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MACROMOLECULAR RESEARCH · 2019 ·Vol. 28 ·期 1 ·51-56 · IF 1.758

A Selective Colorimetric Sensor for Pb2+ Detection by Using Phenylboronic Acid Functionalized Polydiacetylene Liposomes

Zhang Siyu,Shi Baoli,Yang Guang

Due to the high toxicity for brain and the nervous system of humans and other living organisms, the design and fabrication of a robust and sensitive method for the detection of Pb 2+ in the aqueous solution has attracted the increasing attention among scientists. Herein, a colorimetric and fluorometric sensor for the detection of Pb 2+ in the aqueous solution by incorporating a new phenylboronic acid functionalized polydiacetylene liposome was designed. The molar ratio of 4:1 between the monomers, 10,12-pentacosadiynoic acid (PCDA) and phenylboronic acid functionalized PCDA (PCDA-pBA) not only offered sufficient binding sites for Pb 2+ , but also interrupted the efficient π -conjugation backbone of polydiacetylene (PDA) chains associated with the color and fluorescence changes. Compared with other metal ions, only Pb 2+ could cause the color change and the fluorescence enhancement. Moreover, the hybrid PDA liposomes exhibited high sensitivity, fast response time (10 s), and a reasonable detection limit for Pb 2+ (0.1 µM). This work not only provides a versatile methodology for the fabrication of sensors for Pb 2+ detection, but also is of great fundamental value for a deeper understanding of the complexion-induced color changes based on polydiacetylene materials, and may pave the way for fabrication a new method for recognizing other metal ions.

研究领域: 分析化学 · 材料科学 · 环境科学
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Journal of Materials Chemistry A · 2014 ·Vol. 2 ·期 25 ·9559-9565 · IF 0

A 2-D photonic crystal hydrogel for selective sensing of glucose

Fei Xue,Zihui Meng,Fengyan Wang,Qiuhong Wang,Min Xue,Zhibin Xu

A novel 2-D photonic crystal (PC) sensing material for the visual detection of glucose with high selectivity at a physiological ionic strength (150 mM) is developed. A monolayer polystyrene crystalline colloidal array (CCA) is embedded in a phenylboronic acid (PBA) functionalized hydrogel film to diffract light to sensitively report on the hydrogel surface area. This 2-D PC sensor is superior to the previously reported 3-D PC sensors due to its fast preparation and simple detection. The binding of glucose would increase the cross-linking of the hydrogel that could shrink the hydrogel to increase the Debye diffraction ring diameter. At a physiological ionic strength of 150 mM, the 2-D PC sensor exhibits significant sensitivity for glucose across the entire human physiological glucose range. Additionally, the 2-D PC sensor shows high selectivity for glucose rather than other sugars (fructose and galactose). The diffraction color change of the 2-D PC sensor can be observed. For validation, the prepared 2-D PC hydrogel sensor is applied for the sensing of glucose in the artificial tear fluid.

研究领域: 生物传感 · 材料科学 · 分析化学
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MACROMOLECULAR BIOSCIENCE · 2016 ·Vol. 17 ·期 3 ·1600227 · IF 3.68

Phenylboronic Acid-Cross-Linked Nanoparticles with Improved Stability as Dual Acid-Responsive Drug Carriers

Chunran Wang,Jinze Wang,Xiaofei Chen,Xu Zheng,Zhigang Xie,Li Chen,Xuesi Chen

Herein, a kind of dual acid-sensitive nanoparticles based on monomethoxy poly(ethylene glycol)-imine-β-cyclodextrin is constructed by a facile phenylboronic acid-cross-linked way. The data of dynamic light scattering and transmission electron microscope reveal the cross-linked nanoparticles have improved stability. The cross-linked nanoparticles could easily self-assemble and load the anticancer drug at neutral pH condition. However, when the drug-loaded nanoparticles are delivered to extracellular tumor sites (pH ≈6.8), the surface of the nanoparticles would be amino positively charged and easily internalized by tumor cell due to the cleavage of the acid-labile benzoic–imine. Subsequently, with the acidity in subcellular compartments significantly increasing (such as the endosome pH ≈5.3), the loaded drug would fast release from the endocytosis carriers due to the hydrolysis of boronate ester. These features suggest that these dual acid-sensitive cross-linked nanoparticles not only possess excellent biocompatibility but also can efficiently load and deliver anticancer drug into tumor cells to enhance the inhibition of cellular proliferation, outlining a favorable platform as drug carriers.

CAS / MDL: 619-66-9
研究领域: 药剂学 · 肿瘤学 · 生物材料学
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Journal of Materials Chemistry C · 2017 ·Vol. 5 ·期 18 ·4400-4407 · IF 5.256

Motion-based glucose sensing based on a fish-like enzymeless motor

Mingtong Li,Hui Zhang,Mei Liu,Bin Dong

In this paper, we report a fish-like enzymeless motor, which consists of a phenylboronic acid modified poly(N-isopropylacrylamide) hydrogel and a surfactant, i.e. sodium dodecyl sulfate. The motor is capable of moving autonomously upon exposure to the glucose molecule. This phenomenon originates from the complexation between glucose and phenylboronic acid, which leads to the swelling of the hydrogel and the release of the surfactant, thus propelling the whole structure based on the Marangoni effect. Interestingly, the motor's moving velocity is directly proportional to the glucose concentration. Through the introduction of a magnetically responsive material, the motion direction of the motor can be manipulated. More interestingly, the combination of the glucose-dependent motion and magnetically steerable motion allows us to directly visualize the glucose concentration in human serum or urine. We thus believe that the motor reported in the current study may have potential for application in the field of glucose sensing for the detection and monitoring of diabetes.

研究领域: 生物医学工程 · 分析化学 · 材料科学
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POLYMER ENGINEERING AND SCIENCE · 2018 ·Vol. 58 ·期 12 ·2304-2310 · IF 1.551

Synthesis of anisotropic Janus composite particles based on poly(urushiol borate)

Jianrong Xia,Baoling Chen,Qinhui Chen

Urushiol, the main component of the natural product of raw lacquer, can react with ester easily owing to its two adjacent phenolic hydroxyls, and urushiol-ester compounds can polymerize further attributing to its unsaturated side chain. In this work, poly(urushiol borate) (PUB) was coated on the surface of polystyrene (PS) microspheres by transesterification between urushiol and tributyl borate. Then, the core–shell composite microspheres of polystyrene@poly(urushiol borate) (PS@PUB) were obtained. Finally, we used a general method to synthesize anisotropic grenade-like Janus composite particles of PUB/PS, that is, the core–shell composite microspheres of PS@PUB were swelled assisted protrusion in the emulsion of organic monomer and water. The morphologies of PUB/PS Janus composite particles could be tuned by changing the swelling time and the dosage of organic monomer. POLYM. ENG. SCI., 58:2304–2310, 2018. © 2018 Society of Plastics Engineers

研究领域: 材料科学 · 化学工程
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Nano Research · 2014 ·Vol. 8 ·期 3 ·920-930 · IF 6.963

A colorimetric method for α-glucosidase activity assay and its inhibitor screening based on aggregation of gold nanoparticles induced by specific recognition between phenylenediboronic acid and 4-aminophenyl-α-d-glucopyranoside

Zhang Juan,Liu Ying,Lv Jun,Li Genxi

A colorimetric method has been established for α-glucosidase activity assay and its inhibitor screening. The method is based on the specific recognition between 1,4-phenylenediboronic acid (PDBA) and 4-aminophenyl-α- d -glucopyranoside (pAPG), which may induce aggregation of pAPG-functionalized gold nanoparticles (AuNPs) to achieve color change of the test solution. Because pAPG is the substrate of α-glucosidase, the aggregation of AuNPs will be influenced by α-glucosidase since there is no coordination reactivity between PDBA and 4-aminobenzene, the hydrolyzed product of pAPG catalyzed by the enzyme. Therefore, a simple and easily-operated colorimetric method for the assay of α-glucosidase activity can be developed. Under the optimized experimental conditions, the ratios of absorbance at a wavelength of 650 nm to that at 520 nm vary linearly with the α-glucosidase activity within a range from 0.05 to 1.1 U/mL with a lowest detection limit of 0.004 U/mL. Moreover, using the proposed method, the inhibition effect of gallic acid and quercetin on α-glucosidase activity can be tested with IC 50 values of 1.16 mM and 1.82 μM, respectively. Thus, the method has a great potential not only for the detection of α-glucosidase activity, but also for the screening of its inhibitors.

研究领域: 生物化学 · 医学检测 · 纳米技术
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ACS Applied Materials & Interfaces · 2019 · IF 8.456

Thiol–Ene Click Synthesis of Phenylboronic Acid-Functionalized Covalent Organic Framework for Selective Catechol Removal from Aqueous Medium

Shi-Lei Ji,Hai-Long Qian,Cheng-Xiong Yang,Xu Zhao,Xiu-Ping Yan

We report a thiol–ene click strategy for the preparation of a novel phenylboronic acid-functionalized covalent organic framework (COF) for selective removal of catechol in aqueous solution. Vinyl-functionalized 2,5-diallyloxyterephthalaldehyde (Da-V) was prepared as a building ligand. Da-V was then condensed with 1,3,5-tris(4-aminophenyl)benzene (Tab) to give a vinyl-functionalized COF DhaTab-V. Subsequently, 4-mercaptophenylboronic acid (4-MPBA) was covalently linked on DhaTab-V via thiol–ene click reaction to give phenylboronic acid-functionalized COF DhaTab-PBA. The adsorption isotherms, energetics and kinetics, and reusability of DhaTab-PBA for the adsorption and removal of catechol from aqueous solution were investigated in detail. This phenylboronic acid-functionalized COF is promising as sorbent for selective removal of catechol from aqueous medium with large adsorption capacity and good reusability.

研究领域: 材料科学 · 环境科学 · 化学工程
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MOLECULES · 2023 ·Vol. 28 ·期 11 ·4461 · IF 4.6

Efficient pH-Responsive Nano-Drug Delivery System Based on Dynamic Boronic Acid/Ester Transformation

Weijun Chen,Wanxuan Xie,Guangkuo Zhao,Qi Shuai

Chemotherapy is currently one of the most widely used treatments for cancer. However, traditional chemotherapy drugs normally have poor tumor selectivity, leading to insufficient accumulation at the tumor site and high systemic cytotoxicity. To address this issue, we designed and prepared a boronic acid/ester-based pH-responsive nano-drug delivery system that targets the acidic microenvironment of tumors. We synthesized hydrophobic polyesters with multiple pendent phenylboronic acid groups (PBA-PAL) and hydrophilic PEGs terminated with dopamine (mPEG-DA). These two types of polymers formed amphiphilic structures through phenylboronic ester linkages, which self-assembled to form stable PTX-loaded nanoparticles (PTX/PBA NPs) using the nanoprecipitation method. The resulting PTX/PBA NPs demonstrated excellent drug encapsulation efficiency and pH-triggered drug-release capacity. In vitro and in vivo evaluations of the anticancer activity of PTX/PBA NPs showed that they improved the pharmacokinetics of drugs and exhibited high anticancer activity while with low systemic toxicity. This novel phenylboronic acid/ester-based pH-responsive nano-drug delivery system can enhance the therapeutic effect of anticancer drugs and may have high potential for clinical transformations.

CAS / MDL: 7787-70-4 3030-47-5
研究领域: 药学 · 生物医学工程 · 肿瘤学
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Journal of Materials Chemistry B · 2015 ·Vol. 3 ·期 18 ·3840-3847 · IF 4.726

Development of phenylboronic acid-functionalized nanoparticles for emodin delivery

Bo Wang,Limin Chen,Yingjuan Sun,Youliang Zhu,Zhaoyan Sun,Tiezhu An,Yuhua Li,Yuan Lin,Daping Fan,Qian Wang

Stable and monodisperse phenylboronic acid-functionalized nanoparticles (PBA-NPs) were fabricated using the 3-((acrylamido)methyl)phenylboronic acid homopolymer (PBAH) via the solvent displacement technique. The effect of operating parameters, including stirring time, initial polymer concentration and the proportion of methanol, on the self-assembly process was systematically investigated. The diameters of PBA-NPs were increased by increasing the initial PBAH concentration and the proportion of methanol. Likewise, there was a linear dependence between the size of self-assembled nanoparticles and the polymer concentration. Moreover, the dissipative particle dynamics (DPD) simulation technique was used to investigate the mechanism of self-assembly behavior of the PBAH, which indicated that the interior of PBA-NPs was hydrophobic and compact, and boronic acid groups were displayed on both the exterior and interior of PBA-NPs. The resulting PBA-NPs could successfully encapsulate emodin through PBA–diol interaction and the encapsulation efficiency (EE%) and drug loading content (DLC%) of drug-loaded PBA-NPs were 78% and 2.1%, respectively. Owing to the acid-labile feature of the boronate linkage, a reduction in environmental pH from 7.4 to 5.0 could trigger the disassociation of the boronate ester bonds, which could accelerate the drug release from PBA–emodin-NPs. Besides, PBA–emodin-NPs showed a much higher cytotoxicity to HepG2 cells (cancer cells) than MC-3T3-E1 cells (normal cells). These results imply that PBA-NPs would be a promising scaffold for the delivery of polyphenolic drugs.

CAS / MDL: 814-68-6 16940-66-2
研究领域: 药剂学 · 纳米医学 · 生物材料
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MICROCHIMICA ACTA · 2023 ·Vol. 190 ·期 10 ·1-11 · IF 5.7

A new sandwich-type electrochemiluminescence sensor based on HPSNs-NH2@Au NPs and AuPdPt NPs for determination of α(2,3)-sial-Gs

Tian Jiangman,Zhu Qihao,Huang Xiaojing,Li Yuan

A novel sandwich-type “on-off” electrochemiluminescence (ECL) biosensor for the determination of α(2,3)-sial-Gs was designed. Specifically, amino-functionalized porous silica nanoparticles (HPSNs-NH 2 ) were first prepared and then decorated with gold nanoparticles (Au NPs) to form HPSNs-NH 2 @Au NP nanocomposite, which exhibited a strong ability to enhance ECL intensity with K 2 S 2 O 8 as co-reactant (signal-on) and could immobilize the target-specific binding molecules of maackia amurensis lectin (MAL). Additionally, AuPdPt trimetallic nanoparticles were prepared to serve as a quenched ECL signal indicator (signal-off) with the ability of capturing the target non-specific binding molecules of 3-aminophenylboronic acid (APBA) to form a signal label. The sandwich-type ECL biosensor was constructed based on the structure of MAL-α(2,3)-sial-Gs-APBA and achieved a determination toward α(2,3)-sial-Gs with a wide linear range from 1 fg mL −1 to 10 ng mL −1 and a low detection limit of 0.5 fg mL −1 . Furthermore, the proposed ECL biosensor showed satisfactory selectivity, stability, and reproducibility for α(2,3)-sial-Gs determination. Graphical Abstract

研究领域: 分析化学 · 生物医学工程 · 纳米科技
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CHEMISTRY OF MATERIALS · 2019 · IF 10.159

Natural Polyphenols Augment Cytosolic Protein Delivery by a Functional Polymer

Chongyi Liu,Wanwan Shen,Bonan Li,Tianfu Li,Hong Chang,Yiyun Cheng

Cytosolic protein delivery is of great importance for basic cell biology and the discovery of novel protein-based biotherapeutics. It remains a challenging task because of the limited binding sites on proteins and their relatively large size. As a result, most current approaches for cytosolic protein delivery need covalent modification on native proteins, which is usually involved with complicated synthesis, reduced protein bioactivity, and unexpected safety concerns. In this study, we proposed a novel strategy to deliver proteins of different molecular sizes and isoelectric points by specific recognitions between natural polyphenols and boronic acid-containing polymers. Protein molecules were decorated with polyphenols via noncovalent hydrogen-bond/hydrophobic interactions or reversible dynamic covalent bonds. The natural polyphenols increase the binding affinity between proteins and boronic acid-containing polymers, allow the release of bound proteins in acidic environments because of pH-sensitive property of catechol–boronate esters, and thus greatly promote the cytosolic delivery efficiency. This strategy showed robust efficiency in the delivery of various proteins such as bovine serum albumin, phycoerythrin, and ribonuclease A and maintained the protein bioactivity after intracellular release. The reported strategy permits the development of a polyphenol-involved polymer platform for cytosolic protein delivery.

CAS / MDL: 98-10-2
研究领域: 生物技术 · 药学 · 细胞生物学
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