References of "Riva, Raphaël"
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See detailPolyphosphoesters as a new platform for the design of particulate drug delivery systems
Vanslambrouck, Stéphanie; Ergul Yilmaz, Zeynep; Debuigne, Antoine ULg et al

Conference (2016, June)

Thanks to their biocompatibility and degradability properties, polyphosphates are appealing polymers for biomedical applications. In contrast to aliphatic polyesters, such as poly(ε-caprolactone) and poly ... [more ▼]

Thanks to their biocompatibility and degradability properties, polyphosphates are appealing polymers for biomedical applications. In contrast to aliphatic polyesters, such as poly(ε-caprolactone) and poly(lactide), the pentavalency of the phosphorus atom allows the easy modification of the polyphosphate properties by simply adjusting the nature, the length and the functionality of the polyphosphate pendant groups. Therefore, macromolecular engineering of polyphosphoesters was applied to design well-defined architectures and functionalities adapted to drug nanocarriers. In a first approach, amphiphilic block copolymers are synthesized by organo-catalyzed ring-opening polymerization process for the synthesis of a range of PEO-b-polyphosphate bearing various pendant groups. Post-polymerization thiol-ene click reactions preformed on PEO-b-polyphosphate copolymers was also investigated to improve the hydrophobicity of the polyphosphate. The self-assembly of these PEO-b-polyphosphate copolymers into micelles was investigated, particularly, the effect of the nature of the polyphosphate pendant groups (i) on the micelles characteristics, (ii) on the encapsulation of a poorly soluble drug and (iii) on the drug release profile. The toxicity of the different amphiphilic block copolymers was also evaluated by live/dead cell viability assays. In a second approach, double hydrophilic copolymers based on polyphosphoesters have been used as templating agent for the synthesis of calcium carbonate particles. Indeed, the use of such microparticles is becoming more and more attractive in many fields especially for biomedical applications for which fine tuning of size, morphology and crystalline form of CaCO3 particles is crucial. Although some structuring compounds, like hyaluronic acid, give satisfying results, the control of the particle structure still has to be improved. To this end, we evaluated the CaCO3 structuring capacity of the well-defined double hydrophilic block copolymers composed of poly(ethylene oxide) and of a polyphosphoester segment with affinity for calcium like poly(phosphotriester)s bearing pendant carboxylic acids or poly(phosphodiester)s with a negatively charged oxygen atom on each repeating monomer unit. [less ▲]

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See detailPolyphosphoester containing amphiphilic block copolymers as drug nanocarriers
Yilmaz-Ergül, Zeynep ULg; Vanslambrouck, Stéphanie; Thiry, Justine ULg et al

Poster (2016, May 23)

The design of drug delivery systems (DDS) often requires biodegradable and biocompatible materials that allow safe retention and controlled release of the drug. In this respect, poly(ethylene oxide)-b ... [more ▼]

The design of drug delivery systems (DDS) often requires biodegradable and biocompatible materials that allow safe retention and controlled release of the drug. In this respect, poly(ethylene oxide)-b-polyphosphoester amphiphilic block copolymers are known to self-assemble into polymer micelles when placed in water are appropriate drug carriers. In this work, an unsaturated alkene side-chain was introduced on the cyclic phosphate monomer according to a one-step reaction followed by its organocatalyzed polymerization initiated by a poly(ethylene oxide) macroinitiator. After self-assembly into water, the micelles were cross-linked by UV irradiation. Then, these cross-linked micelles have been loaded by doxorubicin, which is a drug to use in cancer therapy. We observed that the doxorubicin loading increased with the number of double bonds on the polyphosphate block of non-cross-linked micelles. This diblock amphiphilic copolymer bearing pendant unsaturations appears thus particularly promising candidate to build micellar drug delivery systems for intravenous injection. [less ▲]

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See detailComprehensive study of the thermo-reversibility of Diels-Alder based PCL polymer networks
Defize, Thomas ULg; Thomassin, Jean-Michel ULg; Alexandre, Michaël et al

in Polymer (2016), 84

Chemical crosslinking is an efficient tool to improve or impart new properties to conventional polymers. Especially, crosslinking imparts remarkable shapeememory properties to poly-ε-caprolactone (PCL ... [more ▼]

Chemical crosslinking is an efficient tool to improve or impart new properties to conventional polymers. Especially, crosslinking imparts remarkable shapeememory properties to poly-ε-caprolactone (PCL) materials. Nevertheless, the processing of networks is often tricky due to infusibility and insolubility of cross-linked chains. Therefore, the synthesis of PCL networks including thermo-reversible crosslinks based on (retro)-Diels-Alder (DA) reaction were developed to allowpreserving the melt-processing while keeping the required mechanical properties below the melting point. This paper aims at studying in depth, such thermo-dependent network formation and stability. Besides conventional swelling experi- ments, Raman spectroscopy was revealed as a powerful tool to follow the formation of the DA adduct during the crosslinking. In combination with rheological measurements, we were able to determine the most appropriate temperatures to form the network (DA crosslinking) and to process it (retro-DA re- action) without degradation of the material. [less ▲]

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See detailCore cross-linked micelles of polyphosphoester containing amphiphilic block copolymers as drug nanocarriers
Ergül, Zeynep ULg; Vanslambrouck, Stéphanie; Cajot, Sébastien et al

in RSC Advances (2016), 6(48), 42081-42088

Poly(ethylene oxide)-b-polyphosphoester amphiphilic block copolymers are known to self-assemble into polymer micelles when dissolved into water. This work aims at reporting on the improvement of the ... [more ▼]

Poly(ethylene oxide)-b-polyphosphoester amphiphilic block copolymers are known to self-assemble into polymer micelles when dissolved into water. This work aims at reporting on the improvement of the stability of the micelles at high dilution by crosslinking the hydrophobic polyphosphoester micellar core. Typically, an unsaturated alkene side-chain was introduced on the cyclic phosphate monomer according to a one-step reaction followed by its organocatalyzed polymerization initiated by a poly(ethylene oxide) macroinitiator. This strategy avoids the use of any organometallic compounds in order to facilitate the purification and meet the stringent requirements of biomedical applications. After self-assembly into water, the micelles were cross-linked by simple UV irradiation. These cross-linked micelles have then been loaded by doxorubicin to evaluate their potential as drug nanocarriers and monitor the impact of crosslinking on the release profile. [less ▲]

Detailed reference viewed: 30 (11 ULg)
See detailSynthesis of functional polyphosphates for hydrogel and particle drug delivery systems
Vanslambrouck, Stéphanie; Ergül, Zeynep ULg; Clément, Benoit et al

Conference (2015, December 02)

Thanks to their biocompatibility and degradability properties, polyphosphates are appealing polymers for biomedical applications. In contrast to aliphatic polyesters, such as poly(ε-caprolactone) and poly ... [more ▼]

Thanks to their biocompatibility and degradability properties, polyphosphates are appealing polymers for biomedical applications. In contrast to aliphatic polyesters, such as poly(ε-caprolactone) and poly(lactide), the pentavalency of the phosphorus atom allows the easy modification of the polyphosphate properties by simply adjusting the nature, the length and the functionality of the polyphosphate pendant groups. Macromolecular engineering of polyphosphoesters was applied to design well-defined architectures and functionalities adapted to drug nanocarriers. In a first approach, amphiphilic block copolymers are synthesized by organo-catalyzed ring-opening polymerization process for the synthesis of a range of PEO-b-polyphosphate bearing various pendant groups. Post-polymerization thiol-ene click reactions preformed on PEO-b-polyphosphate copolymers was also investigated to improve the hydrophobicity of the polyphosphate. The self-assembly of these PEO-b-polyphosphate copolymers into micelles was investigated, particularly, the effect of the nature of the polyphosphate pendant groups (i) on the micelles characteristics, (ii) on the encapsulation of a poorly soluble drug and (iii) on the drug release profile. The toxicity of the different amphiphilic block copolymers was also evaluated by live/dead cell viability assays. In a second approach, double hydrophilic copolymers based on polyphosphoesters have been used as templating agent for the synthesis of calcium carbonate particles. Indeed, the use of such microparticles is becoming more and more attractive in many fields especially for biomedical applications for which fine tuning of size, morphology and crystalline form of CaCO3 particles is crucial. Although some structuring compounds, like hyaluronic acid, give satisfying results, the control of the particle structure still has to be improved. To this end, we evaluated the CaCO3 structuring capacity of the well-defined double hydrophilic block copolymers composed of poly(ethylene oxide) and of a polyphosphoester segment with affinity for calcium like poly(phosphotriester)s bearing pendant carboxylic acids or poly(phosphodiester)s with a negatively charged oxygen atom on each repeating monomer unit. [less ▲]

Detailed reference viewed: 59 (8 ULg)
See detailDevelopment of photo- or thermo-reversible cross-linked recyclable shape-memory materials
Defize, Thomas ULg; Riva, Raphaël ULg; Thomassin, Jean-Michel ULg et al

Conference (2015, September 01)

Shape-memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus ... [more ▼]

Shape-memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus, such as heat or light. Typically, the shape-memory property is generally observed for chemically or physically cross-linked polymers that exhibit an elastomeric behavior above a phase transition, e.g. glass or melting transition. As an example, cross-linked semi-crystalline poly(ε-caprolactone) (PCL) is widely studied for the development of SMPs. As most of SMPs are irreversibly cross-linked material, their reprocessing is impossible preventing any recycling. Thereby, reversible reactions, allowing the formation/cleavage of the network, raise tremendous interest for the development of new SMPs. Recently, we reported the preparation reversibly cross-linked PCL-based SMP using the Diels-Alder (DA) reaction between furan and maleimide end-groups of 4-arm star-shaped PCL, well-known to create reversible bonds. After implementation, this shape-memory material was demonstrated to be recyclable, and was characterized by excellent fixity and recovery before and after recycling experiments. However, the relatively low retro DA temperature of the furan-maleimide adducts led to an inelastic deformation during shape-memory tensile cycles. In order to get rid of this drawback, an alternative approach was investigated. The substitution of the DA reaction by a photo-reversible reaction, typically the photo-induced (2+2) cycloaddition of coumarins, was proposed to prepare cross-linked PCL matrix presenting one-way and two-way memory properties, since photolabile adducts are supposed to be stable during shape-memory tensile cycles. [less ▲]

Detailed reference viewed: 67 (5 ULg)
See detailCross-linked polymer micelles made of polyphosphate containing amphiphilic copolymers for drug delivery
Riva, Raphaël ULg; Vanslambrouck, Stéphanie ULg; Ergül, Zeynep ULg et al

Conference (2015, September 01)

In the pharmaceutical field, amphiphilic block copolymers are of great interest for the nanovectorization of active principles in Drug Delivery. Indeed, new drugs are synthesized each day but in too many ... [more ▼]

In the pharmaceutical field, amphiphilic block copolymers are of great interest for the nanovectorization of active principles in Drug Delivery. Indeed, new drugs are synthesized each day but in too many cases, their high hydrophobicity makes them useless because of the absence of an appropriated administration method. Typically, amphiphilic block copolymers present the remarkable property to self-assemble in water with formation, in most cases, of spherical micelles characterized by a hydrophobic core and a hydrophylic corona. Rapidly, their ability to encapsulate a hydrophobic drug in their hydrophiobic core was investigated to increase the solubility of the drug in aqueous media, prevent its degradation and decrease its toxicity. However, polymer micelles suffer of the main drawback to be unstable in diluted medium, leading to a premature release of the drug, when the concentration falls down the critical micellar concentration (CMC), which it is rapidly observed after intravenous injection. This work aims at reporting on the development of a drug delivery device based on a new amphiphilic block copolymers made of degradable polyphosphate and bioeliminable poly(ethylene oxide). Thanks to their biocompatibility, biodegradability and their structure similar to natural biomacromolecules, polyphosphates are appealing polymers for biomedical applications. In contrast to aliphatic polyesters, polyphosphate properties and functionality are easily tuned via the chemical nature of the lateral chains R. In order to get rid of the CMC, the crosslinking of the micelle’s core was realized by UV radiation, in order to fulfill the increasingly stringent requirements of biomedical applications. For this purpose, photo-cross-linkable groups were introduced on the polyphosphate backbone. The effect of the crosslinking rate on the drug loading and the drug release was evaluated using doxorubicin as model drug. [less ▲]

Detailed reference viewed: 321 (8 ULg)
See detailPhoto- and thermo-reversible crosslinked recyclable shape memory materials
Defize, Thomas ULg; Riva, Raphaël ULg; Thomassin, Jean-Michel ULg et al

Poster (2015, July 02)

Shape memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus ... [more ▼]

Shape memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus; such as heat or light. Typically; the shape memory property is generally observed for chemically or physically cross-linked polymers that exhibit an elastomeric behavior above a phase transition; e.g. glass or melting transition. As an example; cross-linked semi-crystalline poly(ε-caprolactone) (PCL) is widely studied for the development of SMPs. As most of SMPs are irreversibly cross-linked material; their reprocessing is impossible preventing any recycling. Thereby; reversible reactions; allowing the formation/cleavage of the network; raise tremendous interest for the development of new SMPs. Recently, we reported the preparation reversibly cross-linked PCL-based SMP using the Diels-Alder (DA) reaction between furan and maleimide end-groups of 4-arm star-shaped PCL, well-known to create reversible bonds. After implementation, this shape memory material was demonstrated to be recyclable, and was characterized by excellent fixity and recovery before and after recycling experiments. However, the relatively low retro DA temperature of the furan-maleimide adducts led to an inelastic deformation during shape memory tensile cycles. In order to get rid of this drawback, an alternative approach was investigated. The substitution of the DA reaction by a photo-reversible reaction, typically the photo-induced (2+2) cycloaddition of coumarins, was proposed to prepare cross-linked PCL matrix presenting one-way and two-way memory properties, since photolabile adducts are supposed to be stable during shape memory tensile cycles. [less ▲]

Detailed reference viewed: 82 (6 ULg)
See detailAliphatic polyphosphates: a promising family of polymers for drug delivery
Vanslambrouck, Stéphanie ULg; Clément, Benoit; Riva, Raphaël ULg et al

Poster (2015, May 18)

Thanks to their biocompatibility and biodegradability, polyphosphates are appealing polymers for biomedical applications. In contrast to polyesters, polyphosphate properties and functionality are easily ... [more ▼]

Thanks to their biocompatibility and biodegradability, polyphosphates are appealing polymers for biomedical applications. In contrast to polyesters, polyphosphate properties and functionality are easily tuned via the chemical nature of the lateral chains. In this work, a series of amphiphilic PEO-block-polyphosphate copolymers were synthesized by organo-catalyzed ring-opening polymerization of cyclic phosphates. These polymers are directly dissolved in water in the absence of any organic solvent and they self-assemble to form nanoparticles Our work aims at changing the lateral chain of polyphosphates to investigate the influence of this structural modification on (i) the size of the nanoparticles, (ii) the critical aggregation concentration, (iii) the encapsulation of an hydrophobic drug in the core of the nanoparticles and, finally, (iv) the release of the drug. [less ▲]

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See detailPoly(ethylene glycol) grafted polylactide based copolymers for the preparation of PLA-based nanocarriers and hybrid hydrogel
Riva, Raphaël ULg; Schmeits, Stéphanie; Croisier, Florence ULg et al

in Clinical Hemorheology and Microcirculation (2015), 60

In previous works, poly(D,L-lactide-co-?CL-poly(ethylene glycol) (poly(D,L-La-co-?PEG?CL) amphiphilic graft- 10 copolymers were successfully synthesized according to a copper azide-alkyne cycloaddition ... [more ▼]

In previous works, poly(D,L-lactide-co-?CL-poly(ethylene glycol) (poly(D,L-La-co-?PEG?CL) amphiphilic graft- 10 copolymers were successfully synthesized according to a copper azide-alkyne cycloaddition (CuAAC) strategy. This paper aims 11 at reporting on the behavior of this amphiphilic copolymer in water, which was not studied in the previous paper. Moreover, 12 the ability of the copolymer to stabilize a PLA nanoparticles aqueous suspension is presented. For this purpose, dynamic 13 light scattering (DLS) and transmission electron microscopy (TEM) are proposed to characterize the nanoparticles in solution. 14 Otherwise, the strategy developed for the synthesis of the amphiphilic copolymers was adapted and extended to the synthesis of 15 PLA-based degradable hydrogel, potentially applicable as drug-loaded degradable polymer implant. [less ▲]

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See detailSynthesis and tensioactive properties of PEO-b-polyphosphate copolymers
Vanslambrouck, Stéphanie ULg; Clément, Benoit; Riva, Raphaël ULg et al

in RSC Advances (2015), 5(35), 27330-37337

Poly(ethylene oxide) (PEO)-b-polyphosphate copolymers made of hydrophilic PEO and hydrophobic polyphosphates are amphiphilic copolymers prone to self-assemble in water into nanoparticles. In this work ... [more ▼]

Poly(ethylene oxide) (PEO)-b-polyphosphate copolymers made of hydrophilic PEO and hydrophobic polyphosphates are amphiphilic copolymers prone to self-assemble in water into nanoparticles. In this work, nanoparticles are obtained by the self-assembly of PEO-b-polyphosphate copolymers in water in the absence of any organic co-solvent whatever the length of the pendant alkyl chain (between 4 and 7 carbon atoms) of the polyphosphate block. Remarkably, this solvent-free process remains efficient even for the most hydrophobic polyphosphate blocks. The critical aggregation concentration (CAC) of the block copolymers was determined by pyrene probe fluorescence. Finally, the efficiency of these copolymer surfactants to decrease the air–water interface was measured by air-bubble tensiometry. [less ▲]

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See detailDirect route to well-defined poly(ionic liquid)s by controlled radical polymerization in water
Cordella, Daniela ULg; Kermagoret, Anthony ULg; Debuigne, Antoine ULg et al

in ACS Macro Letters (2014), 3

The precision synthesis of poly(ionic liquid)s (PILs) in water is achieved for the first time by the cobalt-mediated radical polymerization (CMRP) of N-vinyl-3-alkylimidazolium-type monomers following two ... [more ▼]

The precision synthesis of poly(ionic liquid)s (PILs) in water is achieved for the first time by the cobalt-mediated radical polymerization (CMRP) of N-vinyl-3-alkylimidazolium-type monomers following two distinct protocols. The first involves the CMRP of various 1-vinyl-3-alkylimidazolium bromides conducted in water in the presence of an alkyl–cobalt(III) complex acting as a monocomponent initiator and mediating agent. Excellent control over molar mass and dispersity is achieved at 30 °C. Polymerizations are complete in a few hours, and PIL chain-end fidelity is demonstrated up to high monomer conversions. The second route uses the commercially available bis(acetylacetonato)cobalt(II) (Co(acac)2) in conjunction with a simple hydroperoxide initiator (tert-butyl hydroperoxide) at 30, 40, and 50 °C in water, facilitating the scaling-up of the technology. Both routes prove robust and straightforward, opening new perspectives onto the tailored synthesis of PILs under mild experimental conditions in water. [less ▲]

Detailed reference viewed: 67 (13 ULg)
See detailRecyclable shape-memory materials based on photo or thermo-reversible crosslinking
Defize, Thomas ULg; Riva, Raphaël ULg; Wauters, Céline et al

Poster (2014, November 11)

Shape memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus ... [more ▼]

Shape memory polymers (SMPs) are remarkable materials able to switch from a stressed deformed state (temporary shape) to their initial relaxed state (permanent shape) by the application of a stimulus, such as heat or light. Typically, the shape memory property is generally observed for chemically or physically cross-linked polymers that exhibit an elastomeric behavior above a phase transition, e.g. glass or melting transition. Cross-linked semi-crystalline poly(ε-caprolactone) (PCL) is already widely studied for the development of SMPs. However, the tensile strength of standard PCL-based SMPs remains quite low, limiting their use in some applications. A convenient way to enhance the strength of SMPs relies on the introduction of nanofillers, such as silica nanoparticles, leading to an enhancement of mechanical strength. Moreover, silica nanoparticles can be advantageously used as multifunctional crosslinking nodes, with the purpose to increase the cross-linking density of the material. As most of SMPs are irreversibly cross-linked material, their reprocessing is impossible preventing any recycling. Thereby, reversible reactions, allowing the formation/cleavage of the network, raise tremendous interest in macromolecular engineering. Recently, a reversibly cross-linked 4-arm star-shaped PCL-based SMP was prepared using the Diels-Alder (DA) reaction between furan and maleimide moieties, well-known to create reversible bonds. This shape memory material demonstrated to be implementable, and so recyclable, and was characterized by excellent fixity and recovery before and after recycling experiments. However, the relatively low retro-DA temperature of the furan- maleimide adducts led to an inelastic deformation during shape memory tensile cycles. In order to get rid of this drawback, two alternative approaches were investigated. Firstly, the substitution of the DA reaction by a photo-reversible reaction, typically the photo- induced (2+2) cycloaddition of coumarins, was proposed to crosslink the PCL matrix. The second approach is based on the use of surface functionalized silica nanoparticles as crosslinking nodes with the purpose to increase the crosslinking density of the material. The network formation and cleavage were studied by solid-state NMR and rheology.4 The resulting shape memory materials were characterized by excellent one-way and two-way shape memory properties as demonstrated by dynamical mechanical analysis. [less ▲]

Detailed reference viewed: 56 (2 ULg)
See detailSmart cross-linked polymer micelles for drug delivery
Riva, Raphaël ULg; Vanslambrouck, Stéphanie ULg; Ergül, Zeynep ULg et al

Conference (2014, November 11)

Nowadays, polymer crosslinking is widely used in industry to improve or to impart new properties to existing polymer material. In the pharmaceutical field, polymer crosslinking is of great interest for ... [more ▼]

Nowadays, polymer crosslinking is widely used in industry to improve or to impart new properties to existing polymer material. In the pharmaceutical field, polymer crosslinking is of great interest for the elaboration of drug delivery devices, mostly hydrogels. Nevertheless, crosslinking is also very useful in nanovectorization of active principle. Indeed, each day, new drugs are synthesized and available on the market but in too many cases, the high hydrophobicity of some drugs makes them useless because of the absence of an appropriated administration method. The encapsulation of the drug into a nanocarrier, typically in the hydrophobic core of a polymer micelle, allows a significant increase of the drugs concentration in water in addition to the protection of the active principle against degradation. However, polymer micelles suffer of the main drawback to not be stable, leading to a premature release of the drug, when the concentration falls down the critical micellar concentration (CMC), which it is rapidly observed after intravenous injection. In order to get rid of the CMC, crosslinking of the micelle core is the most proposed strategy. Nevertheless, the crosslinking of the micelle core may have a non-negligible effect on the drug loading but mainly on the drug release due to the sequestration of the drug in the network. Over the last years, our lab investigated several strategies for the crosslinking of the micelle core made of amphiphilic and biocompatible block copolymers generally by UV radiation in order to fulfill the increasingly stringent requirements of biomedical applications. These strategies are very helpful to prepare injectable nanosized cross-linked particles loaded with an active particle. For some systems, the effect of the crosslinking rate on the drug loading and the drug release was evaluated using a model drug. As the crosslinking may interfere with the drug release after internalization of the carrier into the cell, a reversible crosslinking of the micelle core was proposed. Typically, the introduction of disulfide bond as inter-chain links allowed to delay the drug release by diffusion whereas into the cell, the reduction of the disulfide bridges into corresponding thiol led to the fast disassemble of the micelle and the specific release of the drug into cytoplasm. [less ▲]

Detailed reference viewed: 172 (10 ULg)
See detailAmphiphilic copolymers containing polyphosphates for drug delivery applications
Vanslambrouck, Stéphanie ULg; Clément, Benoit; Riva, Raphaël ULg et al

Poster (2014, September 19)

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See detailMicellization of PEO-b-polyphosphate for drug delivery applications
Vanslambrouck, Stéphanie ULg; Clément, Benoit; Riva, Raphaël ULg et al

Conference (2014, July 11)

Detailed reference viewed: 35 (12 ULg)
See detailStructure-morphology relationship of polyphosphate containing polymer micelles
Vanslambrouck, Stéphanie ULg; Clément, Benoit; Riva, Raphaël ULg et al

Conference (2014, June 18)

Detailed reference viewed: 18 (5 ULg)