scholarly journals Bio-Inspired Amphiphilic Block-Copolymers Based on Synthetic Glycopolymer and Poly(Amino Acid) as Potential Drug Delivery Systems

Polymers ◽  
2020 ◽  
Vol 12 (1) ◽  
pp. 183 ◽  
Author(s):  
Mariia Levit ◽  
Natalia Zashikhina ◽  
Alena Vdovchenko ◽  
Anatoliy Dobrodumov ◽  
Natalya Zakharova ◽  
...  
Keyword(s):  
Amino Acid ◽  
Block Copolymers ◽  
Raft Polymerization ◽  
Amphiphilic Block Copolymers ◽  
Breast Adenocarcinoma ◽  
Hydrodynamic Diameter ◽  
Amphiphilic Copolymers ◽  
Lung Carcinoma Cells ◽  
Biodegradable Poly ◽  
Human Lung Carcinoma

In this work, a method to prepare hybrid amphiphilic block copolymers consisting of biocompatible synthetic glycopolymer with non-degradable backbone and biodegradable poly(amino acid) (PAA) was developed. The glycopolymer, poly(2-deoxy-2-methacrylamido-D-glucose) (PMAG), was synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization. Two methods for modifying the terminal dithiobenzoate-group of PMAG was investigated to obtain the macroinitiator bearing a primary aliphatic amino group, which is required for ring-opening polymerization of N-carboxyanhydrides of hydrophobic α-amino acids. The synthesized amphiphilic block copolymers were carefully analyzed using a set of different physico-chemical methods to establish their composition and molecular weight. The developed amphiphilic copolymers tended to self-assemble in nanoparticles of different morphology that depended on the nature of the hydrophobic amino acid present in the copolymer. The hydrodynamic diameter, morphology, and cytotoxicity of polymer particles based on PMAG-b-PAA were evaluated using dynamic light scattering (DLS) and transmission electron microscopy (TEM), as well as CellTiter-Blue (CTB) assay, respectively. The redox-responsive properties of nanoparticles were evaluated in the presence of glutathione taken at different concentrations. Moreover, the encapsulation of paclitaxel into PMAG-b-PAA particles and their cytotoxicity on human lung carcinoma cells (A549) and human breast adenocarcinoma cells (MCF-7) were studied.

scholarly journals Glucose-bearing biodegradable poly(amino acid) and poly(amino acid)-poly(ester) conjugates for controlled payload release

2016 ◽  
Vol 4 (12) ◽  
pp. 1792-1801 ◽  
Author(s):  
Mthulisi Khuphe ◽  
Clare S. Mahon ◽  
Paul D. Thornton
Keyword(s):  
Aqueous Solution ◽  
Amino Acid ◽  
Block Copolymers ◽  
Self Assembly ◽  
Ring Opening ◽  
Amphiphilic Block Copolymers ◽  
Biodegradable Poly

The glucoseamine-initiated ring-opening polymerisation of amino acid N-carboxyanhydrides and O-carboxanhydrides to yield amphiphilic block copolymers that are capable of self-assembly in aqueous solution to form well-defined, glucose-presenting, particles is reported.

scholarly journals Self-Assembled Nanoparticles Based on Block-Copolymers of Poly(2-deoxy-2-methacrylamido-d-glucose)/Poly(N-vinyl succinamic acid) with Poly(O-cholesteryl methacrylate) for Delivery of Hydrophobic Drugs

2021 ◽  
Vol 22 (21) ◽  
pp. 11457
Author(s):  
Mariia Levit ◽  
Alena Vdovchenko ◽  
Apollinariia Dzhuzha ◽  
Natalia Zashikhina ◽  
Elena Katernyuk ◽  
...  
Keyword(s):  
Block Copolymers ◽  
Chain Transfer ◽  
Aqueous Media ◽  
Spherical Shape ◽  
Amphiphilic Block Copolymers ◽  
Hydrodynamic Diameter ◽  
Amphiphilic Copolymers ◽  
Succinamic Acid ◽  
Cholesteryl Methacrylate

The self-assembly of amphiphilic block-copolymers is a convenient way to obtain soft nanomaterials of different morphology and scale. In turn, the use of a biomimetic approach makes it possible to synthesize polymers with fragments similar to natural macromolecules but more resistant to biodegradation. In this study, we synthesized the novel bio-inspired amphiphilic block-copolymers consisting of poly(N-methacrylamido-d-glucose) or poly(N-vinyl succinamic acid) as a hydrophilic fragment and poly(O-cholesteryl methacrylate) as a hydrophobic fragment. Block-copolymers were synthesized by radical addition–fragmentation chain-transfer (RAFT) polymerization using dithiobenzoate or trithiocarbonate chain-transfer agent depending on the first monomer, further forming the hydrophilic block. Both homopolymers and copolymers were characterized by 1H NMR and Fourier transform infrared spectroscopy, as well as thermogravimetric analysis. The obtained copolymers had low dispersity (1.05–1.37) and molecular weights in the range of ~13,000–32,000. The amphiphilic copolymers demonstrated enhanced thermal stability in comparison with hydrophilic precursors. According to dynamic light scattering and nanoparticle tracking analysis, the obtained amphiphilic copolymers were able to self-assemble in aqueous media into nanoparticles with a hydrodynamic diameter of approximately 200 nm. An investigation of nanoparticles by transmission electron microscopy revealed their spherical shape. The obtained nanoparticles did not demonstrate cytotoxicity against human embryonic kidney (HEK293) and bronchial epithelial (BEAS-2B) cells, and they were characterized by a low uptake by macrophages in vitro. Paclitaxel loaded into the developed polymer nanoparticles retained biological activity against lung adenocarcinoma epithelial cells (A549).

One-step synthesis of poly(2-oxazoline)-based amphiphilic block copolymers using a dual initiator for RAFT polymerization and CROP

Polymer ◽  
2014 ◽  
Vol 55 (23) ◽  
pp. 5986-5990 ◽  
Author(s):  
Young Chang Yu ◽  
Hang Sung Cho ◽  
Woong-Ryeol Yu ◽  
Ji Ho Youk
Keyword(s):  
Block Copolymers ◽  
Raft Polymerization ◽  
Amphiphilic Block Copolymers ◽  
One Step

Synthesis of amphiphilic block copolymers based on poly(dimethylsiloxane) via fragmentation chain transfer (RAFT) polymerization

Polymer ◽  
2004 ◽  
Vol 45 (13) ◽  
pp. 4383-4389 ◽  
Author(s):  
Tommy S.C Pai ◽  
Christopher Barner-Kowollik ◽  
Thomas P Davis ◽  
Martina H Stenzel
Keyword(s):  
Block Copolymers ◽  
Chain Transfer ◽  
Raft Polymerization ◽  
Amphiphilic Block Copolymers

scholarly journals Photo-Responsive Polymersomes as Drug Delivery System for Potential Medical Applications

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5147
Author(s):  
Wanting Hou ◽  
Ruiqi Liu ◽  
Siwei Bi ◽  
Qian He ◽  
Haibo Wang ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Block Copolymers ◽  
Drug Delivery System ◽  
Delivery System ◽  
Raft Polymerization ◽  
Amphiphilic Block Copolymers ◽  
Medical Applications ◽  
Drug Molecules ◽  
Reversible Addition ◽  
Raft Agent

Due to a strong retardation effect of o-nitrobenzyl ester on polymerization, it is still a great challenge to prepare amphiphilic block copolymers for polymersomes with a o-nitrobenzyl ester-based hydrophobic block. Herein, we present one such solution to prepare amphiphilic block copolymers with pure poly (o-nitrobenzyl acrylate) (PNBA) as the hydrophobic block and poly (N,N’-dimethylacrylamide) (PDMA) as the hydrophilic block using bulk reversible addition-fragmentation chain transfer (RAFT) polymerization of o-nitrobenzyl acrylate using a PDMA macro-RAFT agent. The developed amphiphilic block copolymers have a suitable hydrophobic/hydrophilic ratio and can self-assemble into photoresponsive polymersomes for co-loading hydrophobic and hydrophilic cargos into hydrophobic membranes and aqueous compartments of the polymersomes. The polymersomes demonstrate a clear photo-responsive characteristic. Exposure to light irradiation at 365 nm can trigger a photocleavage reaction of o-nitrobenzyl groups, which results in dissociation of the polymersomes with simultaneous co-release of hydrophilic and hydrophobic cargoes on demand. Therefore, these polymersomes have great potential as a smart drug delivery nanocarrier for controllable loading and releasing of hydrophilic and hydrophobic drug molecules. Moreover, taking advantage of the conditional releasing of hydrophilic and hydrophobic drugs, the drug delivery system has potential use in medical applications such as cancer therapy.

Synthesis of Y-shaped amphiphilic copolymers by macromolecular azo coupling reaction

RSC Advances ◽  
2015 ◽  
Vol 5 (13) ◽  
pp. 9476-9481 ◽  
Author(s):  
Jilei Wang ◽  
Yuqi Zhou ◽  
Xiaogong Wang ◽  
Yaning He
Keyword(s):  
Block Copolymers ◽  
Coupling Reaction ◽  
Amphiphilic Block Copolymers ◽  
Amphiphilic Copolymers ◽  
Azo Coupling

The synthesis of well-defined AB2 Y-shaped amphiphilic block copolymers by macromolecular azo coupling reaction is reported.

Fluorinated amphiphilic block copolymers via RAFT polymerization and their application as surf-RAFT agent in miniemulsion polymerization

RSC Advances ◽  
2015 ◽  
Vol 5 (20) ◽  
pp. 15461-15468 ◽  
Author(s):  
Bishnu P. Koiry ◽  
Arindam Chakrabarty ◽  
Nikhil K. Singha
Keyword(s):  
Block Copolymer ◽  
Block Copolymers ◽  
Ethylene Glycol ◽  
Raft Polymerization ◽  
Miniemulsion Polymerization ◽  
Amphiphilic Block Copolymers ◽  
Poly Ethylene Glycol ◽  
Raft Agent ◽  
Poly Ethylene ◽  
Glycol Methyl Ether

Preparation of an amphiphilic block copolymer (Am-BCP) based on poly(ethylene glycol) methyl ether methacrylate (PEGMA) and heptafluorobutyl acrylate (HFBA) via RAFT polymerization and application of this Am-BCP as surf-RAFT agent for polymerization of styrene.

Analysis of Thiol-sensitive Core-cross-linked Polymeric Micelles Carrying Nucleoside Pendant Groups using 'On-line' Methods: Effect of Hydrophobicity on Cross-linking and Degradation

2011 ◽  
Vol 64 (6) ◽  
pp. 766 ◽  
Author(s):  
Bianca M. Blunden ◽  
Donald S. Thomas ◽  
Martina H. Stenzel
Keyword(s):  
Block Copolymers ◽  
Polymeric Micelles ◽  
Raft Polymerization ◽  
Amphiphilic Block Copolymers ◽  
Cross Linking ◽  
Copolymer Composition ◽  
Reversible Addition ◽  
On Line ◽  
Styrene Content ◽  
Poly Ethylene

Amphiphilic block copolymers were prepared via reversible–addition fragmentation chain transfer (RAFT) polymerization and their synthesis, cross-linking, and degradation were studied using on-line monitoring. The focus of this work is the systematic alteration of the hydrophobic block using copolymers based on 5′-O-methacryloyluridine (MAU) and styrene at different compositions to determine the effect of the copolymer composition on the properties of the micelle. A poly(poly(ethylene glycol) methyl ether methacrylate) (PEGMA) macroRAFT agent was chain extended with a mixture of styrene and MAU. In both systems, an increasing fraction of styrene was found to reduce the rate of polymerization, but the functionality of the RAFT system was always maintained. The amphiphilic block copolymers were dialyzed against water to generate micelles with sizes between 17 and 25 nm according to dynamic light scattering (DLS). Increasing styrene content lead to smaller micelles (determined by DLS and transmission electron microscopy) and to lower critical micelle concentrations, which was measured using surface tensiometry. The micelles were further stabilized via core-cross-linking using bis(2-methacroyloxyethyl) disulfide as crosslinker. NMR analysis revealed a faster consumption of crosslinker with higher styrene content. These stable cross-linked micelles were investigated regarding their ability to degrade in the presence of dithiothreitol as a model reductant. Increasing the styrene content resulted in a faster degradation of the cross-linked micelles into unimers.

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