Novel self-assembled micelles of amphiphilic poly(2-ethyl-2-oxazoline) -poly(L-lactide) diblock copolymers for sustained drug delivery

Su, Feng; Peng, Yun; Li, Chenglong; Li, Rongye; Xi, Laishun; Wang, Yuandou; Chen, Yangsheng; Li, Suming

doi:10.1016/j.colsurfa.2019.01.015

Cited by 25 publications

(23 citation statements)

References 41 publications

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“…Among the wide range of biocompatible and biodegradable polymers utilized for preparation of nanoparticles, amphiphilic copolymers allow for the simple formation of nanostructures of different morphology (polymersomes, micelles, nanospheres) due to their ability to self-assemble in aqueous media [4][5][6]. Self-assembled nanoparticles are suitable for encapsulation of hydrophobic, hydrophilic and amphiphilic drugs [7][8][9]. Nowadays, a wide variety of amphiphilic copolymers of different structure and composition have been described and discussed [4,10,11].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2020

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“…As outlined in the introduction part, the synthesis of PEtOx-b-PLA co-polymers, such as the synthesis poly (2-ethyl-2-oxazoline)-b-poly(L-lactide) 8 (Scheme 1(a)) and poly(2-ethyl-2-oxazoline)/poly(L-lactide) triblock copolymers, [10][11][12] have been well-documented in the literature. Furthermore, the latter building block was utilized in the preparation of thermoreversible hydrogel, which is likely to find application in controlled drug release.…”

Section: Discussionmentioning

confidence: 99%

“…Whereas the azide group of 4 allows the grafting of PLA block through Click chemistry, 37,38 the allyl group paves the way for conjugating peptides via well‐established photoinduced thiol‐ene click reaction in the subsequent reaction 39 . In comparison to the procedures reported in, 10–12 ours is conformed with the expeditious synthesis of tumor‐homing agents‐PEG‐ b ‐PLA block copolymers conjugates. In this manuscript, we present our methodology to access 1a and 1b and discuss experimental details, regarding the grafting of two different peptides on these molecules for tailor targeted drug delivery systems.…”

Section: Introductionmentioning

confidence: 99%

“…2 In this context, it is worth noting that the hydrophobic nature of PLA posed a problem as it augments the uptake of drug-loaded nanoparticles (NPs) through the mononuclear phagocyte system, resulting in diminished therapeutic efficiency. 3 Thus, many research groups explored the notion of decorating the surface of PLA with hydrophilic polymers, which resulted in amphiphilic block-co-polymers, such as PLA-grafted dextran, 4 PLA-b-poly(2-methacryloyloxyethylphosphorylcholine), 5 PLA-b-poly(N,N-dimethylaminoethyl methacrylate), 6 PEG-b-PLA, 7 poly(oxazoline)-b-PLA [8][9][10][11][12] and so forth.…”

Section: Introductionmentioning

confidence: 99%

“…[21][22][23] It is needless to say that this control provides freedom for an orthogonal conjugation of biomolecules (such as drugs, fluorescent labels, targeting agents and so forth). To this end, PEOz-PLA diblock copolymer (Scheme 1(a)) 10 and PEOz-PLA-PEOz triblock co-polymers 11,12 has been developed for in situ drug and cell delivery.…”

Section: Introductionmentioning

confidence: 99%

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The synthesis of peptide‐conjugated poly(2‐ethyl‐2‐oxazoline)‐b‐poly(L‐lactide) (PEtOx‐b‐PLA) polymeric systems through the combination of controlled polymerization techniques and click reactions

Özköse

Gülyüz

Khalily

et al. 2020

J of Applied Polymer Sci

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To optimize the therapeutic effect of pharmaceutical agents, drug delivery systems tailored from FDA‐approved polymers like poly(L‐lactide) (PLA) is an effective strategy. Because of their hydrophobic character, these systems greatly suffer from reduced circulation time thus, amphiphilic block copolymers became favorable to overcome this limitation. Of them, poly(oxazoline)‐b‐poly(L‐lactide) are of choice as poly(oxazoline) (PEtOx) is compatible, biodegradable, while exhibiting minimum cytotoxicity. To tailor selective drug targeting drug delivery systems, whereby their selectivity for tumor tissues is maximized, these polymers should be decorated with so‐called tumor‐homing agents, such as antibodies, peptides and so forth. To this respect, we designed a new block copolymer, allyl‐poly(2‐ethyl‐2‐oxazoline)‐b‐poly(L‐lactide) allyl‐(PEtOx‐b‐PLA) and its subsequent conjugation to tumor‐homing peptides, peptide‐18, and peptide‐563 at the terminal position. In this manuscript, we report our synthetic route to obtain this building block and its conjugation to tumor‐homing agents.

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Biocompatibility, drug release, and anti‐tumor effect of pH‐sensitive micelles prepared from poly(2‐ethyl‐2‐oxazoline)‐poly(DL‐lactide) block copolymers

Wang

Zhang

Shen

et al. 2021

Polymers for Advanced Techs

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Various ratios PEOz-PDLLA diblock copolymers were synthesized through ringopening polymerization of DL-lactide initiated by monohydroxyl terminated poly (2-ethyl-2-oxazoline) (PEOz-OH). The chemical composition and molar mass of the resulting copolymers were determined by using NMR and GPC. Spherical micelles with a diameter from 104 to 136 nm were obtained via self-assembly of PEOz-PDLLA in water, as evidenced by TEM and DLS. The CMC of copolymers was well below 0.01 mg/mL, and showed a decreasing trend with increase of PDLLA block length. A two-step procedure was applied to encapsulate curcumin taken as a hydrophobic model drug. Copolymers with longer PDLLA block exhibit enhanced drug loading capacity. In vitro drug release was carried out in phosphate buffered saline (PBS) at physiological and slightly acidic pH values. A pH-sensitive biphasic drug release behavior was detected with an initial burst release followed by slower prolonged release. Lower pH or shorter PDLLA block length leads to higher drug release rate because of faster degradation of micelles. Hemo-and cytocompatibility studies illustrated the excellent biocompatibility of PEOz-PDLLA micelles. MTT assay showed a significant cytotoxicity of curcumin-loaded micelles against A549 lung cancer cells. Therefore, it can be inferred that PEOz-PDLLA block copolymers with outstanding biocompatibility, controllable drug loading performance, and prolonged drug release present a good potential as nano-carrier of hydrophobic drugs.

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Novel self-assembled micelles of amphiphilic poly(2-ethyl-2-oxazoline) -poly(L-lactide) diblock copolymers for sustained drug delivery

Cited by 25 publications

References 41 publications

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

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

The synthesis of peptide‐conjugated poly(2‐ethyl‐2‐oxazoline)‐b‐poly(L‐lactide) (PEtOx‐b‐PLA) polymeric systems through the combination of controlled polymerization techniques and click reactions

Biocompatibility, drug release, and anti‐tumor effect of pH‐sensitive micelles prepared from poly(2‐ethyl‐2‐oxazoline)‐poly(DL‐lactide) block copolymers

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