A Pseudopolyrotaxane for Glucose-Responsive Insulin Release: The Effect of Binding Ability and Spatial Arrangement of Phenylboronic Acid Group

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

doi:10.1021/acs.molpharmaceut.6b00599

Cited by 24 publications

(21 citation statements)

References 37 publications

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“…[5b,7] Typically, insulin is embedded in a matrix consisting of glucose‐sensing elements via certain interactions. Here three classical glucose‐sensing moieties are often utilized: phenylboronic acid (PBA) derivatives, glucose‐binding proteins (e.g., concanavalin A, Con A), and glucose oxidase (GOx) . The former two moieties are flawed in different ways.…”

Section: Introductionmentioning

confidence: 99%

Erythrocyte‐Membrane‐Camouflaged Nanoplatform for Intravenous Glucose‐Responsive Insulin Delivery

Liu

Wang

et al. 2018

Adv Funct Materials

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An artificial "closed-loop" system that mimics the glucose-responsive insulin secretion of pancreas β-cells can potentially improve the treatment efficacy for diabetes. Herein, a lipid bilayer-coated polymeric nanoparticle (NP) with "core-shell" structure is designed. As far as it is known, it is the first and only intravenous nanoplatform utilizing enzymatic-oxidation scheme to achieve glucose-responsive insulin delivery so far. Ethoxy acetal-derivatized dextran nanoparticles (Ace-DEX NPs) are constructed as "inner core" loaded with insulin, and coloading glucose oxidase (GOx) and catalase (CAT) endow the "inner core" excellent glucose-sensitive ability. Red blood cell membrane (RBCm)-derived coating is adopted as "outer shell." It collectively provides a closed microenvironment for GOx-based enzymatic-oxidation scheme and camouflages it from elimination. Above all, the anchored glucose transporters (GLUTs) on the "outer shell" are able to sense blood glucose levels and facilitate the transport of outer blood glucose getting inside. Under a hyperglycemic condition, the internalized glucose is catalytically converted into gluconic acid with the aid of the GOx and subsequently triggers acid degradation of the "inner core" to secrete insulin. By governing the blood glucose levels on an automatic and continuous basis, the RBCm-Ace-DEX NPs can effectively respond to hyperglycemia and turn to resting conditions under normoglycemia.

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Section: Introductionmentioning

confidence: 99%

Erythrocyte‐Membrane‐Camouflaged Nanoplatform for Intravenous Glucose‐Responsive Insulin Delivery

Liu

Wang

et al. 2018

Adv Funct Materials

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“…This is a new concept for chemical-responsive materials based on the use of guest-modified CyDs, and has potential applications. Recently, Seki et al 37) prepared a PPRX comprising 3-carboxy-5-nitrophrnylboronic acid-modified γ-CyD (NPBA-γ-CyD) and naphthalene-modified PEG (Naph-PEG) as a sugar-responsive supramolecular structure. The Naph-PEG/NPBA-γ-CyD PPRX exhibited improved sugar responsivity.…”

Section: Controlled Release For Pegylated Proteins Usingmentioning

confidence: 99%

Potential Use of Cyclodextrins as Drug Carriers and Active Pharmaceutical Ingredients

2017

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Cyclodextrins (CyDs) are extensively used in various fields, and especially have been widely utilized as pharmaceutical excipients and drug carriers in the pharmaceutical field. Owing to the multi-functional and biocompatible characteristics, CyDs can improve the undesirable properties of drug molecules. This review outlines the current application of CyDs in pharmaceutical formulations, focusing on their use as CyD-based drug carriers for several kinds of drugs. Additionally, CyDs have great potential as active pharmaceutical ingredients against various diseases with few side effects.

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“…Recently, we proposed the concept of pPRXs using phenylboronic acid (PBA) as a sugar recognition motif. The pPRXs containing PBA showed sugar-induced disintegration [11][12][13]. PBA is a Lewis acid that coordinates with OHto form a boronate.…”

Section: Introductionmentioning

confidence: 99%

Polyol-responsive pseudopolyrotaxanes based on phenylboronic acid-modified polyethylene glycol and cyclodextrins

Kojima

Okano

Seki

et al. 2017

J Incl Phenom Macrocycl Chem

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Phenylboronic acid (PBA), which reacts with polyols to form cyclic esters, was attached to the amino terminal of polyethylene glycol (PEG) via amide bonds. PBA-PEG was used to prepare pseudopolyrotaxanes (pPRXs) by combining it with cyclodextrins (CyDs). In the case of α-CyD, a single stranded pPRX formed that disintegrated in the presence of catechol (CA), D-fructose (Fru), and D-glucose (Glc). The order of response was CA > Fru > Glc, which corresponds with the affinities between the PBA moiety and the polyols. In contrast, a pPRX using γ-CyD, which has a double-stranded structure, showed sugar-induced disintegration but did not show a response to CA.We explained these apparently curious responses of the pPRXs using a mechanism based on the penetrability of the polyol-bound PBA toward the cavities of the CyDs. The pPRXs, which are a class of molecular machine, show two selectivities; one is derived from polyol selectivity, and the other is based on the penetrability for CyDs.

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A Pseudopolyrotaxane for Glucose-Responsive Insulin Release: The Effect of Binding Ability and Spatial Arrangement of Phenylboronic Acid Group

Cited by 24 publications

References 37 publications

Erythrocyte‐Membrane‐Camouflaged Nanoplatform for Intravenous Glucose‐Responsive Insulin Delivery

Erythrocyte‐Membrane‐Camouflaged Nanoplatform for Intravenous Glucose‐Responsive Insulin Delivery

Potential Use of Cyclodextrins as Drug Carriers and Active Pharmaceutical Ingredients

Polyol-responsive pseudopolyrotaxanes based on phenylboronic acid-modified polyethylene glycol and cyclodextrins

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