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Bioorg Med Chem ; 15(13): 4537-42, 2007 Jul 01.
Article in English | MEDLINE | ID: mdl-17467997

ABSTRACT

A water-soluble 8-aminoquinolino-beta-cyclodextrin/1-adamantaneacetic acid (1/ADA) system is prepared in situ and exhibits a unique switch-on fluorescence response to Zn(2+) over other common metal ions. Spectrophotometric studies demonstrate that this system can strongly coordinate Zn(2+) through a cyclodextrin/substrate/metal triple recognition mode, and the resulting 1/ADA/Zn(2+) ternary complex emits the blue-green fluorescence (lambda=490nm) that can be easily distinguished by eyes in aqueous solution. Significantly, the switch-on fluorescence response of 1/ADA to Zn(2+) is barely affected by various metal ions except Cu(2+). As a result, this system can behave as an efficient supramolecular fluorescence sensor for Zn(2+) in water.


Subject(s)
Acetates/chemistry , Adamantane/analogs & derivatives , Aminoquinolines/chemistry , Zinc/chemistry , beta-Cyclodextrins/chemistry , Acetates/chemical synthesis , Adamantane/chemical synthesis , Adamantane/chemistry , Aminoquinolines/chemical synthesis , Fluorescence , Indicators and Reagents , Models, Molecular , Reproducibility of Results , Spectrometry, Fluorescence , Water/chemistry , beta-Cyclodextrins/chemical synthesis
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