Polymer Microcapsules with Carbohydrate‐Sensitive Properties

Levy, Tatjana; Déjugnat, Christophe; Sukhorukov, Gleb B.

doi:10.1002/adfm.200701291

Cited by 109 publications

(122 citation statements)

References 41 publications

(49 reference statements)

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“…[113][114][115] Glucose-sensitive LbL microcapsules that decompose in response to glucose have been prepared using phenylboronic acid (PBA)-bearing polymers. [116][117][118] LbL microcapsules consisting of PBA polymers decomposed in response to glucose at pH 9.0 or higher. However, the glucose sensitivity of these microcapsules was not satisfactory in the physiological pH range, because of the lower affinity of the PBA moiety for glucose.…”

Section: ·2 Controlled Release From Lbl Microcapsulesmentioning

confidence: 99%

Layer-by-layer Thin Films and Microcapsules for Biosensors and Controlled Release

2012

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We present an overview of the preparation and properties of layer-by-layer (LbL) deposited thin films and microcapsules in relation to their use in the development of biosensors and controlled release systems. Enzyme biosensors can be constructed by immobilizing enzymes on the surface of electrodes by LbL deposition without loss of their catalytic activity. In addition to synthetic polymers, binding proteins, such as avidin and lectin, are also used for constructing LbL films through avidin-biotin and lectin-sugar interactions. The performance characteristics of LbL film-based biosensors can be tuned by controlling the number of layers and by the choice of film components. The permeability of polyelectrolyte LbL films to ions and molecules is discussed in relation to the use of the films for eliminating interference in biosensors. The possible use of polysaccharide LbL film-coated electrodes for the construction of biosensors is highlighted, and examples of LbL film-and microcapsule-based optical sensors are described. We then focus on the use of LbL films and microcapsules as vehicles for controlled release, in particular on recent progress in the controlled release of insulin from LbL films and microcapsules. LbL films composed of insulin and polymers are sensitive to environmental pH, and release insulin in response to pH changes, suggesting that insulin LbL films can be used in the development of orally administered insulin. The construction of glucose-dependent insulin release systems using LbL insulin microcapsules functionalized with phenylboronic acid, lectin, and glucose oxidase is also examined.

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Section: ·2 Controlled Release From Lbl Microcapsulesmentioning

confidence: 99%

Layer-by-layer Thin Films and Microcapsules for Biosensors and Controlled Release

2012

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“…Finally, the resonance frequency in the QCM decreased by a total of 700 Hz. Considering that the area of the QCM resonator was 0.20 cm 2 , we calculated that the total loading of the film (PVA/PBAIns) 5 to be 3.7×10 −6 g cm −2 based on the assumption that the deposition of 1.068 ng of a substance on the 9 MHz resonator will induce a −1 Hz change in the frequency. 23) In a similar manner, we used a pH 5.0 buffer (10 mM acetic acid buffer, containing 150 mM NaCl) for washing and the PBA-Ins was also suspended in the pH 5.0 buffer.…”

Section: Resultsmentioning

confidence: 99%

“…Sugar Response of the (PVA/PBA-Ins) 5 Film The sugar response of the (PVA/PBA-Ins) 5 film is shown in Fig. 4.…”

Section: )mentioning

confidence: 99%

“…[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.…”

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“…Although the report described a small response in the LbL film in the presence of sugar at pH 8.5, the report did not discuss the hypoglycemic activity of the PVA-appended insulin. The activity of the PVA-appended insulin was likely lost because the molecular weight (MW) of PVA used in the study was too large (MW 1.59×10 5 ). In this study, we prepared PBA-appended insulin for use in the fabrication of an LbL film with PVA (Chart 1).…”

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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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Switchable Polymers

2012

Polymeric Sensors and Actuators

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Polymer Microcapsules with Carbohydrate‐Sensitive Properties

Cited by 109 publications

References 41 publications

Layer-by-layer Thin Films and Microcapsules for Biosensors and Controlled Release

Layer-by-layer Thin Films and Microcapsules for Biosensors and Controlled Release

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

Switchable Polymers

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