Poly(2-oxazoline)–Pterostilbene Block Copolymer Nanoparticles for Dual-Anticancer Drug Delivery

Romio, Matteo; Morgese, Giulia; Trachsel, Lucca; Babity, Samuel; Paradisi, Cristina; Brambilla, Davide; Benetti, Edmondo M.

doi:10.1021/acs.biomac.7b01279

Cited by 30 publications

(18 citation statements)

References 50 publications

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“…Within the class of chain-growth polymerization, two important techniques for the synthesis of functional polymers are cationic ring opening polymerization (CROP) of 2-oxazolines 20–23 and reversible deactivation radical polymerization (RDRP) of vinyl monomers (e.g., styrene and (meth)acrylates). For CROP, poly(2-alkyl-2-oxazoline)s (PAOx) with methyl ester functionalized side chains are specifically interesting as they can undergo a direct amidation or can be hydrolyzed to a carboxylic acid, making them versatile functional copolymers for conjugation 6,7,24–30 . For RDRP, an important technique is atom transfer radical polymerization (ATRP) with e.g., N -propyl maleimide or glycidyl methacrylate as functional comonomer prone to conjugation or further chemical modification 31,32 .…”

Section: Introductionmentioning

confidence: 99%

Visualization and design of the functional group distribution during statistical copolymerization

et al. 2019

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Even though functional copolymers with a low percentage of functional comonomer units (up to 20 mol%) are widely used, for instance for the development of polymer therapeutics and hydrogels, insights in the functional group distribution over the actual chains are lacking and the average composition is conventionally used to describe the functionalization degree. Here we report the visualization of the monomer distribution over the different polymer chains by a synergetic combination of experimental and theoretical analysis aiming at the construction of functionality-chain length distributions (FUNC-CLDs). A successful design of the chemical structure of the comonomer pair, the initial functional comonomer amount (13 mol%), and the temperature (100 °C) is performed to tune the FUNC-CLD of copoly(2-oxazoline)s toward high functionalization degree for both low (100) and high (400) target degrees of polymerization. The proposed research strategy is generic and extendable to a broad range of copolymerization chemistries, including reversible deactivation radical polymerization.

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Section: Introductionmentioning

confidence: 99%

Visualization and design of the functional group distribution during statistical copolymerization

et al. 2019

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“…Copolymers have been developed as delivery systems for medicinal products as well as various carriers for therapeutic agents and different contrast agents in diagnostic imaging applications [1][2][3][4]. With the structure of amphiphilic polymeric micelles, hydrophobic drug compounds are soluble within the hydrophobic nuclei, while the shell retains a hydration barrier that protects the integrity of each microcell [5,6].…”

Section: Introductionmentioning

confidence: 99%

Biotin-functionalized copolymeric PEG-PCL micelles for in vivo tumour-targeted delivery of artemisinin

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Barzegari

Danafar

et al. 2019

Artificial Cells, Nanomedicine, and Biotechnology

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Artemisinin is used as an antimalarial and anticancer agent with minimal toxic effects on the host body. Biotin-PEG-PCL polymers have been used for targeted drug delivery to cancer, as well as to improve the pharmacokinetics of the drug and reduce its effects. In this study, biotin-conjugated copolymers were fabricated with polymerization of the ring opening method and the properties of copolymer and nanoparticles were investigated using various techniques. The toxicity of artemisinin and its nanoparticles have been investigated on MCF-7 and normal HFF2 cells. The results showed that the encapsulation efficacy of artemisinin in nanoparticles was 45.5 ± 0.41%. The release profile of the drug indicates that the release is slow and controlled and is approximately pH dependent. The results of artemisinin cell culture on human breast cancer cells showed that biotin-PEG-PCL nanoparticles had an inhibitory effect on MCF-7 cells and had no toxic effects on HFF2 cells. Anticancer activity in vivo in the 4T1 breast cancer model showed that tumour volumes were decreased up 40 mm 3 by ART-loaded micelles and 76 mm 3 by free ART, compared to the control group (2150 mm). In vivo results showed that this formulation significantly increases the accumulation of substances in the tumours. Therefore, the molecular formulation of ART-based copolymers can be a desirable process for cancer treatment purposes.

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“…In vitro cytotoxicity of PNVP- b - dendr (Phe-Lys) n (n = 2, 3) against human lung epithelial cells (BEAS-2B) and human liver cancer cells (SMMC-7721) was evaluated using the colorimetric MTS assay [48]. Briefly, BEAS-2B cells were seeded into a 96-well plate at a density of 5 × 10 3 cells per well in 100 μL of Dulbecco’s modified Eagle’s medium (DMEM; Sigma), supplemented with 10% fetal bovine serum (FBS), and incubated in a humidified atmosphere (37 °C, 5% CO 2 ) for 24 h. After 24 h, the polymer solutions (100 μL in normal saline) at different concentrations were added to each well.…”

Section: Methodsmentioning

confidence: 99%

Self-Assembly and Enzyme Responsiveness of Amphiphilic Linear-Dendritic Block Copolymers Based on Poly(N-vinylpyrrolidone) and Dendritic Phenylalanyl-lysine Dipeptides

et al. 2019

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In this study, we present the synthesis, self-assembly, and enzyme responsive nature of a unique class of well-defined amphiphilic linear-dendritic block copolymers (PNVP-b-dendr(Phe-Lys)n, n = 1–3) based on linear poly(N-vinylpyrrolidone) (PNVP) and dendritic phenylalanyl-lysine (Phe-Lys) dipeptides. The copolymers were prepared via a combination ofreversible addition-fragmentation chain transfer (RAFT)/xanthates (MADIX) polymerization of N-vinylpyrrolidone and stepwise peptide chemistry. The results of fluorescence spectroscopy, 1H NMR analyses, transmission electron microscopy (TEM), and particle size analysis demonstrated that the copolymers self-assemble in aqueous solution into micellar nanocontainers that can disassemble and release encapsulated anticancer drug doxorubicin or hydrophobic dye Nile red by trigger of a serine protease trypsin under physiological conditions. The disassembly of the formed micelles and release rates of the drug or dye can be adjusted by changing the generation of dendrons in PNVP-b-dendr(Phe-Lys)n. Furthermore, the cytocompatibility of the copolymers have been confirmed using human lung epithelial cells (BEAS-2B) and human liver cancer cells (SMMC-7721). Due to the fact of their enzyme responsive properties and good biocompatibility, the copolymers may have potential applicability in smart controlled release systems capable of site-specific response.

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Poly(2-oxazoline)–Pterostilbene Block Copolymer Nanoparticles for Dual-Anticancer Drug Delivery

Cited by 30 publications

References 50 publications

Visualization and design of the functional group distribution during statistical copolymerization

Visualization and design of the functional group distribution during statistical copolymerization

Biotin-functionalized copolymeric PEG-PCL micelles for in vivo tumour-targeted delivery of artemisinin

Self-Assembly and Enzyme Responsiveness of Amphiphilic Linear-Dendritic Block Copolymers Based on Poly(N-vinylpyrrolidone) and Dendritic Phenylalanyl-lysine Dipeptides

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