Glucose Recognition by a Supramolecular Complex of Boronic Acid Fluorophore with Boronic Acid-Modified Cyclodextrin in Water

Glucose Recognition by a Supramolecular Complex of Boronic Acid Fluorophore with Boronic Acid-Modified Cyclodextrin in Water
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DOI:
10.2116/analsci.28.121
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发表时间:
2012-02-01
影响因子:
1.6
通讯作者:
Hayashita, Takashi
Hayashita, Takashi
中科院分区:
化学4区
文献类型:
--
作者:
Kumai, Mio;Kozuka, Satoko;Hayashita, Takashi

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设计了一种硼酸荧光团(C1-APB)/硼酸修饰的γ-环糊精(3-PB-gamma-CyD)复合物作为超分子传感器,用于水中葡萄糖的选择性识别. C1-APB/3-PB-gamma-CyD复合物在各种pH条件下的荧光响应行为表明,含有葡萄糖的C1-APB/3-PB-gamma-CyD复合物溶液在碱性pH条件下显示出荧光强度的大幅增加。相比之下,果糖和无糖溶液的荧光强度仅略有增加。对C1-APB/3-PB-gamma-CyD复合物的响应选择性顺序为葡萄糖>>半乳糖,甘露糖>果糖。C1-APB/3-PB-gamma-CyD复合物的包合常数较大(K-L.CyD = 6.5 x 10(3)M-1)、H-1 NMR谱显著增宽以及葡萄糖结合诱导的环状非线性(ICD)强度增强等证据支持C1-APB/3-PB-gamma-CyD复合物与葡萄糖的多点相互作用。这些结果表明,C1-APB/3-PB-gamma-CyD复合物作为一个有效的超分子传感器选择性识别葡萄糖在水中。
A boronic acid fluorophore (C1-APB)/boronic acid-modified gamma-cyclodextrin (3-PB-gamma-CyD) complex as a supramolecular sensor has been designed for selective glucose recognition in water. The fluorescent response behavior of the C1-APB/3-PB-gamma-CyD complex under various pH conditions revealed that a C1-APB/3-PB-gamma-CyD complex solution containing glucose showed a large increase in the fluorescence intensity under alkaline pH conditions. In contrast, only small increases in the fluorescence intensity were noted for fructose and without sugar solutions. The observed response selectivity for the C1-APB/3-PB-gamma-CyD complex was on the order of glucose >> galactose, mannose > fructose. The evidence on a large value of the inclusion constant (K-L.CyD = 6.5 x 10(3) M-1), a marked broadening of the H-1 NMR spectra, and an enhancement of induced circular dichloism (ICD) intensity for the C1-APB/3-PB-gamma-CyD complex by glucose binding supported the multi-point interaction of the C1-APB/3-PB-gamma-CyD complex with glucose. These results demonstrated that the C1-APB/3-PB-gamma-CyD complex functioned as an efficient supramolecular sensor for selective glucose recognition in water.