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Journal of Materials Chemistry A · 2018 ·Vol. 6 ·期 42 ·21193-21206 · IF 9.931

Synthesis of glycopolymer nanosponges with enhanced adsorption performances for boron removal and water treatment

Xueping Liao,Bingyu Wang,Qiang Zhang

The high-affinity interactions between cis-diols and boric/boronic acid have been widely employed as a tool for carbohydrate analysis, protein separation and boron removal. Herein we report the design and synthesis of cyclodextrin-scaffolded glycopolymers as bifunctional nanosponges for boron removal and water treatment for the first time. Different glycopolymer nanosponges (GNs) have been successfully synthesized from monosaccharides and β-cyclodextrin via a combination of a cross-linking reaction, Fischer glycosylation and a click reaction. Such functional GNs are mesoporous polymer frameworks with cis-diol-containing saccharides immobilized on the surface, which have exhibited selective adsorption behaviour towards boric acid depending on the structure of the GNs and the loaded saccharides. The GNs have also shown remarkable adsorption rates and capacities for an organic dye as a model pollutant in this work. Secondary bonding, such as hydrogen bonding and van der Waals forces between the immobilized saccharides and the adsorbates is believed to be responsible for the significantly enhanced adsorption rates and capacities. Such bifunctional materials may exhibit potential applications in seawater desalination and water treatment.

研究领域: 材料科学 · 环境科学 · 化学工程
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Journal of Analytical Methods in Chemistry · 2019 · IF 1.589

A Simple, Rapid, Fluorometric Assay for Dopamine by In Situ Reaction of Boronic Acids and cis-Diol

Xiaoxia Liu,Miaomiao Tian,Wenmei Gao,Jinzhong Zhao

An efficient, sensitive, and low-cost method has been developed for turn-on fluorescence sensing of dopamine (DA). The method relies on the rapid reaction of DA and 3-Hydroxyphenylboronic acid (3-HPBA) via specific recognition between boronic acids and cis-diol of DA in alkaline solution. The reaction product shows an excitation wavelength of 417 nm and the maximum emission peak at 470 nm. The proposed method allows the determination of DA in the range of 50 nM–25 μM, and the whole detection can be completed within 5 minutes. Furthermore, the presented approach has good selectivity and has been successfully applied to DA sensing in human serum samples, showing great potential in clinical diagnosis.

研究领域: 分析化学 · 生物医学 · 临床诊断
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SENSORS AND ACTUATORS B-CHEMICAL · 2025 · IF 7.7

Boronate affinity-mediated multi-mode visual sensing of cis-diol compounds in both biological and food samples

Mengzhen Jiang,Ruohan Xu,Chunyan Yang,Haili Wang,Jinyuan Cai,Yanrong Wen,Mingfu Ye,Tingxuan Yan,Shuangshou Wang

cis -Diol compounds are of great biological and clinical values, but their detection is usually instrument-inseparable. Herein, a flexible sensing strategy was proposed at the first time for multi-mode visualization of cis -diol compounds based on boronate affinity (BA)-mediated colorimetry and fluorometry. Boronic acid-decorated sensors with color-/fluorescence-derived binary responsivity were designed using cis -diol fluorescent dyes or dyes-fluorophore counterparts as response units, inducing competitive BA when cis -diol analytes were existed. Consequently, colors and fluorescence of sensors changed simultaneously, and both signals were linearly varied versus the dosages of cis -diol analytes in certain ranges. As proofs of concept, dual-mode visual sensing of glucose in normal/hyperglycemic human serum and sucrose in canned white fungus and edible mushroom plant beverage was achieved with sensing time as short as 1   min and limit of detection as low as 0.18   mg/mL. Furtherly, color information of colorimetric/fluorometric cards and tested sensors was picked by a smartphone APP for digital image analysis, by which the validity of dual-mode visual sensing assays was reinforced by avoiding possible errors from subjective judgement on colors and fluorescence. Besides, the credibility of visual sensing was cross-validated by fluorescent quantification and classical tools such as portable blood glucose meter and phenol-sulfuric acid method-based halochromic reaction.

研究领域: 分析化学 · 生物医学
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MICROCHEMICAL JOURNAL · 2020 · IF 3.594

Analyte-triggered autoacceleration of 4-mercaptophenylboronic acid-mediated aggregation of silver nanoparticles for facile and one-step ratiometric colorimetric method for detection of ascorbic acid

Shengnan Wei,Xuechen Wang,Bo Pang,Hang Li,Xuening Shi,Chao Zhao,Juan Li,Juan Wang

A simple, fast, one-step method is described for ratiometric colorimetric detection of ascorbic acid (AA) based on 4-mercaptophenylboronic acid (4-MPBA) and silver nanoparticles (AgNPs). In the presence of AA, the aggregation process of AgNPs can be triggered and accelerated, due to the interaction between 4-MPBA and the cis 1,2-diol moieties of AA through a reversible esterification, resulting in a distinguish color change from yellow to brownish red. The AA concentration-dependent color change can be quantified by the bare eyes or a UV–Vis spectrometer. The whole AA detection procedure was able to complete in 10 min with an excellent linear relationship (1–500 μM) and a low limit of detection (0.70 μM). The proposed approach was also used to accurately evaluate AA levels in orange juice. In our perception, this assay is rapid, sensitive, and specific, which demonstrates its potential on constructing biochemical and clinical sensors.

研究领域: 分析化学 · 生物化学
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TALANTA · 2017 · IF 4.162

Silica – Boronate affinity material for quick enrichment of intracellular nucleosides

Shuxia Wang,Huihui Li,Xiujuan Guan,Ting Cheng,Haixia Zhang

Boronic acid modified materials have been widely used to adsorb nucleosides , but their adsorption capacities require further improvement. Most cis -diol containing biomolecules are in very low abundance along with interfering components in real samples, and need to be enriched specially. In this study, we synthesize a kind of silica absorbent modified with boronic acid derivative, using amorphous silica as raw material and obtaining high adsorption capacity for adenosine. In addition, the adsorption equilibrium can be completed within 10   s and 1   min for the desorption. Finally, the material was successfully applied to enrich nucleosides from cells and the spiked recoveries were found between 82.21% and 118.9%. The results showed that the prepared adsorbent has potential to effectively enrich cis-diol substances from cell samples.

研究领域: 分析化学 · 生物化学
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ANALYTICA CHIMICA ACTA · 2023 · IF 6.2

Boronic acid-functionalized magnetic porphyrin-based covalent organic framework for selective enrichment of cis-diol-containing nucleosides

Ziyi Wang,Ting Zou,Shitao Feng,Fengshou Wu,Juan Zhang

In this study, a novel boronic acid-functionalized magnetic porphyrin-based covalent organic framework (COF) with a core-shell structure was designed and synthesized for the selective enrichment and detection of nucleosides . Firstly, brominated porphyrin-based COF was in situ grown on Fe 3 O 4 -NH 2 nanospheres (denoted as Fe 3 O 4 @Br-COF), then a post-synthetic modification strategy was used to introduce boronic acid into the framework via Suzuki-Miyaura cross-coupling reaction to obtain boronic acid functionalized magnetic COF (denoted as Fe 3 O 4 @BA-COF). Suzuki-Miyaura cross-coupling possesses the advantages of mild synthesis conditions, high tolerance to functionalities, and ease of handling and separation, which is considered as a promising candidate for functionalizing COF. It is worth mentioning that the porphyrin-based COF possesses a unique nitrogen-rich skeleton and “trap” structure formed by four pyrrole rings, which can provide hydrogen bond and make it more suitable for trapping analytes than other types of COF. The boronic acid group provides boronate affinity, which enables better selective enrichment of cis -diol-containing nucleoside. The morphology and structure of the prepared Fe 3 O 4 @BA-COF was characterized by various methods. Based on the Fe 3 O 4 @BA-COF, a facile magnetic solid phase extraction coupled with high performance liquid chromatography method (MSPE-HPLC) was used to extract and detect adenosine, guanosine , uridine , and cytidine in urine samples. This work not only provides a mild and feasible post-synthetic modification method for fabrication of boronic acid-functionalized magnetic COF, but also provides an efficient and rapid method to selectively enrich and detect hydrophilic nucleosides.

研究领域: 分析化学 · 材料科学 · 生物医学
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BIOMEDICAL CHROMATOGRAPHY · 2015 ·Vol. 29 ·期 8 ·1133-1136 · IF 1.723

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

Li Zhang,Chaozhan Wang,Yinmao Wei

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. Copyright © 2015 John Wiley & Sons, Ltd.

研究领域: 生物化学 · 药物化学
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ADVANCED FUNCTIONAL MATERIALS · 2015 ·Vol. 25 ·期 25 ·3847-3854 · IF 11.805

Metal–Organic Frameworks with Boronic Acid Suspended and Their Implication for cis-Diol Moieties Binding

Xiangyang Zhu,Jinlou Gu,Junying Zhu,Yongsheng Li,Liming Zhao,Jianlin Shi

Introduction of accessible boronic acid functionality into metal–organic frameworks (MOFs) might to endow them with desired properties for potential applications in recognition and isolation of cis -diol containing biomolecules (CDBs). However, no investigation is found to address this topic until now. Herein, Cr-based MOFs of MIL-100 (MIL stands for Materials from Institut Lavoisier) integrated with different pendent boronic acid group (MIL-100-B) are reported. This new functional material is successfully prepared using a simple metal–ligand–fragment coassembly (MLFC) strategy with isostructure to the parent MIL-100 as verified by X-ray diffraction characterization. The integration and content tunability of the boronic acid group in the framework are confirmed by X-ray photoelectron spectroscopy and 11 B NMR. Transmission electron microscopy reveals that MIL-100-B can evolve into well-defined morphology and nanoscale size at optimized boronic acid incorporating level. The obtained MOFs exhibit comparable surface areas and pore volumes with parent MIL-100 and present exceptional chemical stability in a wide pH range. The inherent boronic acid components in MIL-100-B can effectively serve as the recognition units for the cis -diol moieties and consequently enhance the capture capabilities for CDBs. The exceptional chemical stability, high porosity, and good reusability as well as the intrinsic cis -diol moieties recognition function prefigure great potential of the current MIL-100-B in CDBs purification, sensing, and separation applications.

研究领域: 材料科学 · 生物化学
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MICROCHIMICA ACTA · 2018 ·Vol. 185 ·期 3 ·1-8 · IF 5.705

Preparation of a boronate affinity material with ultrahigh binding capacity for cis-diols by grafting polymer brush from polydopamine-coated magnetized graphene oxide

Deng Ya’nan,Gao Qin,Ma Juan,Wang Chaozhan,Wei Yinmao

Poly(3-acrylamidophenylboronic acid) (PAAPBA) was grafted onto polydopamine-coated magnetic graphene oxide via surface-initiated atom transfer radical polymerization to obtain a new kind of boronate affinity material (BAM). The BAM possesses good water dispersity and adsorption capacities as high as 154, 357, 588 and 1111 μmol·g −1 for adenosine, salbutamol, dopamine and catechol, respectively. For the molecules without nitrogen atoms, the BAM can selectively capture the cis -diols under the interference of non- cis -diols. For molecules containing nitrogen, the non- cis -diols are also retained, but much less than the cis -diols. The selectivity can be improved by adding salts to facilitate complexation and to suppress the electrostatic interaction between cis -diols and the boronic acid ligand. The BAM was successfully employed to the enrichment of catecholamines from real urine samples. Results indicate that it is a promising material for the pretreatment of real samples. Schematic of the preparation of an ultrahigh capacity boronate affinity material by grafting polymer brush from polydopamine coated magnetic graphene oxide. The material has good selectivity to cis -diol-containing molecules and can be applied to enrich catecholamines in urine samples.

研究领域: 分析化学 · 材料科学 · 生物医学
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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Structure-Assisted Boronic Acid Implanted Mesoporous Metal–Organic Frameworks for Specific Extraction of cis-Diol Molecules

Jiacheng Dong,Ailan Huang,Tianrun Wu,Yang Chen,Zijun Bie

cis-Diol-containing molecules, an essential type of compounds in living organisms, have attracted intensive research interest from various fields. The analysis of cis-diol-containing molecules is still suffering from some drawbacks, including low abundance and abundant interference. Metal–organic frameworks (MOFs) have proven to be an ideal sorbent for sample preparation. However, most of the reported MOFs are mainly restricted to a microporous regime (pore size <2 nm), which greatly limits the application. Herein, a facile strategy is established to construction of boronate affinity MOFs via the postsynthetic ligand-exchange process. Owing to the fact that the ligand-exchange process was assisted by the structural integrity of the primitive metal–organic framework and the great compatibility of click chemistry, the obtained EPBA-PCN-333(Fe) is able to realize the maximum maintaining the porosity and crystallinity of the parent material. Several intriguing features of EPBA-PCN-333(Fe) (e.g., excellent selectivity, efficient diffusion, good accessibility, and size exclusion effect) are experimentally demonstrated via a series of cis-diol-containing molecules with different molecular sizes (small molecules, glycopeptides, and glycoproteins). The binding performance of EPBA-PCN-333(Fe) is evaluated by employing catechol as the test molecule (binding capacity: 0.25 mmol/g, LOD: 200 ng/mL). Finally, the real-world applications of EPBA-PCN-333(Fe) were demonstrated by the detection of nucleosides of human urine samples.

研究领域: 分析化学 · 材料科学 · 生物医学
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RSC Advances · 2016 ·Vol. 6 ·期 49 ·43648-43655 · IF 3.289

Polyethyleneimine-facilitated high-capacity boronate affinity membrane and its application for the adsorption and enrichment of cis-diol-containing molecules

Juan Ma,Chaozhan Wang,Yinmao Wei

Membrane separation has notably important applications in many fields. Boronate affinity provides a method to specifically recognize cis-diol-containing molecules. However, there is no report on the preparation and application of boronate affinity membranes. In the present study, high-capacity boronate affinity membranes were synthesized by grafting polyethyleneimine (PEI) to regenerated-cellulose (RC) membranes and subsequently coupling 4-formylphenylboronic acid. Detailed physical characterizations using Attenuated Total Reflection Fourier transform infrared (ATR-FTIR) spectroscopy and X-ray photoelectron spectroscopy (XPS) revealed the success of the synthesis. The morphology of the membranes, which were characterized using an atomic force microscope (AFM), indicates that the membrane became smoother after the polymer was grafted. The boronate affinity membrane had high selectivity and a high adsorption capacity for cis-diol-containing molecules; its saturated adsorption capacity for catechol, salbutamol, dopamine and adenosine was 511, 103, 472 and 120 μmol g−1, respectively, which is much higher than that of most reported particulate or monolithic adsorbents. In addition, the membrane showed notably fast adsorption and desorption equilibration for the cis-diol-containing molecules. It was successfully used to enrich dopamine in urine samples with notably efficient reusability, which indicates its promising application in the pretreatment of real complex samples.

CAS / MDL: 9002-98-6 25895-60-7
研究领域: 生物化学 · 材料科学 · 分析化学
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Analytical Methods · 2023 ·Vol. 15 ·期 43 ·5803-5812 · IF 3.1

Discrimination of cis-diol-containing molecules using fluorescent boronate affinity probes by principal component analysis

Fenying Wang,Shuqing Xiong,Tingting Wang,Yadan Hou,Qianjin Li

Fluorescent boronate affinity molecules have gained increasing attention in the field of fluorescence sensing and detection due to their selective recognition capability towards cis-diol-containing molecules (cis-diols). However, the conventional fluorescent boronate affinity molecules face a challenge in differentiating the type of cis-diol only by their fluorescence responses. In this study, a simple method was used to discriminate different types of cis-diols, including nucleosides, nucleotides, sugars, and glycoproteins based on the phenylboronic acid-functionalized fluorescent molecules combined with principal component analysis (PCA). Both fluorescent molecules were simply synthesized by the covalent interaction between the amino group in 3-aminophenyl boronic acid and the isothiocyanate group in fluorescein or rhodamine B. In view of their fluorescence-responsive behaviors to these cis-diols directly, it is impossible to differentiate their types even under the optimized experimental conditions. When PCA was employed to treat the fluorescence response data and the quenching constants with their molecular weight, different types of cis-diols can be distinguished successfully. As a result, by integrating the fluorescence response of the boronate affinity probes with PCA, it can greatly improve the specific recognition capability of the boronic acids, providing a simple and direct way to distinguish and identify different types of cis-diols.

研究领域: 生物化学 · 分析化学
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