Differential Sensing of Saccharides Based on an Array of Fluorinated Benzosiloxaborole Receptors

Abstract

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.

Oxazoline scaffold in synthesis of benzosiloxaboroles and related ring-expanded heterocycles: diverse reactivity, structural peculiarities and antimicrobial activity

“…6 Other applications of benzosiloxaboroles involved chemometric differential sensing of selected sugars. 7 On the other hand, oxazolines and closely related oxazole heterocycles are useful synthons in medicinal chemistry. [8][9][10][11][12] Examples of boronated aryl oxazolines are rare.…”

Heteroelement Analogues of Benzoxaborole and Related Ring Expanded Systems

“…Association constants K s with dopamine, ribose, glucose, fructose, sorbitol, and adenosine and its monophosphate (AMP) were determined using the Springsteen and Wang method, with ARS as a fluorescent probe [ 41 ]. Later on, compounds 72 , 75 , 76 , 96 , and 102 were employed for the chemometric differential fluorescence-based sensing of saccharides such as glucose, fructose, ribose, sorbitol, lactose, and sucrose [ 46 ].…”

“…The formation of a third C-C bond and the cleavage of two B-C bonds was observed when THF was used as the solvent. The 1 H NMR studies on the structural behaviour of 44 revealed that it exists in equilibrium with the respective diborinic acid (45) upon the addition of water, whereas complete conversion to the dibromo derivative (46) occurs upon heating with an excess of BBr 3 . Compound 46 is readily reconverted back to 44 upon the addition of water.…”

Exploring the effect of substitution patterns on the symmetry of hydrogen-bonded supramolecular motifs in functionalized benzosiloxaboroles

“…Benzosiloxaboroles also show high affinity towards biologically relevant diols such as dopamine, AMP and selected sugars, indicating their possible application in chemosensing devices. 35,38 Synthetic routes are generally different between benzoxa-and benzosiloxaboroles, opening new possibilities for functionalization, especially at the C6 and C7 positions, e.g., in the vicinity of the silicon atom. 39 Thus, over one hundred benzosiloxaboroles with diverse substitution patterns have already been obtained with the prospect of being able to synthesize hundreds more.…”