Development of ratiometric carbohydrate sensor based on boron dipyrromethene (BODIPY) scaffold
Development of ratiometric carbohydrate sensor based on boron dipyrromethene (BODIPY) scaffold
复制标题
基于硼二吡咯亚甲基（BODIPY）支架的比率式碳水化合物传感器的开发
DOI：
10.1016/j.bmcl.2019.126684
复制
发表时间：
2019
影响因子：
2.7
通讯作者：
Urano Yasuteru
中科院分区：
文献类型：
--
作者：
Cheruthu Nusaiba Madappuram;Komatsu Toru;Ueno Tasuku;Hanaoka Kenjiro;Urano Yasuteru
基于BODIPY的吸光度/荧光波长对取代基的依赖性，我们设计了一种比例碳水化合物传感器，由硼二吡咯甲烷荧光团在2位取代硼酸组成。取代基在硼酸B(OH)2和硼酸B(OH)3−两种形式之间处于平衡状态，这两种形式在可见光区具有不同的吸光度/荧光波长。硼酸部分与碳水化合物羟基的反应产生环状酯，使平衡向硼酸（B(OR)3−）形式转移，导致荧光比随碳水化合物浓度的变化。因此，该传感器BA-BODIPY可以在pH值接近环酯形成的pka1时比例检测碳水化合物。
We designed a ratiometric carbohydrate sensor consisting of the boron dipyrromethene fluorophore substituted with boronic acid at the 2-position, based upon the strong substituent dependency of the absorbance/fluorescence wavelengths of BODIPY. The substituent is in equilibrium between the boronic acid B(OH)2and boronate (B(OH)3−) forms, which have different absorbance/fluorescence wavelengths in the visible region. Reaction of the boronic acid moiety with hydroxy groups of carbohydrate affords a cyclic ester and shifts the equilibrium in favor of the boronate (B(OR)3−) form, resulting in a carbohydrate-concentration-dependent change of the fluorescence ratio. Thus, the sensor, BA-BODIPY, can ratiometrically detect carbohydrate at a pH near the pKaof cyclic ester formation.