A wavelength-ratiometric fluoride-sensitive probe based on the quinolinium nucleus and boronic acid moiety
A wavelength-ratiometric fluoride-sensitive probe based on the quinolinium nucleus and boronic acid moiety
复制标题
DOI：
10.1016/j.snb.2004.04.119
复制
发表时间：
2005-01-03
影响因子：
8.4
通讯作者：
Geddes, CD
中科院分区：
文献类型：
--
作者：
Badugu, R;Lakowicz, JR;Geddes, CD
我们报道了一种新的水溶性荧光探针敏感的含水氟化物。在氟化物存在的情况下，探针以波长比法和比色法显示出光谱位移和强度变化，从而可以在可见光波长检测到氟浓度，浓度范围约为1-300 mm。探针的响应基于硼酸基团与氟化物相互作用的能力，从中性形式的硼酸基团[R-B(OH)(2)]转变为阴离子形式的三氟化合物[R-B- f3]。它是给电子基。在喹啉骨架上，缺电子的四杂环氮中心和6位的强给电子氨基的存在，提供了氟化物与硼酸基团结合时观察到的光谱响应。有趣的是，喹啉骨架上6位氨基的存在抑制了含氟基团的硼酸对生物液体和食品中存在的单糖（如葡萄糖和果糖）的反应，这可能导致主要的氟化物敏感性。除了生理糖外，我们还讨论了作为潜在干扰物的水卤化物的响应，或者确实是要检测的分析物，并表明新探针在其他物种的高背景存在下对水氟化物的响应良好，例如在50 mM葡萄糖，50 mM Cl-和5 mM果糖的生物鸡尾酒中。(C) 2004 Elsevier B.V.版权所有
We report a new water-soluble fluorescent probe sensitive to aqueous fluoride. The probe shows spectral shifts and intensity changes in the presence of fluoride, in a wavelength ratiometric and colorimetric manner, enabling the detection of fluoride concentrations at visible wavelengths, in the concentration range approximate to 1-300 mM.The probes response is based on the ability of the boronic acid group to interact with fluoride, changing from the neutral form of the boronic acid group [R-B(OH)(2)] to the anionic trifluoro form [R-B-F3], which is an electron donating group. The presence of an electron-deficient quaternary heterocyclic nitrogen center and a strong electron donating amino group in the 6-position, on the quinolinium backbone, provides for the spectral responses observed upon fluoride binding to the boronic acid group. Interestingly, the presence of the amino group on the 6-position of the quinolinium backbone suppresses the response of the boronic acid containing fluorophore towards monosaccharides, such as glucose and fructose, which are present in biological fluids and food stuffs, potentially allowing for the predominant fluoride sensitivity.In addition to physiological sugars, we discuss the response of aqueous halides as potential interferents, or indeed analytes to be sensed, and show that the new probe responds well to aqueous fluoride in the presence of a high background of other species, such as in a biological cocktail of 50 mM glucose, 50 mM aqueous Cl- and 5 mM fructose. (C) 2004 Elsevier B.V. All rights reserved.