Masayori Hagimori, T. Uto, Naoko Mizuyama
May 1, 2013
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0
Influential Citations
36
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Journal
Sensors and Actuators B-chemical
Abstract
Abstract We report a novel series of fluorescent Zn 2+ sensors based on a pyridine–pyridone core structure, which functions as both the chelating part for Zn 2+ and as the fluorophore. Pyridine–pyridone derivatives obtained by replacement of an electron-donating group with an electronic-withdrawing group at the 3-position of the pyridone ring showed almost no background fluorescence because electron transfer to the fluorophore was inhibited. However, these derivatives showed strong fluorescence with Zn 2+ . Coordination with Zn 2+ greatly influenced the electron transfer of the fluorophore, and, as a result, enabled fluorescence ON/OFF switching. In these sensors, 4-[4-(methylsulfanyl)-2-oxo-6-(pyridin-2-yl)-1,2-dihydropyridin-3-yl]benzoic acid ( 5 ) displayed excellent properties: small molecular weight (MW = 338), good water solubility, large Stokes shift (132 nm), and fluorescence ON/OFF switching with Zn 2+ . In addition, fluorescence images of Zn 2+ with 5 in living cells show that the new fluorescent sensor is useful for biological applications.