Fluorescence ON/OFF switching Zn2+ sensor based on pyridine–pyridone scaffold
Fluorescence ON/OFF switching Zn2+ sensor based on pyridine–pyridone scaffold
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DOI：
10.1016/j.snb.2013.02.033
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发表时间：
2013-05
影响因子：
8.4
通讯作者：
Masayori Hagimori;T. Uto;Naoko Mizuyama;T. Temma;Y. Yamaguchi;Y. Tominaga;H. Saji
中科院分区：
文献类型：
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作者：
Masayori Hagimori;T. Uto;Naoko Mizuyama;T. Temma;Y. Yamaguchi;Y. Tominaga;H. Saji
我们报道了一种新型的基于吡啶-吡啶酮核心结构的Zn 2+荧光传感器，该结构既作为Zn 2+的螯合部分又作为荧光团。通过在吡啶酮环的3-位用吸电子基团取代给电子基团获得的吡啶-吡啶酮衍生物显示几乎没有背景荧光，因为电子转移到荧光团被抑制。然而，这些衍生物显示出强烈的荧光与Zn 2+。与Zn 2+的配位极大地影响了荧光团的电子转移，并且因此使荧光ON/OFF切换成为可能。在这些传感器中，4-[4-（甲硫基）-2-氧代-6-（吡啶-2-基）-1，2-二氢吡啶-3-基]苯甲酸（5）表现出优异的性质：分子量小（MW=338），水溶性好，Stokes位移大（132 nm），与Zn ~（2+）的荧光开关。此外，在活细胞中的Zn 2+与5的荧光图像表明，新的荧光传感器是有用的生物应用。
We report a novel series of fluorescent Zn2+sensors based on a pyridine–pyridone core structure, which functions as both the chelating part for Zn2+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 Zn2+. Coordination with Zn2+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 (132nm), and fluorescence ON/OFF switching with Zn2+. In addition, fluorescence images of Zn2+with 5 in living cells show that the new fluorescent sensor is useful for biological applications.