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1. Characterization of Organic Molecules Grafted to Silica or Bismuth Nanoparticles by NMR

Author

Céline Henoumont, Gauthier Hallot, Estelle Lipani, Catherine Gomez, Robert N. Muller, Luce Vander Elst, Marc Port, and Sophie Laurent

Subjects
nanoparticles surface, DOSY, NMR, Technology
Abstract

NMR is a powerful characterization tool and we propose to study the surface of silica or bismuth nanoparticles dedicated to medical applications in order to evidence the covalent grafting of organic molecules on their surface. For that aim, DOSY experiments are particularly useful and allow for the discrimination of molecules interacting strongly with the nanoparticle surface from molecules simply weakly adsorbed at the surface. We were able to characterize thoroughly the surface of different silica and bismuth nanoparticles.

Published
2021
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2. Performances of Homogeneous and Heterogenized Methylene Blue on Silica Under Red Light in Batch and Continuous Flow Photochemical Reactors

Author

Maxime Lancel, Catherine Gomez, Marc Port, and Zacharias Amara

Subjects
photochemistry, flow chemistry, green chemistry, heterogeneous photocatalysis, catalysis, singlet oxygen, Technology, Chemical technology, TP1-1185
Abstract

Methylene blue was efficiently immobilized on silica micro- and nanoparticles by electrostatic interactions and the performances of the heterogenized photocatalysts were compared against the homogeneous conditions using the photooxidation of citronellol as a model reaction under red light, in a batch and a continuous flow photochemical reactor. In batch, the heterogeneous photocatalyst outperforms the homogeneous one, presumably due to kinetic and stability effects. The two catalytic systems are also compared in a flow reactor displaying improved mass transfer properties. We demonstrate that this results in a dramatic enhancement in photocatalyst stability, reactivity and productivity. This study highlights the importance of photocatalyst stability under homogeneous versus heterogenized conditions and in batch versus flow photochemistry.

Published
2021
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3. Medical Applications of Metallic Bismuth Nanoparticles

Author

Catherine Gomez, Gauthier Hallot, Sophie Laurent, and Marc Port

Subjects
bismuth, nanoparticles, theranostic agents, biocompatibility, Pharmacy and materia medica, RS1-441
Abstract

Recent reviews described the efficient syntheses of metallic bismuth nanoparticles. Nevertheless, few studies have been published on the medical applications of these nanoparticles compared to the number of studies on the well-documented clinical use of the bismuth(III) complex. An analysis of the literature revealed the significant potential of metallic bismuth nanoparticles in different theranostic applications. In the diagnostic field, preclinical proofs of concept have been demonstrated for X-ray, photoacoustic and fluorescence imaging. In the therapeutic field, several preclinical studies have shown the potential of bismuth nanoparticles as X-ray radiosensitizers for use in radiotherapy and as photothermal agents for applications in near infrared phototherapy. The properties of these metallic bismuth nanoparticles as bactericidal, fungicidal, antiparasitic and antibiofilm agents have also been studied. Although information concerning the toxic effects of these nanoparticles has been collected, these data are insufficient when considering the immediate clinical use of these new nanoparticles.

Published
2021
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4. Self-Sensitized Photooxidation of Naphthols to Naphthoquinones and the Use of Naphthoquinones as Visible Light Photocatalysts in Batch and Continuous Flow Reactors

Author

Maxime Lancel, Pierre Zimberlin, Catherine Gomez, Marc Port, Lhoussain Khrouz, Cyrille Monnereau, Zacharias Amara, Laboratoire Génomique, bioinformatique et chimie moléculaire (GBCM), Conservatoire National des Arts et Métiers [CNAM] (CNAM), HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM)-HESAM Université - Communauté d'universités et d'établissements Hautes écoles Sorbonne Arts et métiers université (HESAM), Laboratoire de Chimie - UMR5182 (LC), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, [CHIM]Chemical Sciences
Abstract

Visible light photooxidation of naphthols to produce naphthoquinones, such as the natural product juglone, has been known for decades and has been widely utilized to benchmark the performances of a variety of photocatalytic systems. We discovered that these transformations can occur without the help of a photocatalyst and, even more intriguingly, that the photocatatyst-free process provides higher yields compared to control experiments utilizing state-of-the-art photocatalysts. In addition, we demonstrate that naphthoquinones and their corresponding naphthol precursors can act as alternatives to commonly used organic and organometallic photocatalysts with applications to challenging targets, such as the antimalarial drug artemisinin. This approach was finally transposed in continuous flow reactors where high photocatalyst stability and process efficiency are demonstrated with a 23× improvement in the space-time yield.

Published
2023
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5. Characterization of Organic Molecules Grafted to Silica or Bismuth Nanoparticles by NMR

Author

Luce Vander Elst, Sophie Laurent, Estelle Lipani, Marc Port, Robert N. Muller, Catherine Gomez, Gauthier Hallot, Céline Henoumont, NMR Laboratory, Université de Mons, Université de Mons (UMons), Laboratoire Génomique, bioinformatique et chimie moléculaire (GBCM), Conservatoire National des Arts et Métiers [CNAM] (CNAM), Center for Microscopy and Molecular Imaging (IBMM - CMMI), and Université libre de Bruxelles (ULB)

Subjects
Technology, Materials science, Geography, Planning and Development, Nanoparticle, DOSY, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Grafting, 01 natural sciences, Bismuth nanoparticles, NMR, 0104 chemical sciences, Organic molecules, Characterization (materials science), Adsorption, Chemical engineering, Covalent bond, Molecule, [CHIM]Chemical Sciences, nanoparticles surface, 0210 nano-technology
Abstract

International audience; NMR is a powerful characterization tool and we propose to study the surface of silica or bismuth nanoparticles dedicated to medical applications in order to evidence the covalent grafting of organic molecules on their surface. For that aim, DOSY experiments are particularly useful and allow for the discrimination of molecules interacting strongly with the nanoparticle surface from molecules simply weakly adsorbed at the surface. We were able to characterize thoroughly the surface of different silica and bismuth nanoparticles.

Published
2021
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6. Medical Applications of Metallic Bismuth Nanoparticles

Author

Sophie Laurent, Marc Port, Gauthier Hallot, Catherine Gomez, Laboratoire Génomique, bioinformatique et chimie moléculaire (GBCM), Conservatoire National des Arts et Métiers [CNAM] (CNAM), Université de Mons (UMons), and NMR Laboratory, Université de Mons

Subjects
Materials science, Biocompatibility, Pharmaceutical Science, Photoacoustic imaging in biomedicine, Nanoparticle, chemistry.chemical_element, Nanotechnology, 02 engineering and technology, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Review, 010402 general chemistry, 01 natural sciences, Bismuth, Metal, Pharmacy and materia medica, biocompatibility, theranostic agents, bismuth, [CHIM]Chemical Sciences, Photothermal therapy, 021001 nanoscience & nanotechnology, Bismuth nanoparticles, 0104 chemical sciences, RS1-441, chemistry, visual_art, visual_art.visual_art_medium, nanoparticles, 0210 nano-technology
Abstract

International audience; Recent reviews described the efficient syntheses of metallic bismuth nanoparticles. Nevertheless, few studies have been published on the medical applications of these nanoparticles compared to the number of studies on the well-documented clinical use of the bismuth(III) complex. An analysis of the literature revealed the significant potential of metallic bismuth nanoparticles in different theranostic applications. In the diagnostic field, preclinical proofs of concept have been demonstrated for X-ray, photoacoustic and fluorescence imaging. In the therapeutic field, several preclinical studies have shown the potential of bismuth nanoparticles as X-ray radiosensitizers for use in radiotherapy and as photothermal agents for applications in near infrared phototherapy. The properties of these metallic bismuth nanoparticles as bactericidal, fungicidal, antiparasitic and antibiofilm agents have also been studied. Although information concerning the toxic effects of these nanoparticles has been collected, these data are insufficient when considering the immediate clinical use of these new nanoparticles.

Published
2021
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7. A Greener Chemistry Process Using Microwaves in Continuous Flow to Synthesize Metallic Bismuth Nanoparticles

Author

Marc Port, Sophie Laurent, Virginie Cagan, Gauthier Hallot, Catherine Gomez, Laboratoire Génomique, bioinformatique et chimie moléculaire (GBCM), Conservatoire National des Arts et Métiers [CNAM] (CNAM), and Université de Mons (UMons)

Subjects
Renewable Energy, Sustainability and the Environment, Continuous flow, Chemistry, General Chemical Engineering, Nanotechnology, 02 engineering and technology, General Chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Bismuth nanoparticles, 0104 chemical sciences, Metal, reproductibility, Scientific method, visual_art, bismuth, visual_art.visual_art_medium, Environmental Chemistry, continuous flow, [CHIM]Chemical Sciences, green nanochemistry, 0210 nano-technology, Microwave
Abstract

International audience; To address environmental concerns, improving synthesis processes in the nanoparticle field was a major challenge. Several processes of bismuth nanoparticle synthesis have been proposed in the past 10 years, but none of them have answered to all green chemistry principles suitable for nanomaterials. In this work, two syntheses of bismuth nanoparticles involving conventional thermal heating and microwave irradiation were compared in batch. All parameters have been studied to optimize the size and distribution of metallic bismuth nanoparticles. The choice of precursor, reducing agent, coating agent, solvents, the evaluation of quantities and the follow-up of reduction step, never documented before, have been fully described in this work. Following this optimization, the validation of synthesis reproducibility confirmed that microwave irradiation was the best process for obtaining bismuth nanoparticles according to green chemistry criteria. This study was continued using a millifluidic process to increase productivity. This continuous flow synthesis under microwave irradiation responded to industrial challenges and provided access to monodisperse bismuth nanoparticles that were characterized by several techniques.

Published
2021
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8. Metallic bismuth nanoparticles: Towards a robust, productive and ultrasound assisted synthesis from batch to flow-continuous chemistry

Author

Sophie Laurent, Emilie Brun, Alexandra Pastor, Gauthier Hallot, Cécile Sicard-Roselli, Catherine Gomez, Marc Port, Laboratoire Génomique, bioinformatique et chimie moléculaire (GBCM), Conservatoire National des Arts et Métiers [CNAM] (CNAM), Université de Mons (UMons), Laboratoire de Chimie Physique D'Orsay (LCPO), and Université Paris-Sud - Paris 11 (UP11)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
inorganic chemicals, Green chemistry, Acoustics and Ultrasonics, Sonication, Oxide, chemistry.chemical_element, Nanoparticle, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Robust process, Bismuth, Inorganic Chemistry, chemistry.chemical_compound, Dynamic light scattering, Chemical Engineering (miscellaneous), Environmental Chemistry, [SDV.BBM]Life Sciences [q-bio]/Biochemistry, Molecular Biology, Radiology, Nuclear Medicine and imaging, Flow chemistry, Productivity, Organic Chemistry, 021001 nanoscience & nanotechnology, [SDV.BIBS]Life Sciences [q-bio]/Quantitative Methods [q-bio.QM], 0104 chemical sciences, chemistry, Chemical engineering, Ultrasound assisted synthesis, d-Glucose, 13. Climate action, Nanoparticles, 0210 nano-technology, Stoichiometry
Abstract

International audience; Bismuth is a highly biocompatible and inexpensive metal with a high atomic number, which confers an important X-rays opacity. While bismuth oxide or bismuth sulphide have been extensively studied in imaging, little is known about metallic bismuth nanoparticles. The latter are more attractive for X-rays imaging because they contain neither oxygen nor sulfur, so that a high amount of metal atoms is contained within the nanoparticles. We report here a robust, efficient and green ultrasound assisted synthesis to obtain metallic bismuth NPs. The procedure, which has been optimized to get a reproducible synthesis, will also tend to minimize chemical hazards to health and environment. By applying the green chemistry principles, several experimental parameters have been studied such as reaction time, reactants stoichiometry, temperature, starting material quantities and purification steps number. Two energy delivery system (classical heating and sonication) were compared. The production of small metallic bismuth NPs on a large scale by flow chemistry coupled to sonication was showed for the first time. These optimizations of the process were completed by a comparison of two purification methods (centrifugation and ultrafiltration) to isolate purified thin black powders of d-glucose-coated bismuth NPs. Several analytical techniques were used to characterize products (structures, sizes and morphology) such as Fourier Transform InfraRed (FT-IR) spectroscopy, Dynamic Light Scattering (DLS), Transmission Electron Microscopy (TEM), Energy-dispersive X-ray spectrometry (EDX) and X-Ray Diffraction (XRD). All these analyses corroborated well with the structure of metallic bismuth NPs coated with a d-glucose shell.

Published
2018
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9. Inhibition of p53-Murine Double Minute 2 (MDM2) Interactions with 3,3'-Spirocyclopentene Oxindole Derivatives

Author

Eric Jacquet, Olivier Pamlard, Maxime Gicquel, Arnaud Voituriez, Catherine Gomez, Maria Concepcion Garcia Alvarez, Jérôme Bignon, Vincent Guérineau, Angela Marinetti, Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS), Laboratoire de synthèse organique (DCSO), Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Ecole Nationale Supérieure de Chimie de Lille (ENSCL)

Subjects
Models, Molecular, [SDV]Life Sciences [q-bio], Molecular Conformation, Antineoplastic Agents, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Structure-Activity Relationship, Western blot, Drug Discovery, P53 status, medicine, Structure–activity relationship, Humans, Oxindole, Spiro Compounds, IC50, ComputingMilieux_MISCELLANEOUS, Cell Proliferation, biology, medicine.diagnostic_test, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Proto-Oncogene Proteins c-mdm2, HCT116 Cells, In vitro, 0104 chemical sciences, 3. Good health, Oxindoles, Biochemistry, chemistry, Drug Design, Antiproliferative Agents, biology.protein, Molecular Medicine, Mdm2, Tumor Suppressor Protein p53, Protein Binding
Abstract

International audience; 3,3'-Spirocyclopentene oxindoles structurally related to Wang's spiropyrrolidine oxindoles have been highlighted as a new class of antiproliferative agents against cancer cell lines with wild-type p53 status (IC50 up to 0.96 μM on SJSA-1 and 2.9 μM in HCT116 p53-wt). Inhibition of the MDM2-p53 interactions has been demonstrated through in vitro HTRF assays (IC50 up to 3.1 nM), while Western blot analysis showed activation of p53 selectively in HCT116 cancer cell lines with wild-type p53.

Published
2018
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10. Potent 3‐Hydroxy‐2‐Pyridine Aldoxime Reactivators of Organophosphate‐Inhibited Cholinesterases with Predicted Blood–Brain Barrier Penetration

Author

Martin Weik, Ludovic Jean, Guillaume Mercey, Romain Mougeot, Tamara Zorbaz, Nikolina Maček Hrvat, Nikola Maraković, Florian Nachon, Maja Katalinić, Joel L. Sussman, Eugenio de la Mora, Anissa Braïki, Zrinka Kovarik, Belén Pérez, Pierre-Yves Renard, Catherine Gomez, Julien Renou, Rachid Baati, Israel Silman, Institute for Medical Research and Occupational Health, 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 de biologie structurale (IBS - UMR 5075 ), Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), 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)-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)-Centre National de la Recherche Scientifique (CNRS), Weizmann Institute of Science [Rehovot, Israël], Universitat Autònoma de Barcelona (UAB), Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Matériaux et nanosciences d'Alsace (FMNGE), Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche Biomédicale des Armées (IRBA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), 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 de biologie structurale (IBS - UMR 5075), Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Grenoble Alpes (UGA)-Centre National de la Recherche Scientifique (CNRS), Weizmann Institute of Science, Laboratoire d'étude des Interactions Sol - Agrosystème - Hydrosystème (UMR LISAH), Institut de Recherche pour le Développement (IRD)-Institut National de la Recherche Agronomique (INRA)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Institut de Recherche pour le Développement (IRD [ Madagascar])-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), UMR 5567-CNRS, University of Montpellier II, France, Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS), Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace, Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique Fine (IRCOF), 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), Université de Caen Normandie (UNICAEN), 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)-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), Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut de Recherche Interdisciplinaire de Grenoble (IRIG), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), and Institut de Recherche Biomédicale des Armées [Brétigny-sur-Orge] (IRBA)

Subjects
0301 basic medicine, Sarin, Stereochemistry, Cyclosarin, Catalysis, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Oximes, medicine, Humans, [CHIM]Chemical Sciences, HI-6, pesticide, sarin, VX, acetylcholinesterase, butyrylcholinesterase, CNS active, PAMPA, Butyrylcholinesterase, Tabun, Paraoxon, Organic Chemistry, Organophosphate, General Chemistry, Oxime, Acetylcholinesterase, Organophosphates, 030104 developmental biology, chemistry, Blood-Brain Barrier, 030217 neurology & neurosurgery, medicine.drug
Abstract

International audience; A new series of 3‐hydroxy‐2‐pyridine aldoxime compounds have been designed, synthesised and tested in vitro, in silico, and ex vivo as reactivators of human acetylcholinesterase (hAChE) and butyrylcholinesterase (hBChE) inhibited by organophosphates (OPs), for example, VX, sarin, cyclosarin, tabun, and paraoxon. The reactivation rates of three oximes (16–18) were determined to be greater than that of 2‐PAM and comparable to that of HI‐6, two pyridinium aldoximes currently used by the armies of several countries. The interactions important for a productive orientation of the oxime group within the OP‐inhibited enzyme have been clarified by molecular‐modelling studies, and by the resolution of the crystal structure of the complex of oxime 17 with Torpedo californica AChE. Blood–brain barrier penetration was predicted for oximes 15–18 based on their physicochemical properties and an in vitro brain membrane permeation assay. Among the evaluated compounds, two morpholine‐3‐hydroxypyridine aldoxime conjugates proved to be promising reactivators of OP‐inhibited cholinesterases. Moreover, efficient ex vivo reactivation of phosphylated native cholinesterases by selected oximes enabled significant hydrolysis of VX, sarin, paraoxon, and cyclosarin in whole human blood, which indicates that the oximes have scavenging potential.

Published
2018
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11. List of Contributors

Author

Niyati S. Acharya, Sanjeev R. Acharya, Mena Aioub, Bernardo G. Almeida, João P. Araújo, Lauren A. Austin, Paramdeep S. Bagga, Ayan K. Barui, Elmars Blums, Bárbara J.P. Borges, Graciela Borthagaray, Lara S. Carminati, Elisabete M.S. Castanheira, Paulo J.G. Coutinho, Namdev L. Dhas, Mostafa A. El-Sayed, Pinar Erkekoglu, Gianella Facchin, Syeda J. Fathima, A. Alberto R. Fernandes, Patricia M.B. Fernandes, Catherine Gomez, Catherine M. Greene, Gauthier Hallot, Nallamuthu Ilaiyaraja, Sana Iram, Didem Şen Karaman, Helene Kettiger, Mohd S. Khan, Salman Khan, Farhath Khanum, Belma Kocer-Gumusel, Rajesh Kotcherlakota, Ritu R. Kudarha, Mikhail Maiorov, Raúl J. Martín-Palma, Melina Mondelli, Chitta R. Patra, Ramón J. Peláez, Marc Port, Maria-João R.P. Queiroz, Moniba Rahim, Habiba Ramzan, Nisith J. Raval, Gonzalo Recio-Sánchez, Syed M.D. Rizvi, Ana Rita O. Rodrigues, Izolda Segal, María H. Torre, Sebastian F. Vencken, Zubaida Yousaf, Alla Zablotskaya, and Dmitry Zablotsky

Published
2018
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12. Bismuth metallic nanoparticles

Author

Catherine Gomez, Marc Port, Gauthier Hallot, and Conservatoire National des Arts et Métiers [CNAM] (CNAM)

Subjects
Materials science, synthesis, Oxide, Nanoparticle, chemistry.chemical_element, Nanotechnology, 02 engineering and technology, reductive agents, 010402 general chemistry, Bismuth metallic nanoparticles, 01 natural sciences, Bismuth, Metal, chemistry.chemical_compound, bismuth, [CHIM]Chemical Sciences, characterization, chemistry.chemical_classification, green chemistry, medical applications, Polymer, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Characterization (materials science), Solvent, Monomer, chemistry, visual_art, visual_art.visual_art_medium, capping agents, 0210 nano-technology
Abstract

International audience; Numerous studies are published on the synthesis and characterization of bismuth oxide or bismuth sulfide nanoparticles. Only a few works are dealing with the synthesis and applications of spherical bismuth metallic nanoparticles. However, this field of research is emerging and so in this chapter, different strategies to synthesize spherical metallic bismuth nanoparticles are reviewed. Two pathways are referenced: the top-down and, more described, bottom-up approaches. All procedures are critically compared to show how they could be improved and directed towards greener strategies. The different capping agents (polymers, hydrophilic or hydrophobic monomers) used to control size, morphology, and stability of these nanoparticles are discussed, as well as the choice of solvent. The relevance of heating techniques (classical heating or irradiation under microwaves) and purification are compared to green processes. Finally, bismuth metallic nanoparticles are discussed in different medical applications, such as theranostic applications as X-ray contrast agent, or X-ray radiosensitizers.

Published
2018
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13. Perindopril and ramipril phosphonate analogues as a new class of angiotensin converting enzyme inhibitors

Author

Sabine Berteina-Raboin, Gérald Guillaumet, Guillaume De Nanteuil, and Catherine Gomez

Subjects
Ramipril, Clinical Biochemistry, Organophosphonates, Pharmaceutical Science, Angiotensin-Converting Enzyme Inhibitors, Peptidyl-Dipeptidase A, Pharmacology, Biochemistry, chemistry.chemical_compound, Catalytic Domain, Drug Discovery, Perindopril, medicine, Humans, Molecular Biology, Binding Sites, biology, Chemistry, Organic Chemistry, Stereoisomerism, Angiotensin-converting enzyme, Phosphonate, Enzyme Activation, Molecular Docking Simulation, biology.protein, Molecular Medicine, Protein Binding, circulatory and respiratory physiology, medicine.drug
Abstract

A series of phosphonate analogues related to perindopril and ramipril were prepared and tested to estimate their ability to inhibit angiotensin converting enzyme. These new synthesized compounds were active ACE inhibitors with a promising activity.

Published
2013
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14. Heterocyclic Spiranes and Dispiranes via Enantioselective Phosphine-Catalyzed [3+2] Annulations

Author

Angela Marinetti, Pascal Retailleau, Nathalie Pinto, Jean-François Betzer, Arnaud Voituriez, Catherine Gomez, Deepti Duvvuru, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Enantioselective synthesis, chemistry.chemical_element, General Chemistry, 010402 general chemistry, 01 natural sciences, Sulfur, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, chemistry, Organic chemistry, ComputingMilieux_MISCELLANEOUS, Phosphine
Abstract

The synthesis of highly functionalized heterocyclic spiranes has been carried out by [3+2] cyclizations between allenoates and enones, under phosphine catalysis. Excellent enantioselectivity levels (ees up to 99%) have been attained in FerroPHANE-promoted cyclizations of this class, leading to chiral sulfides with unprecedented spiranic structures. The corresponding sulfoxides have been obtained then via a subsequent, highly diastereoselective oxidation of the prostereogenic sulfur centre.

Published
2012
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15. Exploring the Reactivity of Carbon(0)/Borane-Based Frustrated Lewis Pairs

Author

Richard Goddard, Catherine Gomez, Manuel Alcarazo, and Sigrid Holle

Subjects
Chemistry, Stereochemistry, Hydrogen bond, Imine, chemistry.chemical_element, Boranes, General Medicine, General Chemistry, Borane, Photochemistry, Catalysis, Frustrated Lewis pair, chemistry.chemical_compound, Reactivity (chemistry), Lewis acids and bases, Carbon
Abstract

DOI 10.1002/anie.201002119 In a series of papers predating the current frustrated Lewis pair (FLP) terminology, the hydrosilation of carbonyl[1] and imine[2] functions as well as the silation of alcohols[3] has been achieved. Strong kinetic arguments point towards a Si H bond activation via a FLP-type mechanism in these processes. The authors would like to thank Prof. W. E. Piers for bringing this precedent to their attention.

Published
2010
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16. Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

Author

Sophie Beauvière, Catherine Gomez, Jean Philippe Goddard, Louis Fensterbank, Rocio Martinez Mallorquin, Max Malacria, Ilan Marek, Adi Abramovitch, Franck Brebion, Guillaume Vincent, Saloua Cheli, Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Schulich faculty of chemistry, Technion - Israel Institute of Technology [Haifa], UPMC, CNRS, IUF, ANR CREDOX [ANR-10-BLAN-0701], Radicaux Verts [ANR-06-BLAN-0309], ANR-10-BLAN-0701,Credox,Catalyse Redox pour une Synthèse Radicalaire Ecocompatible(2010), ANR-06-BLAN-0309,Radicaux verts,Synthèse radicalaire verte(2006), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie Physique des Réactions (DCPR), Centre National de la Recherche Scientifique (CNRS) - Institut National Polytechnique de Lorraine (INPL), Unité de Pharmacologie Chimique et Génétique (UPCG), Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP) - IFR71 - Université Paris Descartes - Paris 5 (UPD5) - Institut National de la Santé et de la Recherche Médicale (INSERM) - Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans (UO) - Institut National de la Santé et de la Recherche Médicale (INSERM) - Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétéroéléments et Coordination (DCPH), Polytechnique - X - Centre National de la Recherche Scientifique (CNRS), Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, and Université Pierre et Marie Curie - Paris 6 (UPMC) - Centre National de la Recherche Scientifique (CNRS)

Subjects
Allylic rearrangement, Chemistry(all), General Chemical Engineering, Radical, Ionic bonding, 010402 general chemistry, Red-ox, Tandem, 01 natural sciences, Medicinal chemistry, Deprotonation, Nucleophile, Organic chemistry, Carbanion, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Conjugate addition, Alkylidene bis-sulfoxide, General Chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, 0104 chemical sciences, Enantiopure drug, Chemical Engineering(all)
Abstract

International audience; [1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.

Published
2016
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17. Enolate Conjugate Addition to Alkylidene Bis-Sulfoxides: Sphaeric Acid Synthesis and Absolute Configuration Determination

Author

Louis Fensterbank, Max Malacria, Jean-Philippe Goddard, Franck Brebion, and Catherine Gomez

Subjects
chemistry.chemical_compound, Sphaeric acid, chemistry, Succinic acid, Organic Chemistry, Absolute configuration, Organic chemistry, Stereoselectivity, Conjugate
Abstract

The first stereoselective synthesis of sphaeric acid is described. The key step of this synthesis is an efficient ester enolate conjugate addition onto alkylidene bis-sulfoxides with good to high diastereoselectivity. Formation of sphaeric acid allowed the determination of its absolute configuration as 2R.3R.

Published
2006
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18. Phosphoryl Compounds

Author

Pierre-Yves Renard, Christopher M. Timperley, Catherine Gomez, 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), Defence Science and Technology Laboratory (Dstl), and Ministry of Defence (UK) (MOD)

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, 010405 organic chemistry, Chemistry, Aryl, Perkow reaction, [CHIM]Chemical Sciences, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, ComputingMilieux_MISCELLANEOUS, Alkyl, 0104 chemical sciences
Abstract

Synthetic methods for phosphoryl compounds are described. The methods cover 75 classes of compounds. These include dialkyl/diaryl phosphoryl substances of general structure: ROP(O)Cl2, ArOP(O)Cl2, ROP(O)F2, ArOP(O)F2, ROP(O)(NR2)2, ROP(O)(NHNHR)2, ROP(O)(NCO)2, ROP(O)(NCS)2, ROP(O)(OH)2, ROP(O)(SR)2, RO(RS)P(O)Cl, RO(R2N)P(O)Cl, RS(R2N)P(O)Cl, (RS)2P(O)Cl, RO(RS)P(O)F, RO(R2N)P(O)F, (RO)2P(O)H, RO(R′O)P(O)H, (ArO)2P(O)H, (RO)2P(O)X (X = F, Cl, Br, I, and CN), (ArO)2P(O)Cl, (RO)2P(O)C(O)X (X = OR, SR, NR2, and NHOR), (RO)2P(O)C(S)SR, (RO)2P(O)OX (X = H, OR, R, NCR2 and CRCR2), RO(R′O)P(O)OH, (ArO)2P(O)OR, (ArO)3PO, (RO)2P(O)N3, (RO)2P(O)NR2, (RO)2P(O)NHAr, (ArO)2P(O)NR2, (RO)2P(O)N(Me)P(X)R2 (X = O or S), (RO)2P(O)N(Me)COR, (RO)2P(O)N(Cl)Ar, (RO)2P(O)NX2 (X = Cl or Br), (RO)2P(O)NHOR (R = H or alkyl), (RO)2P(O)NHNH2, (RO)2P(O)NCO, (RO)2P(O)NCS, (RO)2P(O)NSO, (RO)2P(O)NHSO2NHP(O)(OR)2, (RO)2P(O)NCHR, (RO)2P(O)NC(NR2)2, (RO)2P(O)SR (R = H, alkyl/aryl, SR, and OR), (RO)2P(O)S(O)OR, (RO)2P(O)XP(O)(OR)2 (X = O, S, SS, and SO), RNHP(O)Cl2, R2NP(O)X2 (X = Cl and F), (R2N)2P(O)X (X = H, Cl, F, and N3), (R2N)2P(O)OP(O)(NR2)2, (RNH)3PO and (R2N)3PO.

Published
2015
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19. Contributors

Author

Nicholas Cooper, Catherine Gomez, Guoxiong Hua, Pierre-Yves Renard, James Riches, John Tattersall, Christopher M. Timperley, and Derek Woollins

Published
2015
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20. ChemInform Abstract: Synthesis of 3,3′-Spirocyclic Oxindoles via Phosphine Catalyzed [4 + 2] Cyclizations

Author

Arnaud Voituriez, Maxime Gicquel, Catherine Gomez, Angela Marinetti, and Pascal Retailleau

Subjects
chemistry.chemical_compound, Chemistry, Synthon, General Medicine, Triphenylphosphine, Medicinal chemistry, Phosphine, Catalysis, Stereocenter
Abstract

Triphenylphosphine promoted reactions between 3-arylideneoxindoles and δ-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted δ-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.

Published
2013
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21. Synthesis of 3,3'-spirocyclic oxindoles via phosphine catalyzed [4 + 2] cyclizations

Author

Arnaud Voituriez, Maxime Gicquel, Catherine Gomez, Angela Marinetti, Pascal Retailleau, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Indoles, Phosphines, 010402 general chemistry, 01 natural sciences, Biochemistry, Catalysis, Stereocenter, chemistry.chemical_compound, Organophosphorus Compounds, X-Ray Diffraction, Organic chemistry, Spiro Compounds, Physical and Theoretical Chemistry, Triphenylphosphine, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, Synthon, Stereoisomerism, 0104 chemical sciences, Oxindoles, chemistry, Cyclization, Phosphine
Abstract

International audience; Triphenylphosphine promoted reactions between 3-arylideneoxindoles and δ-aryl-substituted penta-2,3-dienoates afford an unprecedented access to spirocyclic oxindoles with functionalized six-membered rings. In these new [4 + 2] cyclization processes, the allenoates operate as the four-carbon synthons, thanks to the involvement of the substituted δ-carbons. These reactions give excellent control of the relative stereochemistry of the three stereogenic centers. The stereochemistry of the final product has been ascertained by X-ray diffraction studies.

Published
2013
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23. ChemInform Abstract: Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

Author

Jean-Christophe Carry, Laurent Schio, Catherine Gomez, Arnaud Voituriez, Angela Marinetti, Pascal Retailleau, and Maxime Gicquel

Subjects
chemistry.chemical_compound, chemistry, Stereochemistry, Cyclopentene, Stereoselectivity, General Medicine, Phosphine, Stereocenter, Catalysis
Abstract

The phosphine-promoted [3 + 2] cyclizations between γ-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh(3) operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

Published
2013
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24. New Advances in Bis(Sulfoxides) Chemistry

Author

Sophie Beauvière, Ophélie Kwasnieski, Jean-Philippe Goddard, Guillaume Vincent, Louis Fensterbank, Benedicte Delouvrie, Maxime R. Vitale, Etienne Derat, Ilan Marek, Max Malacria, Francisco Najera, Saloua Chelli, Catherine Gomez, Rocio Martinez Mallorquin, Franck Brebion, Unité de Pharmacologie Chimique et Génétique (UPCG - UMR_S 640/UMR 8151), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Paris Descartes - Paris 5 (UPD5)-Institut des sciences du Médicament -Toxicologie - Chimie - Environnement (IFR71), Institut National de la Santé et de la Recherche Médicale (INSERM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC), Laboratoire Hétéroéléments et Coordination (DCPH), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Organique et Analytique (ICOA), Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Orléans (UO)-Institut de Chimie du CNRS (INC), Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, CNRS, UPMC, ANR BLAN ``Radicaux Verts', ANR BLAN ``CREDOX', DGA, Fondation de Gif, IUF, Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut des sciences du Médicament -Toxicologie - Chimie - Environnement (IFR71), Institut de Recherche pour le Développement (IRD)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Unité de Pharmacologie Chimique et Génétique ( UPCG - UMR_S 640/UMR 8151 ), Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL ( ENSCP ) -Institut des sciences du Médicament -Toxicologie - Chimie - Environnement ( IFR71 ), Institut National de la Santé et de la Recherche Médicale ( INSERM ) -Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL ( ENSCP ) -Centre National de la Recherche Scientifique ( CNRS ) -Institut de Recherche pour le Développement ( IRD ) -Université Paris Descartes - Paris 5 ( UPD5 ) -Institut National de la Santé et de la Recherche Médicale ( INSERM ) -Centre National de la Recherche Scientifique ( CNRS ) -Institut de Recherche pour le Développement ( IRD ) -Université Paris Descartes - Paris 5 ( UPD5 ) -Université Paris Descartes - Paris 5 ( UPD5 ) -Institut National de la Santé et de la Recherche Médicale ( INSERM ) -Centre National de la Recherche Scientifique ( CNRS ), Laboratoire Hétéroéléments et Coordination ( DCPH ), École polytechnique ( X ) -Centre National de la Recherche Scientifique ( CNRS ), Institut de Chimie Organique et Analytique ( ICOA ), Centre National de la Recherche Scientifique ( CNRS ) -Institut National de la Santé et de la Recherche Médicale ( INSERM ) -Université d'Orléans ( UO ), Institut Parisien de Chimie Moléculaire ( IPCM ), Université Pierre et Marie Curie - Paris 6 ( UPMC ) -Centre National de la Recherche Scientifique ( CNRS ), Département de Chimie Physique des Réactions ( DCPR ), Institut National Polytechnique de Lorraine ( INPL ) -Centre National de la Recherche Scientifique ( CNRS ), Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-Institut des sciences du Médicament -Toxicologie - Chimie - Environnement (IFR71), Institut National de la Santé et de la Recherche Médicale (INSERM)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Paris Descartes - Paris 5 (UPD5)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie Physique des Réactions (DCPR), Institut National Polytechnique de Lorraine (INPL)-Centre National de la Recherche Scientifique (CNRS), and Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)

Subjects
bis(sulfoxides), radical, 010405 organic chemistry, Chemistry, ligands, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, 3. Good health, 0104 chemical sciences, Inorganic Chemistry, [ CHIM.ORGA ] Chemical Sciences/Organic chemistry, Michael addition, Michael reaction, Organic chemistry
Abstract

International audience; The chemistry of bis(sulfoxides) is discussed from two starting materials, (Ss,Ss)-bis-p-tolylsulfinylmethane and (Ss,Ss)-bis-p-tolylsulfinyl alkylidenes. Reactions presented include Michael additions, ionic-radical crossover processes and coordination complexes formations.

Published
2013
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25. Phosphine-Catalyzed Synthesis of 3,3-Spirocyclopenteneoxindoles from γ-Substituted Allenoates: Systematic Studies and Targeted Applications

Author

Jean-Christophe Carry, Catherine Gomez, Laurent Schio, Maxime Gicquel, Angela Marinetti, Arnaud Voituriez, Pascal Retailleau, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
Indoles, Molecular Structure, 010405 organic chemistry, Stereochemistry, Chemistry, Phosphines, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Cyclopentanes, 010402 general chemistry, 01 natural sciences, Catalysis, 3. Good health, 0104 chemical sciences, Stereocenter, Alkadienes, chemistry.chemical_compound, Cyclization, Molecule, Cyclopentene, Stereoselectivity, Spiro Compounds, Phosphine
Abstract

International audience; The phosphine-promoted [3 + 2] cyclizations between γ-substituted allenoates and arylideneoxindoles have been applied to the stereoselective synthesis of spiro(cyclopentene)oxindoles with trisubstituted cyclopentene units. It has been demonstrated that PPh(3) operates a very efficient control of the relative stereochemistry of the three stereogenic centers of the final spiranic products. Focused experiments have been carried out then so as to access carbocyclic analogues of an important series of anticancer agents inhibiting MDM2-p53 interactions.

Published
2013
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26. Phosphine organocatalysis in the synthesis of natural products and bioactive compounds

Author

Angela Marinetti, Catherine Gomez, Arnaud Voituriez, Jean-François Betzer, Institut de Chimie des Substances Naturelles (ICSN), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Total synthesis, 010402 general chemistry, 01 natural sciences, Small molecule, Catalysis, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, chemistry, Intramolecular force, Organocatalysis, Organic chemistry, Physical and Theoretical Chemistry, Phosphine, ComputingMilieux_MISCELLANEOUS
Abstract

During the last few years, synthetic methods based on phosphine organocatalysis have experienced extremely fast developments. This short overview is intended to demonstrate that these methods can afford suitable tools for the constitution of either focused or diversity-oriented-synthesis (DOS) inspired libraries of small molecules for biological screening. It also reports selected examples where these organocatalytic methods have been used conveniently as key steps in the formal or total synthesis of complex natural products. Especially, synthetic applications of the inter- and intramolecular cyclizations of unsaturated substrates have been considered in this review.

Published
2013
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27. Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis

Author

Catherine Gomez, Guillaume Anquetin, Prishila Ponien, Alexandra Aubry, Aazdine Lamouri, Estelle Capton, Nawal Serradji, Vincent Jarlier, Alix Pantel, Institut de Chimie Organique et Analytique (ICOA), and Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Université d'Orléans (UO)-Institut de Chimie du CNRS (INC)

Subjects
medicine.drug_class, Moxifloxacin, Clinical Biochemistry, Antitubercular Agents, Pharmaceutical Science, Microbial Sensitivity Tests, Gatifloxacin, Biochemistry, DNA gyrase, Microbiology, Mycobacterium tuberculosis, Structure-Activity Relationship, 03 medical and health sciences, chemistry.chemical_compound, Drug Discovery, medicine, Topoisomerase II Inhibitors, DNA Cleavage, Molecular Biology, Mycobacterium leprae, 030304 developmental biology, Aza Compounds, 0303 health sciences, biology, 030306 microbiology, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Quinolone, biology.organism_classification, 3. Good health, DNA Gyrase, Mutation, Quinolines, Molecular Medicine, DNA supercoil, Ofloxacin, DNA, Fluoroquinolones, medicine.drug
Abstract

International audience; Novel 3'-piperazinyl derivatives of the 8-hydrogeno and 8-methoxy-6-fluoro-1-cyclopropyl-4-quinolone-3-carboxylic acid scaffolds were designed, synthesized and characterized by (1)H, (13)C and (19)F NMR, and HRMS. The activity of these derivatives against pathogenic mycobacteria (M. leprae and M. tuberculosis), wild-type (WT) strains or strains harboring mutations implicated in quinolone resistance, were determined by measuring drug concentrations inhibiting cell growth (MIC) and/or DNA supercoiling by DNA gyrase (IC(50)), or inducing 25% DNA cleavage by DNA gyrase (CC(25)). Compound 4 (with a methoxy in R(8) and a secondary carbamate in R(3)') and compound 5 (with a hydrogen in R(8) and an ethyl ester in R(3)') displayed biological activities close to those of ofloxacin but inferior to those of gatifloxacin and moxifloxacin against M. tuberculosis and M. leprae WT DNA gyrases, whereas all of the compounds were less active in inhibiting M. tuberculosis growth and M. leprae mutant DNA gyrases. Since R(3)' substitutions have been poorly investigated previously, our results may help to design new quinolone derivatives in the future.

Published
2012
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29. Aprendizaje organizacional de la cadena productiva del transporte de carga por carretera en el Valle del Cauca: variables de satisfaccion del canal de miembros

Author

Carolina Bedoya Ospina, Henry Alberto Mosquera Abadia, Ricardo Alonso Cardenas, and Catherine Gomez Sierra

Subjects
Recompensa, Lealtad, General Arts and Humanities, Repetición de la compra, Cadena productiva, Post-compra, Aprendizaje organizacional, Actitud, Expectativa, Eslabones
Abstract

En este artículo se presentan las variables de satisfacción de miembro es de la cadena de transporte de carga por carretera, como una manera de lograr el aprendizaje organizacional de esta. Las variables mencionadas son conceptos desarrollado por Churchill y Suprenant (J982), quienes afirman que conceptualmente la satisfacción es el resultado de comprar y resultante del uso, comparando la recompensa y costos de la compra con relación a las consecuencias previstas o anticipadas por parte del comprador. Para este caso se presentan estas variables organizadas en cinco (5) grupos que son: Normatividad y en Aspectos Operativos, Culturales, Socio Económicos y Tecnológicos. Esta cadena está conformada por los siguientes eslabones a saber: Generador de Carga, Empresa de Transporte o transportista (propietario de vehículo) y Cliente final. Para efectos del análisis únicamente se consideraron los dos (2) primeros eslabones

Published
2011

30. Highly Diastereoselective Ionic/Radical Domino Reactions: Single Electron Transfer Induced Cyclization of Bis-sulfoxides

Author

Louis Fensterbank, Catherine Gomez, Jean-Philippe Goddard, Sophie Beauvière, Max Malacria, and Franck Brebion

Subjects
Tandem, Radical, Metals and Alloys, Enantioselective synthesis, Ionic bonding, General Chemistry, General Medicine, Medicinal chemistry, Radical cyclization, Combinatorial chemistry, Catalysis, Domino, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Single electron, chemistry.chemical_compound, chemistry, Materials Chemistry, Ceramics and Composites, Organic chemistry, Methylene, Heterocyclic derivatives
Abstract

SET oxidation of bis-sulfinyl anions has enabled the uses of bis-sulfinyl radical as a synthetic equivalent of chiral acyl and methylene radicals involved in tandem reactions leading to the enantioselective construction of various carbo- and heterocyclic derivatives.

Published
2007
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33. Highly diastereoselective ionic/radical domino reactions: single electron transfer induced cyclization of bis-sulfoxidesIn memory of our dear colleague and friend Charles Mioskowski.

Author

Jean-Philippe Goddard, Catherine Gomez, Franck Brebion, Sophie Beauvière, Louis Fensterbank, and Max Malacria

Subjects
*PARTICLES (Nuclear physics), *CHARGE exchange, *RING formation (Chemistry), *SULFOXIDES
Abstract

SET oxidation of bis-sulfinyl anions has enabled the uses of bis-sulfinyl radical as a synthetic equivalent of chiral acyl and methylene radicals involved in tandem reactions leading to the enantioselective construction of various carbo- and heterocyclic derivatives. [ABSTRACT FROM AUTHOR]

Published
2007
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34. LA AMBIENTALIZACIÓN DE LA EDUCACIÓN SUPERIOR: ESTUDIO DE CASO EN TRES INSTITUCIONES DE MEDELLÍN, COLOMBIA.

Author

CATHERINE GÓMEZ and CAMILO M. BOTERO

Subjects
Ambientalización, educación superior, educación ambiental, análisis institucional., Geography. Anthropology. Recreation, Environmental sciences, GE1-350
Abstract

La incorporación de una 'variable ambiental' en el quehacer universitario ha tomado fuerza desde finales del siglo XX, siendo su implementación en Colombia una realidad. Esta investigación evaluó el grado de incorporación de tal variable en procesos misionales de tres instituciones de educación superior en Medellín (Colombia). Incluyó dos niveles diferentes de formación (profesional y técnico) y utilizó técnicas cualitativas (entrevistas a dos docentes por institución, visitas de una hora a dos cursos por institución y aplicación de listas de chequeo a cada visita y al análisis institucional). En los tres casos el tema ambiental hace parte de los compromisos institucionales, incluyendo sus procesos de formación, investigación, gestión y extensión. Esto se reflejó en la inclusión de la ambientalización en los currículos, el fomento a la investigación en temas ambientales, la cooperación interdisciplinaria y la adopción de políticas internas. Este trabajo identifica algunos elementos para desarrollar la educación ambiental como herramienta de comprensión integral de la sociedad y su entorno, constituye una base para discusiones, muestra el avance de las tres instituciones de estudio y descubre que existen deficiencias por cubrir.

Published
2012

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