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1. Bipyrrole boomerangs via Pd-mediated tandem cyclization–oxygenation. Controlling reaction selectivity and electronic properties

Author

Joanna Cybińska, Piotr J. Chmielewski, Marika Żyła-Karwowska, Ludovic Favereau, Marcin Stępień, Liliia Moshniaha, Uniwersytet Wroclawski, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), National Science Center of Poland [UMO-2017/27/N/ST5/00613], Foundation for Polish ScienceFoundation for Polish Science [TEAM POIR.04.04.00-00-5BF1/17-00], Ministere de l'Education Nationale, de la Recherche et de la Technologie, Centre National de la Recherche Scientifique (CNRS)Centre National de la Recherche Scientifique (CNRS), Rennes MetropoleRegion Bretagne, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)

Subjects
donor-acceptor systems, 010402 general chemistry, Photochemistry, 01 natural sciences, Full Research Paper, double C-H bond activation, lcsh:QD241-441, helicenes, chemistry.chemical_compound, double C–H bond activation, lcsh:Organic chemistry, pyrroles, lcsh:Science, donor–acceptor systems, Quantum, Electronic properties, Tandem, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, Toluene, 0104 chemical sciences, lcsh:Q, Selectivity, Luminescence
Abstract

International audience; Boomerang-shaped bipyrroles containing donor-acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C-H bond activation, and a double alpha-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to alpha-unsubstituted boomerangs for the first time. These "alpha-free" systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Preliminary measurements show that helicene-like boomerangs may be usable as circularly polarized luminescent materials.

Published
2020
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2. Apigenin, a Partial Antagonist of the Estrogen Receptor (ER), Inhibits ER-Positive Breast Cancer Cell Proliferation through Akt/FOXM1 Signaling

Author

Frédéric Percevault, Gilles Flouriot, Yann Le Page, François Ferrière, Farzad Pakdel, Thu Ha Pham, Institut de recherche en santé, environnement et travail (Irset), Université d'Angers (UA)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-École des Hautes Études en Santé Publique [EHESP] (EHESP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), FUI mVolio, Rennes metropoleRegion Bretagne, Region BretagneRegion Bretagne, MENRT scholarships, Université d'Angers (UA)-Université de Rennes (UR)-École des Hautes Études en Santé Publique [EHESP] (EHESP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), and Chard-Hutchinson, Xavier

Subjects
0301 basic medicine, Cell, Clone (cell biology), Estrogen receptor, lcsh:Chemistry, chemistry.chemical_compound, 0302 clinical medicine, skin and connective tissue diseases, lcsh:QH301-705.5, Spectroscopy, [SDV.MHEP.EM] Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, Chemistry, General Medicine, [SDV.MHEP.EM]Life Sciences [q-bio]/Human health and pathology/Endocrinology and metabolism, Cell cycle, 3. Good health, Computer Science Applications, medicine.anatomical_structure, Receptors, Estrogen, [SDV.SP.PHARMA] Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, 030220 oncology & carcinogenesis, Apigenin, MCF-7 Cells, Female, Signal transduction, Signal Transduction, [SDV.CAN]Life Sciences [q-bio]/Cancer, Breast Neoplasms, Catalysis, Article, Inorganic Chemistry, endocrine resistance, 03 medical and health sciences, breast cancer, [SDV.CAN] Life Sciences [q-bio]/Cancer, Cell Line, Tumor, medicine, Humans, Physical and Theoretical Chemistry, Molecular Biology, Protein kinase B, Cell Proliferation, apigenin, Cell growth, Akt, Forkhead Box Protein M1, Organic Chemistry, FOXM1, Estrogens, phytochemicals, 030104 developmental biology, lcsh:Biology (General), lcsh:QD1-999, ER, [SDV.SP.PHARMA]Life Sciences [q-bio]/Pharmaceutical sciences/Pharmacology, Cancer research, Endocrine Cells, Proto-Oncogene Proteins c-akt
Abstract

Approximately 80% of breast cancer (BC) cases express the estrogen receptor (ER), and 30&ndash, 40% of these cases acquire resistance to endocrine therapies over time. Hyperactivation of Akt is one of the mechanisms by which endocrine resistance is acquired. Apigenin (Api), a flavone found in several plant foods, has shown beneficial effects in cancer and chronic diseases. Here, we studied the therapeutic potential of Api in the treatment of ER-positive, endocrine therapy-resistant BC. To achieve this objective, we stably overexpressed the constitutively active form of the Akt protein in MCF-7 cells (named the MCF-7/Akt clone). The proliferation of MCF-7/Akt cells is partially independent of estradiol (E2) and exhibits an incomplete response to the anti-estrogen agent 4-hydroxytamoxifen, demonstrating the resistance of these cells to hormone therapy. Api exerts an antiproliferative effect on the MCF-7/Akt clone. Api inhibits the proliferative effect of E2 by inducing G2/M phase cell cycle arrest and apoptosis. Importantly, Api inhibits the Akt/FOXM1 signaling pathway by decreasing the expression of FOXM1, a key transcription factor involved in the cell cycle. Api also alters the expression of genes regulated by FOXM1, including cell cycle-related genes, particularly in the MCF-7/Akt clone. Together, our results strengthen the therapeutic potential of Api for the treatment of endocrine-resistant BC.

Published
2021
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3. Three dimensional resistance mapping of self-organized Sr3V2O8 nanorods on metallic perovskite SrVO3 matrix

Author

Matthieu Euchin, Louis Biadala, Mathieu Frégnaux, Vincent Notot, Rosine Coq Germanicus, Damien Aureau, Alexis Boileau, Bruno Berini, Ulrike Lüders, Bruno Grandidier, Valérie Demange, Arnaud Fouchet, Yves Dumont, Maxime Berthe, Andréia Márcia Santos de Souza David, Wilfrid Prellier, Yoan Bourlier, Laboratoire de cristallographie et sciences des matériaux (CRISMAT), École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC), Institut Lavoisier de Versailles (ILV), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut d’Électronique, de Microélectronique et de Nanotechnologie - UMR 8520 (IEMN), Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF), Groupe d'Etude de la Matière Condensée (GEMAC), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Synthèse Caractérisation Analyse de la Matière (ScanMAT), Centre National de la Recherche Scientifique (CNRS)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut de Chimie du CNRS (INC), Physique-IEMN (PHYSIQUE-IEMN), Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF)-Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF), French Agence Nationale de la Recherche (ANR)French National Research Agency (ANR) [ANR-17-CE08-0012], Reseaux d'Interets Normands RIN PLACENANO, EQUIPEX program Excelsior [ANR-11-EQPX-0015], H2020 program [PITN-GA-2016-722176], RENATECH network from IDEX Paris-Saclay [ANR-11-LABEX-0039], Labex CHARMMMAT from IDEX Paris-Saclay [ANR-11-LABEX-0039], Region BretagneRegion Bretagne, Rennes MetropoleRegion Bretagne, Departement d'Ille et Vilaine, European UnionEuropean Union (EU) [39126, 37339], Renatech Network, PCMP PCP, ANR-17-CE08-0012,Polynash,Substrats bas couts polycristallins et Nanofeuillets de germination(2017), ANR-11-EQPX-0015,Excelsior,Centre expérimental pour l'étude des propriétés des nanodispositifs dans un large spectre du DC au moyen Infra-rouge.(2011), ANR-11-LABX-0039,CHARMMMAT,CHimie des ARchitectures MoléculairesMultifonctionnelles et des MATériaux(2011), European Project: 722176,H2020, H2020-MSCA-ITN-2016,INDEED(2017), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-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)-Institut de Recherche sur les Matériaux Avancés (IRMA), Normandie Université (NU)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-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)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-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), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Physique - IEMN (PHYSIQUE - IEMN)

Subjects
Materials science, EELS, Spreading resistance profiling, Annealing (metallurgy), STM, General Physics and Astronomy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, law.invention, law, 3D-SSRM, Microscopy, Functional perovskite oxide, [CHIM]Chemical Sciences, Thin film, business.industry, Electron energy loss spectroscopy, Surfaces and Interfaces, General Chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, Surfaces, Coatings and Films, Electron diffraction, Optoelectronics, Vanadate, Nanorod, Nanorods, Scanning tunneling microscope, AFM, 0210 nano-technology, business
Abstract

International audience; Self-organized epitaxial nanorods, obtained by an adapted annealing process after deposition of metallic strontium vanadate perovskite (SrVO3) thin films, are analyzed to determine their structural, chemical and electrical properties. After the identification of the Sr3V2O8 phase of the nanorods by electron diffraction; Electron Energy Loss Spectroscopy investigations show the vanadium oxidation state (V5+ ) for the nanorods. Two scanning probe techniques are deployed to determine the specific local electrical properties of these Sr3V2O8 nanorods. In ambient conditions, local electrical properties are studied by Scanning Spreading Resistance Microscopy based on an Atomic Force Microscope and multiple probe scanning tunneling microscopy is used for the study in ultrahigh vacuum. Both techniques reveal that local electrical resistances of the nanorods are five order of magnitude higher than the resistance of the perovskite SrVO3 matrix. Futhermore, the nanorods are found to be etched by repeating scanning of the conducive Atomic Force Microcopy probe, enabling a three-dimensional depth profile of the nanorods resistance with 3D-Spreading Resistance Microscopy mode. A partial embedding of the nanorods in the underlying SrVO3 film is proved and the impact of the water meniscus at the origin of the selective etching observed during Scanning Spreading Resistance Microscopy, in ambient conditions, is discussed.

Published
2020
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4. Inverse identification of constitutive parameters from heat source fields: A local approach applied to hyperelasticity

Author

Jean-Benoit Le Cam, Sylvain Charlès, Institut de Physique de Rennes (IPR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), PCM Technologies S.A.S, Region BretagneRegion Bretagne, Rennes MetropoleRegion Bretagne, and Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Physics, heat source reconstruction, [PHYS]Physics [physics], Work (thermodynamics), Digital image correlation, Field (physics), Mechanical Engineering, 02 engineering and technology, Kinematics, Mechanics, 01 natural sciences, Source field, 010309 optics, inverse identification, 020303 mechanical engineering & transports, 0203 mechanical engineering, Mechanics of Materials, Hyperelastic material, 0103 physical sciences, infrared thermography, digital image correlation, Heat equation, Boundary value problem, hyperelasticity, elastomer
Abstract

International audience; In this paper, a new inverse identification method of constitutive parameters is developed from full kinematic and thermal field measurements. It consists in reconstructing the heat source field from two different approaches by using the heat diffusion equation. The first one requires the temperature field measurement and the value of the thermophysical parameters. The second one is based on the kinematic field measurement and the choice of a thermo-hyperelastic model that contains the parameters to be identified. The identification is carried out at the local scale, ie, at any point of the heat source field, without using the boundary conditions. In the present work, the method is applied to the challenging case of hyperelasticity from a heterogeneous test. Due to large deformations undergone by the rubber specimen tested, a motion compensation technique is developed to plot the kinematic and the thermal fields at the same points before reconstructing the heterogeneous heat source field. In the present case, the constitutive parameter of the Neo-Hookean model has been identified, and its distribution has been characterized with respect to the strain state at the surface of a cross-shaped specimen.

Published
2020
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5. Self-assembly of a terbium(III) 1D coordination polymer on mica

Author

Andrea Caneschi, Matteo Mannini, Quentin Evrard, Guillaume Calvez, Carole Daiguebonne, Yan Suffren, Olivier Guillou, Felix Houard, Giuseppe Cucinotta, Kevin Bernot, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), National Interuniversity Consortium of Materials Science and Technology (INSTM ), Università degli Studi di Firenze = University of Florence [Firenze] (UNIFI), Institut Universitaire de France (IUF), Ministère de l'Education nationale, de l’Enseignement supérieur et de la Recherche (M.E.N.E.S.R.), Rennes MetropoleRegion Bretagne, INSA Rennes, CNRSCentre National de la Recherche Scientifique (CNRS), Fondazione Ente Cassa Risparmio di Firenze (progetto SPIN-E)Fondazione Cassa Risparmio Firenze [2017.0730], MIUR-Italy ('Progetto Dipartimenti di Eccellenza 2018-2022) [B96C1700020008], Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Università degli Studi di Firenze = University of Florence (UniFI)

Subjects
Materials science, Coordination polymer, polymer, General Physics and Astronomy, chemistry.chemical_element, Terbium, 02 engineering and technology, engineering.material, 010402 general chemistry, Epitaxy, lcsh:Chemical technology, 01 natural sciences, lcsh:Technology, Full Research Paper, chemistry.chemical_compound, Adsorption, nanostructuration, luminescence, Nanotechnology, surface, [CHIM]Chemical Sciences, General Materials Science, lcsh:TP1-1185, atomic force microscopy (AFM), Electrical and Electronic Engineering, lcsh:Science, lcsh:T, Muscovite, self-assembly, 021001 nanoscience & nanotechnology, lcsh:QC1-999, 0104 chemical sciences, Crystallography, Nanoscience, chemistry, engineering, lcsh:Q, Self-assembly, Mica, terbium complexes, 0210 nano-technology, Luminescence, lcsh:Physics
Abstract

The terbium(III) ion is a particularly suitable candidate for the creation of surface-based magnetic and luminescent devices. In the present work, we report the epitaxial growth of needle-like objects composed of [Tb(hfac)3·2H2O]n (where hfac = hexafluoroacetylacetonate) polymeric units on muscovite mica, which is observed by atomic force microscopy. The needle-like shape mimics the structure observed in the crystalline bulk material. The growth of this molecular organization is assisted by water adsorption on the freshly air-cleaved muscovite mica. This deposition technique allows for the observation of a significant amount of nanochains grown along three preferential directions 60° apart from another. The magnetic properties and the luminescence of the nanochains can be detected without the need of surface-dedicated instrumentation. The intermediate value of the observed luminescence lifetime of the deposits (132 µs) compared to that of the bulk (375 µs) and the CHCl3 solution (13 µs) further reinforces the idea of water-induced growth.

Published
2019
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6. Reaction Conditions for the Regiodivergent Direct Arylations at C2-or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts

Author

Xinzhe Shi, Henri Doucet, Jean-François Soulé, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), CNRS Centre National de la Recherche Scientifique (CNRS), Rennes MetropoleRegion Bretagne, [ANR-16-CE07-0001], ANR-16-CE07-0001,ALCATRAS,Ligands hybrides modulables en catalyse d'activation de liaisons stables C–H et C–O(2016), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Reaction conditions, C-H bond functionalization, 010405 organic chemistry, direct arylation, oxazole, chemistry.chemical_element, General Chemistry, 010402 general chemistry, palladium, 01 natural sciences, C-C bond formation, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, C c coupling, chemistry, Polymer chemistry, [CHIM]Chemical Sciences, Phosphine, Oxazole, Palladium
Abstract

International audience; Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)(2)/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)(2)/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)(2)/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C-H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C-H bond functionalization steps. The Ru-catalyzed C-H arylation of the aryl unit of 2-aryloxazoles is also described.

Published
2019
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