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