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Open AccessArticle

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

Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan
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Pharmaceuticals 2019, 12(3), 121; https://doi.org/10.3390/ph12030121
Received: 22 July 2019 / Revised: 11 August 2019 / Accepted: 13 August 2019 / Published: 19 August 2019
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. View Full-Text
Keywords: phenylboronic acid; cell adhesive; insulin; diabetes; long-acting insulin; red blood cell phenylboronic acid; cell adhesive; insulin; diabetes; long-acting insulin; red blood cell
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MDPI and ACS Style

Ohno, Y.; Kawakami, M.; Seki, T.; Miki, R.; Seki, T.; Egawa, Y. Cell Adhesive Character of Phenylboronic Acid-Modified Insulin and Its Potential as Long-Acting Insulin. Pharmaceuticals 2019, 12, 121.

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