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1. 1H-1,2,3-triazolyl-1,6-naphthyridin-7(6H)-ones as Potential Fluorescent Nucleoside Analogues: Synthesis and Optical Properties

Author

Anissa Beghennou, Océane Rondot, Vincent Corcé, and Candice Botuha

Subjects
nucleoside, 1,2,3 triazole, CuAAC reaction, fluorescence, solvatochromism, Organic chemistry, QD241-441
Abstract

In this article, we present the synthesis and the optical properties of three original molecules as potential fluorescent ribonucleoside analogues incorporating a 1,6-naphthyridin-7(6H)-one scaffold as a fluorescent nucleobase and a 1,2,3-triazole as a linkage. The nucleosides were prepared via a Cu alkyne-azide cycloaddition (CuAAC) reaction between a ribofuranosyl azide and a 4-ethynylpyridine partner. Construction of substituted 1,6-naphthyridin-7(6H)-ones was achieved through two additional steps. Optical property studies were investigated on nucleoside analogues. Powerful fluorescence properties have been evidenced with a remarkable change of emissivity depending on the polarity of the solvent, making these molecules suitable as a new class of artificial fluorescent nucleosides for investigating enzyme binding sites as well as probing nucleic acids. In addition, we are convinced that such analogues could be of great interest in the search for new antiviral or antitumoral drugs based on nucleosides.

Published
2024
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2. Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp 2-Csp cross-coupling

Author

Fen Zhao, Mehdi Abdellaoui, Wided Hagui, Maria Ballarin-Marion, Jérôme Berthet, Vincent Corcé, Stéphanie Delbaere, Héloïse Dossmann, Agathe Espagne, Jérémy Forté, Ludovic Jullien, Thomas Le Saux, Virginie Mouriès-Mansuy, Cyril Ollivier, and Louis Fensterbank

Subjects
Science
Abstract

Dual photo- and metal-catalysis is generally not well-understood when the metal catalyst is a gold complex. Here the authors show that a variation of a known metallaphotoredox annulation is possible without an added photocatalyst, proceeding putatively through a gold–intermediate photosensitization by the aggregate of a potassium amide reactant, and yielding indole derivatives.

Published
2022
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3. Synthetic Applications of Intramolecular Thiol-Ene 'Click' Reactions

Author

Eoin M. Scanlan, Vincent Corcé, and Aoife Malone

Subjects
free radical, organic synthesis, carbohydrate, peptide, Organic chemistry, QD241-441
Abstract

The intermolecular thiol-ene reaction is emerging as a highly efficient; free-radical mediated “click” process with diverse applications in biofunctionalisation and materials science. The related intramolecular thiol-ene reactions offer significant potential for the preparation of a wide range of sulphur containing heterocycles including synthetic therapeutics such as cyclic peptides and thiosugars. Herein, we review recent advances in intramolecular thiyl-radical mediated reactions and their applications for synthetic and medicinal chemistry.

Published
2014
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4. 1,6-Naphthyridin-7(6H)-ones: synthesis and optical properties

Author

Anissa Beghennou, Geoffrey Gontard, Héloïse Dossmann, Kévin Passador, Serge Thorimbert, Vincent Corcé, and Candice Botuha

Subjects
Organic Chemistry, Physical and Theoretical Chemistry, Biochemistry
Abstract

Original fluorescent dyes containing 1,6-naphthyridin-7(6H)-one have been synthesized and their optical properties have been studied.

Published
2023

5. Martin Silicates as Versatile Radical Precursors in Photoredox/ Nickel Dual Catalysis

Author

Louis Fensterbank, Cyril Ollivier, Gilles Lemière, Mehdi Abdellaoui, Maxim-Aleksa Wiethoff, Thomas Deis, and Vincent Corcé

Subjects
Organic Chemistry
Abstract

A cross-coupling methodology is described based on the nickel-catalyzed connection of an aryl moiety to an alkyl radical generated by photoinduced single-electron oxidation of a silicate formed from a Martin spirosilane. Complementary to the other anionic radical precursors in photoredox catalysis, Martin silicates permit access to highly reactive alkyl radicals directly engageable in smooth C(sp2)–C(sp3) bond-formation reactions.

Published
2023

6. Boron, silicon, nitrogen and sulfur-based contemporary precursors for the generation of alkyl radicals by single electron transfer and their synthetic utilization

Author

Vincent Corcé, Cyril Ollivier, and Louis Fensterbank

Subjects
General Chemistry
Abstract

Recent developments in the use of boron, silicon, nitrogen and sulfur derivatives in single-electron transfer reactions for the generation of alkyl radicals are described. Photoredox catalyzed, electrochemistry promoted or thermally-induced oxidative and reductive processes are discussed highlighting their synthetic scope and discussing their mechanistic pathways.

Published
2022

7. Phenyl Silicates with Substituted Catecholate Ligands: Synthesis, Structural Studies and Reactivity

Author

Heng-Rui Zhang, Etienne Derat, Louis Fensterbank, Aurélie Bernard, Etienne Levernier, Khaoula Jaouadi, Geoffrey Gontard, Laurence Grimaud, Cyril Ollivier, Vincent Corcé, Claire Troufflard, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire des biomolécules (LBM UMR 7203), Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM), Méthodes et Application en Chimie Organique (MACO), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Département de Chimie - ENS Paris, Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Ollivier, Cyril

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Ligand, Aryl, Radical, Organic Chemistry, Photoredox catalysis, General Chemistry, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, [CHIM.THEO] Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Moiety, Reactivity (chemistry), Alkyl
Abstract

International audience; While the generation of aryl radicals by photoredox catalysis is well-documented under reductive conditions, it has remained challenging under an oxidative pathway. Because of the easy photooxidation of alkyl bis-catecholato silicates, a general study on phenyl silicates bearing substituted catecholate ligands has been achieved. The newly synthesized phenyl silicates have been fully characterized and their reactivity has been explored. It was found that thanks to the substitution of the catecholate moiety and notably with the 4-cyanocatecholato ligand, the phenyl radical could be generated and trapped. Computational studies provided a rationale for these findings.

Published
2021

8. Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp2-Csp cross-coupling

Author

Fen Zhao, Mehdi Abdellaoui, Wided Hagui, Maria Ballarin-Marion, Jérôme Berthet, Vincent Corcé, Stéphanie Delbaere, Héloïse Dossmann, Agathe Espagne, Jérémy Forté, Ludovic Jullien, Thomas Le Saux, Virginie Mouriès-Mansuy, Cyril Ollivier, Louis Fensterbank, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Lille Neurosciences & Cognition - U 1172 (LilNCog), Institut National de la Santé et de la Recherche Médicale (INSERM)-Université de Lille-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille), Département de Chimie - ENS Paris, Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL), Pigeon, Pascal, CHU Lille, Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), ESPAGNE, Agathe, ANR-17-CE07-0018,HyperSiLight,Utilisation de dérivés hypervalents du silicium en catalyse photoredox et duale(2017), and ANR-20-CE07-0038,LuxOr,Catalyse à l'or sous lumière visible(2020)

Subjects
Multidisciplinary, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM] Chemical Sciences, [CHIM]Chemical Sciences, General Physics and Astronomy, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Chemistry, [CHIM.COOR] Chemical Sciences/Coordination chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, General Biochemistry, Genetics and Molecular Biology
Abstract

Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process is observed. Of note, 2-iodo-ynamides can be used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

Published
2022

9. Synthetic Strategy Studies for a Concise Access to Functionalized Pyrano[4,3‐ b ]pyridin‐7‐ones: An Entry to Semi‐Rigid Analogs of Antihistamines

Author

Anissa Beghennou, Vincent Corcé, Anthony Passador, Candice Botuha, Serge Thorimbert, Kevin Passador, Chemical Biology (CHEMBIO), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Chemistry, Organic Chemistry, [CHIM]Chemical Sciences, Pinner reaction, Physical and Theoretical Chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, ComputingMilieux_MISCELLANEOUS, δ lactone, 3. Good health, 0104 chemical sciences
Abstract

International audience

Published
2020

10. Reactant-induced photoactivation of in situ generated organogold intermediates leading to alkynylated indoles via Csp

Author

Fen, Zhao, Mehdi, Abdellaoui, Wided, Hagui, Maria, Ballarin-Marion, Jérôme, Berthet, Vincent, Corcé, Stéphanie, Delbaere, Héloïse, Dossmann, Agathe, Espagne, Jérémy, Forté, Ludovic, Jullien, Thomas, Le Saux, Virginie, Mouriès-Mansuy, Cyril, Ollivier, and Louis, Fensterbank

Abstract

Photosensitization of organogold intermediates is an emerging field in catalysis. In this context, an access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process is observed. Of note, 2-iodo-ynamides can be used as electrophiles in this cross-coupling reaction. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converge on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

Published
2021

11. Reactant-Induced Photoactivation of a Gold-Catalyzed Csp2-Csp Cross-Coupling Leading to Indoles

Author

Vincent Corcé, Jérôme Berthet, Mehdi Abdellaoui, Héloïse Dossmann, Louis Fensterbank, Fen Zhao, Cyril Ollivier, Virginie Mouriès-Mansuy, Stéphanie Delbaere, Thomas Le Saux, Jérémy Forté, Ludovic Jullein, and Agathe Espagne

Subjects
Sulfonyl, chemistry.chemical_classification, chemistry.chemical_compound, Aniline, Quenching (fluorescence), Chemistry, Amide, Electrophile, Photochemistry, Oxidative addition, Reductive elimination, Catalysis
Abstract

A novel access to 2,3-disubstituted indoles from o-alkynyl aniline and iodoalkyne derivatives via a gold-catalyzed sequence under visible-light irradiation and in the absence of an exogenous photocatalyst was uncovered. A wide scope of the process was observed. Of note, 2-iodo-ynamides that have never been used in any organometallic cross-coupling reaction could be used as electrophiles. The resulting N-alkynyl indoles lend themselves to post-functionalization affording valuable scaffolds, notably benzo[a]carbazoles. Mechanistic studies converged on the fact that a potassium sulfonyl amide generates emissive aggregates in the reaction medium. Static quenching of these aggregates by a vinylgold(I) intermediate yields to an excited state of the latter, which can react with an electrophile via oxidative addition and reductive elimination to forge the key C-C bond. This reactant-induced photoactivation of an organogold intermediate opens rich perspectives in the field of cross-coupling reactions.

Published
2021

12. Cross coupling of alkylsilicates with acyl chlorides via photoredox/nickel dual catalysis: a new synthesis method for ketones

Author

Michael Tatoulian, Louise-Marie Rakotoarison, Etienne Levernier, Adrien Smith, Mengxue Zhang, Cyril Ollivier, Vincent Corcé, Louis Fensterbank, Stéphanie Ognier, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche de Chimie Paris (IRCP), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ministère de la Culture (MC)

Subjects
Coupling, Silicon, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Flow chemistry, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, 0104 chemical sciences, Catalysis, Nickel, chemistry, Electrophile, [CHIM]Chemical Sciences
Abstract

International audience; Photoredox/Nickel dual catalysis using easy oxydized bis-catecholato hypercoordinated silicon derivatives as radical sources and acylchlorides as electrophile allows a new method of formation of dialkyl and alkyl-aryl ketones as well as dibenzyl ketones which are less easily accessed. Flow chemistry can be used

Published
2019

13. Novel luminescent benzopyranothiophene- and BODIPY-derived aroylhydrazonic ligands and their dicopper(II) complexes: syntheses, antiproliferative activity and cellular uptake studies

Author

Nicolás A. Rey, Claude-Marie Bachelet, Geoffrey Gontard, Michèle Salmain, Jérémy Forté, Vincent Corcé, Jesica Paola Rada, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Pontifical Catholic University of Rio de Janeiro (PUC), Institut du Cerveau et de la Moëlle Epinière = Brain and Spine Institute (ICM), Institut National de la Santé et de la Recherche Médicale (INSERM)-CHU Pitié-Salpêtrière [AP-HP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Institut du Cerveau = Paris Brain Institute (ICM), Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Institut National de la Santé et de la Recherche Médicale (INSERM)-CHU Pitié-Salpêtrière [AP-HP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Sorbonne Université (SU)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), and Pigeon, Pascal

Subjects
Boron Compounds, [CHIM.THER] Chemical Sciences/Medicinal Chemistry, [SDV.CAN]Life Sciences [q-bio]/Cancer, Antineoplastic Agents, Triple Negative Breast Neoplasms, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Crystal structure, Thiophenes, 010402 general chemistry, 01 natural sciences, Biochemistry, Inorganic Chemistry, anticancer agents, chemistry.chemical_compound, [SDV.CAN] Life Sciences [q-bio]/Cancer, Cell Line, Tumor, Fluorescence microscope, aroylhydrazones, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, copper complexes, Spectroscopy, Cytotoxicity, Molecular Structure, 010405 organic chemistry, Ligand, cellular uptake, [CHIM.COOR] Chemical Sciences/Coordination chemistry, Fluorescence, Combinatorial chemistry, 0104 chemical sciences, 3. Good health, chemistry, Microscopy, Fluorescence, cytotoxicity, Female, BODIPY, Luminescence, Copper
Abstract

International audience; Two novel unsymmetrical binucleating aroylhydrazonic ligands and four dicopper(II) complexes carrying fluorescent benzopyranothiophene (BPT) or boron dipyrromethene (BODIPY) entities were synthesized and fully characterized. Complex 1, derived from the BPT-containing ligand H3L1, had its crystal structure elucidated through X-ray diffraction measurements. The absorption and fluorescence profiles of all the compounds obtained were discussed. Additionally, the stability of the ligands and complexes was monitored by UV–vis spectroscopy in DMSO and biologically relevant media. All the compounds showed moderate to high cytotoxicity towards the triple negative human breast cancer cell line MDA-MB-231. BPT derivatives were the most cytotoxic, specially H3L1, reaching an IC50 value up to the nanomolar range. Finally, fluorescence microscopy imaging studies employing mitochondria- and nucleus-staining dyes showed that the BODIPY-carrying ligand H3L2 was highly cell permeant and suggested that the compound preferentially accumulates in the mitochondria.

Published
2021

14. Photoredox Catalysis, an Opportunity for Sustainable Radical Chemistry

Author

Vincent Corcé, Christophe Lévêque, Cyril Ollivier, Etienne Levernier, Max Malacria, Louis Fensterbank, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Radical, Photoredox catalysis, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Photochemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2020

15. Photoredox/Nickel Dual Catalysis for the C(sp3 )-C(sp3 ) Cross-Coupling of Alkylsilicates with Alkyl Halides

Author

Ludwig Chenneberg, Vincent Corcé, Cyril Ollivier, Louis Fensterbank, and Christophe Lévêque

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Halide, 010402 general chemistry, Photochemistry, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, 3. Good health, Catalysis, Nickel, chemistry, Physical and Theoretical Chemistry, Alkyl
Abstract

Alkylsilicates were engaged under photoredox/nickel dual catalysis conditions with alkyl halides for the first time. The C(sp3)–C(sp3) cross-coupling products were obtained in moderate yields and were accompanied by the homocoupling products of the alkyl halide derivatives. These promising findings are strongly suggestive of the high synthetic potential of the dual catalytic approach for the forging of alkyl carbon–carbon bonds.

Published
2017

16. Photosensitized oxidative addition to gold(i) enables alkynylative cyclization of o-alkylnylphenols with iodoalkynes

Author

Zhonghua Xia, Fen Zhao, Louis Fensterbank, Cédric Przybylski, Thomas Le Saux, Cyril Ollivier, Ludovic Jullien, Vincent Corcé, Agathe Espagne, Yves Gimbert, Virginie Mouriès-Mansuy, Héloïse Dossmann, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL), Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Département de Chimie Moléculaire (DCM), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])

Subjects
chemistry.chemical_classification, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemical Engineering, Iodide, chemistry.chemical_element, General Chemistry, 010402 general chemistry, 01 natural sciences, Redox, Combinatorial chemistry, Oxidative addition, Reductive elimination, 0104 chemical sciences, Catalysis, chemistry, Transition metal, Reagent, Iridium, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

International audience; The well-established oxidative addition-reductive elimination pathway is the most followed one in transition metal catalyzed cross coupling reactions. While readily occurring with a series of transition metals, it does not take place with gold(I) complexes which have shown some reluctance to undergo oxidative addition unless special sets of ligands on gold(I), reagents or reaction conditions are used. A new possibility to overcome this hurdle has been devised. Upon visible light irradiation, an iridium photocatalyst triggers via triplet sensitization the oxidative addition of an al-kynyliodide onto a vinylgold(I) intermediate to deliver Csp 2-Csp coupling products after reductive elimination. Mechanistic and modeling studies support that an energy transfer takes place and not a redox pathway. This novel mode of activation in gold homogenous catalysis was applied in several dual catalytic processes. Alkynylbenzofuran derivatives were obtained from o-alkynylphenols and iodoalkynes in the presence of catalytic gold(I) and iridium(III) complexes under blue LED irradiation. Over the last two decades, homogeneous gold catalysis has been extensively used to efficiently and selectively promote a variety of cyclization processes. 1-3 The typical casting involves bifunctional substrates bearing an unsaturation prompt to electrophilic activation and a judiciously positioned internal nucleophile. A protodemetalation of the organogold intermediates to afford hydrofunctional-ized products generally terminates the catalytic cycles. 4 Pursuing the step economy principle and also aiming at higher level of molecular complexity, some in situ post-functionalization reactions of the organogold 5 intermediate have been devised such as electrophilic halogenation or cross-coupling reactions. Although palladium catalyzed cross coupling from an organogold(I) intermediate has been

Published
2019

17. pH‐Sensitive Poly(ethylene glycol)/Poly(ethoxyethyl glycidyl ether) Block Copolymers: Synthesis, Characterization, Encapsulation, and Delivery of a Hydrophobic Drug

Author

Michèle Salmain, Nicolas Illy, Philippe Guégan, Vincent Corcé, Vincent Molinié, Jéril Degrouard, Mélanie Labourel, Guillaume Tresset, Jeremy M. Zimbron, Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Physique des Solides (LPS), and Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)

Subjects
Polymers and Plastics, curcumin encapsulation, 02 engineering and technology, amphiphilic polyether, 010402 general chemistry, 01 natural sciences, Micelle, chemistry.chemical_compound, Amphiphile, Polymer chemistry, Materials Chemistry, Copolymer, Physical and Theoretical Chemistry, Solubility, anionic-ring opening polymerization, Aqueous solution, Organic Chemistry, self-assembly, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, 3. Good health, [CHIM.POLY]Chemical Sciences/Polymers, [SDV.SP.PG]Life Sciences [q-bio]/Pharmaceutical sciences/Galenic pharmacology, chemistry, Polymerization, pH-sensitive copolymer, Curcumin, 0210 nano-technology, Ethylene glycol
Abstract

International audience; Curcumin is a natural polyphenolic compound known for its numerous pharmacological properties. However, its low water solubility and instability at neutral pH are serious drawbacks preventing its use as an oral drug. Well‐defined amphiphilic poly(ethylene glycol)‐block‐poly(ethoxyethyl glycidyl ether) (PEG‐b‐PEEGE) block copolymers carrying acid‐labile acetal groups are synthesized by anionic ring‐opening polymerization and investigated as potential pH‐sensitive nano‐carriers for delivery of curcumin to cancer cells. The nanoparticles, resulting from copolymer self‐assembly in aqueous media, are characterized by dynamic light scattering and cryo‐transmission electron microscopy. The nanoparticles’ stabilities are evaluated in three different phosphate buffers (pH = 7.2, 6.4, and 5.3). The stability decreases at lower pH and a complete disappearance of the nanoparticles is noticed after 4 days at pH 5.3. Curcumin is encapsulated in hydrophobic core of mPEG40‐b‐PEEGE25 nanoparticles allowing significant enhancements of curcumin solubility in water and lifetime at neutral pH. In vitro curcumin release is studied at different pH by UV‐spectroscopy and high‐performance liquid chromatography (HPLC). The cytotoxicity of curcumin and curcumin encapsulated in micelles is evaluated by cell viability 3‐(4,5‐Dimethyl‐2‐thiazolyl)‐2,5‐diphenyl‐2H‐tetrazolium bromide (MTT) assay on MDA‐MB‐231 human breast cancer cells

Published
2019

18. 15 Silicates in Photocatalysis

Author

Cyril Ollivier, Christophe Lévêque, Louis Fensterbank, Vincent Corcé, Chemical Biology (CHEMBIO), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Méthodes et Application en Chimie Organique (MACO), and König, B.

Subjects
Materials science, CHEMBIO, Chemical engineering, POLE 3, POLE 1, Photocatalysis, [CHIM]Chemical Sciences, MACO, ComputingMilieux_MISCELLANEOUS, 3. Good health
Abstract

Bis(catecholato)silicates have emerged as robust alkyl radical sources under photocatalysis. This chapter describes the preparation of various silicates and their utilization under photocatalytic conditions for the formation of C–C and C–O bonds. The last section focuses on the use of silicates in photoredox/nickel dual catalysis.

Published
2019

19. Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis

Author

Etienne Levernier, Takahide Fukuyama, Cyril Ollivier, Ilhyong Ryu, Vincent Corcé, Louis Fensterbank, Alex Cartier, Anne-Lise Dhimane, Osaka Prefecture University, Méthodes et Application en Chimie Organique (MACO), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), and Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Primary (chemistry), 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Photoredox catalysis, Alkyl radicals, General Chemistry, General Medicine, Photochemistry, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Carbonylation, Visible spectrum, Carbon monoxide
Abstract

International audience; Primary, secondary and tertiary alkyl radicals, formed by photocatalyzed oxidation of organosilicates, can be involved efficiently in radical carbonylation with carbon monoxide (CO), which leads to a variety of unsymmetrical ketones. This work constitutes the first example of radical carbonylation under a photooxidative regime.

Published
2019

20. Single-Electron-Transfer Oxidation of Trifluoroborates and Silicates with Organic Reagents: A Comparative Study

Author

Cyril Ollivier, Jean-Philippe Goddard, Vincent Corcé, Louis Fensterbank, Ludwig Chenneberg, Christophe Lévêque, Alexandre Baralle, 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), Laboratoire de Biotechnologies et de Chimie Bio-organique (LBCBO), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), and La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, oxidation, 010405 organic chemistry, Radical, Organic Chemistry, Inorganic chemistry, Salt (chemistry), radicals, 010402 general chemistry, Photochemistry, dyes, 01 natural sciences, 0104 chemical sciences, Single electron, single electron transfer, silicates, chemistry, Reagent, Photocatalysis, [CHIM]Chemical Sciences, trifluoroborates, photocatalysis, Alkyl
Abstract

International audience; In this report, the single-electron-transfer oxidation of alkyl trifluoroborates and silicates has been studied. Different types of oxidation reagents have been examined, focusing on organic oxidants and particularly the use of dyes in photocatalytic oxidations. Both trifluoroborates and silicates could provide C-centered radicals when using a tritylium salt or the Ledwith–Weitz aminium salt. Photocatalysis with the Fukuzumi reagent suggested that trifluoroborates are more easily oxidized than biscatecholato silicates under these conditions.

Published
2016

21. Recent advances in cancer treatment by iron chelators

Author

David Deniaud, Vincent Corcé, Stéphanie Renaud, Sébastien G. Gouin, François Gaboriau, Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Foie, métabolismes et cancer, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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 ), Société d'Accélération du Transfert de Technologies (SATT OUEST VALORISATION), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-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 Jonchère, Laurent

Subjects
0301 basic medicine, Stereochemistry, [SDV]Life Sciences [q-bio], Iron, Clinical Biochemistry, Metal chelators, Pharmaceutical Science, [SDV.CAN]Life Sciences [q-bio]/Cancer, Antineoplastic Agents, Iron Chelating Agents, Biochemistry, 03 medical and health sciences, [SDV.CAN] Life Sciences [q-bio]/Cancer, polyamine, Neoplasms, Drug Discovery, Animals, Humans, Chelation, Molecular Biology, Chemistry, Cancer cell proliferation, Organic Chemistry, 3. Good health, Cancer treatment, [SDV] Life Sciences [q-bio], Metal chelation, 030104 developmental biology, Cancer research, Molecular Medicine, Tumor vectorisation, 8-Hydroxyquinoline, Iron depletion
Abstract

International audience; The development of new therapeutic alternatives for cancers is a major public health priority. Among the more promising approaches, the iron depletion strategy based on metal chelation in the tumoral environment has been particularly studied in recent decades. After a short description of the importance of iron for cancer cell proliferation, we will review the different iron chelators developed as potential chemotherapeutics. Finally, the recent efforts to vectorize the chelating agents specifically in the microtumoral environment will be discussed in detail

Published
2016

22. Versatile Access to Martin’s Spirosilanes and Their Hypervalent Derivatives

Author

Hugo Lenormand, Louis Fensterbank, Christine Chhun, Geoffroy Sorin, Vincent Corcé, Jean-Philippe Goddard, Emilie-Laure Zins, Lahouari Krim, Lise-Marie Chamoreau, Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), De la Molécule aux Nanos-objets : Réactivité, Interactions et Spectroscopies (MONARIS), Méthodes et Application en Chimie Organique (MACO), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-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), DGA, ANR [BLAN0309, NHCX ANR-11-BS07-008], LabEx MiChem part of French state funds [ANR-11-IDEX-0004-02], Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Trifluoromethyl, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, Aryl, Organic Chemistry, Hypervalent molecule, Ring (chemistry), Combinatorial chemistry, chemistry.chemical_compound, Nucleophile, Alkoxy group, Organic chemistry, Lewis acids and bases, Alkyl
Abstract

International audience; A new route to Martins spirosilanes has been devised. The original synthesis does not allow diversely substituted spirosilane derivatives to be synthesized, and thus their corresponding silicates. In this report, Martins spirosilanes bearing alkyl, aryl, halogen, alkoxy, and trifluoromethyl substituents on the aryl ring have been prepared through a versatile four-step route. Addition of fluoride onto these Lewis acids as a prototypical reaction with a nucleophile yielded a library of stable fluorosilicates. Both sets of compounds have been characterized by X-ray crystallograph

Published
2015

23. Synthetic Applications of Intramolecular Thiol-Ene 'Click' Reactions

Author

Vincent Corcé, Eoin M. Scanlan, and Aoife Malone

Subjects
Free Radicals, Pharmaceutical Science, Review, 010402 general chemistry, Peptides, Cyclic, 01 natural sciences, Analytical Chemistry, Thiosugars, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, Drug Discovery, Organic chemistry, Sulfhydryl Compounds, Physical and Theoretical Chemistry, Ene reaction, free radical, chemistry.chemical_classification, 010405 organic chemistry, Organic Chemistry, Intermolecular force, organic synthesis, Combinatorial chemistry, peptide, Cyclic peptide, 0104 chemical sciences, chemistry, carbohydrate, Chemistry (miscellaneous), Intramolecular force, Thiol, Molecular Medicine, Click Chemistry, Organic synthesis
Abstract

The intermolecular thiol-ene reaction is emerging as a highly efficient; free-radical mediated “click” process with diverse applications in biofunctionalisation and materials science. The related intramolecular thiol-ene reactions offer significant potential for the preparation of a wide range of sulphur containing heterocycles including synthetic therapeutics such as cyclic peptides and thiosugars. Herein, we review recent advances in intramolecular thiyl-radical mediated reactions and their applications for synthetic and medicinal chemistry.

Published
2014

24. Intramolecular thiol–yne cyclisation as a novel strategy for thioglycal synthesis

Author

Aoife Malone, Vincent Corcé, Eoin M. Scanlan, and Lauren McSweeney

Subjects
Exclusive access, chemistry.chemical_classification, Chemistry, Molecular Conformation, Metals and Alloys, Ionic bonding, General Chemistry, Catalysis, Molecular conformation, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Cyclization, Alkynes, Intramolecular force, Materials Chemistry, Ceramics and Composites, Thiol, Organic chemistry, Glycosides, Sulfhydryl Compounds
Abstract

A novel intramolecular thiol-yne cyclisation strategy has been developed for the synthesis of thioglycals. Both ionic and radical mediated cyclisation pathways have been investigated for D- and L-sugars. The ionic cyclisation provides exclusive access to 5-exo products directly from the thioesters whereas the radical cyclisation provides access to both 5-exo and 6-endo products upon photochemical irradiation of the free thiols. These are the first examples of intramolecular thiol-yne cyclisation reactions applied to thiosugar synthesis.

Published
2015

25. ChemInform Abstract: Recent Advances in Cancer Treatment by Iron Chelators

Author

Vincent Corcé, David Deniaud, Sébastien G. Gouin, Stéphanie Renaud, and François Gaboriau

Subjects
Metal chelation, Chemistry, Cancer cell proliferation, Cancer research, Chelation, General Medicine, Iron depletion, Cancer treatment
Abstract

The development of new therapeutic alternatives for cancers is a major public health priority. Among the more promising approaches, the iron depletion strategy based on metal chelation in the tumoral environment has been particularly studied in recent decades. After a short description of the importance of iron for cancer cell proliferation, we will review the different iron chelators developed as potential chemotherapeutics. Finally, the recent efforts to vectorize the chelating agents specifically in the microtumoral environment will be discussed in detail.

Published
2016

26. A well-defined low-valent cobalt catalyst Co(PMe3)4 with dimethylzinc: a simple catalytic approach for the reductive dimerization of benzyl halides

Author

Vincent Corcé, Franck Ferreira, Muriel Amatore, Alejandro Perez-Luna, Marc Petit, Fabrice Chemla, Corinne Aubert, Brendan J. Fallon, 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), Méthodes et Application en Chimie Organique (MACO), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-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), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-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)

Subjects
inorganic chemicals, 010405 organic chemistry, Chemistry, Dimethylzinc, Halide, chemistry.chemical_element, General Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, 3. Good health, Cobalt catalyst, Single electron, chemistry.chemical_compound, Polymer chemistry, Materials Chemistry, [CHIM]Chemical Sciences, Cobalt
Abstract

International audience; Herein, we report the first catalytic version of a cobalt-catalysed reductive homocoupling of benzyl halides which proceeds with low catalyst loadings (0.5 to 5 mol%). By synthetizing each cobalt intermediate we demonstrate that reaction proceeds through two single electron transfers (SET) and that dimethylzinc is only involved in the regeneration of the catalytic species.

Published
2016

27. Organic photoredox catalysis for the oxidation of silicates: applications in radical synthesis and dual catalysis

Author

Louis Fensterbank, Ludwig Chenneberg, Christophe Lévêque, Cyril Ollivier, Vincent Corcé, 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 Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, 010405 organic chemistry, Chemistry, Metals and Alloys, Alkyl radicals, chemistry.chemical_element, Photoredox catalysis, General Chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Homolysis, Nickel, Metal free, Organic dye, Materials Chemistry, Ceramics and Composites, [CHIM]Chemical Sciences, Alkyl
Abstract

International audience; Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN) allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to provide homolytic addition products or in photoredox/nickel dual catalysis reactions to obtain cross-coupling products.

Published
2016

28. Primary alkyl bis-catecholato silicates in dual photoredox/nickel catalysis: aryl- and heteroaryl-alkyl cross coupling reactions

Author

Ludwig Chenneberg, Jean-Philippe Goddard, Louis Fensterbank, Christophe Lévêque, Cyril Ollivier, Vincent Corcé, 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), Laboratoire de chimie organique et bioorganique EA 4566, Ecole Nationale Supérieure de Chimie de Mulhouse, Laboratoire de Chimie organique et bioorganique (COB), and Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Primary (chemistry), 010405 organic chemistry, Aryl, Radical, Organic Chemistry, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Coupling reaction, 0104 chemical sciences, Catalysis, chemistry.chemical_compound, Nickel, chemistry, Bromide, Organic chemistry, [CHIM]Chemical Sciences, Alkyl
Abstract

International audience; Primary alkyl bis-catecholato silicates have been successfully engaged with aryl and heteroaryl bromide substrates in photoredox/nickel dual catalysis to provide aryl- and heteroaryl-alkyl cross coupling products. The scope of the transformation is wide and the process appears to be tolerant of various functional groups present. Of note, most examples rely on the challenging use of highly reactive primary radicals which constitutes a significant advance in these cross coupling reactions.

Published
2016

31. Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds

Author

Cyril Ollivier, Etienne Derat, Jean-Philippe Goddard, Louis Fensterbank, Vincent Corcé, Lise-Marie Chamoreau, Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), Laboratoire de Chimie organique et bioorganique (COB), Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS), UPMC, UHA, CNRS, IUF, ANR NHCX [11-BS07-008], COST Action [CM1201], Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie organique et bioorganique EA 4566, and Ecole Nationale Supérieure de Chimie de Mulhouse

Subjects
oxidation, Radical, chemistry.chemical_element, 010402 general chemistry, Photochemistry, 01 natural sciences, 7. Clean energy, Catalysis, Bipyridine, chemistry.chemical_compound, silicates, Iridium, Alkyl, chemistry.chemical_classification, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Hypervalent molecule, General Medicine, General Chemistry, hypervalent compounds, radicals, 0104 chemical sciences, Homolysis, chemistry, Photocatalysis, photocatalysis
Abstract

International audience; This works introduces hypervalent bis-catecholato silicon compounds as versatile sources of alkyl radicals upon visible-light photocatalysis. Using Ir[(dF(CF3)ppy)(2)(bpy)]-(PF6) (dF(CF3)ppy = 2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy = bipyridine) as catalytic photooxidant, a series of alkyl radicals, including highly reactive primary ones can be generated and engaged in various intermolecular homolytic reactions. Based on cyclic voltammetry, Stern-Volmer studies, and supported by calculations, a mechanism involving a single-electron transfer from the silicate to the photoactivated iridium complex has been proposed. This oxidative photocatalyzed process can be efficiently merged with nickel-catalyzed C-sp2-C-sp3 cross-coupling reactions.

Published
2015

33. Quilamine HQ1-44, an iron chelator vectorized toward tumor cells by the polyamine transport system, inhibits HCT116 tumor growth without adverse effect

Author

Olivier Loréal, Martine Ropert, François Gaboriau, Sylvie Lepage, Vincent Corcé, Isabelle Cannie, David Deniaud, Stéphanie Renaud, Foie, métabolismes et cancer, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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 ), Société d'Accélération du Transfert de Technologies (SATT OUEST VALORISATION), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), CHU Pontchaillou [Rennes], Laboratoire de Toxicologie Biologique et Médico-Légale, Hôpital Pontchaillou-CHU Pontchaillou [Rennes], This work was supported by the development funds SATT Ouest-Valorisation and FEDER Europe (Brittany region). The authors are grateful to the Conseil Régional Pays de la Loire, to the French Ministry of Education, to the Ligue Nationale contre le Cancer (LNCC, Ille et Vilaine/Loire Atlantique), to the Association pour la Recherche sur le Cancer (ARC) and to the Centre National de la Recherche Scientifique (CNRS) for financial support.The authors thank P. Loyer (Inserm UMR991, Rennes, France) and I. Morel (CHU Pontchaillou, Rennes, France) for scientific assistance in the flow cytometry and LC/MSMS analyses, respectively.In vivo experiments were carried out in the animal handling facility of the university, the ARCHE platform of the Structure Fédérative de Recherche BIOSIT in Rennes (BiogenOuest and Cancéropôle Grand Ouest network).The histological analysis were carried out in the histopathological platform H2P2 of the Structure Fédérative de Recherche BIOSIT in Rennes (BiogenOuest and Cancéropôle Grand Ouest network)., Université de Rennes (UR)-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 ), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Jonchère, Laurent

Subjects
MESH: Colonic Neoplasms/pathology, [SDV]Life Sciences [q-bio], MESH: Colonic Neoplasms/drug therapy, Endogeny, polyamine transport system, Biochemistry, Mice, chemistry.chemical_compound, 0302 clinical medicine, MESH: Biological Transport/drug effects, polyamine, MESH: Molecular Targeted Therapy, Polyamines, MESH: Animals, Molecular Targeted Therapy, Cancer, 0303 health sciences, Iron chelator, Chemistry, MESH: Antineoplastic Agents/pharmacology, Cell Cycle, MESH: Iron Chelating Agents/pharmacology, DNA, Neoplasm, Cell cycle, Tumor Burden, 3. Good health, [SDV] Life Sciences [q-bio], 030220 oncology & carcinogenesis, Colonic Neoplasms, Female, Intracellular, MESH: Cell Cycle/drug effects, Eflornithine, Cell Survival, MESH: DNA, Neoplasm/antagonists & inhibitors, MESH: HCT116 Cells, Iron, Transplantation, Heterologous, Mice, Nude, Antineoplastic Agents, [SDV.CAN]Life Sciences [q-bio]/Cancer, Iron Chelating Agents, 03 medical and health sciences, [SDV.CAN] Life Sciences [q-bio]/Cancer, In vivo, MESH: Mice, Nude, Animals, Humans, MESH: Mice, 030304 developmental biology, Pharmacology, Polyamine transport, Cell growth, MESH: DNA, Neoplasm/biosynthesis, Biological Transport, MESH: Colonic Neoplasms/metabolism, HCT116 Cells, In vitro, MESH: Eflornithine/pharmacology, colon adenocarcinoma, tumor vectorization, Cancer research, MESH: Polyamines/antagonists & inhibitors, Polyamine, MESH: Cell Survival/drug effects, MESH: Female, Neoplasm Transplantation, MESH: Neoplasm Transplantation
Abstract

International audience; Tumor cell growth requires large iron quantities and the deprivation of this metal induced by synthetic metal chelators is therefore an attractive method for limiting the cancer cell proliferation. The antiproliferative effect of the Quilamine HQ1-44, a new iron chelator vectorized toward tumor cells by a polyamine chain, is related to its high selectivity for the Polyamine Transport System (PTS), allowing its preferential uptake by tumoral cells. The difference in PTS activation between healthy cells and tumor cells enables tumor cells to be targeted, whereas the strong dependence of these cells on iron ensures a secondary targeting. Here, we demonstrated in vitro that HQ1-44 inhibits DNA synthesis and cell proliferation of HCT116 cells by modulating the intracellular metabolism of both iron and polyamines. Moreover, in vivo, in xenografted athymic nude mice, we found that HQ1-44 was as effective as cis-platin in reducing HCT116 tumor growth, without its side effects. Furthermore, as suggested by in vitro data, the depletion in exogenous or endogenous polyamines, known to activate the PTS, dramatically enhanced the antitumor efficiency of HQ1-44. These data support the need for further studies to assess the value of HQ1-44 as an adjuvant treatment in cancer

Published
2015

34. Synthesis and biological properties of Quilamines II, new iron chelators with antiproliferative activities

Author

Vincent Corcé, François Gaboriau, Sébastien G. Gouin, Stéphanie Renaud, Karine Julienne, Olivier Loréal, David Deniaud, Isabelle Cannie, Foie, métabolismes et cancer, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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 ), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Société d'Accélération du Transfert de Technologies (SATT OUEST VALORISATION), Université de Rennes (UR)-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 Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Spectrometry, Mass, Electrospray Ionization, Magnetic Resonance Spectroscopy, Biomedical Engineering, Pharmaceutical Science, Bioengineering, CHO Cells, Iron Chelating Agents, 01 natural sciences, Reductive amination, 03 medical and health sciences, chemistry.chemical_compound, Cricetulus, Cricetinae, [CHIM]Chemical Sciences, Animals, Amines, 030304 developmental biology, Cell Proliferation, Pharmacology, 0303 health sciences, Polyamine transport, 010405 organic chemistry, Chinese hamster ovary cell, Organic Chemistry, Biological activity, 0104 chemical sciences, Calcein, chemistry, Biochemistry, Polyamine, Linker, Lead compound, Biotechnology
Abstract

International audience; To selectively target tumor cells expressing an overactive Polyamine Transport System (PTS), we designed, synthesized, and evaluated the biological activity of a new generation of iron chelators, derived from the lead compound HQ1-44, which we named Quilamines II. The structures of four new antiproliferative agents were developed. They differ in the size of the linker (HQ0-44 and HQ2-44) or in the nature of the linker (HQCO-44 and HQCS-44) between a hydroxyquinoline moiety (HQ) and a homospermidine (44) chain, the best polyamine vector. The Quilamines II were obtained after 6 to 9 steps by Michael addition, peptide linkage, and reductive amination or by using the Willgerodt-Kindler reaction. The biological evaluation of these second-generation Quilamines showed that modifying the size of the linker increased the selectivity of these compounds for the PTS. In addition, measurement of the toxicity of Quilamines HQ0-44 and HQ2-44 highlighted their marked antiproliferative nature on several cancerous cell lines as well as a differential activity on nontransformed cells (fibroblasts). In contrast, Quilamines HQCO-44 and HQCS-44 presented low selectivity for the PTS, probably due to a loss of electrostatic interaction. We also demonstrated that the HCT116 cell line, originating from a human colon adenocarcinoma, was the most responsive to the various Quilamines. As deduced from the calcein and HVA assays, the higher iron chelating capacity of HQ1-44 could explain its higher antiproliferative efficiency.

Published
2014

35. Polyaminoquinoline iron chelators for vectorization of antiproliferative agents: design, synthesis, and validation

Author

David Deniaud, Sébastien G. Gouin, Raphaël Tripier, Solène Guihéneuf, Luís M. P. Lima, Karine Julienne, Eric Renault, Stéphanie Renaud, Emmanuelle Morin, Olivier Loréal, Vincent Corcé, François Gaboriau, Isabelle Cannie, Foie, métabolismes et cancer, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-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 ), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Chimie, Electrochimie Moléculaires et Chimie Analytique (CEMCA), Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO)-Université de Brest (UBO)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université de Rennes (UR)-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 ), Université de Nantes (UN)-Université de Nantes (UN)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Brest (UBO)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Brestois Santé Agro Matière (IBSAM), Université de Brest (UBO), and Le Corre, Morgane

Subjects
Magnetic Resonance Spectroscopy, Spectrophotometry, Infrared, Stereochemistry, Biomedical Engineering, Pharmaceutical Science, Bioengineering, MESH: Drug Design, Iron Chelating Agents, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, [CHIM] Chemical Sciences, MESH: Aminoquinolines, Moiety, [CHIM]Chemical Sciences, Cytotoxicity, 030304 developmental biology, Pharmacology, 0303 health sciences, Polyamine transport, Chemistry, MESH: Magnetic Resonance Spectroscopy, MESH: Spectrophotometry, Infrared, Chinese hamster ovary cell, Organic Chemistry, Biological activity, [SDV.MHEP.HEG]Life Sciences [q-bio]/Human health and pathology/Hépatology and Gastroenterology, [SDV.MHEP.HEG] Life Sciences [q-bio]/Human health and pathology/Hépatology and Gastroenterology, MESH: Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, MESH: Iron Chelating Agents, Drug Design, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, 030220 oncology & carcinogenesis, Aminoquinolines, MESH: Cell Division, Selectivity, Polyamine, Cell Division, Biotechnology
Abstract

International audience; Iron chelation in tumoral cells has been reported as potentially useful during antitumoral treatment. Our aim was to develop new polyaminoquinoline iron chelators targeting tumoral cells. For this purpose, we designed, synthesized, and evaluated the biological activity of a new generation of iron chelators, which we named Quilamines, based on an 8-hydroxyquinoline (8-HQ) scaffold linked to linear polyamine vectors. These were designed to target tumor cells expressing an overactive polyamine transport system (PTS). A set of Quilamines bearing variable polyamine chains was designed and assessed for their ability to interact with iron. Quilamines were also screened for their cytostatic/cytotoxic effects and their selective uptake by the PTS in the CHO cell line. Our results show that both the 8-HQ moiety and the polyamine part participate in the iron coordination. HQ1-44, the most promising Quilamine identified, presents a homospermidine moiety and was shown to be highly taken up by the PTS and to display an efficient antiproliferative activity that occurred in the micromolar range. In addition, cytotoxicity was only observed at concentrations higher than 100 μM. We also demonstrated the high complexation capacity of HQ1-44 with iron while much weaker complexes were formed with other cations, indicative of a high selectivity. We applied the density functional theory to study the binding energy and the electronic structure of prototypical iron(III)-Quilamine complexes. On the basis of these calculations, Quilamine HQ1-44 is a strong tridentate ligand for iron(III) especially in the form of a 1:2 complex.

Published
2012

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