Amphiphilic polymers based on polyoxazoline as relevant nanovectors for photodynamic therapy

Oudin, Amandine; Chauvin, Julie; Gibot, Laure; Rols, Marie‐Pierre; Balor, Stéphanie; Goudounèche, Dominique; Payré, Bruno; Lonetti, Barbara; Vicendo, Patricia; Mingotaud, Anne‐Françoise; Lapinte, Vincent

doi:10.1039/c9tb00118b

Cited by 17 publications

(15 citation statements)

References 51 publications

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“…Graft copolymers with hydrophobic polytyrosine or polycaprolactone backbones and hydrophilic POx side chains and heterografted comb polymers comprising PLA and PEtOx side chains are capable of self-assembly and of encapsulating hydrophobic dyes. For instance, the micellization of poly(2-nitrobenzyl acrylate) as a hydrophobic building block and PEtOx was more straightforward in a graft copolymer architecture than that of the linear block copolymer. , Also, more complex systems comprising coumarin moieties revealed micellization and enabled the encapsulation of a hydrophobic photosensitizer. , However, to the best of our knowledge, the in vivo performance of POx-based graft copolymer micelles has not been reported so far.…”

Section: Introductionmentioning

confidence: 98%

“…28,29 Also, more complex systems comprising coumarin moieties revealed micellization and enabled the encapsulation of a hydrophobic photosensitizer. 30,31 However, to the best of our knowledge, the in vivo performance of POx-based graft copolymer micelles has not been reported so far. Graft copolymers enable a more flexible design than linear block copolymers.…”

Section: Introductionmentioning

confidence: 98%

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Stealth Effect of Short Polyoxazolines in Graft Copolymers: Minor Changes of Backbone End Group Determine Liver Cell-Type Specificity

et al. 2021

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Dye-loaded micelles of 10 nm diameter formed from amphiphilic graft copolymers composed of a hydrophobic poly(methyl methacrylate) backbone and hydrophilic poly(2-ethyl-2-oxazoline) side chains with a degree of polymerization of 15 were investigated concerning their cellular interaction and uptake in vitro as well as their interaction with local and circulating cells of the reticuloendothelial system in the liver by intravital microscopy. Despite the high molar mass of the individual macromolecules (M n ≈ 20 kg mol–1), backbone end group modification by attachment of a hydrophilic anionic fluorescent probe strongly affected the in vivo performance. To understand these effects, the end group was additionally modified by the attachment of four methacrylic acid repeating units. Although various micelles appeared similar in dynamic light scattering and cryo-transmission electron microscopy, changes in the micelles were evident from principal component analysis of the Raman spectra. Whereas an efficient stealth effect was found for micelles formed from polymers with anionically charged or thiol end groups, a hydrophobic end group altered the micelles’ structure sufficiently to adapt cell-type specificity and stealth properties in the liver.

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 98%

Stealth Effect of Short Polyoxazolines in Graft Copolymers: Minor Changes of Backbone End Group Determine Liver Cell-Type Specificity

et al. 2021

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“…Herein, the challenge was to combine poly(2-ethyl-2-oxazoline) (POx) backbone with phosphonic acid moieties. Polyoxazoline was chosen for its biocompatibility, nontoxicity, its versatility, tunable properties, [47][48][49][50][51] and to ensure hydrosolubility. It was first partially hydrolyzed to lead to poly(2-alkyl-2-oxazoline)-stat-poly(ethylenimine) (POx-st-PEI), which allowed the introduction of phosphonated moieties.…”

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confidence: 99%

Hydrosoluble phosphonic acid functionalized poly(2‐ethyl‐2‐oxazoline) chelating polymers for the sorption of metallic cations

Benkhaled

Montheil

Lapinte

et al. 2020

Journal of Polymer Science

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In the present contribution, the synthesis of well-defined water-soluble phosphonic-acid based poly(2-ethyl-2-oxazoline) and the preliminary study of their sorption properties were reported. For such purpose, poly(2-ethyl-2-oxazoline) (POx) was first prepared. Then, controlled hydrolysis allowed the obtaining of statistical poly(2-ethyl-2-oxazoline)-stat-poly(ethyleneimine) (POx-st-PEI) with 20% of ethyleneimine units, which allowed maintaining water solubility of the copolymers. The latter were successfully functionalized with either dimethyl(acryloyloxymethyl) phosphonate (APC1) or diethyl-2-(acrylamido)ethylphosphonate (DAAmEP) using Michael reaction. Phosphonated esters were hydrolyzed to produce phosphonic acid groups, thus, leading to hPOx-st-PEI-APC1 and hPOx-st-PEI-DAAmEP copolymers. Finally, functionalized statistical copolymers were successfully used for the sorption of divalent or trivalent metallic cations. The reported work aims at reporting the synthesis of original polyoxazoline materials functionalized with phosphonic acid groups that could be further employed for water treatment in polymer enhanced ultrafiltration processes.

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“…18−21 They are regularly discussed as one of the potential alternatives to PEG. 11,20,22−25 Accordingly, pMeOx and pEtOx have been used widely as hydrophilic polymer components, e.g., in polymer nanoparticles 26 and micelles (in combination with other hydrophobic POx, e.g., with 2-butyl, 2-nonyl, or 2isopropyl-2-oxazoline 27 ), polymer−peptide conjugates, 28,29 polymer−protein conjugates, 30 lipopolymers for liposome stabilization, 19 polymer−drug conjugates, 31 and antimicrobial polymers. 32 While the toolbox of 2-substituted 2-oxazolines and their corresponding polymers has been expanding rapidly, however, work on monomers and polymers with additional substituents in the 4-and 5-position is quite limited.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Investigation of Chiral Poly(2,4-disubstituted-2-oxazoline)-Based Triblock Copolymers, Their Self-Assembly, and Formulation with Chiral and Achiral Drugs

Yang¹,

Haider²,

Forster³

et al. 2022

Macromolecules

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Considering the largely chiral nature of biological systems, there is interest in chiral drug delivery systems. Here, we investigate for the first time polymer micelles based on poly(2-oxazoline) (POx) ABA-type triblock copolymers with chiral and racemic hydrophobic blocks for the formulation of chiral and achiral drugs. Specifically, poly(2-ethyl-4-ethyl-2oxazoline) (pEtEtOx) and poly(2-propyl-4-methyl-2-oxazoline) (pPrMeOx) were used as hydrophobic block B and poly(2-methyl-2-oxazoline) (pMeOx) as hydrophilic block A. Using these triblock copolymers, nanoformulations of curcumin (CUR), paclitaxel (PTX), and chiral (R and S) and racemic ibuprofen were prepared. For CUR and PTX, the maximum drug loading was significantly dependent on the structure of the hydrophobic repeat units, but not the chirality. In contrast, the maximum drug loading with chiral/racemic ibuprofen was affected neither by the polymer structure nor by chirality, but minor effects were observed with respect to the size and size distribution of the drug-loaded micelles.

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Amphiphilic polymers based on polyoxazoline as relevant nanovectors for photodynamic therapy

Abstract: Coumarin crosslinked polyoxazoline-based vectors developed for efficient photodynamic therapy.

Cited by 17 publications

References 51 publications

Stealth Effect of Short Polyoxazolines in Graft Copolymers: Minor Changes of Backbone End Group Determine Liver Cell-Type Specificity

Stealth Effect of Short Polyoxazolines in Graft Copolymers: Minor Changes of Backbone End Group Determine Liver Cell-Type Specificity

Hydrosoluble phosphonic acid functionalized poly(2‐ethyl‐2‐oxazoline) chelating polymers for the sorption of metallic cations

Synthesis and Investigation of Chiral Poly(2,4-disubstituted-2-oxazoline)-Based Triblock Copolymers, Their Self-Assembly, and Formulation with Chiral and Achiral Drugs

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