Design and synthesis of a library of BODIPY-based environmental polarity sensors utilizing photoinduced electron-transfer-controlled fluorescence ON/OFF switching
Design and synthesis of a library of BODIPY-based environmental polarity sensors utilizing photoinduced electron-transfer-controlled fluorescence ON/OFF switching
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DOI：
10.1021/ja068551y
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发表时间：
2007-05-02
影响因子：
15
通讯作者：
Nagano, Tetsuo
中科院分区：
文献类型：
--
作者：
Sunahara, Hisato;Urano, Yasuteru;Nagano, Tetsuo
我们系统地研究了BODIPY（硼二吡咯亚甲基）荧光团的荧光ON/OFF阈值的溶剂极性依赖性的机制和光诱导电子转移（PeT）的作用。在一系列的BODIPY衍生物与各种取代的苯部分在8-位，苯部分的氧化电位变得更加积极和BODIPY荧光团的还原电位变得更加负的溶剂极性降低，因此，从苯部分的PeT的自由能变化变得更大，在一个更非极性的环境。利用这一发现，我们设计并合成了一个探针库，其中荧光ON/OFF切换的阈值对应于不同水平的溶剂极性。这些环境敏感的探针被用来检查牛血清白蛋白（BSA）和活细胞。白蛋白表面的极性与丙酮相似，而HeLa细胞内膜的极性与二氯甲烷相似。
We systematically examined the mechanism of the solvent polarity dependence of the fluorescence ON/OFF threshold of the BODIPY (boron dipyrromethene) fluorophore and the role of photoinduced electron transfer (PeT). In a series of BODIPY derivatives with variously substituted benzene moieties at the 8-position, the oxidation potential of the benzene moiety became more positive and the reduction potential of the BODIPY fluorophore became more negative as the solvent polarity was decreased; consequently, the free energy change of PeT from the benzene moiety becomes larger in a more nonpolar environment. Utilizing this finding, we designed and synthesized a library of probes in which the threshold of fluorescence ON/OFF switching corresponds to different levels of solvent polarity. These environment-sensitive probes were used to examine bovine serum albumin (BSA) and living cells. The polarity at the surface of albumin was concluded to be similar to that of acetone, while the polarity of the internal membranes of HeLa cells was similar to that of dichloromethane.