Premium
Benzenesulfonamidoquinolino‐β‐cyclodextrin as a Cell‐Impermeable Fluorescent Sensor for Zn 2+
Author(s) -
Zhang Ning,
Chen Yong,
Yu Miao,
Liu Yu
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900233
Subject(s) - cyclodextrin , fluorescence , linker , metal ions in aqueous solution , chemistry , bilayer , yield (engineering) , membrane , beta cyclodextrins , biophysics , metal , nuclear chemistry , materials science , biochemistry , organic chemistry , biology , physics , quantum mechanics , computer science , metallurgy , operating system
A water‐soluble benzenesulfonamidoquinolino‐β‐cyclodextrin has been successfully synthesized in 30 % yield by incorporating a N ‐(8‐quinolyl)‐ p ‐aminobenzenesulfonamide (HQAS) group to β‐cyclodextrin through a flexible linker. This compound exhibits a good fluorescence response in the presence of Zn 2+ in water but gives poor fluorescence responses with other metal ions commonly present in a physiological environment under similar conditions. Fluorescence microscopic and two‐dimensional NMR experiments showed that benzenesulfonamidoquinolino‐β‐cyclodextrin could bind to the loose bilayer membranes. As a result, benzenesulfonamidoquinolino‐β‐cyclodextrin was found to act as an efficient cell‐impermeable Zn 2+ probe, showing a specific fluorescent sensing ability to Zn 2+ ‐containing damaged cells whilst exhibiting no response in the presence of healthy cells.