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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2014 ·Vol. 406 ·期 11 ·2687-2693 · IF 3.578

A fast and biocompatible living virus labeling method based on sialic acid-phenylboronic acid recognition system

Huang Li-Li,Jin Yong-Jie,Zhao Dongxu,Yu Chao,Hao Jian,Xie Hai-Yan

The sialic acid (SA)-phenylboronic acid (PBA) recognition system is of particular interest in the bioconjugation field, because it is simple, fast, efficient, and biocompatible. In this paper, we report a novel method for reversibly labeling living virus with quantum dots (QDs) by taking advantage of this SA-PBA recognition system. The QDs were initially modified with PBA (QDs-PBA) to target them to the surface of vesicular stomatitis virus (VSV), which has abundant with SA on its envelope. The QDs-PBA was of good monodispersity and strong fluorescence, and could be conjugated with VSV by simply incubating with native VSV for 10 min at 37 °C, producing QDs-VSV that was capable of being imaged at the single virion level. The labeling efficiency attained 83 ± 4.3 % (mean ± SD); meanwhile, the activity and recognition ability of the labeled virus were minimally affected. This method was simple, rapid, and reversible. This work promotes the virus labeling development to a new step. That is, native viruses can be reversibly labeled without any modification. Initially, the 3-amino-phenylboronic acid (APBA) reacted with QDs-COOH to prepare the PBA capped QDs (QDs-PBA). Then, the vesicular stomatitis virus (VSV), on which the surface of the envelope is abundant with sialic acid (SA), could be labeled efficiently and specifically with QDs-PBA in one step based on sialic acid-phenylboronic acid recognition system. The labeling efficiency attained to (83 ± 4.3 %) (mean ± SD). The labeled VSA (QDs-VSV) was still infectious and capable of being imaged at the single virion level

研究领域: 生物化学 · 病毒学 · 纳米生物学
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Analytical Methods · 2024 · IF 2.7

Phenylboronic acid modification-based novel dumbbell-shaped Au-Ag nanorods SERS substrates for ultrasensitive detection of SO42-

Kang Shen,Caili Bi,Haifan Yang,Miaowen Xu,Lili Huang,Youwei Wang

Based on the coordination principle of Lewis acid, the 4-mercaptophenylboronic acid (4-MPBA)-modified novel dumbbell-shaped Au-Ag nanorods (4-MPBA@DS Au-AgNRs) substrate has been developed, which could be combined with the surface-enhanced Raman scattering (SERS) technique to detect SO42- with high sensitivity and specificity. DS Au-AgNRs synthesized in this paper with dumbbell particular structure have been verified by finite-difference time domain (FDTD) simulation to be capable of stimulating strong localized electromagnetic enhancement (EM) at nano-edge, gap, generating a large number of “hot spots” exhibiting excellent SERS performance. The 4-MPBA modified on its surface could specifically recognize SO42-, producing a change in the spectral peak at 1382 cm-1, thus realizing highly sensitive and specific sensing of SO42-. Under optimized conditions, this SERS sensor responded rapidly to SO42- within 2 minutes and demonstrated uncommon immunity. Ratio calculation by the ratio of the characteristic peaks at 1382 and 1070 cm-1 (I1382/I1070) enabled quantitative detection of SO42- in the range of 1 × 10-8-1 × 10-3 M, and the detection threshold was as low as 1 nM, which was superior to that of similar detection methods. Importantly, the utility and reliability of this SERS substrate for the determination of SO42- in actual samples were evaluated using ion chromatography as the gold standard, and there was no significant difference between the two protocols (P > 0.05), and the RSD was less than 6% with a satisfactory recovery rate (97.6-102.3%). Therefore, the present protocol has the advantages of simplicity and rapidity, high sensitivity, specificity, stability, and practicability in the determination of SO42- in aqueous solution, providing a reliable solution for tracing SO42- in the field of food safety and environmental testing.

CAS / MDL: 110-54-3 16940-66-2
研究领域: 分析化学 · 环境科学 · 食品安全
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JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY · 2024 · IF 2.8

Selective extraction of 1,3-propanediol by phenylboronic acid-based ternary extraction system

Lusheng Huang,Xu Zhou,Nasha Wu,Yaqin Sun,Zhilong Xiu

BACKGROUND Conventional methods for the separation of 1,3-propanediol (1,3-PDO) are problematic in many ways. The study of a simple and efficient separation process was the key to solving the bottlenecks that have restricted the large-scale development of 1,3-PDO. In order to solve the difficulty of separating 1,3-PDO from fermentation broths, a ternary selective extraction system was constructed to separate 1,3-PDO from a simulated solution and fermentation broth. RESULTS In this study, quantum chemistry calculation and wave function analysis showed that the reaction between phenylboronic acid and 1,3-PDO is thermodynamically feasible, stable and covalently reversible. The ternary extraction system was composed of 1-naphthylboric acid, dichloromethane and Aliquat 336. After optimization of the extraction conditions, a high extraction efficiency of 82.6% could be achieved for 1,3-PDO. Meanwhile, the stripping recovery of 1,3-PDO was over 90%, with a high purity (98.6%), from a simulated solution using 0.4 mol L −1 hydrochloric acid as stripping solution. The extraction selectivity of 1,3-PDO to glycerol, acetic acid and butyric acid in the fermentation broth reached 12.9, 230.6 and 233.7, respectively, implying a high selective performance compared with the aldehyde-based traditional reactive extraction. CONCLUSION The ternary extraction system exhibited good extraction performance, highlighting the potential for selective extraction of diol biochemicals from fermentation broths. © 2024 Society of Chemical Industry (SCI).

研究领域: 生物工程 · 化学工程
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Science China-Chemistry · 2015 ·Vol. 58 ·期 6 ·1056-1064 · IF 1.695

Polydopamine-mediated immobilization of phenylboronic acid on magnetic microspheres for selective enrichment of glycoproteins and glycopeptides

Zheng Jiangnan,Lin Zian,Zhang Lan,Yang Huanghao

In this work, we demonstrate for the first time, a method to synthesize phenylboronic acid-Fe 3 O 4 @polydopamine (Fe 3 O 4 @PDA-PBA) magnetic microspheres via the combination of mussel-inspired polydopamine coating and click chemistry. Uniform-size and core-shell structured Fe 3 O 4 @PDA-PBA magnetic microspheres with a core diameter of ∼240 nm and a shell thickness of ∼13 nm were obtained as identified by the characterization of the morphology, structure and composition of the synthesized microspheres. We evaluated the selectivity and binding capacity of the Fe 3 O 4 @PDA-PBA magnetic microspheres by using standard glycoproteins (ovalbumin, immunoglobulin G and catalase) and nonglycoproteins (human serum albumin, bovine hemoglobin, myoglobin, lysozyme, and ribonuclease A) as model proteins. Adsorption experiments, SDS-PAGE and mass spectrometry analysis demonstrated that the Fe 3 O 4 @PDA-PBA magnetic microspheres had much high binding capacity and selectivity for glycoproteins/glycopeptides compared to nonglycoproteins/nonglycopeptides. In addition, the practicability of the Fe 3 O 4 @PDA-PBA magnetic microspheres was further assessed by selective capture of glycoproteins from healthy human serum. The good results demonstrated its potential in glycoproteome analysis.

CAS / MDL: 25322-68-3 134-03-2
研究领域: 生物化学 · 分析化学 · 材料科学
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Matter · 2024 · IF 17.3

Nanopore signatures of major alcoholic beverages

Pingping Fan,Kui Li,Tian Li,Panke Zhang,Shuo Huang

Alcoholic beverages, such as wine, beer, and distilled spirits, are widely produced and consumed in different nations. Different types of alcoholic beverages contain different combinations of flavor compounds. However, rapid and simultaneous analysis of a large variety of compounds in alcoholic beverages by a miniatured and portable device remains a challenge. In this paper, a Mycobacterium smegmatis porin A (MspA) nanopore modified with a phenylboronic acid (PBA) adapter is applied for rapid analysis of a variety of alcoholic beverages. By utilizing custom machine learning algorithms, various cis -diols are identified simultaneously in both distilled and fermented alcoholic beverages, generating unique barcodes for each sample type. Nanopore analysis of alcoholic beverages has also never been carried out previously. Rapid grading of wine sweetness and detection of additives, including sucrose and D-tartaric acid, are also demonstrated, showcasing the significance of this technique in the administration of wine production.

研究领域: 生物技术 · 食品科学
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NEW JOURNAL OF CHEMISTRY · 2021 ·Vol. 45 ·期 24 ·10711-10717 · IF 3.591

A cyclodextrin-phenylboronic acid cross-linked hydrogel with drug hosting, self-healing and pH-sensitive properties for sustained drug release

Daijun Chen,Guanglei Ren,Xiaoli Zhao,Jinni Luo,Huanxia Wang,Pengxiang Jia

The rapid drug release and poor self-healing properties of drug-loaded hydrogels largely limit their practical application. Herein, we present a simple method to prepare hydrogels with self-healing, drug hosting and pH-sensitive properties for sustained drug release. First, salicylic acid was loaded into β-CD through host–guest interactions. The hydrogel was then constructed through the polymerization of acrylamide using cyclodextrin-phenylboronic acid as a reversible, pH-sensitive cross-linker. The obtained hydrogel exhibited outstanding stretchability (1150%), good tensile strength (42 kPa), excellent self-healing properties (90%) and high biocompatibility. Besides, the introduction of the cyclodextrin-phenylboronic acid cross-linker endowed the hydrogel with pH-sensitive and sustained drug release properties. These functions enable cyclodextrin-phenylboronic acid cross-linked hydrogels to be drug hosting, self-healing and pH-sensitive flexible materials for sustained drug release, making them a powerful platform for various biomedical applications.

研究领域: 材料科学 · 生物医学工程 · 药剂学
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Soft Matter · 2024 · IF 2.9

pH and glucose dual-responsive phenylboronic acid hydrogels for smart insulin delivery

Keke Yang,Hou Bo,Dewei Ma,Mingwei Peng,Qinglong Liu,Ziwen Heng,Zhongwei Gu,Xuhan Liu,Siyuan Chen

Phenylboronic acid (PBA) is a widely exploited glucose-sensitive element for constructing glucose-responsive hydrogels to enable smart insulin delivery. However, its relatively high intrinsic pKa affects its binding with glucose under physiological conditions and thus limits its application. Herein, we developed a series of boronate-containing PLP–PBA polymers by conjugating glucose-sensitive 3-aminophenylboronic acid (3-PBA) onto the backbone of a metabolite-derived, pH-responsive poly-L-lysine isophthalamide (PLP) polymer with a pKa value of 4.4 at various substitution degrees. Dual-responsive LME–(PLP–PBA) hydrogels were further synthesized by crosslinking the PLP–PBA polymers with L-lysine methyl ester (LME). The rheological properties and swelling ratio of the hydrogel could be manipulated by the PBA grafting degree and crosslinking ratio. With the increase of pH and glucose concentration, the pore size of the hydrogel enhanced, thus promoting the release of loaded insulin. Under physiological conditions, the hydrogel with optimal formulation could establish acute pH-responsive and glucose-responsive insulin release. The development of this dual-responsive hydrogel suggests a strategy to overcome the high pKa problem associated with PBA and provide a promising delivery system for smart insulin delivery.

研究领域: 材料科学 · 生物医学工程 · 药物递送系统 · 聚合物化学
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Chemical Science · 2015 ·Vol. 7 ·期 2 ·1487-1495 · IF 9.211

A novel probe based on phenylboronic acid functionalized carbon nanotubes for ultrasensitive carbohydrate determination in biofluids and semi-solid biotissues

Guosheng Chen,Junlang Qiu,Jianqiao Xu,Xu'an Fang,Yan Liu,Shuqin Liu,Songbo Wei,Ruifen Jiang,Tiangang Luan,Feng Zeng,Fang Zhu,Gangfeng Ouyang

Carbohydrates are known to be involved in a wide range of biological and pathological processes. However, due to the presence of multiple hydroxyl groups, carbohydrate recognition is a particular challenge. Herein, we reported an ultrasensitive solid-phase microextraction (SPME) probe based on phenylboronic acid (PBA) functionalized carbon nanotubes (CNTs) for direct in vitro or in vivo recognition of carbohydrates in biofluids as well as semi-solid biotissues. The coating of the proposed probe possessed a 3D interconnected porous architecture formed by the stacking of CNTs. As a result, the binding capacity toward carbohydrates was excellent. The proposed approach was demonstrated to be much superior to most carbohydrate sensors, including higher sensitivity, wider linear range, and excellent qualitative ability in multi-carbohydrate systems. Thus, this approach opens up new avenues for the facile and efficient recognition of carbohydrates for important applications such as glycomics.

研究领域: 分析化学 · 生物化学 · 医学检测
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CARBOHYDRATE POLYMERS · 2021 · IF 9.381

Injectable DMEM-induced phenylboronic acid-modified hyaluronic acid self-crosslinking hydrogel for potential applications in tissue repair

Huichang Gao,Chenxi Yu,Qingtao Li,Xiaodong Cao

Most of traditional injectable hydrogels based on light curing or enzyme crosslinking are difficult to control the crosslinking time accurately and lack tissue adhesion, which leads to difficult clinical application and poor tissue repair effect. In this study, a novel injectable DMEM (Dulbecco’s Modified Eagle’s Medium)-induced phenylboronic acid-modified hyaluronic acid self-crosslinking hydrogel was designed and prepared by combining the phenylboronic acid and a diol on hyaluronic acid as the main network, in which dynamically reversible phenylboronic acid esters imparted good self-healing properties and tissue adhesion properties to the hydrogels. Cell medium that induced the formation of the hydrogel could simulate the pH of the physiological environment and provide uniform nutrients for the encapsulated cells. In addition, in vitro cell experiments indicated that the DMEM-induced phenylboronic acid-modified hyaluronic acid self-crosslinking hydrogel was capable of supporting cell loading and proliferation, thus being a promising candidate for tissue repair materials.

CAS / MDL: 30418-59-8
研究领域: 生物材料学 · 组织工程学
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POLYMER · 2021 · IF 4.43

Phosphate enhanced self-healing property of phenylborate-based hydrogel at neutral environment

Yongjie Dong,Siqi Chen,Piao Ning,Ka Lu,Song Ma,Yingjie Wang,Shaoyu Lü

Self-healing hydrogels based on phenylboronate ester bonds are of huge interest in polymer science. However, most of these hydrogels only heal themselves at pH above their pKa (mostly > 8.0), which reduces their potential application in physiologic environments. Here, we showed that a small amount of phosphate produced stable hydrogels, able to support their self-healing at neutral pH. The hydrogel was formed by poly (3-acryloxymethylphenylboronic acid- co -N, N-dimethyl acrylamide) and poly (D-gluconamidoethyl methacrylate- co -N, N-dimethyl acrylamide) in phosphate buffer. Self-healing was observed at pH = 7.0. Intermolecular interactions between phenylboronic acid and phosphate were suggested by rheology, DSC determination and QTAIM calculations. The study represents a new mechanism to promote phenylboronate-based hydrogel formation and self-healing at neutral environment and, more importantly, provides considerable insight into their application in physiologic conditions including sensors and tissue engineering.

研究领域: 材料科学 · 生物医学工程
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2022 · IF 5.518

Efficient detection of glucose by graphene-based non-enzymatic sensing material based on carbon dot

Jingxin Zhou,Ran Wang,Weiwei Su,Lexin Zhang,Adan Li,Tifeng Jiao

Diabetes is one of the global chronic diseases, which is mainly caused by the abnormal increase of blood sugar level. Therefore, it is particularly important to monitor glucose in real time. In this work, based on the principle that phenylboronic acid can react with diol rapidly and reversibly in aqueous medium, phenylboronic acid functionalized reduced graphene oxide (rGO-PBA) and polyhydroxy modified carbon spot fluorescent probe (CD1) were designed for detecting important glucose molecules. Among them, reduced graphene oxide (rGO) has high specific surface area and strong fluorescence quenching performance. When CD1 is close to the surface of rGO-PBA, the fluorescence of carbon dots was quenched. With the addition of glucose, the fluorescence of carbon dots increased continuously. The detection of small molecule glucose can be realized quickly and sensitively by using the "on" and "off" strategies of fluorescence.

研究领域: 生物化学 · 材料科学 · 医学检测
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JOURNAL OF MATERIALS SCIENCE · 2019 ·Vol. 54 ·期 7 ·5695-5711 · IF 3.442

Phenylboronic acid-functionalized ultra-pH-sensitive micelles for enhanced tumor penetration and inhibition in vitro

Qin Jiejie,Huang Yan,Yan Guoqing,Wang Jun,Hu Liefeng,Zhang Panpan,Tang Rupei

In this work, the tumor-targeted ultra-pH-responsive conjugates (PBA/Dex-g-OE) and nontargeted conjugates (Dex-g-OE) were successfully prepared and could easily self-assemble into stable micelles with lower CMC values in neutral aqueous solution. Transmission electron microscopy and dynamic light scattering measurement indicated that the resulting micelles have desirable size distribution and regular spherical shape. The PBA/Dex-g-OE micelles possessed high stability in physiological condition and were pH sensitive to both extracellular and intracellular acidic conditions. Doxorubicin (DOX) was efficiently loaded to give the DOX-loaded micelles (PBA/Dex-g-OE-DOX and Dex-g-OE-DOX) with the desirable drug loading contents. In vitro cellular uptake and growth inhibition assays suggested that PBA/Dex-g-OE-DOX micelles were more efficiently internalized by monolayer tumor cells and three-dimensional multicellular tumor spheroids (MCTS) than nontargeted micelles (Dex-g-OE-DOX), leading to the fast and complete destruction of MCTS in vitro.

CAS / MDL: 30418-59-8
研究领域: 药剂学 · 肿瘤学
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