Synthesis and evaluation of dual wavelength fluorescent benzo[b]thiophene boronic acid derivatives for sugar sensing
Synthesis and evaluation of dual wavelength fluorescent benzo[b]thiophene boronic acid derivatives for sugar sensing
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DOI：
10.1111/j.1747-0285.2007.00563.x
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发表时间：
2007-10-01
影响因子：
3
通讯作者：
Wang, Binghe
中科院分区：
文献类型：
--
作者：
Akay, Senol;Yang, Wenqian;Wang, Binghe
细胞表面糖蛋白在多种生理和病理过程中起着非常重要的作用。能够识别碳水化合物的小分子化合物在传感、诊断和治疗试剂的开发中非常有用。沿着这条路线，我们有兴趣开发用于碳水化合物识别的水溶性荧光硼酸化合物。因此，我们合成了一系列苯并[b]噻吩硼酸衍生物，并分析了它们在生理pH下的荧光性质。苯并[b]噻吩衍生物是一种新型的荧光报告化合物，在生理pH条件下具有双重荧光发射能力。化合物1、3、4、5和6在与糖结合时表现出不寻常的发射波长变化。这些硼酸将是构建用于生物应用的糖蛋白生物传感器的有用工具。
Cell surface glycoproteins have been known to play very important roles in various physiologic and pathologic processes. Small molecule compounds capable of carbohydrate recognition can be very useful for the development of sensing, diagnostic, and therapeutic agents. Along this line, we are interested in developing water-soluble fluorescent boronic acid compounds for carbohydrate recognition. As such, a series of benzo[b]thiophene boronic acid derivatives have been synthesized and their fluorescent properties analyzed at physiologic pH. Benzo[b]thiophene derivatives were found to be a new type of fluorescent reporter compounds capable of dual fluorescent emission under physiologic pH conditions. Compounds 1, 3, 4, 5, and 6 showed unusual emission wavelength shifts upon binding of sugars. These boronic acids will be useful tools for building glycoprotein biosensors for biologic applications.