Boronate affinity adsorption of cis‐diol‐containing biomolecules in nonaqueous solvent

Abstract

Boronate affinity has attracted much attention in recent years. It has been broadly used for selective isolation and enrichment of cis-diol-containing molecules. Conventionally, the cis-diols are adsorbed in mild alkaline aqueous solutions. In this work, for the first time, we found that boronate affinity adsorption could also be performed in nonaqueous solvent at nonbasic pH. Cis-diol-containing compounds present in herbal medicines were used for the adsorption test. The results indicated that all compounds obtained higher recoveries in the organic solvents (methanol, acetonitrile, ethyl acetate) compared with alkaline buffer. The adsorption of vicinal cis-diol-containing molecules in organic solvents could be accomplished rapidly, with high selectivity and high recoveries (>80%). These results shed light on the possibility of boronate affinity adsorption in nonaqueous solvents. The results are very important for the isolation and enrichment of cis-diols, which have poor solubility in water, especially for those in herbal medicines.

Imprinted polymer and Cu2O-graphene oxide nanocomposite for the detection of disease biomarkers

“…The MIP-Cu 2 O-rGO hybrid coatings are fabricated on QCM devices and are characterized. Boronateaffinity MIP can reversibly anchor cis-diol containing biomolecules (nucleotides, saccharides, glycoproteins, ribonuclease, and glycans) through their active boronic acid group [28,29]. The designed MIP-Cu 2 O-rGO/QCM sensor exhibits suitable α 1 -AGp recognition performance in complex mixtures such as human serum samples, thereby exhibiting its applicability in clinical diagnostics.…”

Efficient Enrichment and Analysis of Vicinal-Diol-Containing Flavonoid Molecules Using Boronic-Acid-Functionalized Particles and Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry

“…The use of MALDI–TOF MS as an analytical tool for small molecules offers many advantages over other conventional methods in terms of easy sample preparation, rapidity, high sensitivity, low background signals, and no false-positive signals. − In addition, mass spectrometry (MS) analysis has excellent multiplexing capability because it provides molecular weights of analytes and, thus, distinctively discriminates multiple analytes, despite structural similarity. In our strategy, boronic-acid-functionalized polyacrylamide particles (BAPs) were harnessed for selective isolation of vicinal-diol-containing flavonoid molecules, where boronic acids dominantly form boronate monoester complexes with vicinal diols at basic pH, while decomplexation occurs in the acidic environment, resulting in the recovery of boronic acid and vicinal diol functionality. − Using this characteristic, boronic-acid-functionalized materials have been widely used for the analysis of vicinal-diol-containing hydrophilic biomolecules, mostly saccharides, − nucleosides, glycopeptides, and glycoproteins, − and for various applications, including drug delivery systems, enzymatic inhibitions, and cell-capture/release systems. ,− However, very few examples have been reported for the study of hydrophobic molecules, such as flavonoids, because of its low water solubility and interference of other vicinal-diol-containing biomolecules existing in biological systems in high abundance. , As a typical example, Zhang et al introduced boronate affinity adsorption of cis -diol-containing hydrophobic molecules in non-aqueous solvents, such as methanol, acetonitrile, and ethyl acetate …”

“…In our strategy, boronic-acid-functionalized polyacrylamide particles (BAPs) were harnessed for selective isolation of vicinal-diolcontaining flavonoid molecules, where boronic acids dominantly form boronate monoester complexes with vicinal diols at basic pH, while decomplexation occurs in the acidic environment, resulting in the recovery of boronic acid and vicinal diol functionality. 27−30 Using this characteristic, boronic-acidfunctionalized materials have been widely used for the analysis of vicinal-diol-containing hydrophilic biomolecules, mostly 43 In the current study, the selectivity of the BAPs toward vicinal-diol-containing flavonoids was evaluated in the presence of other flavonoids in a highly excess amount, which have multiple hydroxyl groups and carbonyl groups that potentially interact with boronic acids. Next, the practical applicability was assessed by quantitating quercetin spiked in fetal bovine serum (FBS).…”