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19 results on '"Emmanuelle Dubost"'

1. Controlled Access to C 1 ‐Symmetrical Cyclotriveratrylenes (CTVs) by Using a Sequential Barluenga Boronic Coupling (BBC) Approach

Author

Emmanuelle Dubost, Frédéric Fabis, Clément Vigier, Thomas Cailly, Pierre Fossé, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), and Normandie Université (NU)-Normandie Université (NU)

Subjects
010405 organic chemistry, Chemistry, Supramolecular chemistry, Cyclotriveratrylene, General Chemistry, 010402 general chemistry, 01 natural sciences, Crown Compounds, 3. Good health, 0104 chemical sciences, Coupling (electronics), chemistry.chemical_compound, Computational chemistry, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2021

2. Recent Advances in Synthetic Methods for Radioiodination

Author

Andrew Sutherland, Thomas Cailly, Holly McErlain, Victor Babin, Emmanuelle Dubost, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), and University of Glasgow

Subjects
Anions, 010405 organic chemistry, Chemistry, Organic Chemistry, Precursors, 010402 general chemistry, 01 natural sciences, Hydrocarbons, 0104 chemical sciences, Iodine Radioisotopes, Substitution reactions, Salts, Biochemical engineering, [CHIM.RADIO]Chemical Sciences/Radiochemistry
Abstract

International audience; Organic compounds bearing radioisotopes of iodine are widely used for biological research, diagnostic imaging, and radiotherapy. Early reported synthetic methods for the incorporation of radioiodine have generally involved high temperature reactions or strongly oxidizing conditions. To overcome these limitations and to cope with the demand for novel radioiodinated probes, there has been a surge in the development of new synthetic methodology for radioiodination. This synopsis describes the key transformations developed recently.

Published
2020

3. Design of iodinated radioligands for SPECT imaging of central human 5-HT4R using a ligand lipophilicity efficiency approach

Author

Audrey Davis, Emmanuelle Dubost, Frédéric Fabis, Jean-Philippe Bouillon, Vincent Reboul, Benjamin B. Tournier, Gilbert Pigrée, Philippe Millet, Jean-François Lohier, Thomas Cailly, Victor Babin, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Geneva University Hospital (HUG), Installations de Mise en Oeuvre et de GEstion des Radioéléments [Caen] (IMOGERE), Laboratoire de chimie moléculaire et thioorganique (LCMT), Centre National de la Recherche Scientifique (CNRS)-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), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), 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
010405 organic chemistry, Chemistry, Organic Chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, Serotonin SPECT imaging 5-HT4 Radio-iodination, 0104 chemical sciences, 3. Good health, ddc:616.89, 010404 medicinal & biomolecular chemistry, Lipophilic efficiency, In vivo, Spect imaging, Drug Discovery, [CHIM]Chemical Sciences, Molecular Biology, Binding affinities
Abstract

International audience; A series of iodinated ligands for the SPECT imaging of 5-HT4 receptors was designed starting from the previously reported hit MR-26132. We focused on the modulation of the piperidine-containing lateral chain by introducing hydrophilic groups in order to decrease the liphophilicity of the new ligands. All the synthesized compounds were tested for their binding affinities on 5-HT4Rs and based on the Ligand Lipophilicity Efficiency approach, compound 13 was further selected for radioiodination with iodine-125 and imaging experiments. Compound 13 showed its ability to displace the specific signal of the reference compound [125I]SB-207710 but no significant detection of [125I]13 was observed in vivo in SPECT experiments.

Published
2020

4. Improvements of C–H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics

Author

Gilbert Pigrée, Thomas Cailly, Jean-Philippe Bouillon, Alexandra Hébert, Florian Benoist, Emmanuelle Dubost, Frédéric Fabis, Victor Babin, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Installations de Mise en Oeuvre et de GEstion des Radioéléments [Caen] (IMOGERE), 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
010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Halogenation, 010402 general chemistry, palladium, 01 natural sciences, Combinatorial chemistry, Catalysis, 0104 chemical sciences, chemistry, iodination, C–H activation, radiochemistry, iodine­-125, [CHIM.RADIO]Chemical Sciences/Radiochemistry, Palladium
Abstract

International audience; An improved protocol to perform C–H radio-iodination is described. These new conditions allow rapid and clean formation of radio-iodinated N-acylsulfonamides using [125I]NIS and catalytic amounts of palladium acetate and para-toluenesulfonic acid. No pre-functionalized precursors are required and the products are obtained with radiochemical conversions (RCC) of 27–84%.

Published
2019

5. Palladium-Mediated Site-Selective C–H Radio-iodination

Author

Alain Manrique, Victor Babin, Emmanuelle Dubost, Frédéric Fabis, Céline Chollet, Jean-Philippe Bouillon, Alexandra Hébert, Thomas Cailly, Grégory Pieters, Florian Benoist, Pierre Barbey, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Normandie Université (NU), Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), 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)-Centre National de la Recherche Scientifique (CNRS)-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)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), 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)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Signalisation, électrophysiologie et imagerie des lésions d’ischémie-reperfusion myocardique (SEILIRM), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), 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), 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
Primary (chemistry), 010405 organic chemistry, Organic Chemistry, Halogenation, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Biochemistry, Medicinal chemistry, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Sodium iodide, Site selective, Physical and Theoretical Chemistry, [CHIM.RADIO]Chemical Sciences/Radiochemistry, Palladium
Abstract

International audience; The palladium-mediated C–H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.

Published
2018

6. Understanding a Host-Guest Model System through129Xe NMR Spectroscopic Experiments and Theoretical Studies

Author

Jean-Pierre Dognon, Estelle Léonce, Bernard Rousseau, Yves Boulard, Christophe Dugave, Céline Boutin, Patrick Berthault, Emmanuelle Dubost, Gaëlle Milanole, Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire Structure et Dynamique par Résonance Magnétique (LCF) (LSDRM), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Chemistry, Supramolecular chemistry, Analytical chemistry, chemistry.chemical_element, Model system, General Medicine, General Chemistry, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, 01 natural sciences, Quantum chemistry, Catalysis, Cryptophane, Spectral line, 0104 chemical sciences, symbols.namesake, Xenon, Chemical physics, Physics::Atomic and Molecular Clusters, symbols, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], van der Waals force
Abstract

International audience; Gaining an understanding of the nature of host–guest interactions in supramolecular complexes involving heavy atoms is a difficult task. Described herein is a robust simulation method applied to complexes between xenon and members of a cryptophane family. The calculated chemical shift of xenon caged in a H2O2 probe, as modeled by quantum chemistry with complementary-orbital, topological, and energy-decomposition analyses, is in excellent agreement with that observed in hyperpolarized 129Xe NMR spectra. This approach can be extended to other van der Waals complexes involving heavy atoms.

Published
2014

7. Synthesis and structure-affinity relationships of selective high-affinity 5-HT(4) receptor antagonists: application to the design of new potential single photon emission computed tomography tracers

Author

Fabienne Dulin, Noé Dumas, Céline Ballandonne, Christine Fossey, Thomas Cailly, Emmanuelle Dubost, Frédéric Fabis, Rosa Magnelli, Jana Sopkova de-Oliveira Santos, Sabrina Butt-Gueulle, Philippe Millet, Yves Charnay, Sylvain Rault, Daniel H. Caignard, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Université Grenoble Alpes - UFR Pharmacie (UGA UFRP), Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Embedded System Lab (ESL), Thales Research and Technology, and Hôpitaux Universitaires de Genève (HUG)

Subjects
Serotonin 5-HT4 Receptor Antagonists, Piperidines/pharmacology, Stereochemistry, chemistry.chemical_element, Serotonin 5-HT4 Receptor Antagonists/chemical synthesis/pharmacology, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Ligands, 010402 general chemistry, 01 natural sciences, Article, Dioxanes, Iodine Radioisotopes, Mice, Radioligand Assay, Structure-Activity Relationship, chemistry.chemical_compound, Piperidines, In vivo, Drug Discovery, medicine, Animals, Humans, Receptor, 5-HT receptor, Tomography, Emission-Computed, Single-Photon, Phenanthridine, medicine.diagnostic_test, Dioxanes/pharmacology, 010405 organic chemistry, Antagonist, 0104 chemical sciences, chemistry, Drug Design, Molecular Probes, Fluorine, Molecular Medicine, Receptors, Serotonin, 5-HT4, Receptors, Serotonin, 5-HT4/chemistry/metabolism, Radiopharmaceuticals, Selectivity, Emission computed tomography
Abstract

The work described herein aims at finding new potential ligands for the brain imaging of 5-HT(4) receptors (5-HT(4)Rs) using single-photon emission computed tomography (SPECT). Starting from the nonsubstituted phenanthridine compound 4a, exhibiting a K(i) value of 51 nM on the 5-HT(4)R, we explored the structure-affinity in this series. We found that substitution in position 4 of the tricycle with a fluorine atom gave the best result. Introduction of an additional nitrogen atom inside the tricyclic framework led to an increase of both the affinity and selectivity for 5-HT(4)R, suggesting the design of the antagonist 4v, exhibiting a high affinity of 0.04 nM. Several iodinated analogues were then synthesized as potential SPECT tracers. The iodinated compound 11d was able to displace the reference radioiodinated 5-HT(4)R antagonist (1-butylpiperidin-4-yl)methyl-8-amino-7-iodo[(123)I]-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylate {[(123)I]1, [(123)I]SB 207710} both in vitro and in vivo in brain. Compound 11d was radiolabeled with [(125)I]iodine, providing a potential SPECT candidate for brain imaging of 5-HT(4)R.

Published
2012
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8. ChemInform Abstract: Cross-Coupling of [2-Aryl-1,1,2,2-Tetrafluoroethyl](trimethyl)silanes with Aryl Halides

Author

Miriam L. O’Duill, Emmanuelle Dubost, Veronique Gouverneur, and Lukas Pfeifer

Subjects
chemistry.chemical_compound, Silanes, chemistry, Phenanthroline, Aryl, Pyridine, Halide, Reactivity (chemistry), General Medicine, Key features, Combinatorial chemistry
Abstract

The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu–Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.

Published
2015

9. Novel Multitarget-Directed Ligands (MTDLs) with Acetylcholinesterase (AChE) Inhibitory and Serotonergic Subtype 4 Receptor (5-HT 4 R) Agonist Activities As Potential Agents against Alzheimer’s Disease: The Design of Donecopride

Author

Sylvie Claeysen, Michel Boulouard, Emmanuelle Dubost, Valentine Bouet, David Genest, Céline Ballandonne, Rémi Legay, Patrick Dallemagne, Damien Hedou, Samir Yahiaoui, Thomas Freret, Jana Sopkova-de Oliveira Santos, François Dauphin, Katia Hamidouche, Patrizia Giannoni, Florence Gaven, Christophe Rochais, Sophie Corvaisier, Aurélie Malzert-Fréon, Cédric Lecoutey, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), Institut de Génomique Fonctionnelle (IGF), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Groupe Mémoire et Plasticité comportementale (GMPc), This work was supported by funding from the Conseil Régional de Basse Normandie, France (Dispositif de Soutien aux Projets de Recherche Emergents), French Agence Nationale de la Recherche Projects MALAD ANR-12-JS007-0012-01 and ADAMGUARD ANR-12-BSV4-008-01, and Ligue Européenne Contre la Maladie d’Alzheimer Grant 12721., ANR-12-JS07-0012,MALAD,Developpement de Ligands pluriactifs d'intérêt potentiel dans le traitement de la maladie d'Alzheimer(2012), ANR-12-BSV4-0008,ADAMGUARD,Les réseaux protéiques associés aux récepteurs 5 HT4 : gardes rapprochées du trafic de l'ADAM10 et de l'APP(2012), Cailly, Thomas, Jeunes Chercheuses et Jeunes Chercheurs - Developpement de Ligands pluriactifs d'intérêt potentiel dans le traitement de la maladie d'Alzheimer - - MALAD2012 - ANR-12-JS07-0012 - JC - VALID, BLANC - Les réseaux protéiques associés aux récepteurs 5 HT4 : gardes rapprochées du trafic de l'ADAM10 et de l'APP - - ADAMGUARD2012 - ANR-12-BSV4-0008 - BLANC - VALID, and Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Agonist, Male, medicine.drug_class, Aché, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, Guinea Pigs, Drug Evaluation, Preclinical, Mice, Inbred Strains, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Pharmacology, Serotonergic, Inhibitory postsynaptic potential, Crystallography, X-Ray, Ligands, Alzheimer's Disease, MTDL, chemistry.chemical_compound, Serotonin 5-HT4 Receptor Agonists, Structure-Activity Relationship, Piperidines, In vivo, Alzheimer Disease, Drug Discovery, medicine, Toxicity Tests, Acute, Structure–activity relationship, Animals, Humans, Computer Simulation, Molecular Targeted Therapy, Receptor, Aniline Compounds, Acetylcholinesterase, language.human_language, 3. Good health, Donecopride, Mice, Inbred C57BL, Memory, Short-Term, chemistry, Drug Design, language, Molecular Medicine, Cholinesterase Inhibitors, Receptors, Serotonin, 5-HT4, 5-HT4 Receptors
Abstract

International audience; In this work, we describe the synthesis and in vitro evaluation of a novel series of multitarget-directed ligands (MTDL) displaying both nanomolar dual-binding site (DBS) acetylcholinesterase inhibitory effects and partial 5-HT4R agonist activity, among which donecopride was selected for further in vivo evaluations in mice. The latter displayed procognitive and antiamnesic effects and enhanced sAPPα release, accounting for a potential symptomatic and disease-modifying therapeutic benefit in the treatment of Alzheimer’s disease.

Published
2015

10. ChemInform Abstract: A General Synthesis of Diversely Substituted Indazoles and Hetero-Aromatic Derivatives from O-Halo-(het)arylaldehydes or -phenones

Author

Thomas Cailly, Valérie Collot, Emmanuelle Dubost, Frédéric Fabis, Thibault Ferrary, and Silvia Stiebing

Subjects
chemistry, chemistry.chemical_element, Organic chemistry, General Medicine, Amination, Catalysis, Palladium
Abstract

A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o -halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N -1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.

Published
2015

11. A doubly responsive probe for the detection of Cys4-tagged proteins

Author

Emmanuelle Dubost, Patrick Berthault, Nathalie J. Arhel, Céline Boutin, Thierry Brotin, Edmond Gravel, James R. Cochrane, Jean-Pierre Dutasta, Gaëlle Milanole, Emilie Mari, Eric Doris, Estelle Léonce, Naoko Kotera, Bernard Rousseau, Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), CIC - Biotherapie - Saint Louis ((CIC-BT 301)), Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Université Paris Diderot - Paris 7 (UPD7)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Groupe Hospitalier Saint Louis - Lariboisière - Fernand Widal [Paris], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP), Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Laboratoire Structure et Dynamique par Résonance Magnétique (LCF) (LSDRM), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Palacin, Serge, Génétique et Ecologie des Virus, Génétique des Virus et Pathogénèse des Maladies Virales, Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Paris Diderot - Paris 7 (UPD7), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), and Université Paris Diderot - Paris 7 (UPD7)-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
Molecular Sequence Data, Biosensing Techniques, Living cell, Catalysis, Green fluorescent protein, law.invention, Protein location, law, [CHIM] Chemical Sciences, Organometallic Compounds, Materials Chemistry, [CHIM]Chemical Sciences, Polycyclic Compounds, Amino Acid Sequence, Cysteine, Nuclear Magnetic Resonance, Biomolecular, ComputingMilieux_MISCELLANEOUS, Fluorescent Dyes, [CHIM.MATE] Chemical Sciences/Material chemistry, Protein function, Chemistry, Metals and Alloys, General Chemistry, Nuclear magnetic resonance spectroscopy, [CHIM.MATE]Chemical Sciences/Material chemistry, Fluoresceins, Molecular biology, Fluorescence, Recombinant Proteins, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Spectrometry, Fluorescence, Ceramics and Composites, Recombinant DNA, Biophysics, Xenon Isotopes, Peptides, Function (biology)
Abstract

International audience; Recombinant proteins bearing a tag are crucial tools for assessing protein location or function. Small tags such as Cys4 tag (tetracysteine; Cys–Cys–X–X–Cys–Cys) are less likely disrupt protein function in the living cell than green fluorescent protein. Herein we report the first example of the design and synthesis of a dual fluorescence and hyperpolarized 129Xe NMR-based sensor of Cys4-tagged proteins. This sensor becomes fluorescent when bound to such Cys4-tagged peptides, and the 129Xe NMR spectrum exhibits a specific signal, characteristic of the biosensor-peptide association.

Published
2015

12. Smart Detection of Toxic Metal Ions, Pb2+ and Cd2+, Using a 129Xe NMR-Based Sensor

Author

Naoko Kotera, Nawal Tassali, Yves Boulard, Estelle Léonce, Jean-Pierre Dutasta, Patrick Berthault, Frédéric Taran, Emmanuelle Dubost, Bernard Rousseau, Thierry Brotin, Céline Boutin, Centre de résonance magnétique des systèmes biologiques (CRMSB), Centre National de la Recherche Scientifique (CNRS)-Université de Bordeaux (UB), Service de Chimie Bio-Organique et de Marquage (SCBM), Médicaments et Technologies pour la Santé (MTS), Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE)-Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) (DRF (CEA)), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), Service de Biologie Intégrative et Génétique Moléculaire (SBIGeM), Institut de Biologie Intégrative de la Cellule (I2BC), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Université de Bordeaux (UB)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Résonance magnétique des systèmes biologiques ( RMSB ), Université Bordeaux Segalen - Bordeaux 2-Centre National de la Recherche Scientifique ( CNRS ), Service de Chimie Bio-Organique et de Marquage ( SCBM ), Département Médicaments et Technologies pour la Santé ( DMTS ), Direction de Recherche Fondamentale (CEA) ( DRF (CEA) ), Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Saclay-Direction de Recherche Fondamentale (CEA) ( DRF (CEA) ), Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Saclay, Service de Biologie Intégrative et Génétique Moléculaire ( SBIGeM ), Institut de Biologie Intégrative de la Cellule ( I2BC ), Université Paris-Saclay-Centre National de la Recherche Scientifique ( CNRS ) -Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Sud - Paris 11 ( UP11 ) -Université Paris-Saclay-Centre National de la Recherche Scientifique ( CNRS ) -Commissariat à l'énergie atomique et aux énergies alternatives ( CEA ) -Université Paris-Sud - Paris 11 ( UP11 ), Centre d'Etudes et de Recherche sur le Médicament de Normandie ( CERMN ), Université de Caen Normandie ( UNICAEN ), Normandie Université ( NU ) -Normandie Université ( NU ), Laboratoire de Chimie - UMR5182 ( LC ), École normale supérieure - Lyon ( ENS Lyon ) -Université Claude Bernard Lyon 1 ( UCBL ), and Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique ( CNRS )

Subjects
Cadmium, Magnetic Resonance Spectroscopy, Ligand, Metal ions in aqueous solution, Inorganic chemistry, chemistry.chemical_element, Zinc, Chemistry Techniques, Analytical, Analytical Chemistry, Ion, Metal, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry, Lead, visual_art, [ CHIM.THEO ] Chemical Sciences/Theoretical and/or physical chemistry, visual_art.visual_art_medium, Chelation, Environmental Pollutants, Fast mri
Abstract

International audience; An approach for sensitive magnetic resonance detection of metal cations is proposed. Combining the use of hyperpolarized 129Xe NMR and of a cage-molecule functionalized by a ligand able to chelate different cations, we show that simultaneous detection of lead, zinc, and cadmium ions at nanomolar concentration is possible in short time, thanks to fast MRI sequences based on the HyperCEST scheme.

Published
2014

13. A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from O-halo-(het)arylaldehydes or -phenones

Author

Emmanuelle Dubost, Frédéric Fabis, Thibault Ferrary, Valérie Collot, Thomas Cailly, Silvia Stiebing, Centre d'Etudes et de Recherche sur le Médicament de Normandie ( CERMN ), Université de Caen Normandie ( UNICAEN ), Normandie Université ( NU ) -Normandie Université ( NU ), Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), and Normandie Université (NU)-Normandie Université (NU)

Subjects
Indazole, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Organic Chemistry, chemistry.chemical_element, Heterocycles, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, [ CHIM ] Chemical Sciences, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, CyclizationIndazole, Drug Discovery, Cross-coupling, Palladium, Amination, ComputingMilieux_MISCELLANEOUS
Abstract

International audience; A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.

Published
2014

14. Synthesis of a functionalizable water-soluble cryptophane-111

Author

Patrick Berthault, Estelle Léonce, Bernard Rousseau, Naoko Kotera, Céline Boutin, Yves Boulard, Christophe Dugave, Sébastien Garcia-Argote, and Emmanuelle Dubost

Subjects
Magnetic Resonance Spectroscopy, Xenon, integumentary system, Chemistry, Organic Chemistry, chemistry.chemical_element, Water, Nanotechnology, Biochemistry, Combinatorial chemistry, Water soluble, Cryptophane-111, Solvents, Polycyclic Compounds, Physical and Theoretical Chemistry, Molecular imaging, circulatory and respiratory physiology
Abstract

The development of optimized xenon host systems is of crucial importance for the success of molecular imaging using hyperpolarized (129)Xe MRI. Cryptophane-111 is a promising candidate because of its encapsulation properties. The synthesis of cryptophane-111-based biosensors requires both water-solubilizing and chemically activatable groups. An expeditious synthesis of a water-soluble and functionalizable cryptophane-111 is described.

Published
2013

15. ChemInform Abstract: Selective ortho-Bromination of Substituted Benzaldoximes Using Pd-Catalyzed C-H Activation: Application to the Synthesis of Substituted 2-Bromobenzaldehydes

Author

Sylvain Rault, Christine Fossey, Thomas Cailly, Emmanuelle Dubost, and Frédéric Fabis

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, Hydroxylamine, Chemistry, Halogenation, General Medicine, Medicinal chemistry, Aldehyde, Catalysis
Abstract

The aldehyde substrates are protected with hydroxylamine and subjected to optimal bromination reactions.

Published
2011

16. Selective ortho-bromination of substituted benzaldoximes using Pd-catalyzed C-H activation : Application to the synthesis of substituted 2-bromobenzaldehydes

Author

Emmanuelle Dubost, Frédéric Fabis, Sylvain Rault, Christine Fossey, Thomas Cailly, Centre d'Etudes et de Recherche sur le Médicament de Normandie ( CERMN ), Université de Caen Normandie ( UNICAEN ), Normandie Université ( NU ) -Normandie Université ( NU ), Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), and Lesnard, Aurélien

Subjects
Halogenation, Molecular Structure, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Combinatorial chemistry, Catalysis, [ CHIM.ORGA ] Chemical Sciences/Organic chemistry, Benzaldehydes, Molecule, Palladium, ComputingMilieux_MISCELLANEOUS
Abstract

Substituted 2-bromobenzaldehydes were synthesized from benzaldehydes using a three-step sequence involving a selective palladium-catalyzed ortho-bromination as the key step. O-Methyloxime serves as a directing group in this reaction. A rapid deprotection of substituted 2-bromobenzaldoximes afforded substituted 2-bromobenzaldehydes with good overall yields.

Published
2011

17. ChemInform Abstract: General Method for the Synthesis of Substituted Phenanthridin-6(5H)-ones Using a KOH-Mediated Anionic Ring Closure as the Key Step

Author

Thomas Cailly, Rosa Magnelli, Sylvain Rault, Emmanuelle Dubost, Frédéric Fabis, and Rémi Legay

Subjects
General method, Chemistry, Closure (topology), Organic chemistry, General Medicine, Ring (chemistry), Medicinal chemistry
Abstract

The cyclization proceeds with both 2′-fluorobiphenyl-2-carbonitriles bearing electron-withdrawing and electron-donating groups.

Published
2010

18. General method for the synthesis of substituted phenanthridin-6(5H)-ones using a KOH-mediated anionic ring closure as the key step

Author

Thomas Cailly, Emmanuelle Dubost, Frédéric Fabis, Rosa Magnelli, Sylvain Rault, Rémi Legay, Centre d'Etudes et de Recherche sur le Médicament de Normandie (CERMN), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU), and Cailly, Thomas

Subjects
Potassium hydroxide, General method, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Closure (topology), [CHIM.ORGA] Chemical Sciences/Organic chemistry, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Biochemistry, Medicinal chemistry, Chemical synthesis, 0104 chemical sciences, chemistry.chemical_compound, Suzuki reaction, Drug Discovery, ComputingMilieux_MISCELLANEOUS
Abstract

Substituted phenanthridin-6(5H)-ones were obtained in a two-step procedure involving a Suzuki cross-coupling reaction followed by a KOH-mediated anionic ring closure. The influence of the nature and the position of the substituents on the cyclization step were studied. This methodology offers a general and practical route to diversely substituted phenanthridin-6(5H)-ones.

Published
2010

19. Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides

Author

Emmanuelle Dubost, Veronique Gouverneur, Miriam L. O’Duill, and Lukas Pfeifer

Subjects
Silanes, 010405 organic chemistry, Aryl, Phenanthroline, Organic Chemistry, Halide, 010402 general chemistry, Key features, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Pyridine, Organic chemistry, Reactivity (chemistry), Physical and Theoretical Chemistry
Abstract

The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and the ability to carry out the reaction at 60 °C or room temperature are the key features of this Cu-Ag mediated cross-coupling methodology. The chemistry is compatible with (hetero)aryl halides, offering a platform to develop products of interest in material and medicinal chemistry.

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