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SCIENCE AND TECHNOLOGY OF ADVANCED MATERIALS · 2019 · IF 3.585

Synthesis and characterization of phenylboronic acid-containing polymer for glucose-triggered drug delivery+

Guihua Cui,Kunming Zhao,Kewei You,Zhengguo Gao,Toyoji Kakuchi,Bo Feng,Qian Duan

Thermo-, pH- and glucose-responsive polymeric nanoparticles are of great interest in developing a self-regulated drug delivery system. The novel core-shell nanoparticles were synthesized by self-assembly of a phenylboronic acid-based block copolymer poly-(N-isopropylacrylamide)-block-poly(3-acrylamidophenylboronic acid) (PNIPAM136-b-PAPBA16) and a fluorescent complex glucosamine-poly(N-isopropylacrylamide)/Eu(III) (GA-PNIPAM)/Eu(III) based on the cross-linking between PBA- and GA-containing blocks in this work. The nanoparticles can be tuned via thermo-induced collapse or glucose-induced swelling at appropriate pH and temperatures; they had an average kinetic radius was about 80nm, and which showed excellent fluorescence. MTT assays revealed the nanocarriers had no significant cytotoxic response of the micelle when it was observed in the cell line over the concentration range from 0.1 to 1000 μg/ml at any exposure times.

研究领域: 生物材料学 · 药剂学 · 高分子化学
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MEDICAL ONCOLOGY · 2024 ·Vol. 41 ·期 5 ·1-5 · IF 2.8

Unlocking the potential: phenylboronic acid as a nuclear-targeting boron agent for neutron capture therapy

Chen Jiejian,Li Yonghao,Gan Xiaoning,Weng Chengyin,Fang Xisheng,Liu Guolong

It has been proposed that boron neutron capture therapy (BNCT) holds promise as a treatment modality for melanoma. However, the effectiveness of boron agents in delivery remains a critical issue to be addressed for BNCT. To this end, phenylboronic acid, which exhibits good water solubility and low cytotoxicity similar to BPA, has been investigated as a potential nuclear-targeting boron agent. The boron concentration of phenylboronic acid was found to be 74.47 ± 12.17 ng/10 6 B16F10 cells and 45.77 ± 5.64 ng/10 6 cells in the nuclei. Molecular docking experiments were conducted to investigate the binding of phenylboronic acid to importin proteins involved in nuclear transport. The potential of phenylboronic acid to serve as a desirable nucleus-delivery boron agent for neutron capture therapy in melanoma warrants further exploration.

研究领域: 肿瘤学 · 药理学 · 核医学
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OPTICAL MATERIALS · 2018 · IF 2.32

Molecular assembly and photoluminescence of lanthanide/siliconoxygen network/poly-vinylphenylboronic functionalized SBA-15 hybrids

Zhongyu Wang,Ying Li,Hao Hu,Xia Wang

Novel organic-inorganic mesoporous luminescent polymeric composite materials containing lanthanide (Eu 3+ , Tb 3+ ) complexes covalently bonded to mesoporous silica have been prepared in situ, followed by the polymerization reaction of the monomer 4-vinylphenylboronic acid (VPBA) extending along the mesoporous SBA-15 channels. The obtained materials were investigated by Fourier transform infrared spectroscopy (FT-IR), Ultraviolet absorption spectra (UV), X-ray diffraction (SAXRD), N 2 adsorption/desorption isotherms, Transmission electron microscopy (TEM), thermogravimetry (TG), and luminescence spectroscopy in detail. These characterizations have proved that composite materials possess high surface area, uniform mesoporous structure, good crystallization and relatively excellent luminescence properties. The terminal ligand phen was used to investigate the difference of photo physical and luminescent properties between binary and ternary composite materials. Furthermore, the results have revealed that the composite material Eu(PVPBA-S15) 3 phen showed more efficient intramolecular energy transfer between the europium ion and the ligands, and more excellent characteristic emission of the europium ion under UV irradiation with higher 5 D 0 luminescence quantum efficiency than the composite materials Eu(PVPBA-S15) 3 without phen. The excellent luminescence properties and ordered mesoporous structures could give rise to many potential applications in optical and electronic areas.

CAS / MDL: 2156-04-9
研究领域: 材料科学 · 光学
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BIOMATERIALS · 2016 · IF 8.387

In situ injection of phenylboronic acid based low molecular weight gels for efficient chemotherapy

Wenxia Gao,Yan Liang,Xinyu Peng,Yalong Hu,Longgui Zhang,Huayue Wu,Bin He

Injectable low molecular weight gels (LMWGs) based on the derivatives of phenylboronic acid were prepared and used as substrates for efficient in situ chemotherapy. The gelators as well as LMWGs were characterized by 1 H NMR, UV–vis, FTIR, MS and SEM. Anticancer drug doxorubicin hydrochloride (DOX) was encapsulated in the gels. The rheological properties and rapid recovery capability of both blank and drug-loaded gels were tested. The LMWGs were non-toxic to both 3T3 fibroblasts and 4T1 breast cancer cells. The gels were formed rapidly after injected in vivo. The in vivo anticancer activities of DOX-loaded LMWGs were investigated in breast cancer bearing mice. The intratumoral injection of DOX loaded LMWGs with dose of 30 mg/kg revealed that the gels could coat around the tumor tissues to release DOX sustainingly and maintain effective DOX concentration for chemotherapy. The systemic toxicity of DOX was reduced significantly with the in situ administration of LMWGs formulations. The injectable LMWGs exhibited excellent therapeutic efficacy and low side effects in local chemotherapy.

CAS / MDL: 76-05-1 126-30-7
研究领域: 药学 · 肿瘤学 · 材料科学
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JOURNAL OF CHROMATOGRAPHY A · 2020 · IF 4.049

Preparation of phenylboronic acid based hypercrosslinked polymers for effective adsorption of chlorophenols

Weihua Liu,Juntao Wang,Jiajia Liu,Fangyuan Hou,Qiuhua Wu,Chun Wang,Zhi Wang

Hypercrosslinked polymers (HCPs) have demonstrated effective adsorption capabilities because of their rich porosity and high specific surface area. However, the HCPs prepared with phenylboronic acid based compounds as monomers via Friedel-Crafts alkylation reaction have not been reported yet. Herein, four new HCPs with phenylboronic acid (PBA), 1,4-benzenediboronic acid, 4-hydroxyphenylboronic acid and 4-carboxyphenylboronic acid as the respective monomers were prepared for the first time. Their Brunner-Emmet-Teller surface areas were 909.1 m 2 g −1 , 71.9 m 2 g −1 , 39.8 m 2 g −1 and 29.3 m 2 g −1 , respectively. The prepared HCP with PBA as the monomer (named as PBA-HCP) displayed the best adsorption capability for chlorophenols. Then, it was investigated as a SPE adsorbent for the extraction of some chlorophenols from water and honey-pomelo beverage samples prior to high performance liquid-phase chromatography with diode array detection. The established method had low limits of detection for the analytes in the range from 0.06 to 0.2 ng mL −1 for water samples and from 0.3 to 1.0 ng mL −1 for honey-pomelo beverage samples. The linear response for the analytes was in the range of 0.18–100.0 ng mL −1 for water samples and 0.9–100.0 ng mL −1 for honey-pomelo beverage samples. The method also had a good repeatability with the relative standard deviations less than 7.1% and a fairly good accuracy with the method recoveries falling between 80.0% and 120.0%. The adsorption capacities of the PBA-HCP for 2-chlorophenol, 3-chlorophenol, 2,3-dichlorophenol and 2,4-dichlorophenol were 21.7 mg g −1 , 31.2 mg g −1 , 77.1 mg g −1 and 82.1 mg g −1 , respectively. The PBA-HCP also exhibited excellent extraction capabilities for some other compounds, especially for those that have more hydrogen bonding sites.

研究领域: 环境科学 · 材料科学
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CRYSTAL GROWTH & DESIGN · 2024 · IF 3.2

A Viologen Derivative Transition from Photosilence to Sensitive Photochromism through Ion Exchange

Xuyi Li,Chen Huang,Rui Xue,Jia-Ping Tong,Yuehan Cheng,Bao-Li An,Jiaqiang Xu,Yue-Ling Bai

Viologen has attracted much attention due to its sensitive chromic properties in response to external stimuli, especially its photochromic behavior. Herein, a viologen derivative, 4PV·2Br, was prepared based on our previous studies, which exhibited strong photoluminescence due to the introduction of the thiazolothiazole group but was silent to light, even under 300 W UV light irradiation. By anion exchange with tetraphenylborate, a new viologen derivative, 4PV·2B(Ph)4, was obtained, which not only exhibits strong fluorescence with a quantum yield of 69% and a lifetime of 1.93 ns in solution but also exhibits sensitive photochromism to UV light, even under sunlight within 5 s. It is very sensitive to light and may become a potential excellent solar chromic material. It should be emphasized that the colored 4PV·2B(Ph)4 radical is particularly stable and can maintain its coloring state in air for a long time, while vinegar vapor can cause it to fade in 2 s, giving it good color reversibility. The single-crystal structure before and after UV light excitation shows that UV light shortens the π···π distances between B(Ph)4 anions and 4PV cations, which is beneficial to faster electron transfer between them and the formation of stable viologen radicals. Sensitive photochromism accompanied by strong photoluminescence may endow 4PV·2B(Ph)4 with potential application in information security and provide a good strategy to regulate the functionality of materials by regulating the counteranions of new viologen derivatives.

研究领域: 材料化学 · 光化学
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MACROMOLECULES · 2016 · IF 5.554

Oxidation Degradable Aliphatic Polycarbonates with Pendent Phenylboronic Ester

Fang-Yi Qiu,Mei Zhang,Fu-Sheng Du,Zi-Chen Li

Functional polyesters and poly(carbonate)s (PCs) with controlled and on-demand degradation properties have great advantages for biomedical and pharmaceutical applications. Herein, we report a new kind of aliphatic PC that possesses the feature of oxidation promoted degradation. Two six-membered cyclic carbonates (C1 and C2) containing phenylboronic ester group have been synthesized from serinol (1) and 2-aminomethyl-2-methylpropane-1,3-diol (2), respectively. Both monomers could undergo well-controlled ring-opening polymerization (ROP) catalyzed by an organic base, but the 5,5-disubstituted C2 has the character of equilibrium ROP and a much slower rate than the monosubstituted C1. The copolymerization of C1 or C2 with trimethylene carbonate and its derivative leads to a series of copolymers. Two series of amphiphilic block copolymers (BPC1s and BPC2s) have been prepared from C1 and C2 using poly(ethylene glycol) as the macroinitiator. They are able to form nanoparticles with the diameters less than 150 nm. The H2O2-triggered decomposition of C1, C2, and their corresponding noncyclic model compounds was studied by 1H NMR, showing the consecutive process of oxidation, 1,6-elimination, release of CO2, and intramolecular isomerization or cyclization. The degradation of the block copolymer nanoparticles, investigated by 1H NMR, GPC, laser light scattering (LLS), and Nile Red fluorescence, can also be accelerated drastically by H2O2 following the similar mechanism but is affected by steric hindrance of the polymer chain and heterogeneous microenvironment inside the nanoparticles. The results of 1H NMR and LLS reveal that the nanoparticles of BPC1 and BPC2 exhibited different degradation profiles, with a slightly faster degradation rate for BPC2. Of particular interest, BPC2 nanoparticle is sensitive to as low as 0.02 mM H2O2.

研究领域: 材料科学 · 生物医学工程
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CHINESE CHEMICAL LETTERS · 2013 · IF 1.21

Phenylboronic acid and dopamine as probe set for electrochemical detection of saccharides

Jian Li,Ya-Qin Sun,Yin-Mao Wei,Jian-Bin Zheng

A novel electrochemical approach for detection of saccharides via indicator displacement assay was presented. In this system, 2-fluorophenylboronic acid and dopamine (DA) were performed as probe set. The electrochemical properties of DA and the binding to 2-fluorophenylboronic acid in phosphate buffer at different pH values were investigated by cyclic voltammetry. After addition of fructose to the solution, a competition for the binding 2-fluorophenylboronic acid occurred that led to the release of the DA. The regenerate oxidation current of DA increased with increasing fructose concentration. Under optimized experimental conditions, the peak current was linearly related to fructose concentration in the range of 0.3–5.0   mmol/L with a detection limit of 0.1   mmol/L. In addition, the interaction between 2-fluorophenylboronic acid and other cis -diol compounds such as glucose, galactose and mannose was investigated.

CAS / MDL: 62-31-7
研究领域: 分析化学 · 生物化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2021 · IF 4.098

A new recognition moiety diphenylborinate in the detection of pyruvate via Lewis acid/base sensing pathway and its bioimaging applications

Kanagaraj Rajalakshmi,Selvaraj Muthusamy,Yun-Sik Nam,Yujun Li,Kang-Bong Lee,Yuanguo Xu

Developing new reaction based recognizing units can enhance the specificity of target analyte molecules in practical applications of real samples and biosystems. Therefore, introducing a recognizing moiety diphenylborinate was encountered for the detection of pyruvate biomolecule through Lewis acid-base reaction based sensing strategy. The construction of the Schiff-base back bone between quinoline and N-(diethylamino)salicylaldehyde-diphenylborinate ( QSB) were expressed the red shift from blue emission of quinoline in to green as that of dative bond developed between Schiff base nitrogen and boron atoms. The new sensing approach was involved such a way that fluorophore QSB is a Lewis acid while pyruvate acts as Lewis base, where the elimination of Lewis pair produced a weak green fluorescence including the formation of quinoline, N-(diethylamino)salicylaldehyde ( QS ). The switching products were witnessed through 1 H NMR titration, HR-MS and FT-IR studies. The good selectivity and interference ability were achieved in presence of 1000-fold excess of possible interferences with LOD of 16 nM. Moreover, the tracking ability of the probe was employed towards pyruvate in live HeLa cell imaging for evaluating an exogenous and endogenous signals producing ability and its mitochondria targeting property was investigated successfully. Further, the practical utility of the probe was tested with milk samples and obtained good recovery results.

研究领域: 分析化学 · 生物医学
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Separations · 2022 ·Vol. 10 ·期 1 ·4 · IF 3.344

Facile Preparation of Phenyboronic-Acid-Functionalized Fe3O4 Magnetic Nanoparticles for the Selective Adsorption of Ortho-Dihydroxy-Containing Compounds

Hongmei Zhou,Junhui Zhang,Aihong Duan,Bangjin Wang,Shengming Xie,Liming Yuan

A new facile strategy was designed to prepare the phenyboronic acid-functionalized Fe3O4magnetic nanoparticles (Fe3O4@PBA) via direct silanization and thiol-ene click chemistry for the selective adsorption of ortho-dihydroxy-containing compounds. The three kinds of Fe3O4@PBA nanoparticles obtained showed excellent adsorption capacity and selectivity for ortho-dihydroxy-containing compounds including adenosine ando-dihydroxybenzene. Among them, the Fe3O4@MPS@MPBA exhibited the highest adsorption capacity and selectivity for adenosine ando-dihydroxybenzene, followed by Fe3O4@MPTES@AAPBA and Fe3O4@MPTES@VPBA. A synthesis method of superparamagnetic and boronate affinity nanocomposites with mild reaction conditions and simple process has been developed, which also provides a novel way for the synthesis of other types of enrichment materials of ortho-dihydroxy-containing compounds.Keywords:phenyboronic-acid-functionalized;Fe3O4magnetic nanoparticles;ortho-dihydroxy-containing compounds

研究领域: 化学 · 材料科学
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ACS Omega · 2022 · IF 4.132

Enhancement of the Mechanical Properties of Poly(lactic acid)/Epoxidized Soybean Oil Blends by the Addition of 3-Aminophenylboronic Acid

Jinyu Xie,Kai Gu,Yan Zhao,Jinrong Yao,Xin Chen,Zhengzhong Shao

Here, the high-strength, high-ductility blends of poly(lactic acid) (PLA) with epoxidized soybean oil (ESO) and 3-aminophenylboronic acid (APBA) were successfully prepared via a melt-bending method. The effects of APBA addition on the mechanical and thermal properties, morphologies, and crystallization behavior of the blends were investigated. The results showed that the addition of APBA endowed the PLA/ESO/APBA blends with a good balance of strength and toughness. The yield strength of the PLA/ESO/APBA (90:10:3) blend was 70 MPa, which was 25% higher than that of the corresponding PLA/ESO blend without APBA (56 MPa), while its elongation at break reached 160%, which is greatly superior to that of pure PLA (6.5%). Scanning electron microscopy images showed that the incorporation of APBA significantly improved the compatibility between PLA and ESO, while gel permeation chromatography and rheological analysis suggested the occurrence of complex reactions between the three constituents, which improved the compatibility between PLA and ESO and enhanced the mechanical properties of the blends. Hence, the PLA/ESO/APBA blends possess great potential for application in the manufacture of environmentally friendly degradable plastics.

CAS / MDL: 210907-84-9
研究领域: 材料科学 · 高分子化学
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SENSORS AND ACTUATORS B-CHEMICAL · 2016 · IF 4.758

Surface modification and ratiometric fluorescence dual function enhancement for visual and fluorescent detection of glucose based on dual-emission quantum dots hybrid

Tongfan Hao,Xiao Wei,Yijing Nie,Yeqing Xu,Kai Lu,Yongsheng Yan,Zhiping Zhou

In this work, 3-aminophenylboronic acid (APBA) functionalized dual-emission quantum dots (QDs) were prepared and utilized as the ratiometric fluorescence probe for the onsite naked eye determination of glucose. The unique ratiometric fluorescence probe, which combined ratiometric fluorescence technique with boric acid functional materials into one system, has been prepared by hybridizing red-emitting CdTe QDs (r-QDs) and green-emitting CdTe QDs (g-QDs). The fluorescence of the embedded r-QDs stays constant, whereas the g-QDs functionalized with APBA can selectively bind glucose by the chemistry of boronic acid and cis diol compounds, leading to the fluorescence of g-QDs quenched due to the surface quenching states induced mechanism and resulting in continuous fluorescence color changes (from green to red) of the ratiometric fluorescence probe system. Under optimum conditions, the proposed ratiometric probe was used for selective detection of glucose in a concentration range of 0.1–2.0   mmol/L with a detection limit of 4.5   μmol/L. Moreover, the developed ratiometric fluorescence probe was successfully applied to the detection of glucose in human serum samples. The present study provides an efficient and facile ratiometric fluorescence probe for rapid, convenient, sensitive and selective visual identification of glucose in blood glucose sensing without the need of complex equipment.

研究领域: 生物化学 · 分析化学
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