Phenylboronic Acid-Functionalized Layer-by-Layer Assemblies for Biomedical Applications

Wang, Baozhen; Yoshida, Kentaro; Sato, Katsuhiko; Anzai, Jun Ichi

doi:10.3390/polym9060202

Cited by 27 publications

(25 citation statements)

References 109 publications

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“…Furthermore, functional molecules can be easily immobilized in a film by modifying them with a polymer chain. For example, it has been reported that a multilayer thin film composed of a phenylboronic acid-modified polymer and polyvinyl alcohol decomposes in response to sugar and hydrogen peroxide [ 20 ]. The multilayer thin films composed of functional organic molecules, enzymes, and lectins also respond to substrates, such as pH [ 21 , 22 ], electrical potential [ 23 ], glucose, lactate, and hydrogen peroxide [ 24 , 25 , 26 ].…”

Section: Introductionmentioning

confidence: 99%

Voltammetric pH Measurements Using Azure A-Containing Layer-by-Layer Film Immobilized Electrodes

et al. 2020

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pH is one of the most important properties associated with an aqueous solution and various pH measurement techniques are available. In this study, Azure A-modified poly(methacrylic acid) (AA-PMA) was synthesized used to prepare a layer-by-layer deposited film with poly(allylamine hydrochloride) (PAH) on a glassy carbon electrode via electrostatic interactions and the multilayer film-immobilized electrode was used to measure pH. Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) measurement were performed. Consequently, the oxidation potential of AA on the electrode changed with pH. As per Nernst’s equation, because H+ ions are involved in the redox reaction, the peak potential shifted depending on the pH of the solution. The peak potential shifts are easier to detect by DPV than CV measurement. Accordingly, using electrochemical responses, the pH was successfully measured in the pH range of 3 to 9, and the electrodes were usable for 50 repeated measurements. Moreover, these electrochemical responses were not affected by interfering substances.

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Section: Introductionmentioning

confidence: 99%

Voltammetric pH Measurements Using Azure A-Containing Layer-by-Layer Film Immobilized Electrodes

et al. 2020

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“…These results demonstrate the potential application of microparticles that undergo glucose-induced decomposition in the development of insulin delivery systems. In insulin delivery systems, insulin loading microparticles remain stable at normal levels of blood glucose (~5 mM), and glucose-induced delivery microparticles that release insulin only when the blood glucose is higher than the diabetic level (>10 mM) under physiological conditions are highly desirable [53]. Insulin release system depending on blood glucose will be realized by improving the suitable design of the film composition and the chemical structures of PBA-polymers.…”

Section: Discussionmentioning

confidence: 99%

Preparation of Microparticles Capable of Glucose-Induced Insulin Release under Physiological Conditions

et al. 2018

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Hydrogen peroxide (H2O2)-sensitive layer-by-layer films were prepared based on combining phenyl boronic acid (PBA)-modified poly(allylamine) (PAH) with shikimic acid (SA)-modified-PAH through boronate ester bonds. These PBA-PAH/SA-PAH multilayer films could be prepared in aqueous solutions at pH 7.4 and 9.0 in the presence of NaCl. It is believed that the electrostatic repulsion between the SA-PAH and PBA-PAH was diminished and the formation of ester bonds between the SA and PBA was promoted in the presence of NaCl. These films readily decomposed in the presence of H2O2 because the boronate ester bonds were cleaved by an oxidation reaction. In addition, SA-PAH/PBA-PAH multilayer films combined with glucose oxidase (GOx) were decomposed in the presence of glucose because GOx catalyzes the oxidation of D-glucose to generate H2O2. The surfaces of CaCO3 microparticles were coated with PAH/GOx/(SA-PAH/PBA-PAH)5 films that absorbed insulin. A 1 mg quantity of these particles released up to 10 μg insulin in the presence 10 mM glucose under physiological conditions.

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“…PBA’s ability to form dynamic covalent bonds is expected to be applicable to many fields. In particular, the reaction between PBA and sugars has been widely investigated to develop blood glucose sensors [5,6,7,8,9,10,11,12] and glucose-responsive insulin delivery systems [13,14,15,16] for diabetes patients. However, the bond between PBA derivatives and glucose is not strong.…”

Section: Introductionmentioning

confidence: 99%

Cell Adhesive Character of Phenylboronic Acid-Modified Insulin and Its Potential as Long-Acting Insulin

Ohno¹,

Kawakami²,

Seki³

et al. 2019

Pharmaceuticals

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Phenylboronic acid (PBA) derivatives have attracted substantial attention owing to their unique character of forming dynamic covalent bonds with polyol compounds. Recent studies have shown interactions between PBA and sugar chains on the cell surface; they have interesting applications for sensors and drug delivery systems. In this study, we prepared phenylboronic acid-modified insulin (PBA-Ins) to evaluate its glucose-lowering activity and cell adhesiveness. In the case of intravenous injection, PBA-Ins showed longer glucose-lowering activity than native insulin. We hypothesized that this prolonged effect was the result of the interaction between the PBA moiety and sugar chains on the cell surface. Red blood cells (RBCs) were used as a cell model, and we confirmed PBA-Ins’s affinity for RBCs, which induced RBC agglutination. Interestingly, using an alternative PBA-Ins administration route markedly changed its glucose-lowering activity. Unlike the intravenous injection of PBA-Ins, the subcutaneous injection showed a small effect on glucose level, which indicated that a small amount of PBA-Ins was absorbed into the bloodstream. This suggested the importance of investigating the interaction between the PBA moiety and many types of cells, such as adipocytes, in subcutaneous tissues.

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Phenylboronic Acid-Functionalized Layer-by-Layer Assemblies for Biomedical Applications

Cited by 27 publications

References 109 publications

Voltammetric pH Measurements Using Azure A-Containing Layer-by-Layer Film Immobilized Electrodes

Voltammetric pH Measurements Using Azure A-Containing Layer-by-Layer Film Immobilized Electrodes

Preparation of Microparticles Capable of Glucose-Induced Insulin Release under Physiological Conditions

Cell Adhesive Character of Phenylboronic Acid-Modified Insulin and Its Potential as Long-Acting Insulin

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