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6 results on '"Ludivine Louise"'

1. Immunologically driven antibodies chemical engineering: design and synthesis of a hapten aimed at nerve agent hydrolysis

Author

Charles Mioskowski, Pierre-Yves Renard, Florence Jovic, and Ludivine Louise

Subjects
Chemistry, Stereochemistry, medicine.drug_class, Organic Chemistry, Substrate (chemistry), Monoclonal antibody, Oxime, Biochemistry, Thiophosphate, Hydrolysis, chemistry.chemical_compound, Drug Discovery, medicine, Bioorganic chemistry, Hapten, Nerve agent, medicine.drug
Abstract

In this letter, we describe the design and the synthesis of an organophosphorus hapten aimed at a mixed biotechnological–chemical strategy for the mild decontamination of exceedingly toxic nerve agent VX. Hapten will be used to raise and select monoclonal antibodies (mAbs) able to bind both the nerve agent, and an oxime, derived from pyridinaldoxime, able to specifically hydrolyze its P–S bond. In order to significantly increase the hydrolysis reaction rate, the controlled respective positioning of the oxime and of the substrate will be achieved through the immunization, and in a second step, the oxime will be bound to the mAb in a reactive position towards the reactive thiophosphate functionality of the substrate.

Published
2005
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2. ChemInform Abstract: Design, Synthesis and Evaluation of New α-Nucleophiles for the Hydrolysis of Organophosphorus Nerve Agents: Application to the Reactivation of Phosphorylated Acetylcholinesterase

Author

Alain Wagner, Florian Nachon, Sanjeevarao Kodepelly, Ludivine Louise-Leriche, Géraldine Saint-André, Rachid Baati, Emilie Gillon, Pierre-Yves Renard, and Maria Kliachyna

Subjects
Chemical Warfare Agents, Aryl, General Medicine, Acetylcholinesterase, Combinatorial chemistry, chemistry.chemical_compound, Hydrolysis, chemistry, Design synthesis, Nucleophile, medicine, Organic chemistry, Phosphorylation, Nerve agent, medicine.drug
Abstract

A variety of (het)aryl aldoximes, (het)arylamidoximes and hydroxamic acids, e.g. (I), is tested as nucleophilic agent for the hydrolysis of phenylphosphonothioate (PhX), a member of a class of organophosphorus used as chemical warfare agents.

Published
2011
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3. Optimized strategies to synthesize β-cyclodextrin-oxime conjugates as a new generation of organophosphate scavengers

Author

Franz Worek, Timo Wille, François Estour, Susanne Müller, Georg Reiter, Pierre-Yves Renard, Romain Le Provost, Nicolas Masurier, Olivier Lafont, Ludivine Louise, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Bundeswehr Institute of Pharmacology and Toxicology, UNIROUEN - UFR Santé (UNIROUEN UFR Santé), and Normandie Université (NU)-Normandie Université (NU)

Subjects
Cyclosarin, 010402 general chemistry, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Hydrolysis, Organophosphorus Compounds, Oximes, Organic chemistry, Physical and Theoretical Chemistry, chemistry.chemical_classification, Molecular Structure, Cyclodextrin, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, beta-Cyclodextrins, Organic Chemistry, Organophosphate, Stereoisomerism, Oligosaccharide, Oxime, Potassium fluoride, 0104 chemical sciences, Kinetics, chemistry, Conjugate
Abstract

International audience; A new generation of organophosphate (OP) scavengers was obtained by synthesis of β-cyclodextrin-oxime derivatives 8-12. Selective monosubstitution of β-cyclodextrin was the main difficulty in order to access these compounds, because reaction onto the oligosaccharide was closely related to the nature of the incoming group. For this purpose, non-conventional activation conditions were also evaluated. Intermediates 5 and 7 were then obtained with the better yields under ultrasounds irradiation. Finally, the desired compounds 8-10 were obtained from 5-7 in high purity by desilylation using potassium fluoride. Quaternarisation of compounds 8 and 9 was carried out. OP hydrolytic activity of compounds 8-12 was evaluated against cyclosarin (GF) and VX. None of the tested compounds was active against VX, but these five cyclodextrin derivatives detoxified GF, and the most active scavengers 10 and 11 allowed an almost complete hydrolysis of GF within 10 min. Even more fascinating is the fact that compounds 9 and 10 were able to hydrolyze enantioselectively GF.

Published
2011
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4. Design, synthesis and evaluation of new alpha-nucleophiles for the hydrolysis of organophosphorus nerve agents: application to the reactivation of phosphorylated acetylcholinesterase

Author

Alain Wagner, Sanjeevarao Kodepelly, Rachid Baati, Ludivine Louise-Leriche, Florian Nachon, Emilie Gillon, Pierre-Yves Renard, Maria Kliachyna, Géraldine Saint-André, Centre de Recherches sur les Macromolécules Végétales (CERMAV), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Toxicology, Centre de Recherches du Service de Santé des Armées, Laboratoire de Chimie des Systèmes Fonctionnels, Centre National de la Recherche Scientifique (CNRS), Institut Gilbert-Laustriat : Biomolécules, Biotechnologie, Innovation Thérapeutique, Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes (UGA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), and Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, medicine.medical_treatment, Aryl, Chemical structure, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, Acetylcholinesterase, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, chemistry.chemical_compound, Hydrolysis, chemistry, Nucleophile, Drug Discovery, medicine, Reactivity (chemistry), Antidote, ComputingMilieux_MISCELLANEOUS, Nerve agent, medicine.drug
Abstract

A series of new α-nucleophiles including oximes and amidoximes have been synthesized, and their ability to efficiently and selectively cleave the P–S bond of organophosphorus nerve agents has been evaluated. The relationship between the chemical structure of the α-nucleophiles and their reactivity towards PhX hydrolysis is reported. A significant effect induced by an ortho-hydroxyl group of aryl- and pyridyl-oximes, amidoximes on their organo-phosphono-thioase reactivity was discovered. The evaluation of the initial rates of PhX hydrolysis reaction in the presence of α-nucleophiles allowed the discovery of new uncharged molecules with increased reactivity compared to positively charged 2-pralidoxime used as antidote. The mechanism of their action was studied in details by kinetic analysis, HPLC and LC–MS methods. The most promising structures were then considered as potent in vitro reactivators of phosphylated acetylcholinesterase (AChE), which was confirmed by the preliminary results of AChE reactivation initially inhibited by VX.

Published
2011
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5. A versatile access to new halogenated 7-azidocoumarins for photoaffinity labeling: Synthesis and photophysical properties

Author

Emilia Pǎunescu, Anthony Romieu, Ludovic Jean, Ludivine Louise, Pierre-Yves Renard, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Photoaffinity labeling, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Process Chemistry and Technology, General Chemical Engineering, Aryl, 010402 general chemistry, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Reagent, Organic chemistry, Reactivity (chemistry), Amination
Abstract

International audience; A versatile methodology for the synthesis of 6/8-halogenated 7-aminocoumarins from the corresponding 7-hydroxy analogs using Pd-catalyzed amination reaction as the key step is presented. Further readily conversion into 7-azidocoumarins was performed and the resulting aryl azides proved higher stability and reactivity than the corresponding non-halogenated parent compound. These new compounds may thus constitute attractive scaffolds for designing novel photoaffinity reagents for various challenging bio-labeling applications.

Published
2011
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6. A HTS assay for the detection of organophosphorus nerve agent scavengers

Author

Rachid Baati, Alain Wagner, Anthony Romieu, Ludivine Louise-Leriche, Géraldine Saint-André, Emilia Paunescu, Pierre-Yves Renard, Institut de biologie de Lille - IBL (IBLI), Université de Lille, Sciences et Technologies-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Université de Lille, Droit et Santé-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie des Systèmes Fonctionnels, Centre National de la Recherche Scientifique (CNRS), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut Gilbert-Laustriat : Biomolécules, Biotechnologie, Innovation Thérapeutique, Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), and Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Substrate (chemistry), Screening assay, General Chemistry, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, High-Throughput Screening Assays, Hydrolysis, Organophosphorus Compounds, Cleave, medicine, Acetylcholinesterase, Organic chemistry, Chemical Warfare Agents, Linker, Bond cleavage, Nerve agent, medicine.drug, Fluorescent Dyes
Abstract

International audience; A new pro-fluorescent probe aimed at a HTS assay of scavengers is able to selectively and efficiently cleave the P-S bond of organophosphorus nerve agents and by this provides non-toxic phosphonic acid has been designed and synthesised. The previously described pro-fluorescent probes were based on a conventional activated P-Oaryl bond cleavage, whereas our approach uses a self-immolative linker strategy that allows the detection of phosphonothioase activity with respect to a non-activated P-Salkyl bond. Further, we have also developed and optimised a high-throughput screening assay for the selection of decontaminants (chemical or biochemical scavengers) that could efficiently hydrolyse highly toxic V-type nerve agents. A preliminary screening, realised on a small alpha-nucleophile library, allowed us to identify some preliminary "hits", among which pyridinealdoximes, alpha-oxo oximes, hydroxamic acids and, less active but more original, amidoximes were the most promising. Their selective phosphonothioase activity has been further confirmed by using PhX as the substrate, and thus they offer new perspectives for the synthesis of more potent V nerve agent scavengers.

Published
2010
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