Multilayer films composed of phenylboronic acid-modified dendrimers sensitive to glucose under physiological conditions

Watahiki, Ryota; Sato, Katsuhiko; Suwa, Keisuke; Niina, Satoshi; Egawa, Yuya; Seki, Toshinobu; Anzai, Jun Ichi

doi:10.1039/c4tb00676c

Cited by 42 publications

(40 citation statements)

References 57 publications

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“…4a, the average hydrodynamic radius is increased from 186.5 to 433.2 nm with glucose concentration range from 0 to 10 mg/mL. Phenylboronic acid (PBA) has widely selective glucose sensitivity in aqueous milieu due to the specific interaction between boronic acids and cis-diol compounds by forming a five-or sixmembered boronic cyclic ester [26][27][28][29]. The concentration of charged phenylborates is improved with increasing the concentration of glucose; and the hydrophilicity of the copolymers with pendant phenylborate moieties is improved as well.…”

Section: Resultsmentioning

confidence: 99%

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Jiang

Li³

et al. 2015

Colloid Polym Sci

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The glucose-responsive amphiphilic poly(PEGMAco-AAPBA) copolymer micelles as drug carriers have been developed using 3-phenylpyruvic acid (3-PPA) as photoinitiator. Under the light irradiation, 3-PPA could be self-polymerized into the trimer structure to execute the emulsifier and initiator functions that confirmed by gas chromatography-mass spectrum (GC-MS) analysis. The structure and morphology of resultant poly(PEGMA-co-AAPBA) micelles were characterized by 1 H NMR and TEM. Insulin, as the model drug of diabetes, was loaded into micelles during the photopolymerization process. The as-prepared polymeric micelles exhibited the excellent glucose sensitivity. The loaded insulin could be released from micelles triggered by regulation of temperature and glucose concentration in the environment. The new drug carriers provided a potential application for the therapy of diabetes based on glucose-sensitive controlled drug delivery systems.

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Section: Resultsmentioning

confidence: 99%

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Jiang

Li³

et al. 2015

Colloid Polym Sci

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“…[7][8][9][10] In this study, we also used PVA with PBA-appended insulin incorporated directly in the LbL film. The fabrication process of the LbL films was monitored with QCM using a flow-through cell.…”

Section: Resultsmentioning

confidence: 99%

“…For example, Anzai's group has prepared LbL films composed of a PBA-modified amine dendrimer and poly(vinyl alcohol) (PVA) through interaction between PBA and the 1,3-diol of PVA with great success. [7][8][9] This LbL film disintegrated when the film was immersed in sugar solutions, which is driven by the displacement of PVA by sugar on the PBA moiety.…”

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Sugar-Responsive Layer-by-Layer Film Composed of Phenylboronic Acid-Appended Insulin and Poly(vinyl alcohol)

Takei

Ohno

Seki

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Previous studies have shown that reversible chemical bond formation between phenylboronic acid (PBA) and 1,3-diol can be utilized as the driving force for the preparation of layer-by-layer (LbL) films. The LbL films composed of a PBA-appended polymer and poly(vinyl alcohol) (PVA) disintegrated in the presence of sugar. This type of LbL films has been recognized as a promising approach for sugar-responsive drug release systems, but an issue preventing the practical application of LbL films is combining them with insulin. In this report, we have proposed a solution for this issue by using PBA-appended insulin as a component of the LbL film. We prepared two kinds of PBA-appended insulin derivatives and confirmed that they retained their hypoglycemic activity. The LbL films composed of PBA-appended insulin and PVA were successfully prepared through reversible chemical bond formation between the boronic acid moiety and the 1,3-diol of PVA. The LbL film disintegrated upon treatment with sugars. Based on the results presented herein, we discuss the suitability of the PBA moiety with respect to hypoglycemic activity, binding ability, and selectivity for D-glucose.Key words layer-by-layer; phenylboronic acid; insulin; sugar response; smart materialThe layer-by-layer (LbL) deposition technique has attracted considerable interest for the preparation of nano-sized multilayer films on solid surfaces.1,2) The LbL deposition technique usually leverages the electrostatic interactions between oppositely charged molecules. This type of LbL films is stable on the solid support unless the pH of the surrounding solution is changed, which is advantageous for the construction of thin stable films. However, the good stability of the films, which need to be disintegrated for drug release, causes an issue for drug delivery applications.An LbL film that disintegrates upon exposure to specific stimuli is desirable for drug delivery systems, but requires a reversible driving force for LbL film.3) To meet this demand, the incorporation of phenylboronic acid (PBA) is a promising approach. [4][5][6][7][8][9][10] PBA derivatives show binding ability for the 1,2-diol, and 1,3-diol of sugars, which can result in the formation of a cyclic ester even in aqueous solution. 11,12) The cyclic ester formation is a reversible reaction, which is suitable for stimuli-responsive LbL films. For example, Anzai's group has prepared LbL films composed of a PBA-modified amine dendrimer and poly(vinyl alcohol) (PVA) through interaction between PBA and the 1,3-diol of PVA with great success. 7-9)This LbL film disintegrated when the film was immersed in sugar solutions, which is driven by the displacement of PVA by sugar on the PBA moiety.

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“…In fact, multilayer films were constructed using PBA-modified polymers and polysaccharides or poly(vinyl alcohol) (PVA) [11,13,15,17,18]. We have recently reported the multilayer films consisting of poly(amidoamine) dendrimer (PBA-PAMAM) and PVA [23,24]. The PBA-PAMAM/PVA multilayer films decomposed upon exposure to glucose as a result of competitive binding of glucose, which contains 1,2-diol moiety, to PBA-PAMAM.…”

Section: Introductionmentioning

confidence: 98%

Preparation of multilayer films consisting of glucose oxidase and poly(amidoamine) dendrimer and their stability

2015

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Multilayer films comprising of glucose oxidase (GOx) and phenylboronic acid-modified poly(amidoamine) dendrimer (PBA-PAMAM) were prepared and their pHand glucose-induced decomposition was studied. Multilayered GOx/PBA-PAMAM films were prepared through boronate ester linkages between PBA-PAMAM and carbohydrate chains of GOx. In contrast, preparation of multilayer film was unsuccessful when unmodified PAMAM was used in lieu of PBA-PAMAM, confirming an essential role of PBA residues in constructing multilayer films. The ten-layered (GOx/PBA-PAMAM) 10 film was stable in aqueous solutions of pH 8.5, whereas the multilayer film decomposed in neutral and acidic media as a result of cleavage of the boronate ester bond. The pH threshold for the film decomposition was pH 7.0-8.0. In addition, the (GOx/PBA-PAMAM) 10 film decomposed in glucose solutions owing to the oxidative scission of carbon-boron bond of PBA-PAMAM by enzymatically produced hydrogen peroxide. Thus, the potential use of the (GOx/PBA-PAMAM) 10 film for the development of pH-and glucosesensitive devices is suggested.

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Multilayer films composed of phenylboronic acid-modified dendrimers sensitive to glucose under physiological conditions

Cited by 42 publications

References 57 publications

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Photo-induced synthesis glucose-responsive carriers for controlled release of insulin in vitro

Sugar-Responsive Layer-by-Layer Film Composed of Phenylboronic Acid-Appended Insulin and Poly(vinyl alcohol)

Preparation of multilayer films consisting of glucose oxidase and poly(amidoamine) dendrimer and their stability

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