The use of multicomponent reactions in the development of bis-boronic acids for the detection of ß-sialic acid.

Sialic acid (SA) is a naturally occurring monosaccharide found in glycoproteins and glycolipids. Changes in the expression of SA are associated with several diseases; thus, the detection of SA is of great significance for biological research, cancer diagnosis, and treatment. Boronic acid analogs have emerged as a promising tool for detecting sugars such as SA due to its reversible covalent bonding ability. In this study, 11 bis-boronic acid compounds and 2 mono-boronic acid compounds were synthesized via a highly efficient Ugi-4CR strategy. The synthesized compounds were subjected to affinity fluorescence binding experiments to evaluate their binding capability to SA. Compound A1 was shown to have a promising binding constant of 2602 ± 100 M-1 at pH = 6.0. Density Functional Theory (DFT) calculations examining the binding modes between A1 and SA indicated that the position of the boronic acid functional group was strongly correlated with its interaction with SA's α-hydroxy acid unit. The DFT calculations were consistent with the observations from the fluorescence experiments, demonstrating that the number and relative positions of the boronic acid functional groups are critical factors in enhancing the binding affinity to SA. DFT calculations of both S and R configuration of A1 indicated that the effect of the S/R configuration of A1 on its binding with ß-sialic acid was insignificant as the Ugi-4CR generated racemic products. A fluorine atom was incorporated into the R2 substituent of A1 as an electron-withdrawing group to produce A5, which possessed a significantly higher capability to bind to SA (Keq = 7015 ± 5 M-1 at pH = 6.0). Finally, A1 and A5 were shown to possess exceptional binding selectivity toward ß-sialic acid under pH of 6.0 and 6.5 while preferring to bind with glucose, fructose, and galactose under pH of 7.0 and 7.5.

Multilayered Ag NP-PEDOT-Paper Composite Device for Human-Machine Interfacing.

Flexible pressure sensors have attracted increasing interest because of their potential applications on wearable sensing devices for human-machine interface connections, but challenges regarding material cost, fabrication robustness, signal transduction, sensitivity improvement, detection range, and operation convenience still need to be overcome. Herein, with a simple, low-cost, and scalable approach, a flexible and wearable pressure-sensing device fabricated by utilizing filter paper as the solid support, poly(3,4-ethylenedioxythiophene) to enhance conductivity, and silver nanoparticles to provide a rougher surface is introduced. Sandwiching and laminating composite material layers with two thermoplastic polypropylene films lead to robust integration of sensing devices, where assembling four layers of composite materials results in the best sensitivity toward applied pressure. This practical pressure-sensing device possessing properties such as high sensitivity of 0.119 kPa-1, high durability of 2000 operation cycles, and an ultralow energy consumption level of 10-5 W is a promising candidate for contriving point-of-care wearable electronic devices and applying it to human-machine interface connections.