Chair of Medical Biotechnology, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
Chair of Physical Chemistry, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
Sensors (Basel). 2020 Jun 22;20(12):3540. doi: 10.3390/s20123540.
Fluorinated benzosiloxaboroles-silicon congeners of benzoxaboroles, were synthesized and tested as molecular receptors for mono- and disaccharides. The receptors differed in the Lewis acidity of the boron center as well as in the number of potential binding sites. The calculated stability constants indicated different binding affinity of benzosiloxaborole derivatives towards selected saccharides, enabling their classification using a receptor array-based sensing. Unique fluorescence fingerprints were created on the basis of competitive interactions of the studied receptors with both Alizarin Red S (ARS) and tested saccharide molecules. Detailed chemometric analysis of the obtained fluorescence data (based on partial least squares-discriminant analysis and hierarchical clustering analysis) provided the differential sensing of common saccharides, in particular the differentiation between glucose and fructose. In addition, DFT calculations were carried out to shed light on the binding mechanism under different pH conditions.
氟化苯并硅氧硼烷——苯并硼烷的硅同系物，被合成并测试为单糖和二糖的分子受体。这些受体在硼中心的路易斯酸度以及潜在结合位点的数量上有所不同。计算出的稳定常数表明，苯并硅氧硼烷衍生物对选定的糖具有不同的结合亲和力，从而能够使用基于受体阵列的传感对其进行分类。基于研究的受体与茜素红 S（ARS）和测试的糖分子的竞争性相互作用，创建了独特的荧光指纹。对获得的荧光数据进行详细的化学计量学分析（基于偏最小二乘判别分析和层次聚类分析），实现了对常见糖的差异感应，特别是对葡萄糖和果糖的区分。此外，还进行了 DFT 计算，以阐明不同 pH 条件下的结合机制。
