References of "Lecomte, Philippe"
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See detailRethinking alkylating(-like) agents for solid tumor management
Lajous, Hélène; Lelièvre, Bénédicte; Vauléon, Bénédicte et al

in Trends in Pharmacological Sciences (2019), 40(5), 342-357

Although old molecules, alkylating agents and platinum derivatives are still widely used in the treatment of various solid tumors. However, systemic toxicity and cellular resistance mechanisms impede ... [more ▼]

Although old molecules, alkylating agents and platinum derivatives are still widely used in the treatment of various solid tumors. However, systemic toxicity and cellular resistance mechanisms impede their efficacy. Innovative strategies, including local administration, optimization of treatment schedule/ dosage, synergistic combinations, and the encapsulation of bioactive mole- cules in smart, multifunctional drug delivery systems, have shown promising results in potentiating anticancer activity while circumventing such hurdles. Furthermore, questioning of the old paradigm according to which nuclear DNA is the critical target of their anticancer activity has shed light on subcellular alternative and neglected targets that obviously participate in the mediation of cytotoxicity or resistance. Thus, rethinking of the use of these pivotal anti- neoplastic agents appears critical to improve clinical outcomes in the management of solid tumors. [less ▲]

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See detailGas-Phase Dynamics of Collision Induced Unfolding, Collision Induced Dissociation, and Electron Transfer Dissociation-Activated Polymer Ions
Haler, Jean ULiege; Massonnet, Philippe ULiege; Far, Johann ULiege et al

in Journal of the American Society for Mass Spectrometry (2019), 30(4), 563572

Polymer characterizations are often performed using mass spectrometry (MS). Aside from MS and different tandem MS (MS/MS) tech- niques, ion mobility–mass spectrometry (IM-MS) has been recently added to ... [more ▼]

Polymer characterizations are often performed using mass spectrometry (MS). Aside from MS and different tandem MS (MS/MS) tech- niques, ion mobility–mass spectrometry (IM-MS) has been recently added to the inventory of char- acterization technique. However, only few studies have focused on the reproducibility and robust- ness of polymer IM-MS analyses. Here, we per- form collisional and electron-mediated activation of polymer ions before measuring IM drift times, collision cross-sections (CCS), or reduced ion mobilities (K0). The resulting IM behavior of different activated product ions is then compared to non-activated native intact polymer ions. First, we analyzed collision induced unfolding (CIU) of precursor ions to test the robustness of polymer ion shapes. Then, we focused on fragmen- tation product ions to test for shape retentions from the precursor ions: cation ejection species (CES) and product ions with m/z and charge state values identical to native intact polymer ions. The CES species are formed using both collision induced dissociation (CID) and electron transfer dissociation (ETD, formally ETnoD) experiments. Only small drift time, CCS, or K0 deviations between the activated/formed ions are observed compared to the native intact polymer ions. The polymer ion shapes seem to depend solely on their mass and charge state. The experiments were performed on three synthetic homopolymers: poly(ethoxy phosphate) (PEtP), poly(2-n-propyl- 2-oxazoline) (Pn-PrOx), and poly(ethylene oxide) (PEO). These results confirm the robustness of polymer ion CCSs for IM calibration, especially singly charged polymer ions. The results are also discussed in the context of polymer analyses, CCS predictions, and probing ion–drift gas interaction potentials. [less ▲]

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See detailUgi three-component polymerization toward poly(α-amino amide)s
Stiernet, Pierre ULiege; Lecomte, Philippe ULiege; De Winter, Julien et al

in ACS Macro Letters (2019), 8

Due to their great modularity, ease of implementation, and atom economy, multicomponent reactions (MCRs) are becoming increasingly popular macromolecular engineering tools. In this context, MCRs suitable ... [more ▼]

Due to their great modularity, ease of implementation, and atom economy, multicomponent reactions (MCRs) are becoming increasingly popular macromolecular engineering tools. In this context, MCRs suitable in polymer synthesis are eagerly searched for. This work demonstrates the potential of the Ugi-three component reaction (Ugi-3CR) for the design of polymers and, in particular, of poly(α-amino amide)s. A series of polymers containing amino and amido groups within their backbone were obtained through a one-pot process by reacting aliphatic or aromatic diamines, diisocyanides, and aldehydes. The impact of temperature, concentration, catalyst loading, and substrates on polymerization efficiency is discussed. A preliminary study on the thermal properties and the solution behavior of these poly(α-amino amide)s was carried out. An aliphatic-rich derivative notably showed some pH-responsiveness in water via protonation−deprotonation of its amino groups. [less ▲]

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See detailRing-opening polymerization of lactones
Lecomte, Philippe ULiege; Jérôme, Christine ULiege

in Dove, Andrew; Sardon, Haritz; Naumann, Stefan (Eds.) Organic catalysis for polymerization (2019)

The synthesis of aliphatic polyesters by the ring-opening polymerization of cyclic monoesters was discovered by Carothers in the 1930s. Since then, a plethora of catalysts and initiators have been ... [more ▼]

The synthesis of aliphatic polyesters by the ring-opening polymerization of cyclic monoesters was discovered by Carothers in the 1930s. Since then, a plethora of catalysts and initiators have been discovered to promote this polymerization. Nowadays, steadily increasing attention is paid to organocatalysts and, among them, acids, bases, and H-bond donors and acceptors. Organocatalysts today available for the polymerization of medium size cyclic monoesters such as δ-valerolactone and ε-caprolactone will be reviewed. Special attention will be paid to dual catalysts capable of activating both the initiator and the monomer. The most efficient catalysts promote fast and selective ring-opening polymerization. The mechanism based either on ionic interactions, the establishment of H-bonds or nucleophilic activation will be discussed. The importance of ring size will be highlighted by the organocatalyzed polymerization of β-butyrolactone, γ-butyrolactone and pentadecalactone as a typical macrocyclic monoester. [less ▲]

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See detailHybrid Gd3+/cisplatin cross-linked polymer nanoparticles enhance platinum accumulation and formation of DNA adducts in glioblastoma cell lines
Lajous, Hélène ULiege; Riva, Raphaël ULiege; Lelièvre, Bénédicte et al

in Biomaterials Science (2018), 6(9), 2386-2409

Glioblastoma is the most frequent and aggressive primary malignant tumor of the central nervous system with a gloomy prognosis. Platinum derivatives and one among them, cisplatin, exhibited promising ... [more ▼]

Glioblastoma is the most frequent and aggressive primary malignant tumor of the central nervous system with a gloomy prognosis. Platinum derivatives and one among them, cisplatin, exhibited promising results when locally administered into the brain of glioblastoma bearing rats. Nanovectorization of anticancer agents through polymeric nanoparticles may even promote drug accumulation within cells, thus concen- trating the drug efficiently at its target. Anchorage of gadolinium complexes on the corona of such smart drug delivery systems could further allow magnetic resonance imaging (MRI) monitoring of the nanoplat- form biodistribution in the damaged parenchyma and its therapeutic benefit. For this purpose, a biocom- patible amphiphilic triblock copolymer, made of degradable polyester and polycarbonate and bioelimin- able polyethylene oxide (PEO), was synthesized by successive ring-opening polymerizations. After micelli- zation in water, gadolinium complexes were grafted onto the PEO micelle corona and the carboxylate functions, located at the surface of the micelle’s core, were able to cross-link with Pt(II) complexes. A macromolecular prodrug was therefore recovered in which more than one third of the carboxylate func- tions were linked to a platinum atom. By this strategy, stable cisplatin cross-linked nanoparticles were for- mulated with a mean size in the range of 100.63 ± 12.04 nm consistent with biological investigations. Relaxometry measurements both in water and in plasma at 7 T, 25 °C, confirmed the intrinsic potential of these hybrid nanoparticles as alternative MRI contrast agents with a substantial increase in the r2/r1 ratio by a factor of 3.3 and 2.7, respectively, compared to the conventional low molar mass Gd-DTPA. As a result, their infusion within the striatum of glioblastoma-bearing mice resulted in a hypersignal on T2- weighted MR images that persisted over time. Ultimately, the formulated prodrug exhibited up to 50-fold increased accumulation in human glioblastoma cell lines and up to 32-fold enhanced subsequent Pt- DNA adduct formation in comparison with free cisplatin, thus supporting the potential of this innovative bimodal tool for further applications. [less ▲]

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See detailMicroplastiques et océans: Partie 1
Lecomte, Philippe ULiege

Conference (2018, March 14)

Des microbilles plastiques sont ajoutées à de nombreux produits cosmétiques et d’hygiène, l’objectif étant d’améliorer l’effet nettoyant des objets tels que les exfoliants pour le visage. Bien qu’elles ... [more ▼]

Des microbilles plastiques sont ajoutées à de nombreux produits cosmétiques et d’hygiène, l’objectif étant d’améliorer l’effet nettoyant des objets tels que les exfoliants pour le visage. Bien qu’elles soient très petites, elles représentent un risque considérable pour la faune et la flore marines. À cause des propriétés chimiques, des substances organiques nocives s’attachent à ces petites particules. Confondues avec une proie, elles sont englouties par des mangeurs de plancton ou d’autres animaux. Elles entrent alors dans la chaîne alimentaire. [less ▲]

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See detailEnolates in macromolecular science: current situation and future outlook
Lecomte, Philippe ULiege; Jérôme, Christine ULiege

in Zabicky, Jacob (Ed.) The Chemistry of Metal Enolates (Volume 2) (2018)

Detailed reference viewed: 50 (14 ULiège)
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See detailPredicting Ion Mobility-Mass Spectrometry Trends of Polymers using the Concept of Apparent Densities
Haler, Jean ULiege; Morsa, Denis ULiege; Lecomte, Philippe ULiege et al

in Methods (2018), 144

Ion Mobility (IM) coupled to Mass Spectrometry (MS) has been used for several decades, bringing a fast separation dimension to the MS detection. IM-MS is a convenient tool for structural elucidation. The ... [more ▼]

Ion Mobility (IM) coupled to Mass Spectrometry (MS) has been used for several decades, bringing a fast separation dimension to the MS detection. IM-MS is a convenient tool for structural elucidation. The fold- ing of macromolecules is often assessed with the support of computational chemistry. However, this strat- egy is strongly dependent on computational initial guesses. Here, we propose the analysis of the Collision Cross-Section (CCS) trends of synthetic homopolymers based on a fitting method which does not rely on computational chemistry a prioris of the three-dimensional structures. The CCS trends were evaluated as a function of the polymer chain length and the charge state. This method is also applicable to mobility trends. It leads to two parameters containing all information available through IM(-MS) measurements. One parameter can be interpreted as an apparent density. The second parameter is related to the shape of the ions and leads us to introduce the concept of trends with constant apparent density. Based on the two fitting parameters, a method for IM trend predictions is elaborated. Experimental deviations from the predictions facilitate detect- ing structural rearrangements and three-dimensional structure differences of the cationized polymer ions. This leads for instance to an easy identification and prediction of the presence of different polymer topologies in complex polymer mixtures. The classification of predicted trends could as well allow for software-assisted data processing. Finally, we suggest the link between the CCS trends of homopolymers and those obtained from (monodisperse) biomolecules to interpret potential folding differences during IM-MS studies. [less ▲]

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See detailDesign of polyphosphoester-based drug delivery systems by efficient thiol-ene reaction
Riva, Raphaël ULiege; Vanslambrouck, Stéphanie; Ergül, Zeynep ULiege et al

Poster (2017, May 23)

Thanks to their biocompatibility, biodegradability and their structure similar to natural biomacromolecules, polyphosphoesters (PPE) are appealing polymers for biomedical applications. In contrast to ... [more ▼]

Thanks to their biocompatibility, biodegradability and their structure similar to natural biomacromolecules, polyphosphoesters (PPE) are appealing polymers for biomedical applications. In contrast to polyesters, PPE properties and functionality are easily tuned via the chemical nature of the lateral chains. To enhance the drug loading capacity of PPE-based micelles used as carriers for the delivery of poorly soluble drugs, an efficient strategy to increase the lipophilicity of the PPE block of polyethylene oxide (PEO)-b-PPE amphiphilic copolymers has been investigated. A PEO-b-PPE copolymer bearing pendant vinyl groups along the PPE block was synthesized and then modified by thiol-ene click reaction with thiols bearing either a long linear alkyl chain (dodecyl) or a tocopherol moiety. Ketoconazole was used as model for hydrophobic drugs. Comparison of the loading contents and release profiles with PEO-b-PPE bearing shorter pendant groups is presented evidencing the key role of the structure of the pendant group on the PPE backbone. Finally, the low cytotoxicity of these novel PEO-b-PPE copolymers was also demonstrated. The tocopherol derivative was evidenced as particularly promising for drug delivery systems. [less ▲]

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See detailThiol-ene reaction: an efficient tool to design polyphosphoester-based drug delivery systems
Riva, Raphaël ULiege; Vanslambrouck, Stéphanie; Ergül, Zeynep ULiege et al

Poster (2017, May 04)

Thanks to their biocompatibility, biodegradability and their structure similar to natural biomacromolecules, polyphosphoesters (PPE) are appealing polymers for biomedical applications. In contrast to ... [more ▼]

Thanks to their biocompatibility, biodegradability and their structure similar to natural biomacromolecules, polyphosphoesters (PPE) are appealing polymers for biomedical applications. In contrast to polyesters, PPE properties and functionality are easily tuned via the chemical nature of the lateral chains. To enhance the drug loading capacity of PPE-based micelles used as carriers for the delivery of poorly soluble drugs, an efficient strategy to increase the lipophilicity of the PPE block of polyethylene oxide (PEO)-b-PPE amphiphilic copolymers has been investigated. A PEO-b-PPE copolymer bearing pendant vinyl groups along the PPE block was synthesized and then modified by thiol-ene click reaction with thiols bearing either a long linear alkyl chain (dodecyl) or a tocopherol moiety. Ketoconazole was used as model for hydrophobic drugs. Comparison of the loading contents and release profiles with PEO-b-PPE bearing shorter pendant groups is presented evidencing the key role of the structure of the pendant group on the PPE backbone. Finally, the low cytotoxicity of these novel PEO-b-PPE copolymers was also demonstrated. The tocopherol derivative was evidenced as particularly promising for drug delivery systems. [less ▲]

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See detailSimultaneous anionic ring-opening and condensation reactions for the synthesis of aliphatic–N-alkyl aromatic copolyamides
Bakkali-Hassani, Camille; Tunc, Deniz; Roos, Kevin et al

in Macromolecules (2017), 50(1), 175-181

The copolymerization of ε-caprolactam with ethyl 4-(butylamino)benzoate was shown to occur in the presence of sodium salts and an acyllactam as activator in a one-step bulk reaction. The mechanism is ... [more ▼]

The copolymerization of ε-caprolactam with ethyl 4-(butylamino)benzoate was shown to occur in the presence of sodium salts and an acyllactam as activator in a one-step bulk reaction. The mechanism is based on the deprotonation of the two monomers yielding activated species able to attack an acyllactam or an ester group at the polymer chain ends. Novel copolyamides with different percentages of aromatic/aliphatic units were synthesized in a one-step bulk copolymerization within a few minutes at 140 °C and characterized by NMR spectroscopy, size exclusion chromatography, and thermal analysis (DSC). This methodology, combining simultaneous anionic ring-opening and condensation reactions, affords a new synthetic pathway to introduce an aromatic unit in an aliphatic polyamide backbone, and more specifically a polyamide 6 containing about 20 mol % of N-alkyl aromatic amides was prepared. [less ▲]

Detailed reference viewed: 41 (16 ULiège)
See detailOrganocatalytic ring-opening polymerization towards polyphosphoesters
Clément, Benoit; Vanslambrouck, Stépanie; Carion, Stéphan ULiege et al

Conference (2016, September 13)

Hydrolytically degradable and biocompatible aliphatic polyesters are widely applied for biomedical applications as implants, scaffolds for tissue engineering and, finally, as nanocarriers for drug ... [more ▼]

Hydrolytically degradable and biocompatible aliphatic polyesters are widely applied for biomedical applications as implants, scaffolds for tissue engineering and, finally, as nanocarriers for drug delivery. Aliphatic phophoesters, known since the pioneering work of S. Penczek in the 70’s, exhibit the same properties of hydrolytic degradability and biocompatibility and are thus more and more studied for biomedical applications as well. In the field of materials, anti-fire properties opens up new perspectives. The difference between polyesters and polyphosphoesters in terms of synthesis and properties will be highlighted. Polyphosphosphoesters are synthesized by step-growth and chain growth polymerization. When these polyphosphoesters are synthesized by ring-opening polymerization of cyclic phosphoesters, organocatalysts turned out to be very efficient compared to coodination processes. The last part of the talk will deal with te implementation of ROP of cyclic phosphates towards a series of amphiphilic PEO-block-polyphosphate copolymers of tailored hydrophobicity depending on the length of the lateral alkyl group. These polymers are able to self assemble into nanoparticles by direct dissolution in water, thus in the absernce of any organic solvent. The so-obtained micelles were studied by a set of techniques (Pyrene Fluorescence, Dynamic Light Scattering, Tensiometry). Finally, the influence of the hydrophobicity of the polyphosphate block of the micelle on the encapsulation and the release of a model drug was investigated. [less ▲]

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

Poster (2016, September 12)

The design of drug delivery systems often requires biodegradable and biocompatible materials that allow safe retention and controlled release of the drug. In this respect, supramolecularly self-assembled ... [more ▼]

The design of drug delivery systems often requires biodegradable and biocompatible materials that allow safe retention and controlled release of the drug. In this respect, supramolecularly self-assembled amphiphilic block copolymers into spherical micelles are appropriate carriers for poorly soluble drugs. In that framework, we have designed novel functional poly(ethylene oxide)-b-polyphosphoester amphiphilic block copolymers able to cross-linked under UV and degrade in response to a reduction of the pH from neutral conditions. Therefore, 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, i.e. a drug used 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 detailAnionic flow polymerizations toward functional polyphosphoesters in microreactors: Polymerization and UV-modification
Baeten, Evelien; Vanslambrouck, Stéphanie; Jérôme, Christine ULiege et al

in European Polymer Journal (2016), 80

The polymerization of cyclic phosphates to poly(phosphoester)s, PPEs, is optimized for chip- based microreactors under continuous flow conditions. The anionic ring-opening polymerization of 2-isobutyoxy-2 ... [more ▼]

The polymerization of cyclic phosphates to poly(phosphoester)s, PPEs, is optimized for chip- based microreactors under continuous flow conditions. The anionic ring-opening polymerization of 2-isobutyoxy-2-oxo-1,3,2-dioxaphospholane (iBP) via the use of two organocatalytic systems allowed to polymerize to nearly quantitative monomer conversion within 10 or 3 minutes, respectively at a reaction temperature of 40 °C. Further, the optimized polymerization protocol was applied to 2-butenoxy-2-oxo-1,3,2-dioxaphospholane (BP) which yields a polymer that carries an alkene functionality per monomer repeating unit. This material can be postmodified in an UV-induced radical thiol-ene reaction, which was also shown to proceed with very high efficiency under UV-flow conditions. Eventually, both reactions were coupled in a two-stage reactor setup, showing that the thermally-activated polymerization can be coupled with high efficiency to the UV-activated post-polymerization modification reaction. The introduced reactor setup can in the future be used to produce and screen a broad variety of functional PPE materials with various functionalities and physical properties. [less ▲]

Detailed reference viewed: 90 (34 ULiège)
See detailPolyphosphoesters as a new platform for the design of particulate drug delivery systems
Vanslambrouck, Stéphanie; Ergul Yilmaz, Zeynep; Debuigne, Antoine ULiege 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 ▲]

Detailed reference viewed: 137 (16 ULiège)
See detailPolyphosphoester containing amphiphilic block copolymers as drug nanocarriers
Yilmaz-Ergül, Zeynep ULiege; Vanslambrouck, Stéphanie; Thiry, Justine ULiege 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 detailLes polymères au service de la pharmacologie
Lecomte, Philippe ULiege

Scientific conference (2016, January 12)

Detailed reference viewed: 27 (3 ULiège)