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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2021 · IF 4.539

Vitamin E-tocopheryl polyethylene glycol succinate decorated drug delivery system with synergistic antitumor effects to reverse drug resistance and immunosuppression

Ying-Ying Guan,Shao-Qi Zeng,Yin Qin,Yan Mu,Hong Liu

To overcome cancer drug resistance and to reverse tumor immunosuppression, a vitamin E-tocopheryl polyethylene glycol succinate (TPGS) decorated polymer-based drug delivery system was developed. The effects of the drug delivery system on diverse proteins involved in cell apoptosis, cancer invasion, metastasis and immunosuppression were investigated to provides a more comprehensive understanding of TPGS modified drug delivery systems. Curcumin (CUR), a hydrophobic drug, was loaded in star poly(DL-lactide) with a cholic acid core, and then decorated with TPGS shell to obtain [email protected] /star poly(DL-lactide) nanoparticles ( [email protected] ). Cholic acid cored star poly(DL-lactide) is featured by a rapid degradation rate with a surface erosion characteristic. TPGS not only reverses tumor drug resistance through downregulating P-gp expression of tumor cells but also enhances the anti-tumor efficiency through combined TPGS/CUR therapeutic actions on reversal of tumor immunosuppression mediated by CD47 and PD-L1. As compared with the CUR loaded nanoparticles without TPGS decoration, [email protected] with TPGS decoration results in significantly enhanced intracellular drug accumulation to efficiently induce cell apoptosis in drug resistant tumor cells. More importantly, [email protected] possesses considerably improved efficacy in upregulating p53 and p21 as well as downregulating β-catenin, MMP-9, Snail, CD47 and PD-L1, indicating the TPGS decorated drug delivery system inhibits tumor development and metastasis much more efficiently.

CAS / MDL: 9002-96-4
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AAPS PHARMSCITECH · 2020 ·Vol. 21 ·期 6 ·1-13 · IF 2.401

The Evaluations of Menthol and Propylene Glycol on the Transdermal Delivery System of Dual Drug–Loaded Lyotropic Liquid Crystalline Gels

Tian Chunling,Liu Liu,Xia Mengqiu,Chu Xiao-qin

This study aimed to evaluate the effects of two different structural alcohol permeation enhancers (menthol and propylene glycol) on the internal structure and in vitro properties of the dual drug–loaded lyotropic liquid crystalline (LLC) gels. The LLC gels were prepared and characterized by polarized light microscopy, small-angle X-ray scattering, differential scanning calorimetry, attenuated total reflectance-Fourier transform infrared spectrum, and rheology. Based on the results, the inner structure of the gels was Q II mesophase and exhibited a pseudoplastic fluid behavior. The level of internal order in the LLC mesophase would be affected by introduced 2 wt% menthol (MEN) and propylene glycol (PG). The in vitro release experiment showed that the release behavior of sinomenine hydrochloride (SH) and cinnamaldehyde (CA) from the LLC system was dominated by Fickian diffusion ( n  < 0.43). MEN and PG had the opposite effects on the release of hydrophilic SH, while the MEN and PG both increased the release of lipophilic drug CA . Furthermore, in vitro permeation studies indicated that MEN and PG could both improve the skin permeability of SH and CA, and MEN displayed more pronounced enhancement. All the samples showed no skin irritation on the normal rat skin. Collectively, in our research, monoterpenoid MEN exhibited a better penetration-promoting effect than straight-chain fatty alcohol PG on the dual drug–loaded LLC system.

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COLLOIDS AND SURFACES B-BIOINTERFACES · 2020 · IF 4.389

cRGD mediated redox and pH dual responsive poly(amidoamine) dendrimer-poly(ethylene glycol) conjugates for efficiently intracellular antitumor drug delivery

Yifei Wang,Wen Hu,Bomei Ding,Dawei Chen,Lifang Cheng

To improve antitumor efficiency of chemotherapy and reduce side effect, according to the physiological characteristics of tumor tissues and tumor intracellular microenvironment, a multifunctional drug delivery system with properties of long circulation, active targeting, redox and pH triggered drug release was established based on the Generation 4 polyamidoamine dendrimer (PAMAM). First, the redox cleavable disulfide bonds (S S) were introduced for linking polyethylene glycol (PEG) with PAMAM to form PAMAM-S-S-PEG (PSSP). Then cRGD peptide was applied to the PEG end of PSSP to construct RGD-PSSP conjugates. Finally, encapsulating the antitumor chemotherapy drug doxorubicin (DOX) into the hydrophobic cavity of RGD-PSSP conjugates constructed the RGD-PSSP/DOX drug delivery system. The in vitro experiments displayed that RGD-PSSP/DOX NPs showed obviously redox and pH dual sensitive drug release profile. MTT and cell uptake observation elucidated cRGD modification could increase the cytotoxicity, and promote the uptake of B16 cells and HUVEC cells both overexpressing integrin ανβ3on cell membrane. Cell uptake mechanism investigation further revealed that RGD-PSSP/DOX interacted with plasma membrane via specific recognition of cRGD peptide with integrin ανβ3, and was subsequently internalized mainly through clathrin- and caveolin-mediated endocytosis. Remarkably, RGD-PSSP/DOX presented superior anticancer activity and lower heart and kidney toxicity in vivo , which could be regarded as a potential candidate for efficient antitumor chemotherapy drug delivery.

CAS / MDL: 141-05-9
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POLYMER DEGRADATION AND STABILITY · 2020 · IF 4.032

Degradation of methoxy-poly (ethylene glycol)-block-poly(α-carboxyl-ε-caprolactone)/magnetite nanocomposites in vitro polymer degradation and stability

Yang Li,Yu Liu,Hongyu Zhu,Shirong Shuai,Cong Zhao,Kanghong Zhou,Wei Ge,Jianyuan Hao

Methoxy-poly (ethylene glycol)-block-poly (α-carboxyl-ε-caprolactone)/Fe 3 O 4 nanocomposites (mPEG-b-PCCL@Fe 3 O 4 ) with spherical shape, more negative and smoother surface and core-sell structure were prepared by simply changing the solvent. Their degradation behavior was systematically investigated at 37 °C in distilled water and buffers with different pH values. The mPEG-b-PCCL micelles were used as the contrast. Although the acid inhibition and basic promoting degradation were observed for both mPEG-b-PCCL@Fe 3 O 4 and micelles, the existence of magnetite nanoparticles (MNPs) and more surface –COOH slowed down the degradation of nanocomposites due to the dissociation hindrance of –COOH, the hydrophobicity and the cross-linking effects of MNPs. The degradation of mPEG-b-PCCL@Fe 3 O 4 underwent the surface degradation at initial time and bulk degradation after complete swelling of the hydrophobic core. These investigations suggested that the degradation of mPEG-b-PCCL@Fe 3 O 4 was more designable and controllable than that of micelles.

CAS / MDL: 7558-79-4 7558-80-7
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JOURNAL OF MOLECULAR LIQUIDS · 2020 · IF 5.065

Measurement of density, viscosity and surface tension of tri-ethylene glycol + 1,3-propanediamine mixtures & their computational chemistry and spectral analysis

Fu Li,Bin Li,Ying Zhang,Yaoping Wang,Xiaoqian Jia,Qiang Li,Jianbin Zhang

For liquid and liquid mixtures, density (ρ), viscosity (η) and surface tension (γ) are seen as important basic data. This research reported the data of ρ, η and γ for the binary mixture of tri-ethylene glycol (TEG) + 1,3-propanediamine (PDA) at p  = .1 MPa and T  = (293.15 to 318.15) K within the whole molar fraction range, finding the maximum of η and γ values when the mole fraction of TEG was x 1  ≈ 0.65. After that, excess molar volume ( V m E ), viscosity deviation (Δη), and surface tension deviation (Δγ) were carefully calculated, and the minimum V m E values and the maximum Δγ values were obtained when the molar fraction of TEG was at x 1  ≈ 0.50; however, the maximum Δη values shifted from x 1  ≈ 0.60 to x 1  ≈ 0.66. And then, the Redlich-Kister (R-K) equation fitting was performed on above parameters to evaluate the coefficient and standard deviation, apparent molar volumes ( V φ , 1 and V φ , 2 ) and partial molar volumes ( V 1 ¯ V1¯ and V 2 ¯ V2¯ ). Meanwhile, Gaussian 09 software was used to further analyze the intermolecular force and to calculate the dissociation energy and bond length of the mixture, and the interaction of PDA with TEG were discussed on the basis of FTIR, UV–Vis and FLS spectral technologies. The results showed that there were hydrogen-bond interactions between the nitrogen atoms in PDA and the hydroxyl hydrogen atoms in TEG.

CAS / MDL: 112-27-6
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ELECTROCHIMICA ACTA · 2020 · IF 6.215

Hollow nanotubular clay composited comb-like methoxy poly(ethylene glycol) acrylate polymer as solid polymer electrolyte for lithium metal batteries

Jianwen Feng,Xiaohu Ao,Zhiwen Lei,Jun Wang,Yonghong Deng,Chaoyang Wang

Solid polymer electrolytes (SPEs) shows increasing promise for all-solid-state batteries due to their high safety, high flexibility and low interfacial resistance. However, the low ionic conductivity at room temperature is the main barrier hindering the practical application of SPEs. Herein, hollow nanotubular clay composited comb-like methoxy poly(ethylene glycol) acrylate polymer electrolyte (HCPE) is fabricated by in-situ UV activated radical polymerization , which exhibits an improved ionic conductivity of 5.62 × 10 −5  S cm −1 at room temperature. The introducing of the branched structure helps reduce the regularity of polymer chains and decreases the proportion of crystalline regions of polymers. Moreover, the nanofiller feature and the special structure of halloysite nanotube (HNT) are beneficial for dissociating lithium salt , thus improving the ionic conductivity. Meanwhile, the designed composite solid-state electrolyte demonstrates high thermal stability and compatibility with Li metal, high electrochemical stability. The all-solid-state Li/HCPE/LiFePO 4 cell delivers high rate capability and stable cycling performance at room temperature, which proves the great potential of HCPE for all-solid-state Li metal batteries .

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GREEN CHEMISTRY · 2019 ·Vol. 21 ·期 19 ·5414-5426 · IF 9.405

One-pot synthesized core/shell structured zeolite@copper catalysts for selective hydrogenation of ethylene carbonate to methanol and ethylene glycol

Yu Ding,Jingxia Tian,Wei Chen,Yejun Guan,Hao Xu,Xiaohong Li,Haihong Wu,Peng Wu

Copper-based catalysts, with highly dispersed and stabilized Cu nanoparticles, intensified mass transfer and a well-balanced Cu0/Cu+ ratio at low Cu loadings, are highly desirable for the selective hydrogenation of ethylene carbonate to ethylene glycol and methanol, an efficient indirect route of CO2 utilization. A hierarchically core/shell-structured Silicalite-1@Cu composite was developed via a base-assisted chemoselective host–guest interaction between the silicon species of MFI-type Silicalite-1 and external Cu salt source. In situ generated mesoporosity and strong Cu–silicate interaction made the uniform Cu NPs firmly immobilized and highly dispersed outside the core S-1 crystals. The S-1@Cu hybrid possessed the co-existing Cu0/Cu+ active species with a suitable ratio, and served as a highly active, selective and robust catalyst for selective ethylene carbonate hydrogenation, providing a lifetime >350 h together with >99% ethylene carbonate conversion, >99% ethylene glycol yield, and more importantly 93% methanol yield at a relatively low Cu loading of 21.4 wt%.

CAS / MDL: 96-49-1
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2019 · IF 4.213

Melt electrohydrodynamic 3D printed poly (ε-caprolactone)/polyethylene glycol/roxithromycin scaffold as a potential anti-infective implant in bone repair

Jianfu Bai,Han Wang,Wei Gao,Feng Liang,Zixu Wang,Ying Zhou,Xingzi Lan,Xun Chen,Nian Cai,Weimin Huang,Yadong Tang

Implanted scaffold or bone substitute is a common method to treat bone defects. However, the possible bone infection caused by orthopaedic surgery has created a challenging clinical problem and generally invalidate bone repair and regeneration. In this study, a poly (ε-caprolactone) (PCL)/polyethylene glycol (PEG)/roxithromycin (ROX) composite scaffold was prepared via melt electrohydrodynamic (EHD) 3D printing. Fourier transform infrared spectroscopy (FTIR) spectroscopy was performed to verify the existence of PEG and ROX in the scaffolds. By water contact angle measurement, the addition of both PEG and ROX was found to improve the hydrophilicity of the scaffolds. By in vitro drug release assay, the PCL/PEG/ROX scaffolds showed an initial burst drug release and subsequent long-term sustained release behaviour, which is favourable for the prevention and treatment of bone infections. The antibacterial assays against E. coli and S. aureus demonstrated that the composite scaffold with ROX possessed effective antibacterial activity, especially for S. aureus , the main cause of bone infection. The immunostaining and MTT assay with human osteoblast-like cells (MG63) indicated that cells showed good viability and growth on the scaffolds. Therefore, the melt EHD 3D printed PCL/PEG/ROX scaffold could be a promising anti-infective implant for bone tissue engineering.

CAS / MDL: 109-99-9
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FOOD CHEMISTRY · 2019 · IF 5.399

Ultrasonic impact on viscosity and extraction efficiency of polyethylene glycol: A greener approach for anthocyanins recovery from purple sweet potato

Hao Huang,Qin Xu,Tarun Belwal,Li Li,Halah Aalim,Qiong Wu,Zhenhua Duan,Xuebing Zhang,Zisheng Luo

Purple sweet potatoes are known for its vibrant purple color due to high level of anthocyanins. A polyethylene glycol based ultrasonic-assisted green extraction (PEG-UAE) of anthocyanins from purple sweet potato was proposed. Different types of PEG were tested for anthocyanin extraction along with PEG concentration, liquid-to-solid ratio, ultrasonic temperature and time were investigated for its impact on viscosity and extraction efficiency. The optimum extraction condition, 42 mL/g of ratio, 83% of PEG 200 concentration, 64 °C of ultrasonic temperature and 80 min of sonication time, resulted in better extraction of anthocyanins (83.78 mg CE/100 g DW) and phenolics (994.88 mg GAE/100 g DW). Using UPLC-Triple-TOF/MS, ten anthocyanin and six non-anthocyanin compounds were identified and characterized, with the highest peak area for cyanidin-3-caffeoyl-p-hydroxybenzoyl sophoroside-5-glucoside (25.9%). Moreover, the anthocyanins and phenolics extraction yield along with antioxidant activity were negatively correlated with PEG viscosity, on which ultrasonication has profound effects.

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POLYMERS & POLYMER COMPOSITES · 2019 · IF 0.683

Effect of chain segment length on crystallization behaviors of poly(l-lactide-b-ethylene glycol-b-l-lactide) triblock copolymer

Yongji Gong,Weihua Song,Yifan Wu,Daohai Zhang,Yufei Liu,Qian Zhao,Min He,Xiaolang Chen

The poly(l-lactide-b-ethylene glycol-b-l-lactide) (PLLA-PEG-PLLA) triblock copolymers with different chain segment length are fabricated by ring-opening polymerization. The structure, molecular weight, and crystallization behaviors of the triblock copolymers are characterized by Fourier transform infrared, nuclear magnetic resonance spectroscopy, gel permeation in chromatography, X-ray diffraction, differential scanning calorimetry, and polarizing optical microscopy (POM). The results show that the increase of block length is beneficial to improve its crystallization. In addition, the triblock copolymer exhibits a double crystallization phenomenon. The POM results indicate that PEG and PLLA chains of the copolymer crystallize in their respective crystallization temperature regions. The growth rate of the PLLA spherocrystal decreases and the dendritic spherocrystals appear with increasing the PEG chain length when the PLLA chain of the copolymer is isothermal crystallized at 80°C and PLLA chain length is constant. The growth rate of the PEG spherocrystal decreases and the spherocrystal morphology changes little with increasing PLLA chain length when the PEG chain is isothermal crystallized at 25°C and the length of PEG chain remained unchanged.

CAS / MDL: 25322-68-3
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2019 · IF 2.298

Experimental Determination and Modeling of Liquid–Liquid Equilibrium for Ternary Mixtures of Ethylene Glycol + 1,2-Butanediol + 3-Heptanone or Anisole

Chunli Li,Xuefei Wang,Hao Li,Cong Duan,Le An,Qing Liu

Experimental liquid–liquid equilibrium (LLE) data for the system ethylene glycol (EG) + 1,2-butanediol (1,2-BD) + 3-heptanone were measured at atmospheric pressure at 293.15, 303.15, and 313.15 K and the ternary LLE for systems of EG + 1,2-BD + anisole were also investigated at 303.15 K at 101.3 KPa by using liquid–liquid equilibrium kettle method. Distribution coefficient and selectivity were obtained and applied to evaluate the extraction capacity of 3-heptanone and anisole. The reliability of the experimental data was confirmed by the Hand correlation and the Othmer–Tobias correlation. The experimental LLE data were correlated by NRTL and UNIQUAC models, and the corresponding parameters were obtained. The root-mean-square deviations (RMSD) between the experimental data and calculated values were less than 1.22%. Topological concepts related to the Gibbs stability test were used to validate the consistency between model parameters and experimental data. The liquid–liquid equilibrium data provide the basic physicochemical properties for design of extraction process of 1,2-BD from EG by 3-heptanone and anisole. According to comprehensive correlation coefficient analysis, 3-heptanone is more suitable for the extraction of 1,2-BD from EG than anisole.

CAS / MDL: 100-66-3
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Journal of Zhejiang University-SCIENCE B · 2019 · IF 1.879

Enhanced water solubility, antioxidant activity, and oral absorption of hesperetin by D-α-tocopheryl polyethylene glycol 1000 succinate and phosphatidylcholine

Su-fang Gu,Li-ying Wang,Ying-jie Tian,Zhu-xian Zhou,Jian-bin Tang,Xiang-rui Liu,Hai-ping Jiang,You-qing Shen

Hesperetin, an abundant bioactive component of citrus fruits, is poorly water-soluble, resulting in low oral bioavailability. We developed new formulations to improve the water solubility, antioxidant activity, and oral absorption of hesperetin. Two nano-based formulations were developed, namely hesperetin-TPGS ( D -α-tocopheryl polyethylene glycol 1000 succinate) micelles and hesperetin-phosphatidylcholine (PC) complexes. These two formulations were prepared by a simple technique called solvent dispersion, using US Food and Drug Administration (FDA)-approved excipients for drugs. Differential scanning calorimetry (DSC) and dynamic light scattering (DLS) were used to characterize the formulations’ physical properties. Cytotoxicity analysis, cellular antioxidant activity assay, and a pharmacokinetic study were performed to evaluate the biological properties of these two formulations. The final weight ratios of both hesperetin to TPGS and hesperetin to PC were 1:12 based on their water solubility, which increased to 21.5-and 20.7-fold, respectively. The hesperetin-TPGS micelles had a small particle size of 26.19 nm, whereas the hesperetin-PC complexes exhibited a larger particle size of 219.15 nm. In addition, the cellular antioxidant activity assay indicated that both hesperetin-TPGS micelles and hesperetin-PC complexes increased the antioxidant activity of hesperetin to 4.2-and 3.9-fold, respectively. Importantly, the in vivo oral absorption study on rats indicated that the micelles and complexes significantly increased the peak plasma concentration ( C max ) from 2.64 μg/mL to 20.67 and 33.09 μg/mL and also increased the area under the concentration–time curve of hesperetin after oral administration to 16.2-and 18.0-fold, respectively. The micelles and complexes increased the solubility and remarkably improved the in vitro antioxidant activity and in vivo oral absorption of hesperetin, indicating these formulations’ potential applications in drugs and healthcare products.

CAS / MDL: 9002-96-4
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