A GLUCOSE-SELECTIVE MOLECULAR FLUORESCENCE SENSOR
A GLUCOSE-SELECTIVE MOLECULAR FLUORESCENCE SENSOR
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DOI：
10.1002/anie.199422071
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发表时间：
1994-11-17
期刊：
影响因子：
--
通讯作者：
SHINKAI, S
中科院分区：
文献类型：
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作者：
JAMES, TD;SANDANAYAKE, KRAS;SHINKAI, S
质子和金属离子的荧光分子传感器已经基于光诱导电子转移（PET）设计，但很少有中性小分子的荧光分子传感器是已知的。以PET为基础的选择性检测的目的，有机硼酸和间苯二甲酸之间的相互作用已经使用分子模型进行了研究，显示出一个特定的衍生物与9，10-二氨基甲基蒽骨架提供了一个裂缝，其中葡萄糖分子适合与其1，2-和4，6-羟基完美地间隔和对齐的2个面向内的硼酸基团。所需的硼酸衍生物很容易在3个阶段合成，其荧光强度（在pH 7.77的33.3%甲醇缓冲液中，10 µsmallcap μ M;未说明波长）与smallcap β-D-单糖（葡萄糖、果糖、阿洛糖或半乳糖）或乙二醇（几乎没有响应）的浓度相关。5种配合物的稳定常数（logKa）分别为3.6、2.5、2.8、2.2和-0.2。解释了葡萄糖络合物的~ 1H-NMR谱特征。当葡萄糖（logc从-5到-1）在0.1 mM小分子果糖或半乳糖存在下进行测试时，计算的logK几乎与单独使用葡萄糖时相同。因此，存在用于构建对葡萄糖具有选择性的基于PET的传感器的基础。
Fluorescent molecular sensors for protons and metal ions have been designed on the basis of photoinduced electron transfer (PET), but few fluorescent molecular sensors for small neutral molecules are known. With the aim of PET-based selective detection of saccharides, interactions between organic boronic acids and saccharides have been studied using molecular models, showing that a particular derivative with a 9,10-diaminomethylanthracene skeleton provides a cleft into which the glucose molecule fits with its 1,2- and 4,6- hydroxyl groups perfectly spaced and aligned with the 2 inwardly facing boronic acid groups. The required boronic acid derivative was easily synthesized in 3 stages, and the intensity of its fluorescence (at 10 µsmallcap˜M in aqueous 33.3% methanol buffer at pH 7.77; no wavelength stated) was studied in relation to the concentrationcof smallcap˜D-monosaccharide (glucose, fructose, allose or galactose) or ethyleneglycol (which gave little response). The calculated stability constants of the 5 complexes, expressed as logKa, were 3.6, 2.5, 2.8, 2.2 and -0.2, respectively. Features of the1H-NMR spectrum of the glucose complex are interpreted. When glucose (logcfrom -5 to -1) was tested in the presence of 0.1 msmallcap˜M fructose or galactose, the calculated logKaremained almost the same as with glucose alone. Hence, a basis exists for constructing a PET-based sensor selective for glucose.