Sugar-responsive pseudopolyrotaxanes and their application in sugar-induced release of PEGylated insulin

Seki, Tomohiro; Abe, Keigo; Nakamura, Kiminobu; Egawa, Yuya; Miki, Ryotaro; Juni, Kazuhiko; Seki, Toshinobu

doi:10.1007/s10847-015-0504-0

Cited by 6 publications

(19 citation statements)

References 43 publications

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“…It is widely known that phenylboronic acid derivatives react with the diol moiety of sugars to form a cyclic ester (Scheme 2). This feature is expected to apply to sugar sensors and drug delivery systems related to diabetes [13][14][15]. We copolymerized 4-vinylphenylboronic acid, isoprene, and V-β-CyD to obtain a gel and investigated its sugar response.…”

Section: Methodsmentioning

confidence: 99%

Single-step preparation of topological gels using vinyl-modified β-cyclodextrin as a figure-of-six cross-linker

Kobayashi

Kojima

Miki

et al. 2018

J Incl Phenom Macrocycl Chem

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Herein, we have proposed a single-step preparation of topological gels using vinyl-modified βcyclodextrin (V-β-CyD) and isoprene. Copolymerization of V-β-CyD and isoprene in an aqueous solution resulted in gelation due to V-β-CyD acting as a novel type of copolymer chain cross-linker. The vinyl moiety of V-β-CyD becomes a part of the copolymer, while the β-CyD moiety of V-β-CyD simultaneously incorporates the isoprene component of the copolymer. V-β-CyD is capable of two different modes of cross-linking at each end, i.e., chemically bonding and mechanically interlocking. Due to the shape of the cross-linking point, we refer to it as figure-of-six cross-linking. Nuclear magnetic resonance (NMR) analysis showed that the gel contained V-β-CyD and isoprene in an approximately 1:0.3 stoichiometry. The relatively high content of β-CyD was reflected in the character of the gel; the gel swelled in dimethylformamide (DMF) which is a good solvent of β-CyD. A fluorometric analysis using 6-(p-toluidino)-2-naphthalenesulfonic acid (TNS) showed that the appended β-CyD was able to accommodate guest molecules. Introduction of an additional vinyl monomer into the gel was also successful. Addition of 4-vinylphenylboronic acid to the preparation procedure yielded a sugar-responsive gel that swelled in the presence of D-fructose.

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Section: Methodsmentioning

confidence: 99%

Single-step preparation of topological gels using vinyl-modified β-cyclodextrin as a figure-of-six cross-linker

Kobayashi

Kojima

Miki

et al. 2018

J Incl Phenom Macrocycl Chem

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“…[ 178 ] Egawa and co‐workers endowed such pseudopolyrotaxanes with glucose‐sensitivity by using γ‐cyclodextrins functionalised with arylboronic acid ( Scheme ). [ 179 ] The authors prepared two γ‐cyclodextrin derivatives in form of esters with 4‐carboxyphenylboronic acid or 3‐carboxy‐5‐nitrophenylboronic acid. Pseudopolyrotaxanes with PEG functionalised insulin have been obtained for these derivatives.…”

Section: Cyclodextrin‐derived Materialsmentioning

confidence: 99%

Insulin Delivery Using Dynamic Covalent Boronic Acid/Ester‐Controlled Release

Banach

Williams

Fossey

2021

Advanced Therapeutics

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The number of people affected by diabetes mellitus increases globally year on year. Elevated blood glucose levels may result from a lack of insulin to manage these levels and can, over a prolonged period, lead to serious repercussions. Diabetes mellitus patients must monitor and control their blood‐glucose levels with invasive testing and often alongside administration of intravenous doses of insulin, which can often lead to suboptimal compliance. To mitigate these issues, “closed‐loop” insulin delivery systems are deemed to be among superior options for rapid relief from the demanding and troublesome necessity of self‐directed care. The reversible dynamic covalent chemistry of boronic acid derivatives and their competitive affinity to 1,2‐ and 1,3‐diols (such as those present in saccharides) allows for the design and preparation of responsive self‐regulated insulin delivery materials which respond to elevated and changing glucose levels. A range of meritorious and noteworthy contributions in the domain of boron‐mediated insulin delivery materials is surveyed, and providing a multidisciplinary context in the realisation of the ambitious goal of ultimately addressing the desire to furnish glucose‐responsive insulin delivery materials through innovative synthesis and rigorous testing is targetted.

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“…The carboxylic terminal was linked to amino groups of insulin, and we referred to this conjugate as Naph-PEG-Ins (Fig. 6(b)) [10]. Naphthalene was used because it facilitates the formation of the molecular necklace.…”

Section: -2 Head-to-head Dimer Based On Pba-modified β-Cydmentioning

confidence: 99%

“…A smart material that responds to a chemical stimulus of sugar could find application as an ideal insulin formulation. Using phenylboronic acid (PBA) as a sugar-sensing moiety and cyclodextrin (CyD) as a basic skeleton of smart materials, we have been developing sugar-responsive smart materials for an artificial pancreas [9][10][11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Sugar-responsive smart materials based on phenylboronic acid and cyclodextrin

Egawa

Seki

Miki

et al. 2019

J Incl Phenom Macrocycl Chem

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This review focuses on sugar-responsive materials based on phenylboronic acid (PBA) as a sugar-sensing motif and cyclodextrins (CyDs) as a basic skeleton of smart materials. PBA modified α-CyD (PBA-α-CyD) forms a supramolecular polymer through intermolecular interactions between PBA part and CyD cavity. Similarly, PBA-β-CyD forms a head-to-head dimer. Meanwhile, combining PBA-γ-CyD and polyethylene glycol (PEG) produces a molecular necklace. Additionally, combining PBA-modified PEG and native α-CyD or γ-CyD results in another type of molecular necklace. These supramolecular structures are obtained as powders, and their solubility increases in the presence of sugar. Besides the powder type, a unique gel is formed through crosslinking polyvinyl alcohol (PVA) with PBA-triazole-γ-CyD (PBA-Tri-γ-CyD). This gel can contain model drug, and it shows sugar-responsive drug release.The sugar response of all of these smart materials can be explained by the concept of equilibrium. The smart materials are constructed with CyD-guest interactions. The CyD-guest equilibrium moves by a reaction between sugar and PBA moiety attached to the smart material. In these smart materials, sugar induces a dissociation in the CyD-guest interaction, and this dissociation results in sugar-induced disintegration of CyD-guest supramolecular structures.

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Sugar-responsive pseudopolyrotaxanes and their application in sugar-induced release of PEGylated insulin

Cited by 6 publications

References 43 publications

Single-step preparation of topological gels using vinyl-modified β-cyclodextrin as a figure-of-six cross-linker

Single-step preparation of topological gels using vinyl-modified β-cyclodextrin as a figure-of-six cross-linker

Insulin Delivery Using Dynamic Covalent Boronic Acid/Ester‐Controlled Release

Sugar-responsive smart materials based on phenylboronic acid and cyclodextrin

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