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See detailReversibly crosslinked thermo- and redox-responsive nanogels for controlled drug release
Liu, Ji ULg; Detrembleur, Christophe ULg; Hurtgen, Marie ULg et al

in Polymer Chemistry (2014), 5(1), 77-88

Reversibly crosslinked poly(vinyl alcohol)-b-poly(N-vinylcaprolactam) PVOH-b-PNVCL nanogels were prepared by using a redox-responsive crosslinking agent, 3,30-dithiodipropionic acid (DPA), to crosslink ... [more ▼]

Reversibly crosslinked poly(vinyl alcohol)-b-poly(N-vinylcaprolactam) PVOH-b-PNVCL nanogels were prepared by using a redox-responsive crosslinking agent, 3,30-dithiodipropionic acid (DPA), to crosslink the PVOH corona, above the lower critical solution temperature (LCST) of the PNVCL block. The stability of the as-prepared nanogels against heating and diluting with water was studied by dynamic light scattering (DLS) to follow the evolution of the hydrodynamic diameter and size distribution. Stability under reductive conditions was also studied by DLS and transmission electron microscopy (TEM) after exposure to dithiothreitol (DTT) buffer solutions at different pH. The reversibility of the crosslinking was evaluated by treating the de-crosslinked nanogels with hydrogen peroxide (H2O2) above the LCST. As a hydrophobic drug model, Nile red (NR) was loaded into the nanogels, and triggered release behaviours were studied after exposure to the same DTT buffer solutions. Moreover, two PVOH-b-PNVCL copolymers with different compositions and LCST were used to evaluate the effect of the LCST on the release behaviours of the nanogels. The cytotoxicity of the nanogels against a mouse fibroblast-like L929 cell line was assessed via the MTS assay, and preliminary studies on cellular uptake of the nanogels within human melanoma MEL-5 cells were also carried out by fluorescence microscopy and fluorescence-activated cell sorting. [less ▲]

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See detailPhotochemical properties and activity of water-soluble polymer/C60 nanohybrids for photodynamic therapy
Hurtgen, Marie ULg; Debuigne, Antoine ULg; Hoebeke, Maryse ULg et al

in Macromolecular Bioscience (2013), 13(1), 106-115

Water-soluble star-like poly(vinyl alcohol)/C60 and poly{[poly(ethylene glycol) acrylate]-co- (vinyl acetate)}/C60 nanohybrids are prepared by grafting macroradicals onto C60 and are assessed as ... [more ▼]

Water-soluble star-like poly(vinyl alcohol)/C60 and poly{[poly(ethylene glycol) acrylate]-co- (vinyl acetate)}/C60 nanohybrids are prepared by grafting macroradicals onto C60 and are assessed as photosensitizers for photodynamic therapy. The photophysical and biological properties of both nanohybrids highlight key characteristics influencing their overall efficiency. The macromolecular structure (linear/graft) and nature (presence/absence of hydroxyl groups) of the polymeric arms respectively impact the photodynamic activity and the stealthiness of the nanohybrids. The advantages of both nanohybrids are encountered in a third one, poly[(Nvinylpyrrolidone)- co-(vinyl acetate)]/C60, which has linear grafts without hydroxyl groups, and shows a better photodynamic activity. [less ▲]

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See detailMechanistic investigation and selectivity of the grafting onto C60 of macroradicals prepared by cobalt-mediated radical polymerization
Hurtgen, Marie ULg; Debuigne, Antoine ULg; Gigmes, Didier et al

in Polymer (2012), 53(20), 4353-4358

The grafting mechanism of poly(vinyl acetate) macroradicals prepared by cobalt-mediated radical polymerization onto C60 is investigated. The experimental conditions directly impact the nature and ... [more ▼]

The grafting mechanism of poly(vinyl acetate) macroradicals prepared by cobalt-mediated radical polymerization onto C60 is investigated. The experimental conditions directly impact the nature and stability of the PVAc/C60 adducts. In the presence of residual initiating radicals that can compete with PVAc! macroradicals for addition onto C60, mixtures of PVAc/C60 adducts having between one and eight polymer chains per C60 are formed. PVAc/C60 adducts prepared with low [PVAc]:[C60] ratios may contain weak C60-C60 bonds that further dissociate and account for the instability of the products. The formation of such dimers can be lessened by increasing the temperature from 30 !C to 100 !C. The temperature increase also allows a complete dissociation of the PVAc-Co dormant species into PVAc! macroradicals and an almost quantitative grafting of eight PVAc chains onto C60, leading to well-de!ned C60(PVAc)8 octa-adducts. These results might shed new light on the grafting onto C60 of macroradicals prepared by other CRP techniques. [less ▲]

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See detailOrganometallic-mediated radical polymerization of vinyl amides: Effect of metal coordination
Kermagoret, Anthony ULg; Morin, A.; Hurtgen, Marie ULg et al

Poster (2012, September 04)

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See detailOrganometallic-mediated radical polymerization of vinyl amides: Effect of metal coordination
Kermagoret, Anthony ULg; Morin, A.; Hurtgen, Marie ULg et al

Conference (2012, September 04)

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See detailSynthetic and mechanistic inputs of photochemistry into the bisacetylacetonatocobalt- mediated radical polymerization of n-butyl acrylate and vinyl acetate
Detrembleur, Christophe ULg; Versace, Davy-Louis; Piette, Yasmine et al

in Polymer Chemistry (2012), 3(7), 1856-1866

The input of photochemistry to the Co(acac)2 mediated radical polymerization (CMRP) of n-butyl acrylate and vinyl acetate is investigated for the first time. Upon UV irradiation, photoinitiators are able ... [more ▼]

The input of photochemistry to the Co(acac)2 mediated radical polymerization (CMRP) of n-butyl acrylate and vinyl acetate is investigated for the first time. Upon UV irradiation, photoinitiators are able to initiate the n-butyl acrylate polymerization that remains controlled up to very high molar masses (>4 × 106 g mol−1) with low polydispersities. The photoinitiator as well as the irradiation time must be appropriately chosen to reach acceptable initiator efficiencies while maintaining an optimal control over the polymerization. Laser flash photolysis experiments were then carried out to evidence the addition of alkyl and phosphonyl radicals onto Co(acac)2 and to determine the rate constants (kdeact) of these addition reactions that were still lacking. Finally, both kinetics of polymerization and spin-trapping experiments have evidenced that the C–Co bond at the extremity of the dormant polymer chains can be easily photocleaved. UV irradiation can therefore be considered as an additional lever for tuning the reactivity of the CMRP process mediated by Co(acac)2. [less ▲]

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See detailInterpolymer radical coupling: A toolbox complementary to controlled radical polymerization
Debuigne, Antoine ULg; Hurtgen, Marie ULg; Detrembleur, Christophe ULg et al

in Progress in Polymer Science (2012), 37(7), 1004-1030

The current review focuses on the relevance and practical benefit of interpolymer radical coupling methods. The latter are developing rapidly and constitute a perfectly complementary macromolecular ... [more ▼]

The current review focuses on the relevance and practical benefit of interpolymer radical coupling methods. The latter are developing rapidly and constitute a perfectly complementary macromolecular engineering toolbox to the controlled radical polymerization techniques (CRP). Indeed, all structures formed by CRP are likely to be prone to radical coupling reactions, which multiply the available synthetic possibilities. Basically, the coupling systems can be divided in two main categories. The first one, including the atom transfer radical coupling (ATRC), silane radical atom abstraction (SRAA) and cobalt-mediated radical coupling (CMRC), relies on the recombination of macroradicals produced from a dormant species. The second one, including atom transfer nitroxide radical coupling (ATNRC), single electron transfer nitroxide radical coupling (SETNRC), enhanced spin capturing polymerization (ESCP) and nitrone/nitroso mediated radical coupling (NMRC), makes use of a radical scavenger in order to promote the conjugation of the polymer chains. More than a compilation of macromolecular engineering achievements, the present review additionally aims to emphasize the particularities, synthetic potential and present limitations of each system. [less ▲]

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See detailSynthèse de copolymères amphiphiles originaux par polymérisation radicalaire contrôlée via des complexes de cobalt
Debuigne, Antoine ULg; Hurtgen, Marie ULg; Liu, Ji ULg et al

Conference (2012, June 05)

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See detailSynthesis of novel poly(N-vinyl amide)s containing copolymers by cobalt-mediated radical polymerization
Kermagoret, Anthony ULg; Hurtgen, Marie ULg; Liu, Ji ULg et al

Poster (2012, May 10)

Poly(N-vinyl amide)s are found in many applications due to their valued properties including water solubility, biocompatibility, metal-coordination ability, etc. Although N-vinyl amides are easily ... [more ▼]

Poly(N-vinyl amide)s are found in many applications due to their valued properties including water solubility, biocompatibility, metal-coordination ability, etc. Although N-vinyl amides are easily polymerized via radical pathways, their growing radicals are quite reactive due to the lack of stabilizing group, rendering the synthesis of well-defined poly(N-vinyl amide)s challenging. Thus, we explored the organometallic-mediated radical polymerization (OMRP) of a series of N-vinyl amides using bis(acetylacetonato)cobalt(II) as controlling agent in order to develop a platform for the precision synthesis of poly(N-vinyl amide)s. [less ▲]

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See detailMagnetic hybrid materials for triggered drug delivery and optical properties of intraocular lens
Liu, Ji ULg; Hurtgen, Marie ULg; Mornet, Stephan et al

Poster (2012, March 30)

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such ... [more ▼]

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such as temperature, pH, ionic strength, magnetic field, etc. Nanohybrids bearing an inorganic core and thermo-responsive polymer shell are particularly applicable in target delivery and controlled drug release. Poly (N-vinylcaprolactam) (PNVCL) and its copolymers, exhibiting lower critical solution temperature (LCST) where the transition between hydrophilic and hydrophobic state happens, is one of the optimal choices for this core/shell structure. Here we present the in-situ fabrication of thermo-responsive gold nanohybrids coated with a novel poly (vinyl alcohol)-b-poly (N-vinylcaprolactam) (PVOH-b-PNVCL) block copolymers, which were prepared by the cobalt-mediated radical polymerization (CMRP). The interaction between both PVOH and PNVCL segments and gold nanoparticles was confirmed by FT-IR spectra. A sharp thermo-induced phase transition with a good reversibility upon change in temperature was detected by DLS and UV/vis spectrometer. Furthermore, the presence of hydrophilic PVOH moieties endows the gold nanohybrids with improved colloidal stability above LCST without any flocculation detected. This kind of gold nanohybrids can be envisaged as a new drug delivery vehicle. [less ▲]

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See detailRadical coupling of polymers formed by cobalt-mediated radical polymerization
Debuigne, Antoine ULg; Hurtgen, Marie ULg; Jérôme, Christine ULg et al

in Matyjaszewski, Krzysztof; Sumerlin, Brent; Tsarevsky, Nicolas V. (Eds.) Progress in controlled radical polymerization: mechanisms and techniques (2012)

Considerable progress has been recently made in cobalt-mediated radical polymerization (CMRP), a controlled radical polymerization system based on the temporary deactivation of the polymer chains by a ... [more ▼]

Considerable progress has been recently made in cobalt-mediated radical polymerization (CMRP), a controlled radical polymerization system based on the temporary deactivation of the polymer chains by a cobalt complex, like the improvement of the mechanistic understanding, the extension to a range of monomers and the preparation of novel architectures. However, the real breakthrough in this field concerns the development of efficient radical coupling methods for polymer precursors preformed by CMRP. This book chapter aims to describe the general principle and main characteristics of such radical coupling techniques involving dienes, nitrones, fullerenes or carbon nanotubes. Well-defined and complex architectures obtained by these techniques are provided in order to illustrate their potential for macromolecular engineering. [less ▲]

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See detailSynthesis of thermo-responsive poly(N-vinylcaprolactam)-containing block copolymers by cobalt-mediated radical polymerization
Hurtgen, Marie ULg; Liu, Ji ULg; Debuigne, Antoine ULg et al

in Journal of Polymer Science. Part A, Polymer Chemistry (2012), 50(2), 400-408

Thermo-responsive block copolymers based on poly(N-vinylcaprolactam) (PNVCL) have been prepared by cobalt-mediated radical polymerization (CMRP) for the first time. The homopolymerization of NVCL was ... [more ▼]

Thermo-responsive block copolymers based on poly(N-vinylcaprolactam) (PNVCL) have been prepared by cobalt-mediated radical polymerization (CMRP) for the first time. The homopolymerization of NVCL was controlled by bis(acetylacetonato)cobalt(II) and a molecular weight as high as 46,000 g/mol could be reached with a low polydispersity. The polymerization of NVCL was also initiated from a poly(vinyl acetate)-Co(acac)2 (PVAc-Co(acac)2) macroinitiator to yield well-defined PVAc-b-PNVCL block copolymers with a low polydispersity (Mw/Mn = 1.1) up to high molecular weights (Mn = 87,000 g/mol), which constitutes a significant improvement over other techniques. The amphiphilic PVAc-b-PNVCL copolymers were hydrolyzed into unprecedented double hydrophilic poly(vinyl alcohol)-b-PNVCL (PVOH-b-PNVCL) copolymers and their temperature-dependent solution behavior was studied by turbidimetry and dynamic light scattering. Finally, the so-called cobalt-mediated radical coupling (CMRC) reaction was implemented to PVAc-b-PNVCL-Co(acac)2 precursors to yield novel PVAc-b-PNVCL-b-PVAc symmetrical triblock copolymers. [less ▲]

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See detailContribution of cobalt-mediated radical polymerization to macromolecular engineering and photodynamic therapy
Hurtgen, Marie ULg

Doctoral thesis (2011)

Cobalt-mediated radical polymerization (CMRP) is an emerging class of controlled radical polymerization technique based on the reversible deactivation of the propagating radicals by a cobalt complex. This ... [more ▼]

Cobalt-mediated radical polymerization (CMRP) is an emerging class of controlled radical polymerization technique based on the reversible deactivation of the propagating radicals by a cobalt complex. This thesis aims at broadening the nature, the structure, the properties and the end-use of (co)polymers accessible by CMRP. The first part of this work is devoted to the synthesis of novel statistical, graft and block copolymers by CMRP. First, the statistical copolymerization of conjugated (n-butyl acrylate) with a non-conjugated one (vinyl acetate) has been successfully controlled by bis(acetylacetonato)cobalt(II). The optimal experimental conditions were then implemented to the copolymerization of vinyl acetate with poly(ethylene glycol) acrylate, which yielded (quasi-)diblock amphiphilic graft copolymers for potential biomedical applications in one step. CMRP also revealed successful for the synthesis of well-defined thermo-responsive copolymers based on poly(N-vinylcaprolactam), either amphiphilic or double-hydrophilic at room temperature. In the second part of this thesis, we investigated the potential of CMRP for the synthesis of new agents for cancer photodynamic therapy. The synthesis of such photosensitizers relied on the chain-end functionalization by [60]fullerene of water-soluble (co)polymers (or precursors) prepared by CMRP. The photodynamic activity of poly(vinyl alcohol)/C60, poly(N-vinylpyrrolidone-co-vinyl acetate)/C60 and poly(PEG acrylate-co-vinyl acetate)/C60 nanohybrids were assessed through photophysical and in vitro experiments. Also, the ability of the nanohybrids to avoid recognition by the immune system was evaluated by a protein adsorption test. Finally, some hints on how to improve the synthesis of the nanohybrids - and therefore, their photodynamic activity - were provided by a mechanistic study of the grafting onto C60 of macroradicals released by cobalt end-capped polymers [less ▲]

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See detailStabilization of gold nanoparticles by thermo-responsive poly (vinyl alcohol)-b-poly (N-vinylcaprolactam) copolymers
Liu, Ji ULg; Hurtgen, Marie ULg; Detrembleur, Christophe ULg et al

Poster (2011, November 21)

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such ... [more ▼]

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such as temperature, pH, ionic strength, magnetic field, etc. Nanohybrids bearing an inorganic core and thermo-responsive polymer shell are particularly applicable in target delivery and controlled drug release. Poly (N-vinylcaprolactam) (PNVCL) and its copolymers, exhibiting lower critical solution temperature (LCST) where the transition between hydrophilic and hydrophobic state happens, is one of the optimal choices for this core/shell structure. Here we present the in-situ fabrication of thermo-responsive gold nanohybrids coated with a novel poly(vinyl alcohol)-b-poly(N-vinylcaprolactam) (PVOH-b-PNVCL) block copolymer prepared by the cobalt-mediated radical polymerization (CMRP). The interaction between both PVOH and PNVCL segments and gold nanoparticles was confirmed by FT-IR spectra. A sharp thermo-induced phase transition with a good reversibility upon change in temperature was detected by DLS and UV/vis spectrometer. Furthermore, the presence of hydrophilic PVOH moieties endows the gold nanohybrids with improved colloidal stability above LCST without any flocculation detected, compared with the gold nanoparticles stabilized with PNVCL homopolymer. This kind of gold nanohybrids can be envisaged as a new drug delivery vehicle. [less ▲]

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See detailPreparation and characterization of thermo-responsive gold nanohybrids
Liu, Ji ULg; Hurtgen, Marie ULg; Detrembleur, Christophe ULg et al

Poster (2011, October 25)

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such ... [more ▼]

Stimuli-responsive nano-materials have been playing increasingly important roles in the biomedical field due to their ability to alter the physico-chemical properties in response to external stimuli, such as temperature, pH, ionic strength, magnetic field, etc. Nanohybrids bearing an inorganic core and thermo-responsive polymer shell are particularly applicable in target delivery and controlled drug release. Poly (N-vinylcaprolactam) (PNVCL) and its copolymers, exhibiting lower critical solution temperature (LCST) where the transition between hydrophilic and hydrophobic state happens, is one of the optimal choices for this core/shell structure. Here we present the in-situ fabrication of thermo-responsive gold nanohybrids coated with a novel poly(vinyl alcohol)-b-poly(N-vinylcaprolactam) (PVOH-b-PNVCL) block copolymer prepared by the cobalt-mediated radical polymerization (CMRP). The interaction between both PVOH and PNVCL segments and gold nanoparticles was confirmed by FT-IR spectra. A sharp thermo-induced phase transition with a good reversibility upon change in temperature was detected by DLS and UV/vis spectrometer. Furthermore, the presence of hydrophilic PVOH moieties endows the gold nanohybrids with improved colloidal stability above LCST without any flocculation detected, compared with the gold nanoparticles stabilized with PNVCL homopolymer. This kind of gold nanohybrids can be envisaged as a new drug delivery vehicle. [less ▲]

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See detailSynthesis of 1-vinyl-3-ethylimidazolium-based ionic liquid (co)polymers by cobalt-mediated radical polymerization
Detrembleur, Christophe ULg; Debuigne, Antoine ULg; Hurtgen, Marie ULg et al

in Macromolecules (2011), 44(16), 6397-6404

The cobalt-mediated radical polymerization (CMRP) of 1-vinyl-3-ethylimidazolium bromide (VEtImBr) is described. Polymerizations were performed at 30 °C in solution either in dimethylformamide (DMF) or in ... [more ▼]

The cobalt-mediated radical polymerization (CMRP) of 1-vinyl-3-ethylimidazolium bromide (VEtImBr) is described. Polymerizations were performed at 30 °C in solution either in dimethylformamide (DMF) or in methanol (MeOH) or in a mixture of both solvents, using a preformed alkyl–cobalt(III) adduct, CH3OC(CH3)2CH2–C(CH3)(CN)–(CH2–CHOAc)<4–Co(acac)2, as the mediating agent. Excellent control over molecular weights and dispersities (Mw/Mn 1.05–1.06) was achieved in MeOH, with a linear increase of experimental molecular weights with the monomer conversion. Substituting methanol for DMF induced much faster polymerization process, even under quite high diluted conditions: for instance, about 80% monomer conversion was reached in 30 min in DMF, compared to 10 h in MeOH. However, size exclusion chromatography (SEC) traces of PVEtImBr samples synthesized in DMF revealed a side population in the high molecular weight region, presumably due to the occurrence of irreversible coupling reactions of a small proportion of growing chains. Well-defined diblock copolymers featuring both a poly(vinyl acetate) (PVAc) block and a PVEtImBr-based poly(ionic liquid) block, PVAc-b-PVEtImBr, were next obtained by sequential CMRP of VAc and VEtImBr. To this end, a PVAc-Co(acac)2 was first prepared by CMRP and employed as a macroinitiator for the polymerization of VEtImBr either in methanol or in a mixture of DMF and MeOH (2/1: v/v) at 30 °C. Finally, cobalt-mediated radical coupling (CMRC) of the aforementioned PVAc-b-PVEtImBr diblock copolymers, using isoprene as a simple coupling agent, led to unprecedented and structurally well-defined PVAc-b-PVEtImBr-b-PVAc triblock copolymers. [less ▲]

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See detailOrganometallic-mediated radical polymerization: unusual route toward (quasi-) diblock graft copolymers starting from a mixture of monomers of opposed reactivity
Hurtgen, Marie ULg; Debuigne, Antoine ULg; Fustin, Charles-André et al

in Macromolecules (2011), 44(12), 4623-4631

Graft copolymers have been prepared by one-step organometallic-mediated radical polymerization (OMRP) for the first time. Poly(ethylene glycol) acrylate (PEGA) was copolymerized with vinyl acetate (VAc ... [more ▼]

Graft copolymers have been prepared by one-step organometallic-mediated radical polymerization (OMRP) for the first time. Poly(ethylene glycol) acrylate (PEGA) was copolymerized with vinyl acetate (VAc) to yield well-defined P(PEGA-grad-VAc) gradient graft copolymers using bis(acetylacetonato)cobalt(II) as the control agent. The influence of experimental parameters such as the PEGA/VAc molar ratio, the nature of the initiator, and the temperature on the control of the copolymerization was discussed. The use of an excess of cobalt complex appeared as a key parameter to maintain a good level of control when higher contents of acrylate were used in the comonomer feed. The reactivity ratios were estimated and revealed that PEGA was added around 30 times faster than VAc, which gave access to a gradient P(PEGA-grad-VAc) copolymer or to a P(PEGA-grad-VAc)-b-PVAc diblock copolymer when the VAc polymerization was pursued after the full consumption of PEGA. The amphiphilic character of the copolymers makes them prone to self-assemble into micelles in water, as evidenced by dynamic light scattering. [less ▲]

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