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9. Enhancing Near Infrared II Emission of Gold Nanoclusters via Encapsulation in Small Polymer Nanoparticles.

Author

Haye, Lucie, Diriwari, P. Iyanu, Alhalabi, Abdallah, Gallavardin, Thibault, Combes, Antoine, Klymchenko, Andrey S., Hildebrandt, Niko, Le Guével, Xavier, and Reisch, Andreas

Subjects
GOLD clusters, POLYMERS, CONTRAST media, NANOPARTICLES, ENERGY transfer, PHOTOTHERMAL effect
Abstract

Reduced scattering and autofluorescence in the second near‐infrared window (NIR‐II, 1000–1700 nm) hold the promise of high‐resolution photoluminescence (PL) in vivo imaging at depths well beyond the µm scale. Yet, contrast agents with bright emission in this spectral region remain limited. Ultrasmall gold nanoclusters (AuNCs) are of particular interest for NIR‐II PL imaging. However, they exhibit limited brightness. Here, high amounts of NIR‐II emitting AuNCs are encapsulated in small polymer nanoparticles (NPs) made of poly(ethyl methacrylates). Using nanoprecipitation, loadings of up to 50 wt% can be reached, corresponding to over 10 000 AuNCs per 60 nm NP. PL quantum yields up to 1.3% and NP brightnesses up to 3.8 × 106 M−1 cm−1 are accomplished. Increasing inter‐AuNC interactions at higher loading result in a bathochromic shift of the PL emission. According to time‐resolved PL measurements, this can be attributed to distinct inter‐AuNC energy transfer pathways between the core and surface‐centered PL modes. Evaluation of the nanohybrids in tissue‐mimicking models for in vivo blood vessel imaging shows that the ultrabright and red‐shifted NIR‐II PL results in significantly improved detection sensitivity and resolution, which makes AuNC‐loaded polymer NPs highly promising candidates for advanced in vivo imaging. [ABSTRACT FROM AUTHOR]

Published
2023
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15. New Antibacterial Cadiolide Analogues active Against Antibiotic Bacterial Resistant Strains

Author

Bekri, S, Desriac, Florie, Barreau, Magalie, Clamens, Thomas, Gallavardin, Thibault, Nahenec-Martel, Patricia Le, Vieillard, Julien, Datoussaid, Yazid, Choukchou-Braham, Noureddine, Lesouhaitier, Olivier, Franck, Xavier, Leleu, Stéphane, Laboratoire de Catalyse et Synthèse en Chimie Organique, Université Aboubekr Belkaid - University of Belkaïd Abou Bekr [Tlemcen], Laboratoire de Microbiologie Signaux et Microenvironnement (LMSM), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Antibacterial, Natural products, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Cadiolide analogues, Antibiotic-resistance
Abstract

International audience; The synthesis of new cadiolide analogues was carried out using a one-pot multi component synthesis. The antibacterial activity of these molecules was evaluated on standard and antibiotic resistant bacterial strains chosen for their involvement in human health or in food-born poisoning. Four molecules have shown good activities with MICs of 2 μg/mL−1. The introduction of an indole group or the conversion of the lactone into lactam have highlighted two new families of molecules with promising antibacterial activity. In addition, most of these active molecules are devoid of cytotoxic activity against keratinocyte cells.

Published
2020

17. Two‐Photon Absorption and Cell Imaging of Fluorene‐Functionalized Epicocconone Analogues

Author

Oger, Samuel, Schapman, Damien, Mougeot, Romain, Leleu, Stéphane, Lascoux, Noëlle, Baldeck, Patrice, Bénard, Magalie, Gallavardin, Thibault, Galas, Ludovic, Franck, Xavier, Oger, Samuel, Schapman, Damien, Mougeot, Romain, Leleu, Stéphane, Lascoux, Noëlle, Baldeck, Patrice, Bénard, Magalie, Gallavardin, Thibault, Galas, Ludovic, and Franck, Xavier

Abstract

info:eu-repo/semantics/published

Published
2019

21. (Bio)-conjugués polymères multifonctionnels pour l'imagerie de fluorescence

Author

Adjili, Salim, Cepraga, Cristina, Marotte, Sophie, Gallavardin, Thibault, Massin, Julien, Lanoe, Pierre-Henri, Mulatier, Jean-Christophe, Fargier, Guillaume, Hamard-Peron, Elise, Monnereau, Cyrille, Maury, Olivier, Bretonnière, Yann, Favier, Arnaud, Lerouge, Frédéric, Lindgren, M., Marvel, Jacqueline, Parola, Stéphane, Leverrier, Yann, Muriaux, Delphine, Baldeck, Patrice, Andraud, Chantal, Charreyre, Marie-Thérèse, Ingénierie des Matériaux Polymères (IMP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Immunité infection vaccination (I2V), Université de Lyon-Université de Lyon-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM), Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Centre de recherche en Biologie Cellulaire (CRBM), Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1), Virologie humaine, École normale supérieure - Lyon (ENS Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM), SFR Biosciences, École normale supérieure - Lyon (ENS Lyon)-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de la Santé et de la Recherche Médicale (INSERM), IMBM, École normale supérieure - Lyon (ENS Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM)-École normale supérieure - Lyon (ENS Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM), Laboratoire de Spectrométrie Physique (LSP), Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, Institut National de la Santé et de la Recherche Médicale (INSERM)-IFR128-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Université Jean Monnet - Saint-Étienne (UJM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM), and École normale supérieure de Lyon (ENS de Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM)-École normale supérieure de Lyon (ENS de Lyon)-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM)

Subjects
[CHIM.POLY]Chemical Sciences/Polymers, [CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2013

22. Two-photon absorbing chromophores for photodynamic therapy: molecular engineering and in vivo applications

Author

Monnereau, Cyrille, Kobayashi, Norihisa, Ouchen, Fahima, Gallavardin, Thibault, Armagnat, Chloé, Rau, Ileana, Lanoe, Pierre-Henri, Maury, Olivier, Marotte, Sophie, Leverrier, Yann, Baldeck, Patrice, Andraud, Chantal, Laboratoire de Chimie - UMR5182 (LC), Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École normale supérieure - Lyon (ENS Lyon)-Institut de Chimie du CNRS (INC), Department of General Chemistry, University Politehnica of Bucharest [Romania] (UPB), 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), Immunité infection vaccination (I2V), Institut National de la Santé et de la Recherche Médicale (INSERM)-IFR128-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon, Centre International de Recherche en Infectiologie - UMR (CIRI), Institut National de la Santé et de la Recherche Médicale (INSERM)-École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Spectrométrie Physique (LSP), Université Joseph Fourier - Grenoble 1 (UJF)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure de Lyon (ENS de Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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 Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-IFR128-Institut National de la Santé et de la Recherche Médicale (INSERM), Centre International de Recherche en Infectiologie (CIRI), and Université de Lyon-Université de Lyon-Université Jean Monnet - Saint-Étienne (UJM)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
0303 health sciences, Materials science, 020205 medical informatics, business.industry, medicine.medical_treatment, Photodynamic therapy, 02 engineering and technology, Chromophore, Molecular engineering, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, 03 medical and health sciences, 030301 anatomy & morphology, Two-photon excitation microscopy, In vivo, Amphiphile, 0202 electrical engineering, electronic engineering, information engineering, medicine, Optoelectronics, business, ComputingMilieux_MISCELLANEOUS
Abstract

Recent examples of our works in the field of molecular engineering of chromophores for two-photon photodynamic therapy (PDT), and their vectorization into biological medium are presented and discussed. In a first section of this article, we show that a commercial amphiphilic diblock copolymer can be used as a micellar container for efficient delivery of s standard two-photon PDT sensitizer into cells. In a second section, we show how a simple molecular engineering strategy can be used to improve the performances of two-photon PDT sensitizer in the biological transparency-window.

Published
2011

31. Biocompatible well-defined chromophore–polymer conjugates for photodynamic therapy and two-photon imaging

Author

Cepraga, Cristina, primary, Gallavardin, Thibault, additional, Marotte, Sophie, additional, Lanoë, Pierre-Henri, additional, Mulatier, Jean-Christophe, additional, Lerouge, Frédéric, additional, Parola, Stéphane, additional, Lindgren, Mikael, additional, Baldeck, Patrice L., additional, Marvel, Jacqueline, additional, Maury, Olivier, additional, Monnereau, Cyrille, additional, Favier, Arnaud, additional, Andraud, Chantal, additional, Leverrier, Yann, additional, and Charreyre, Marie-Thérèse, additional

Published
2013
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37. Photodynamic therapy and two-photon bio-imaging applications of hydrophobic chromophores through amphiphilic polymer delivery

Author

Gallavardin, Thibault, primary, Maurin, Mathieu, additional, Marotte, Sophie, additional, Simon, Timea, additional, Gabudean, Ana-Maria, additional, Bretonnière, Yann, additional, Lindgren, Mikael, additional, Lerouge, Frédéric, additional, Baldeck, Patrick L., additional, Stéphan, Olivier, additional, Leverrier, Yann, additional, Marvel, Jacqueline, additional, Parola, Stéphane, additional, Maury, Olivier, additional, and Andraud, Chantal, additional

Published
2011
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39. Multifunctional hybrid nanoparticles for two-photon fluorescence imaging and photodynamic therapy

Author

Baldeck, Patrice L., primary, Maurin, Mathieu, additional, Philipot, Cecile, additional, Zaiba, Soraya, additional, Gallavardin, Thibault, additional, Maury, Olivier, additional, Andraud, Chantal, additional, Dubois, Fabien, additional, Ibanez, Alain, additional, Lerouge, Frédéric, additional, Parola, Stéphane, additional, Stephan, Olivier, additional, and van Der Sanden, Baudwin, additional

Published
2011
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40. Two-Photon “Caging” Groups: Effect ofPosition Isomery on the Photorelease Properties of Aminoquinoline-DerivedPhotolabile Protecting Groups.

Author

Tran, Christine, Gallavardin, Thibault, Petit, Morgane, Slimi, Riadh, Dhimane, Hamid, Blanchard-Desce, Mireille, Acher, Francine C., Ogden, David, and Dalko, Peter I.

Subjects
*QUINOLINE, *PHOTOLABILE compounds, *PROTECTIVE groups (Chemistry), *PHOTOLYSIS (Chemistry), *SOLUBILITY, *SUBSTITUTION reactions
Abstract

Hightwo-photon photolysis cross sections and water solubilityof probes are important to avoid toxicity in biomedical applicationsof photolysis. Systematic variation of the position of a carboxylelectron-withdrawing group (EWG) on photolysis of 8-dimethylaminoquinolineprotecting groups identified the C5-substituted isomer as a privilegeddipole. The 5-benzoyl-8-DMAQ substitution yields a caging group withan enhanced two-photon uncaging cross section (δu= 2.0 GM) and good water solubility (c≤50 mM, pH 7.4). [ABSTRACT FROM AUTHOR]

Published
2015
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41. Unsymmetrical boron diketonates containing strong electron-donating groups as mechanochromic fluorescent solids.

Author

Mehiaoui, Nawel, Leleu, Stéphane, Kibou, Zahira, Choukchou-Braham, Noureddine, Franck, Xavier, and Gallavardin, Thibault

Subjects
*BORON, *SINGLE crystals, *SOLIDS, *QUANTUM states, *MOLECULAR spectra
Abstract

New π-conjugated unsymmetrical β-diketones were synthesized thanks to a modular synthetic approach involving in situ generated acylketenes through thermal degradation of 1,4-dioxin-2-ones. This method gave access to a family of new chromophores featuring either an indoline or a benzothiazole as electron-donating groups in one side and various aromatic moieties in the other side. After complexation with boron difluoride, BDK (Boron DiKetonates) compounds were obtained featuring fluorescence in non-polar solvents. These compounds were also found to be fluorescent in solid state with quantum yield up to 0.22, and their emission wavelength was very sensitive to their crystallinity. Two of these compounds were successfully recrystallized to provide small single crystals and emission spectra were recorded in crystal phase and ground state which showed mechanochromism with a spectral shift of 37 nm. • A method based on the thermal degradation of 1,3-dioxin-4-ones was developed to synthesize unsymmetrical β-diketones. • Corresponding boron diketonates (BDK) were fluorescent in non-polar solvents, featuring a cyanine optical behavior. • In solid state, most of these compounds were fluorescent with quantum up to 0.22, with emission ranging from 575 to 650 nm. • Mecanochromism was evidenced in two recrystallized compounds. [ABSTRACT FROM AUTHOR]

Published
2022
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42. Indazole versus indole-based cationic merocyanines with red shifted in-cellulo emission for selective mitochondria imaging

Author

Ludovic Galas, Magalie Bénard, Xavier Franck, Margot Boujut, Thibault Gallavardin, Arnaud Chevalier, Damien Schapman, Gallavardin, Thibault, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Plate-Forme de Recherche en Imagerie Cellulaire de Haute-Normandie (PRIMACEN), Normandie Université (NU)-Normandie Université (NU)-Institute for Research and Innovation in Biomedicine (IRIB), Normandie Université (NU)-Normandie Université (NU)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-High-tech Research Infrastructures for Life Sciences (HeRacLeS), and Normandie Université (NU)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Indole test, Indazole, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Process Chemistry and Technology, General Chemical Engineering, Cationic polymerization, [SDV.BC.BC]Life Sciences [q-bio]/Cellular Biology/Subcellular Processes [q-bio.SC], Fluorophore, Mitochondrion, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Photochemistry, Mitochondria, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, [CHIM.THEO] Chemical Sciences/Theoretical and/or physical chemistry, chemistry.chemical_compound, Membrane, chemistry, Cationic merocyanine dyes, [SDV.BC.BC] Life Sciences [q-bio]/Cellular Biology/Subcellular Processes [q-bio.SC], Molecule, Cellular biology, Merocyanine, Electrochemical potential
Abstract

International audience; Selective fluorophores are seminal for the development of fluorescent cell imaging allowing the simultaneous monitoring of several biological parameters. Mitochondria are one of the main targets of optical microscopy as their dynamics are related to many biological events. One of the best strategy to target them, is to design cationic dyes which accumulate preferentially in their membranes due to their high electrochemical potential. In this work, indazole scaffold was explored to build new cationic merocyanine dyes and compared with indole scaffold. This nitrogen heteroaromatic structure is still very uncommon in dyes chemistry; therefore, a lot has to be discovered about the effects of pH, solvent polarity and methylation in cyclic nitrogen on their optical properties. Finally, fluorescent imaging revealed that a red shift occurred in the emission of these molecules inside the mitochondria.

Published
2022

43. From One-Photon to Two-Photon Probes: 'Caged' Compounds, Actuators, and Photoswitches

Author

Peter I. Dalko, Guillaume Bort, David Ogden, Thibault Gallavardin, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physiologie cérébrale (LPC - UMR 8118), Université Paris Diderot - Paris 7 (UPD7)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), and Gallavardin, Thibault

Subjects
Laser Microscopy, Macrocyclic Compounds, Photon, Nanotechnology, Molecular systems, 010402 general chemistry, 01 natural sciences, Catalysis, Cell Physiological Phenomena, Absorptiometry, Photon, Two-photon excitation microscopy, [CHIM] Chemical Sciences, cell signaling, [CHIM]Chemical Sciences, Nitrobenzenes, Chelating Agents, Photons, photochemistry, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Photochemical Processes, 0104 chemical sciences, caged compounds, protecting groups, Actuator, signal transduction
Abstract

International audience; Molecular systems that can be remotely controlled by light are gaining increasing importance in cell biology, physiology, and neurosciences because of the spatial and temporal precision that is achievable with laser microscopy. Two‐photon excitation has significant advantages deep in biological tissues, but raises problems in the design of “smart” probes compatible with cell physiology. This Review discusses the chemical challenges in generating suitable two‐photon probes.

Published
2013

44. Substitution Effect on the One- and Two-photon Sensitivity of DMAQ 'Caging' Groups

Author

Francisco Palma-Cerda, Francine Acher, Christine Tran, Morgane Petit, Hamid Dhimane, Peter I. Dalko, Mireille Blanchard-Desce, Thibault Gallavardin, Thomas Roger, David Ogden, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques (LCBPT - UMR 8601), Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de physiologie cérébrale (LPC - UMR 8118), Université Paris Diderot - Paris 7 (UPD7)-Université Paris Descartes - Paris 5 (UPD5)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Gallavardin, Thibault, Université de Rennes 1 (UR1), and Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Stereochemistry, Quinolines/chemistry, Glutamates/chemistry, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Structure-Activity Relationship, Two-photon excitation microscopy, Glutamates, [CHIM] Chemical Sciences, Structure–activity relationship, Molecule, [CHIM]Chemical Sciences, Substitution effect, Physical and Theoretical Chemistry, Photons, Photolysis, Molecular Structure, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Quinoline, Photodissociation, Glutamate receptor, [CHIM.ORGA] Chemical Sciences/Organic chemistry, 3. Good health, 0104 chemical sciences, chemistry, Quinolines, Derivative (chemistry)
Abstract

International audience; The systematic SAR study of a "caging" group showed a strong influence of the position of the donor dimethylamino group on the efficiency of photolysis of the DMAQ (2-hydroxymethylene-(N,N-dimethylamino)quinoline) caged acetate under one-photon near-UV or two-photon near-IR excitation. Photorelease of l-glutamate by the most efficient 8-DMAQ derivative strongly and efficiently activated glutamate receptors, generating large, fast rising responses similar to those elicited by glutamate photoreleased from the widely used MNI-caged glutamate.

Published
2012

45. Two-Photon Absorption and Cell Imaging of Fluorene-Functionalized Epicocconone Analogues.

Author

Oger S, Schapman D, Mougeot R, Leleu S, Lascoux N, Baldeck P, Bénard M, Gallavardin T, Galas L, and Franck X

Subjects
Animals, Benzopyrans chemical synthesis, Catalysis, Fluorenes chemical synthesis, Fluorescent Dyes chemical synthesis, Furans chemical synthesis, Ketones chemical synthesis, Optical Imaging methods, PC12 Cells, Palladium chemistry, Rats, Benzopyrans chemistry, Fluorenes chemistry, Fluorescent Dyes chemistry, Furans chemistry, Ketones chemistry, Microscopy, Fluorescence, Multiphoton methods
Abstract

Epicocconone 1 is a natural chromophore isolated from the fungus Epicoccum nigrum that has shown applications in proteomics and fluorescent microscopy thanks to its unique pro-fluorescence properties. The modification of the skeleton of the natural product by replacing the triene side chain by a fluorenyl scaffold can noticeably increase the fluorophore's absorption coefficient. The synthesis of the analogues of the natural product has been made possible by the use of a palladium-catalyzed carbonylation reaction, allowing the construction of the β-keto-dioxinone key intermediate. Two-photon absorption cross-section measurements of the fluorenyl epicocconone analogues show a structure dependency with values ranging from 60 to 280 GM and live cell imaging show intense staining of intracellular vesicle-like structures around the nucleus., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2019
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46. An optimized procedure for direct access to 1 H -indazole-3-carboxaldehyde derivatives by nitrosation of indoles.

Author

Chevalier A, Ouahrouch A, Arnaud A, Gallavardin T, and Franck X

Abstract

Indazole derivatives are currently drawing more and more attention in medicinal chemistry as kinase inhibitors. 1 H -indazole-3-carboxaldehydes are key intermediates to access to a variety of polyfunctionalized 3-substituted indazoles. We report here a general access to this motif, based on the nitrosation of indoles in a slightly acidic environment. These very mild conditions allow the conversion of both electron-rich and electron-deficient indoles into 1 H -indazole-3-carboxaldehydes., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

Published
2018
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47. Quinoline-derived two-photon sensitive quadrupolar probes.

Author

Dunkel P, Tran C, Gallavardin T, Dhimane H, Ogden D, and Dalko PI

Subjects
Molecular Structure, Photolysis, Photons, Photosensitizing Agents chemistry, Quinolines chemistry
Abstract

The first quadrupolar 8-dimethylaminoquinoline-derived 6-(8-DMAQ-OAc)2 (1c) and 5-(8-DMAQ-OAc)2 (2c) photosensitive probes underwent photolysis under UV (365 nm) and NIR (730 nm two-photon (TP)) irradiation conditions, showing Qu = 9.3% and 6.6% quantum yields and δu = 0.07 GM and 0.40 GM uncaging cross-sections, respectively.

Published
2014
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48. From one-photon to two-photon probes: "caged" compounds, actuators, and photoswitches.

Author

Bort G, Gallavardin T, Ogden D, and Dalko PI

Subjects
Cell Physiological Phenomena, Chelating Agents chemistry, Nitrobenzenes chemistry, Photochemical Processes, Photochemistry, Signal Transduction, Absorptiometry, Photon methods, Macrocyclic Compounds chemistry, Photons
Abstract

Molecular systems that can be remotely controlled by light are gaining increasing importance in cell biology, physiology, and neurosciences because of the spatial and temporal precision that is achievable with laser microscopy. Two-photon excitation has significant advantages deep in biological tissues, but raises problems in the design of "smart" probes compatible with cell physiology. This Review discusses the chemical challenges in generating suitable two-photon probes., (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2013
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