Glucose-Responsive Polymer Bearing a Novel Phenylborate Derivative as a Glucose-Sensing Moiety Operating at Physiological pH Conditions

Matsumoto, Akira; Ikeda, Syuhei; Harada, Atsushi; Kataoka, Kazunori

doi:10.1021/bm034139o

Cited by 338 publications

(261 citation statements)

References 31 publications

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“…Multiple daily injections of insulin are currently the standard treatment for insulin-dependent diabetic patients. 41,42 However, poor patient compliance is associated with this method. Therefore, better ways of insulin administration are being sought.…”

Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Nanoparticles Shelled with Chitosan for Oral Insulin Delivery

et al. 2006

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Nanoparticles (NPs) composed of chitosan (CS) and poly(γ-glutamic acid) (γ-PGA) were prepared by a simple ionic-gelation method for oral insulin delivery. Fourier transform infrared (FT-IR) spectra indicated that CS and γ-PGA were ionized at pH 2.5-6.6, while X-ray diffractograms demonstrated that the crystal structure of CS was disrupted after it was combined with γ-PGA. The diameters of the prepared NPs were in the range of 110-150 nm with a negative or positive surface charge, depending on the relative concentrations of CS to γ-PGA used. The NPs with a positive surface charge (or shelled with CS) could transiently open the tight junctions between Caco-2 cells and thus increased the paracellular permeability. After loading of insulin, the NPs remained spherical and the insulin release profiles were significantly affected by their stability in distinct pH environments. The in vivo results clearly indicated that the insulin-loaded NPs could effectively reduce the blood glucose level in a diabetic rat model.

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Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Nanoparticles Shelled with Chitosan for Oral Insulin Delivery

et al. 2006

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“…Inspired by the use of a PBA‐modified nanostructure to reversibly capture and release tumor cells in vitro,40, 41 we established a very simple strategy to reduce the off‐target effects of NPs. PBA can form reversible, pH‐sensitive borate esters with cis ‐diol‐containing monosaccharides (e.g., glucose, galactose, and d ‐fructose),42, 43 but formed stable links with SA residues, even under intratumoral pH conditions, that is, pH 6.5 ( Figure 1 G) 36. Therefore, we hypothesized that coincubating PLT NPs with monosaccharides beforehand to block PBA could maintain the stability at a physiological pH of 7.4 , inhibiting the interaction between PBA and SA residues in normal tissues.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Melanoma‐Targeted Therapy by “Fru‐Blocked” Phenyboronic Acid‐Modified Multiphase Antimetastatic Micellar Nanoparticles

Long

Mei

et al. 2018

Advanced Science

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Metastasis remains the main driver of mortality in patients suffering from cancer because of the refractoriness resulting from the multi‐phase metastatic cascade. Herein, a multifunctional self‐delivering PBA‐LMWH‐TOS nanoparticle (PLT NP) is established that acts as both nanocarrier and anti‐metastatic agent with effects on most hematogenous metastases of cancers. The hydrophilic segment (low molecular weight heparin, LMWH) inhibits the interactions between tumor cells and platelets. The hydrophobic segment (d‐α‐tocopheryl succinate, TOS) could inhibit the expression of matrix metalloproteinase‐9 (MMP‐9) in B16F10 cells which is first reported in this article. Surprisingly, even the blank NPs showed excellent anti‐metastatic capacity in three mouse models by acting on different phases of the metastatic cascade. Moreover, the overexpression of sialic acid (SA) residues on tumor cells is implicated in the malignant and metastatic phenotypes of cancers. Thus, these 3‐aminophenylboronic acid (PBA)‐modified doxorubicin (DOX)‐loaded NPs offer an efficient approach for the treatment of both solid melanomas and metastases. Furthermore, a simple pH‐sensitive “Fructose (Fru)‐blocking” coping strategy is established to reduce the NP distribution in normal tissues and distinctly increases the accumulation in melanoma tumors. These micellar NPs consisting of biocompatible materials offer a promising approach for the clinical therapy of highly invasive solid tumors and metastases.

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“…The observed pH dependence in our material, which is indicative of the controlled release mechanism, is consistent with those of other literature-reported insulin delivery systems. 20 To further examine the applicability of this system, FITC-G-Ins released by a stepwise treatment of glucose at two diabetic levels (50 and 100 mM) was monitored ( Figure S6 in the SI). A typical decrease in insulin release after the second cycle was observed.…”

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confidence: 99%

Mesoporous Silica Nanoparticle-Based Double Drug Delivery System for Glucose-Responsive Controlled Release of Insulin and Cyclic AMP

et al. 2009

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A boronic acid-functionalized mesoporous silica nanoparticle-based drug delivery system (BA-MSN) for glucose-responsive controlled release of both insulin and cyclic adenosine monophosphate (cAMP) was synthesized. Fluorescein isothiocyanate-labeled, gluconic acid-modified insulin (FITC-G-Ins) proteins were immobilized on the exterior surface of BA-MSN and also served as caps to encapsulate cAMP molecules inside the mesopores of BA-MSN. The release of both G-Ins and cAMP was triggered by the introduction of saccharides. The selectivity of FITC-G-Ins release toward a series of carbohydrate triggers was determined to be fructose > glucose > other saccharides. The unique feature of this double-release system is that the decrease of FITC-G-Ins release with cycles can be balanced by the release of cAMP from mesopores of MSN, which is regulated by the gatekeeper effect of FITC-G-Ins. In vitro controlled release of cAMP was studied at two pH conditions (pH 7.4 and 8.5). Furthermore, the cytotoxicity of cAMP-loaded G-Ins-MSN with four different cell lines was investigated by cell viability and proliferation studies. The cellular uptake properties of cAMP-loaded FITC-BA-MSN with and without G-Ins capping were investigated by flow cytometry and fluorescence confocal microscopy. We envision that this glucose-responsive MSN-based double-release system could lead to a new generation of self-regulated insulin-releasing devices.

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Glucose-Responsive Polymer Bearing a Novel Phenylborate Derivative as a Glucose-Sensing Moiety Operating at Physiological pH Conditions

Cited by 338 publications

References 31 publications

Preparation and Characterization of Nanoparticles Shelled with Chitosan for Oral Insulin Delivery

Preparation and Characterization of Nanoparticles Shelled with Chitosan for Oral Insulin Delivery

Enhanced Melanoma‐Targeted Therapy by “Fru‐Blocked” Phenyboronic Acid‐Modified Multiphase Antimetastatic Micellar Nanoparticles

Mesoporous Silica Nanoparticle-Based Double Drug Delivery System for Glucose-Responsive Controlled Release of Insulin and Cyclic AMP

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