Cell-Trappable Quinoline-Derivatized Fluoresceins for Selective and Reversible Biological Zn(II) Detection
Name
Mcquade and Lippard Inorg Chem.pdf
Size
948.02 KB
Format
Adobe PDF
Checksum (MD5)
88f474616c18ad2bac9a7a74ba85019c
Author(s)
McQuade, Lindsey E.
Lippard, Stephen J.
Date Issued
September 2010
Journal
Inorganic Chemistry
Publisher
American Chemical Society (ACS)
Citation
McQuade, Lindsey E., and Stephen J. Lippard. “Cell-Trappable Quinoline-Derivatized Fluoresceins for Selective and Reversible Biological Zn(II) Detection.” Inorganic Chemistry 49.20 (2010): 9535–9545.
Version
Author's final manuscript
Abstract
The synthesis and spectroscopic characterization of two new, cell-trappable fluorescent probes for Zn(II) are presented. These probes, 2-(4,5-bis(((6-(2-ethoxy-2-oxoethoxy)quinolin-8-yl)amino)methyl)-6-hydroxy-3-oxo-3H-8 xanthen-9-yl)benzoic acid (QZ2E) and 2,2′-((8,8′-(((9-(2-carboxyphenyl)-6-hydroxy-3-oxo-3H-xanthene-4,5-diyl)bis(methylene))bis(azanediyl))bis(quinoline-8,6-diyl))bis(oxy))diacetic acid (QZ2A), are poorly emissive in the off-state but exhibit dramatic increases in fluorescence upon Zn(II) binding (120 ± 10-fold for QZ2E, 30 ± 7-fold for QZ2A). This binding is selective for Zn(II) over other biologically relevant metal cations, toxic heavy metals, and most first-row transition metals and is of appropriate affinity (K[subscript d1](QZ2E) = 150 ± 100 μM, K[subscript d2](QZ2E) = 3.5 ± 0.1 mM, K[subscript d1](QZ2A) = 220 ± 30 μM, K[subscript d2](QZ2A) = 160 ± 80 μM, K[subscript d3](QZ2A) = 9 ± 6 μM) to reversibly bind Zn(II) at physiological levels. In live cells, QZ2E localizes to the Gogli apparatus where it can detect Zn(II). It is cell-membrane-permeable until cleavage of its ester groups by intracellular esterases produces QZ2A, a negatively charged acid form that cannot cross the cell membrane.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike 3.0
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/ic1012507
