Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide
Tunable design strategy for fluorescence probes based on 4-substituted BODIPY chromophore: improvement of highly sensitive fluorescence probe for nitric oxide
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DOI：
10.1007/s00216-006-0587-y
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发表时间：
2006-10-01
影响因子：
4.3
通讯作者：
Nagano, Tetsuo
中科院分区：
文献类型：
--
作者：
Gabe, Yu;Ueno, Tasuku;Nagano, Tetsuo
4，4-二氟-4-硼杂-3a，4a-二氮杂-s-引达省（BODIPY）是众所周知的荧光团，具有高摩尔消光系数和高荧光量子效率（Phi（fl））。此外，其结构可以被修改以改变其激发和发射波长。然而，在B-4位上用其他官能团对氟进行结构修饰的工作却很少。我们以令人满意的产率合成了4-甲氧基取代的BODIPY衍生物，并发现它们在水溶液中表现出改善的溶解度。此外，它们的氧化和还原电位大大降低，而没有任何变化，其吸光度和荧光性质。4-取代的BODIPYs的这些功能可能是有用的，用于开发新的荧光探针的基础上的分子内光诱导电子转移（PeT）机制，因为它是可能的，以优化精确地通过调制的荧光团的电化学性质的PeT过程。这种方法的价值体现在它的应用程序开发一氧化氮的高灵敏度和pH值无关的荧光探针。
4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) is a well-known fluorophore, with a high molar extinction coefficient and high fluorescence quantum efficiency (Phi(fl)). Furthermore, its structure can be modified to change its excitation and emission wavelengths. However, little work has been done on the structural modification of fluorines at the B-4 position with other functional groups. We synthesized 4-methoxy-substituted BODIPY derivatives in satisfactory yields, and found that they exhibited improved solubility in aqueous solution. Moreover, their oxidation and reduction potentials were greatly decreased without any change in their absorbance and fluorescence properties. These features of 4-substituted BODIPYs may be useful for developing novel fluorescence probes based on the intramolecular photoinduced electron transfer (PeT) mechanism, because it is possible to optimize the PeT process precisely by modulating the electrochemical properties of the fluorophore. The value of this approach is exemplified by its application to the development of a highly sensitive and pH-independent fluorescence probe for nitric oxide.