References of "Marchand-Brynaert, Jacqueline"
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See detail2-nitrobenzyl esters of penam and cephem derivatives as inhibitors of penicillin-binding proteins
Brulé, Cédric; Grugier, Jérôme; Brans, Alain ULg et al

in Asian Journal of Organic Chemistry (2013), 2

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See detailMacrocyle-embedded b-lactams as novel inhibitors of the Penicillin Binding Protein PBP2a from MRSA
Dive, Georges ULg; Bouillon, Camille; Sliwa, Aline et al

in European Journal of Medicinal Chemistry (2013), 64

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See detailClickable PEG conjugate obtained by ‘‘clip’’ photochemistry: Synthesis and
Pourcelle, Vincent; Le Duff, Cécile S.; Freichels, Hélène et al

in Journal of Fluorine Chemistry (2012), 140

In this paper, we describe a grafting methodology associated to a quantitative 19F NMR method (qNMR) for the conjugation of small molecules on a PEG building block aimed at click chemistry applications in ... [more ▼]

In this paper, we describe a grafting methodology associated to a quantitative 19F NMR method (qNMR) for the conjugation of small molecules on a PEG building block aimed at click chemistry applications in the domain of drug delivery systems. Acetylenic PEG (PEG-yne) was first derivatized with a fluorinated benzyl amine (TagF6) by means of photografting of a trifluoromethylphenyl diazirine bifunctional linker (TPD-clip). The amount of TagF6 grafted on PEG-yne was calculated by NMR using an internal standard (trifluoroethanol) and adjusting of the acquisition and processing parameters. NMR is used as a valuable alternative to the complex procedures often employed for the quantification of functionalities on biomaterials. The accuracy of the qNMR methodology was attested by controlling its linearity, the determination of limits of quantification and the percentage of recovery. A good assessment of the TagF6 grafting rates was obtained after taking into account the inherent unspecific adsorption that occurs on materials. This versatile methodology that combines simple chemistry and a common analytical tool was, in a second time, applied to the preparation of a PEG conjugated with a RGD (Arg-Gly-Asp) peptidomimetic in a controlled manner. [less ▲]

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See detailSynthesis of poly(lactide-co-glycolide-co-ε-caprolactone)-graft-mannosylated poly(ethylene oxide) copolymers by combination of “clip” and “click” chemistries
Freichels, Hélène; Pourcelle, Vincent; Auzély-Velty, Rachel et al

in Biomacromolecules (2012), 13(3), 760-768

Poly(lactide-co-glycolide) (PLGA) is extensively used in pharmaceutical applications, for example, in targeted drug delivery, because of biocompatibility and degradation rate, which is easily tuned by the ... [more ▼]

Poly(lactide-co-glycolide) (PLGA) is extensively used in pharmaceutical applications, for example, in targeted drug delivery, because of biocompatibility and degradation rate, which is easily tuned by the copolymer composition. Nevertheless, synthesis of sugar-labeled amphiphilic copolymers with a PLGA backbone is quite a challenge because of high sensitivity to hydrolytic degradation. This Article reports on the synthesis of a new amphiphilic copolymer of PLGA grafted by mannosylated poly(ethylene oxide) (PEO). A novel building block, that is, α-methoxy-ω-alkyne PEO-clip-N-hydroxysuccinimide (NHS) ester, was prepared on purpose by photoreaction of a diazirine containing molecular clip. This PEO block was mannosylated by reaction of the NHS ester groups with an aminated sugar, that is, 2-aminoethyl-α-d-mannopyroside. Then, the alkyne ω-end-group of PEO was involved in a copper alkyne- azide coupling (CuAAC) with the pendent azides of the aliphatic copolyester. The targeted mannose-labeled poly(lactide-co-glycolide-co-ε-caprolactone)-graft-poly(ethylene oxide) copolymer was accordingly formed. Copolymerization of d,l-lactide and glycolide with α-chloro-ε-caprolactone, followed by substitution of chlorides by azides provided the azido-functional PLGA backbone. Finally, micelles of the amphiphilic mannosylated graft copolymer were prepared in water, and their interaction with Concanavalin A (ConA), a glyco-receptor protein, was studied by quartz crystal microbalance. This study concluded to the prospect of using this novel bioconjugate in targeted drug delivery. [less ▲]

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See detail12- to 22-membered bridged b-lactams as potential penicillin-binding protein inhibitors
Sliwa, Aline; Dive, Georges ULg; Marchand-Brynaert, Jacqueline

in Chemistry : An Asian Journal (2012), 7(2), 425-434

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See detailNon-symmetrically substituted phenoxazinones from laccase-mediated oxidative cross-coupling of aminophenols: an experimental and theoretical insight
Bruyneel, Frédéric; Dive, Georges ULg; Marchand-Brynaert, Jacqueline

in Organic & Biomolecular Chemistry (2012), 10

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See detail"Clip" and "click" chemistries combination: toward easy PEGylation of degradable aliphatic polyesters
Freichels, Hélène; Pourcelle, Vincent; Le Duff, Cécile S. et al

in Macromolecular Rapid Communications (2011), 32(7), 616-621

The combination of “clip” and “click” reactions provides a versatile and straightforward pathway for the synthesis of functional amphiphilic and degradable copolymers valuable for biomedical applications ... [more ▼]

The combination of “clip” and “click” reactions provides a versatile and straightforward pathway for the synthesis of functional amphiphilic and degradable copolymers valuable for biomedical applications such as targeted drug-delivery vehicles. [less ▲]

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See detailSuperlative Scaffold of 1,2,4-Triazole Derivative of Glycine Steering Linear Chain to a Chiral Helicate
Dirtu, Marinela M; Neuhausen, Christine; Naik, Anil D et al

in Crystal Growth & Design (2011), 11

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See detail(Di)-aminoguanidine Functionalization through Transamination: An Avenue to an Auspicious Class of Supramolecular Synthons
Naik, Anil D; Tinant, Bernard; Léonard, Alexandre ULg et al

in Crystal Growth & Design (2011), 11

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See detailTargeting nanoparticles to M cells with non-peptidic ligands for oral vaccination
Freichels, Hélène ULg; Fievez, Virginie; Plapied, Laurence et al

Poster (2010, March 18)

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See detailHDA cycloadditions of 1-diethoxyphosphonyl-1,3-butadiene with nitroso heterodienophiles: a computational investigation
Monbaliu, Jean-Christophe ULg; Dive, Georges ULg; Marchand-Brynaert, Jacqueline et al

in Journal of Molecular Structure : Theochem (2010), 959

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See detailHetero Diels-Alder (HDA) reactions of 1-phosphono-1,3-butadienes with azo and nitroso dienophiles : an entry towards versatile heterocyclic synthons for aminophosphonic compounds
Monbaliu, Jean-Christophe ULg; Villemin, Elise; Elias, Benjamin et al

in Attanasi, Orazio (Ed.) Targets in heterocyclic systems - Chemistry and Properties (2010)

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See detailStraightforward hetero Diels-Alder cycloadditions of nitroso dienophiles by microreactor technology
Monbaliu, Jean-Christophe ULg; Cukalovic, Ana; Marchand-Brynaert, Jacqueline et al

in Tetrahedron Letters (2010), 51

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See detailNovel chiral 1-phosphono-1,3-butadiene for asymmetric hetero Diels-Alder cycloadditions with nitroso and azodicarboxylate dienophiles
Monbaliu, Jean-Christophe ULg; Tinant, Bernard; Peeters, Daniel et al

in Tetrahedron Letters (2010), 51

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See detailCyclodimerization by ring-closing metathesis: synthesis, computational and biological evaluation of novel bis-azetidinyl-macrocycles
Sliwa, Aline; Dive, Georges ULg; Habib Jiwan, Jean-Louis et al

in Tetrahedron (2010), 66

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See detailTargeting of tumor endothelium by RGD-grafted PLGA-nanoparticles loaded with Paclitaxel
Danhier, Fabienne; Vroman, Benoît; Lecouturier, Nathalie et al

in Journal of Controlled Release (2009), 140(2), 166-173

Paclitaxel (PTX)-loaded PEGylated PLGA-based nanoparticles (NP) have been previously described as more effective in vitro and in vivo than Taxol®. The aim of this study was to test the hypothesis that our ... [more ▼]

Paclitaxel (PTX)-loaded PEGylated PLGA-based nanoparticles (NP) have been previously described as more effective in vitro and in vivo than Taxol®. The aim of this study was to test the hypothesis that our PEGylated PLGA-based nanoparticles grafted with the RGD peptide or RGD-peptidomimetic (RGDp) would target the tumor endothelium and would further enhance the anti-tumor efficacy of PTX. The ligands were grafted on the PEG chain of PCL-b-PEG included in the nanoparticles. We observed in vitro that RGD-grafted nanoparticles were more associated to Human Umbilical Vein Endothelial cells (HUVEC) by binding to αvβ3 integrin than non-targeted nanoparticles. Doxorubicin was also used to confirm the findings observed for PTX. In vivo, we demonstrated the targeting of RGD and RGDp-grafted nanoparticles to tumor vessels as well as the effective retardation of TLT tumor growth and prolonged survival times of mice treated by PTX-loaded RGD-nanoparticles when compared to non-targeted nanoparticles. Hence, the targeting of anti-cancer drug to tumor endothelium by RGD-labeled NP is a promising approach. [less ▲]

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See detailDiscovery of novel lipophilic inhibitors of OXA-10 enzyme (class D beta-lactamase) by screening amino analogs and homologs of citrate and isocitrate.
Beck, Joséphine; Vercheval, Lionel ULg; Bebrone, Carine ULg et al

in Bioorganic & Medicinal Chemistry Letters (2009), 19

Aminocitrate (and homolog) derivatives have been prepared by bis-alkylation of glycinate Schiff bases with bromoacetates (and ethyl acrylate), followed by N-acylation and esters (partial or complete ... [more ▼]

Aminocitrate (and homolog) derivatives have been prepared by bis-alkylation of glycinate Schiff bases with bromoacetates (and ethyl acrylate), followed by N-acylation and esters (partial or complete) deprotection. Aminoisocitrate was similarly obtained by mono-alkylation with diethyl fumarate. Evaluation against representative beta-lactamases revealed that the free acid derivatives are modest inhibitors of class A enzymes, whilst their benzyl esters showed a good inhibition of OXA-10 (class D enzyme). A docking experiment featured hydrophobic interactions in the active site. [less ▲]

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See detailLight induced functionalization of PCL-PEG block copolymers for the covalent immobilization of biomolecules
Pourcelle, Vincent; Freichels, Hélène ULg; Stoffelbach, François et al

in Biomacromolecules (2009), 10(4), 966-974

Functionalized poly-ε-caprolactone-block-polyethyleneglycol (PCL-PEG) amphiphilic copolymers were prepared to be constituents of nanocarriers used for the targeting of specific cells. Hence, we conceived ... [more ▼]

Functionalized poly-ε-caprolactone-block-polyethyleneglycol (PCL-PEG) amphiphilic copolymers were prepared to be constituents of nanocarriers used for the targeting of specific cells. Hence, we conceived a smooth and simple photografting methodology on these copolymers using a bifunctional molecular clip (O-succinimidyl-4-(p-azido-phenyl)butanoate). We prepared PCL-PEGs with pendent N-hydroxysuccinimide esters and studied the grafting with 3H-lysine, which radioactivity was counted by LSC. Several parameters were investigated, such as behavior of homopolymers, initial concentrations, irradiation, and incubation durations. Evidences of a “PEG directed photografting” are discussed and this selectivity could be improved by a selective solvent technique. The photografting on different PCL-PEGs revealed a dependency of the rates to the crystallinity of the copolymers. Several controls by SEC, DLS, and TEM of the treated copolymers were realized. Lastly, the coupling of α-d-mannopyranoside ligand was performed, reaching amounts of 5400 nmol/g of PCL-PEG. This derivatized PCL-PEG enters in the preparation of nanocarriers used for the targeting of antigen presenting cells. [less ▲]

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