Synthesis  of three-arm block copolymer poly(lactic-&lt;em&gt;co&lt;/em&gt;-glycolic acid)&amp;ndash;poly(ethylene glycol) with oxalyl chloride and its application in hydrophobic drug delivery

Zhu, Xiaowei; Liu, Chao; Duan, Jianwei; Liang, Xiaoyu; Li, Xuanling; Sun, Hongfan; Kong, Deling; Yang, Jing

doi:10.2147/ijn.s119446

Cited by 14 publications

(17 citation statements)

References 60 publications

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“…The synthetic route of 3s-PLGA-PO-PEG was depicted as follow. The 3s-PLGA was firstly synthesized using lactide and glycolide by ring-opening polymerizationas previously reported 14 .The block copolymer was obtained when modified 3s-PLGA and PEG linked with oxalyl chloride by acylation reaction. Three-arm PLGA connected to PEG by peroxalate ester bond which breaks in the presence of H2O2.…”

Section: Synthesis Of 3s-plga-po-pegmentioning

confidence: 99%

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Liang

Duan

et al. 2018

Mol. Pharmaceutics

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Currently, development of subunit vaccine based on recombinant antigens or peptides has gradually become an important alternative option for traditional vaccine. However, induction of potent immune response with desired efficacy remains a major challenge. The nanoparticle-based antigen delivery system has been considered a potential carrier system to improve the efficacy of subunit vaccine. In the present study, we have designed an immune-stimulatory delivery system by conjugating three-armed PLGA to PEG via the peroxalate ester bond which is sensitive to hydrogen peroxide (HO), a major reactive oxygen species (ROS). Hyaluronic acid (HA), a ligand for CD44 receptors was also modified onto the outer shell of the 3s-PLGA-PEG nanoparticles to promote immune cell uptake. For in vitro and in vivo immune response assessment, a model antigen ovalbumin (OVA) was enclosed within the core of the 3s-PLGA-PEG nanoparticles to form 3s-PLGA-PO-PEG/HA nanoparticles (PHO NPs). Our results showed that the PHO NPs enhanced dendritic cell maturation, antigen uptake, and antigen presentation in vitro, likely due to enhanced lysosomal escape. In vivo experiments further revealed that the PHO nanovaccine robustly promoted OVA-specific antibody production and T cell response accompanied by modest stimulation of memory T cells. In summary, the ROS-responsive PHO NPs with modified HA may be an effective vehicle antigen delivery system to promote antigen-induced immune response.

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Section: Synthesis Of 3s-plga-po-pegmentioning

confidence: 99%

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Liang

Duan

et al. 2018

Mol. Pharmaceutics

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“…Compared with the traditional synthesis method using dicyclohexylcarbodiimide (DCC) and N-hydroxysuccinimide (NHS), this synthetic method is simple and convenient. 30,31,36 1 H-NMR was used to confirm the chemical structure of 6S-PCL and 6S-PCL-PEG. The resonance peaks a (δ=4.05), b (δ=1.66), c (δ=1.41), and d (δ=2.31) were assigned to the protons of CH 2 in the PCL (Figure 2A).…”

Section: Results and Discussion Characterization Of Copolymermentioning

confidence: 99%

“…Finally, 6S-PCL polymer was obtained after filtering and drying in a vacuum for 24 h. Hydrogen-1 nuclear magnetic resonance ( 1 H-NMR) spectroscopy measurements were performed using a 400 MHz spectrometer (Varian, Palo Alto, CA, USA) with CDCl 3 as the solvent and tetramethylsilane as the internal reference, with a chemical shift of 0 ppm. 31 A Nicolet Nexus 470-ESP Fouriertransform infrared (FTIR) spectrometer (Thermo Fisher Scientific, Waltham, MA, USA) was employed to analyze the main functional groups. The molecular weight of the copolymer was investigated by gel-permeation chromatography (GPC) with polymethyl methacrylate (PMMA) as the standard using a Hitachi L-2490 differential refraction detector and two Agilent PL gel particle columns (7.5×300 mm, 10 mm).…”

Section: Synthesis Of 6s-pclmentioning

confidence: 99%

“…Initial work in this study focused on the preparation of 6S-PCL-PEG by a two-step method which is simple and efficient. 31 Thereafter, ovalbumin (OVA) was used as a model protein and a doubleemulsion solvent evaporation method was employed to prepare the NPs, followed by property analysis, in vitro stability, and release behavior studies of NPs. Further, the in vitro uptake of NPs by NIH-3T3 cells was performed to examine the potential of this formulation in delivering protein into living cells.…”

Section: Introductionmentioning

confidence: 99%

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Protein delivery nanosystem of six-arm copolymer poly(ε-caprolactone)–poly(ethylene glycol) for long-term sustained release

Duan¹,

Liu²,

Liang³

et al. 2018

IJN

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BackgroundTo address the issue of delivery of proteins, a six-arm copolymer, six-arm poly (ε-caprolactone)–poly(ethylene glycol) (6S-PCL-PEG), was synthesized by a simple two-step reaction. Thereafter, the application of 6S-PCL-PEG as a protein carrier was evaluated.Materials and methodsA six-arm copolymer, six-arm poly(ε-caprolactone) (6S-PCL), was synthesized by ring-opening polymerization, with stannous octoate as a catalyst and inositol as an initiator. Then, poly(ethylene glycol) (PEG) was linked with 6S-PCL by oxalyl chloride to obtain 6S-PCL-PEG. Hydrogen-1 nuclear magnetic resonance spectrum, Fourier-transform infrared spectroscopy, and gel-permeation chromatography were conducted to identify the structure of 6S-PCL-PEG. The biocompatibility of the 6S-PCL-PEG was evaluated by a cell counting kit-8 assay. Polymeric nanoparticles (NPs) were prepared by a water-in-oil-in-water double emulsion (W1/O/W2) solvent evaporation method. The size distribution and zeta potential of NPs were determined by dynamic light scattering. Transmission electron microscopy was used to observe the morphology of NPs. Drug-loading capacity, encapsulation efficiency, and the release behavior of ovalbumin (OVA)-loading NPs were tested by the bicinchoninic acid assay kit. The stability and activity of OVA released from NPs were detected and the uptake of NPs was evaluated by NIH-3T3 cells.ResultsAll results indicated the successful synthesis of amphiphilic copolymer 6S-PCL-PEG, which possessed excellent biocompatibility and could formulate NPs easily. High drug-loading capacity and encapsulation efficiency of protein NPs were observed. In vitro, OVA was released slowly and the bioactivity of OVA was maintained for over 28 days.Conclusion6S-PCL-PEG NPs prepared in this study show promising potential for use as a protein carrier.

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“…Meanwhile, the drug load (%) was calculated according to the percentage of the drug in the micelle relative to the amount of total micelle. 27 All characterizations were performed triplicates.…”

Section: Methodsmentioning

confidence: 99%

Assessment of the Effect of PLGA Co-polymers and PEG on the Formation and Characteristics of PLGA-PEG-PLGA Co-block Polymer Using Statistical Approach

et al. 2019

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Purpose: To assess the effect of the lactic acid (LA)-to-glycolic acid (GA) molar ratio and polyethylene glycol (PEG) concentration on the formation of poly-lactide co-glycolide acid (PLGA)-PEG-PLGA co-block polymers simultaneously using statistical approach. Methods: A 22 full factorial design with the addition of a point in the center of the design, namely curvature, was applied. Fourier transform infrared (FTIR), differential scanning calorimetry (DSC), and nuclear magnetic resonance (NMR) were performed to confirm the formation of the co-block polymer. Simvastatin (SMV), a drug model was incorporated into the nano-polymeric micellar (NpM) of PLGA-PEG-PLGA followed by solubility phase, particle size, zeta potential, and entrapment efficiency characterizations. Results: FTIR, DSC, and NMR successfully confirmed the formation of co-block polymers. Solubility of SMV increased from 2 to 44-folds depending on co-block concentration with entrapment efficiency of 59%-80%. The NpM had size in the range of 206 to 402 nm with negative zeta potential. LA to GA ratio had greater effect on particle size reduction and increasing of co-polymer length. In addition, it had higher contributions on increasing of solubility and entrapment efficiency of SMV than PEG. Conclusion: According to these findings, the LA to GA ratio and PEG concentration gained a great consideration in order to prepare the PLGA-PEG-PLGA co-block which fulfilled the quality target product profile of NpM delivery system.

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Synthesis of three-arm block copolymer poly(lactic-<em>co</em>-glycolic acid)–poly(ethylene glycol) with oxalyl chloride and its application in hydrophobic drug delivery

Cited by 14 publications

References 60 publications

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Protein delivery nanosystem of six-arm copolymer poly(ε-caprolactone)–poly(ethylene glycol) for long-term sustained release

Assessment of the Effect of PLGA Co-polymers and PEG on the Formation and Characteristics of PLGA-PEG-PLGA Co-block Polymer Using Statistical Approach

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Synthesis of three-arm block copolymer poly(lactic-<em>co</em>-glycolic acid)&ndash;poly(ethylene glycol) with oxalyl chloride and its application in hydrophobic drug delivery

Cited by 14 publications

References 60 publications

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Nanoparticles with CD44 Targeting and ROS Triggering Properties as Effective in Vivo Antigen Delivery System

Protein delivery nanosystem of six-arm copolymer poly(&epsilon;-caprolactone)&ndash;poly(ethylene glycol) for long-term sustained release

Assessment of the Effect of PLGA Co-polymers and PEG on the Formation and Characteristics of PLGA-PEG-PLGA Co-block Polymer Using Statistical Approach

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Synthesis of three-arm block copolymer poly(lactic-<em>co</em>-glycolic acid)–poly(ethylene glycol) with oxalyl chloride and its application in hydrophobic drug delivery

Protein delivery nanosystem of six-arm copolymer poly(ε-caprolactone)–poly(ethylene glycol) for long-term sustained release