Glucose-Responsive Vehicles Containing Phenylborate Ester for Controlled Insulin Release at Neutral pH

Yao, Yuan; Zhao, Liang; Yang, Junjiao; Yang, Jing

doi:10.1021/bm3003286

Cited by 113 publications

(107 citation statements)

References 46 publications

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“…[22][23][24][25][26] The covalent interactions between phenylbronic acid and the hydroxyl groups of saccharides (1,2-or 1,3-diols) lead to the formation of five-or sixmembered rings and allow bronic acid to be a sensitive detector for saccharides. [25][26][27][28] Figure 4 shows the fluorescent intensity curves vs. glucose concentration controlled at 0-0.8 mg/mL and the concentration of polymer kept at 0.5 wt%. The fluorescent intensity is decreased with the increasing glucose concentration in the solution.…”

Section: Resultsmentioning

confidence: 99%

Facile one-pot synthesis of fluorescent hyperbranched polymers for optical detection of glucose

Jiang

Wang

et al. 2014

Designed Monomers and Polymers

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Fluorescent and glucose-sensitive hyperbranched poly(amidoamine)s (HPAMAMs-B) were synthesized via Michael addition of 1-(2-aminoethyl) piperazine, methyl acrylate, and 3-aminobenzeneboronic acid (APBA). These hyperbranched polymers emitted chartreuse photoluminescence and showed emission band at 378 nm under excitation wavelength. The intensity of emission band was enhanced with increasing the amount of APBA in HPAMAMs-B. The glucose sensitivity of HPAMAMs-B has been investigated at different glucose concentrations and pH conditions. These hyperbranched polymers showed potential for biomedical applications such as fluorescence imaging technology and glucose detecting sensors.

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Section: Resultsmentioning

confidence: 99%

Facile one-pot synthesis of fluorescent hyperbranched polymers for optical detection of glucose

Jiang

Wang

et al. 2014

Designed Monomers and Polymers

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“…The percentage release values observed and the release rates are broadly in agreement with the literature. [49][50][51] of these two materials (ie, had a lower LCST) and further, since AAPBA is very expensive, is more cost-effective than PAD-2-1. PAD-5-1 was thus taken forward into further work.…”

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confidence: 99%

Glucose- and temperature-sensitive nanoparticles for insulin delivery

Wu¹,

Williams²,

Li³

et al. 2017

IJN

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Glucose- and temperature-sensitive polymers of a phenylboronic acid derivative and diethylene glycol dimethacrylate (poly(3-acrylamidophenyl boronic acid- b -diethylene glycol methyl ether methacrylate); p(AAPBA- b -DEGMA)) were prepared by reversible addition–fragmentation chain transfer polymerization. Successful polymerization was evidenced by 1 H nuclear magnetic resonance and infrared spectroscopy, and the polymers were further explored in terms of their glass transition temperatures and by gel permeation chromatography (GPC). The materials were found to be temperature sensitive, with lower critical solution temperatures in the region of 12°C–47°C depending on the monomer ratio used for reaction. The polymers could be self-assembled into nanoparticles (NPs), and the zeta potential and size of these particles were determined as a function of temperature and glucose concentration. Subsequently, the optimum NP formulation was loaded with insulin, and the drug release was studied. We found that insulin was easily encapsulated into the p(AAPBA- b -DEGMA) NPs, with a loading capacity of ~15% and encapsulation efficiency of ~70%. Insulin release could be regulated by changes in temperature and glucose concentration. Furthermore, the NPs were non-toxic both in vitro and in vivo. Finally, the efficacy of the formulations at managing blood glucose levels in a murine hyperglycemic diabetes model was studied. The insulin-loaded NPs could reduce blood glucose levels over an extended period of 48 h. Since they are both temperature and glucose sensitive and offer a sustained-release profile, these systems may comprise potent new formulations for insulin delivery.

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“…The monomer (2-phenylboronic esters-1,3-dioxane-5-methyl) methylacrylate (PBDMMA) and macroinitiator MPEG-(OH) 2 were fabricated according to the method described in the previous work, respectively. [ 35,38 ] …”

Section: Methodsmentioning

confidence: 99%

“…According to the reported method, [ 35 ] FITCinsulin could be loaded to the Y-shaped polymer nanoparticles with interactions of hydrogen bonding, van der Waals force and the hydrophilic-hydrophobic interaction. Through multiple ultrafi ltration centrifuge (MWCO 30 kDa) to completely remove free FITC-insulin, the insulin-loading particles were further measured by DLS and zeta potential.…”

Section: Insulin-loading Of the Polymeric Micelles From Mpeg-(pla-blomentioning

confidence: 99%

Synthesis of Y‐Shaped Copolymers Containing Phenylborate Ester and Biodegradable Poly(lactic acid) Blocks and Their Glucose‐Sensitive Behavior for Controlled Insulin Release

Zhao

Zhang

Yao

et al. 2014

Macro Chemistry & Physics

Self Cite

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This study is devoted to developing amphiphilic, biodegradable, Y-shaped block polymers, which can self-assemble to form nanoparticles, as a glucose-sensitive drug carrier. Y-shaped poly(ethylene glycol)-block -[poly(lactic acid)-block -poly (2-phenylborate esters-1,3-dioxane-5-methyl) methylacrylate)] 2 (MPEG-(PLA-block -PPBDMMA) 2 ) polymers are constructed via a combination of ring-opening polymerization (ROP) and atom transfer radical polymerization (ATRP) with MPEG-(OH) 2 , having double initiation endings, as starting material. These Y-shaped block polymers can disperse in an aqueous medium and self-assemble into micellar aggregates with a spherical core-shell structure. Dynamic laser scattering (DLS), zeta potential measurements, and transmission electron microscopy (TEM) show the solution properties of these polymeric micelles with or without insulin loading. Compared with MPEG-PLA-block -PPBDMMA linear polymer, in vitro insulin release at different glucose concentrations, revealed by the fl uorescence technique, shows that the studied Y-shaped polymers have intelligent glucoseconcentration-dependent manner of insulin release at pH 7.4 and 37 °C. The bulk swelling phenomenon of the polymeric micelles formed from the Y-shaped polymers is detected by DLS in the process of their glucose-responsiveness. Such a Y-shaped glucose-responsive polymer is a promising candidate that holds great potential in the treatment of diabetes. predicted to drastic increase to 440 million by 2030, [ 1 ] and it has become one of the most important health concerns we ought to confront. Currently, the common treatment involves frequent blood glucose monitoring and multi ple daily insulin injections. [ 2 ] This provides some control of the diabetic state, but this is far from the physiologic regulation achieved by a normally functioning pancreas and results in unexpected fl uctuations in blood glucose and long-term complications. [ 3,4 ] Great effort has been 0 1 0 2 0 3 0 4 0 5 0 0 20 40 60 80 100 Cumulative Release % Time (h) [Glc]= 0 mg/mL [Glc]=1.0 mg/mL [Glc]=3.0 mg/mL [Glc]=5.0 mg/mL

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Glucose-Responsive Vehicles Containing Phenylborate Ester for Controlled Insulin Release at Neutral pH

Cited by 113 publications

References 46 publications

Facile one-pot synthesis of fluorescent hyperbranched polymers for optical detection of glucose

Facile one-pot synthesis of fluorescent hyperbranched polymers for optical detection of glucose

Glucose- and temperature-sensitive nanoparticles for insulin delivery

Synthesis of Y‐Shaped Copolymers Containing Phenylborate Ester and Biodegradable Poly(lactic acid) Blocks and Their Glucose‐Sensitive Behavior for Controlled Insulin Release

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