Benzenesulfonamidoquinolino-beta-cyclodextrin as a cell-impermeable fluorescent sensor for Zn2+.
A water-soluble benzenesulfonamidoquinolino-beta-cyclodextrin has been successfully synthesized in 30% yield by incorporating a N-(8-quinolyl)-p-aminobenzenesulfonamide (HQAS) group to beta-cyclodextrin through a flexible linker. This compound exhibits a good fluorescence response in the presence of Zn2+ 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-beta-cyclodextrin could bind to the loose bilayer membranes. As a result, benzenesulfonamidoquinolino-beta-cyclodextrin was found to act as an efficient cell-impermeable Zn2+ probe, showing a specific fluorescent sensing ability to Zn2+-containing damaged cells whilst exhibiting no response in the presence of healthy cells.
Zhang
Ning
N
Department of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, P.R. China.
Chen
Yong
Y
Yu
Miao
M
Liu
Yu
Y
D000818:Animals; D015374:Biosensing Techniques; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D008081:Liposomes / Q000737:chemistry; D008856:Microscopy, Fluorescence; D019906:Nuclear Magnetic Resonance, Biomolecular; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*; D012441:Saccharomyces cerevisiae / Q000737:chemistry; D015032:Zinc / Q000032:analysis*; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
D005456:Fluorescent Dyes; D008081:Liposomes; D011804:Quinolines; C518055:aminobenzenesulfonamidoquinolino-beta-cyclodextrin; D047392:beta-Cyclodextrins; D015032:Zinc