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1. Periodic Mesoporous Organosilica Nanoparticles for CO

Author

Paul, Kirren, Lucile, Barka, Saher, Rahmani, Nicolas, Bondon, Nicolas, Donzel, Philippe, Trens, Aurélie, Bessière, Laurence, Raehm, Clarence, Charnay, and Jean-Olivier, Durand

Subjects
Temperature, Aminopyridines, Humans, Nanoparticles, Adsorption, Carbon Dioxide, Porosity
Abstract

(1) Background: Due to human activities, greenhouse gas (GHG) concentrations in the atmosphere are constantly rising, causing the greenhouse effect. Among GHGs, carbon dioxide (CO

Published
2022

3. Synthesis of Cyclen‐Functionalized Ethenylene‐Based Periodic Mesoporous Organosilica Nanoparticles and Metal‐Ion Adsorption Studies

Author

Gulaim A. Seisenbaeva, Clarence Charnay, Hao Li, Roser Pleixats, Laurence Raehm, Ani Vardanyan, Jean-Olivier Durand, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Swedish University of Agricultural Sciences (SLU), and Universitat Autònoma de Barcelona (UAB)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, Renewable Energy, Sustainability and the Environment, Chemistry, Energy Engineering and Power Technology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Biomaterials, chemistry.chemical_compound, Mesoporous organosilica, Adsorption, Cyclen, Transition metal, Desorption, Polymer chemistry, Materials Chemistry, Click chemistry, Nanorod, Other Chemistry Topics, 0210 nano-technology, Selectivity
Abstract

International audience; The preparation of two cyclens both possessing two triethoxysilyl groups through click chemistry is described. These two cyclens were incorporated into bis(triethoxysilyl)ethenylene‐based periodic mesoporous organosilica nanoparticles (PMO NPs) at different proportions of bis(triethoxysilyl)ethenylene/cyclens (90/10, 75/25). The obtained nanorods were analyzed with different techniques and showed high specific surface areas at low proportion of cyclens. The nanorods containing free amino groups of cyclen were then used for Ni(II) and Co(II) removal from model solutions. The kinetics and isotherms of adsorption of Ni(II) and Co(II) were determined, and the materials showed high uptake of metals (up to 3.9 mmol ⋅ g−1). They demonstrated pronounced selectivity in separation of rare earth elements from late transition metals, e. g. Ni(II) and Co(II) by adsorption and even more so by controlled desorption..

Published
2020

4. Photosensitivity of Different Nanodiamond–PMO Nanoparticles in Two-Photon-Excited Photodynamic Therapy

Author

Nicolas Bondon, Denis Durand, Kamel Hadj-Kaddour, Lamiaa M. A. Ali, Rabah Boukherroub, Nadir Bettache, Magali Gary-Bobo, Laurence Raehm, Jean-Olivier Durand, Christophe Nguyen, Clarence Charnay, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Université de Montpellier (UM), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Institut d’Électronique, de Microélectronique et de Nanotechnologie - UMR 8520 (IEMN), Centrale Lille-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF)-JUNIA (JUNIA), Université catholique de Lille (UCL)-Université catholique de Lille (UCL), NanoBioInterfaces - IEMN (NBI - IEMN), Université catholique de Lille (UCL)-Université catholique de Lille (UCL)-Centrale Lille-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF)-JUNIA (JUNIA), We acknowledge the imaging facility MRI, member of the France-BioImaging national infrastructure, supported by the French National Research Agency (ANR-10-INBS-04, 'Investments for the future') and Erwan Olivieiro from the MEA platform, Université de Montpellier, for the STEM-EDX experiments. ANR-19-CE09-0034 MSN-2hv, ANR-19-CE09-0034,MSN-2hv,Matériaux théranostiques associant les fonctionnalités d'imagerie 2 photons et de thérapie photodynamique pour le ciblage de bactéries et le contrôle des infections lors de la cicatrisation(2019), ANR-10-INBS-0004,France-BioImaging,Développment d'une infrastructure française distribuée coordonnée(2010), Unité Mixte de Recherche sur les Herbivores - UMR 1213 (UMRH), VetAgro Sup - Institut national d'enseignement supérieur et de recherche en alimentation, santé animale, sciences agronomiques et de l'environnement (VAS)-Institut National de Recherche pour l’Agriculture, l’Alimentation et l’Environnement (INRAE), and We acknowledge the imaging facility MRI, member of the France-BioImaging national infrastructure, supported by the French National Research Agency (ANR-10-INBS-04, 'Investments for the future') and Erwan Olivieiro from the MEA platform, Université de Montpellier, for the STEM-EDX experiments.ANR-19-CE09-0034 MSN-2hv

Subjects
K. Ali, R. Bettache, theranostics, J.-O. Nguyen, Hadj-Kaddour, Gary-Bobo, K, J.-O, [SDV.CAN]Life Sciences [q-bio]/Cancer, L.M.A, Bondon, Raehm, General Biochemistry, Genetics and Molecular Biology, M, [SPI]Engineering Sciences [physics], C, et al nanodiamond, Boukherroub, N. Durand, nanodiamond, two-photon excitation, mesoporous organosilica, cancer cells, Durand, L. Durand, Bettache, Ecology, Evolution, Behavior and Systematics, R, D. Hadj-Kaddour, Paleontology, L.M.A. Boukherroub, [CHIM.MATE]Chemical Sciences/Material chemistry, N, L, N. Gary-Bobo, Ali, M. Raehm, Space and Planetary Science, C. et al nanodiamond two-photon excitation mesoporous organosilica theranostics cancer cells, D, [SPI.OPTI]Engineering Sciences [physics]/Optics / Photonic, Nguyen
Abstract

Background: In addition to their great optical properties, nanodiamonds (NDs) have recently proved useful for two-photon-excited photodynamic therapy (TPE-PDT) applications. Indeed, they are able to produce reactive oxygen species (ROS) directly upon two-photon excitation but not with one-photon excitation; Methods: Fluorescent NDs (FNDs) with a 100 nm diameter and detonation NDs (DNDs) of 30 nm were compared. In order to use the gems for cancer-cell theranostics, they were encapsulated in a bis(triethoxysilyl)ethylene-based (ENE) periodic mesoporous organosilica (PMO) shell, and the surface of the formed nanoparticles (NPs) was modified by the direct grafting of polyethylene glycol (PEG) and amino groups using PEG-hexyltriethoxysilane and aminoundecyltriethoxysilane during the sol–gel process. The NPs’ phototoxicity and interaction with MDA-MB-231 breast cancer cells were evaluated afterwards; Results: Transmission electronic microscopy images showed the formation of core–shell NPs. Infrared spectra and zeta-potential measurements confirmed the grafting of PEG and NH2 groups. The encapsulation of the NDs allowed for the imaging of cancer cells with NDs and for the performance of TPE-PDT of MDA-MB-231 cancer cells with significant mortality. Conclusions: Multifunctional ND@PMO core–shell nanosystems were successfully prepared. The NPs demonstrated high biocompatibility and TPE-PDT efficiency in vitro in the cancer cell model. Such systems hold good potential for two-photon-excited PDT applications.

Published
2022

5. Organosilica Nanoparticles for Gemcitabine Monophosphate Delivery in Cancer Cells

Author

Saher Rahmani, Jelena Budimir, Morgane Daurat, Yannick Guari, Laurence Raehm, Peter Hesemann, Sébastien Richeter, Clarence Charnay, Roza Bouchal, Magali Gary-Bobo, Nadir Bettache, Alia Akrout, Christophe Nguyen, Jean-Olivier Durand, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Centre de recherche en Biologie Cellulaire (CRBM), and Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)

Subjects
gemcitabine monophosphate, organosilica nanoparticles, drug delivery, cancer, ionosilica, Renewable Energy, Sustainability and the Environment, Chemistry, Energy Engineering and Power Technology, Nanoparticle, Cancer, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, medicine.disease, 01 natural sciences, Gemcitabine, 0104 chemical sciences, Biomaterials, Cancer cell, Drug delivery, Materials Chemistry, medicine, Cancer research, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, medicine.drug
Abstract

Organosilica nanoparticles hold great promise for nanomedicine applications. These nanoparticles are synthesized from polytrialkoxysilylated precursors without any silica source. In this work we present two kinds of organosilica nanoparticles with either amine or ammonium walls constituting their structure. Both types of nanoparticles are very efficient for gemcitabine monophosphate delivery, a small hydrophilic anticancer drug whose encapsulation is still a challenge. The nanoparticles are endocytosed by MCF-7 breast cancer cells as monitored by confocal microscopy. They are efficient and lead to 60% cancer cell death.

Published
2019

6. Synthesis of triethoxysilylated cyclen derivatives, grafting on magnetic mesoporous silica nanoparticles and application to metal ion adsorption

Author

Erwan Oliviero, Jean-Olivier Durand, Roser Pleixats, Clarence Charnay, Gulaim A. Seisenbaeva, Hao Li, Laurence Raehm, Mathilde Ménard, Ani Vardanyan, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Swedish University of Agricultural Sciences (SLU), Departament de Química [Barcelona] (UAB), and Universitat Autònoma de Barcelona (UAB)

Subjects
Solid-state chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, General Chemical Engineering, Metal ions in aqueous solution, Nanoparticle, 02 engineering and technology, General Chemistry, Mesoporous silica, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, chemistry.chemical_compound, Adsorption, Cyclen, Materials Chemistry, Click chemistry, Surface modification, 0210 nano-technology, Nuclear chemistry
Abstract

International audience; The synthesis through click chemistry of triethoxysilylated cyclen derivative-based ligands is described. Different methods were used such as the copper catalyzed Huisgen's reaction, or thiol-ene reaction for the functionalization of the cyclen scaffold with azidopropyltriethoxysilane or mercaptopropyltriethoxysilane, respectively. These ligands were then grafted on magnetic mesoporous silica nanoparticles (MMSN) for extraction and separation of Ni(II) and Co(II) metal ions from model solutions. The bare and ligand-modified MMSN materials revealed high adsorption capacity (1.0-2.13 mmol g À1) and quick adsorption kinetics, achieving over 80% of the total capacity in 1-2 hours.

Published
2021

7. Fluorescent periodic mesoporous organosilica nanoparticles dual-functionalized via click chemistry for two-photon photodynamic therapy in cells

Author

Marie Maynadier, Laurence Raehm, Jean-Olivier Durand, Xavier Cattoën, Marcel Garcia, Maxime Klausen, Sébastien Picard, Dina Aggad, Guillaume Clermont, Chiara Mauriello Jimenez, Mireille Blanchard-Desce, Jonas G. Croissant, Emilie Genin, Michel Wong Chi Man, Magali Gary-Bobo, Olivier Mongin, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Optique et Matériaux (NEEL - OPTIMA), Institut Néel (NEEL), Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), 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), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Optique et Matériaux (OPTIMA )

Subjects
Fluorophore, Materials science, Singlet oxygen, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Biomedical Engineering, Nanoparticle, 02 engineering and technology, General Chemistry, General Medicine, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Fluorescence, 0104 chemical sciences, chemistry.chemical_compound, Mesoporous organosilica, chemistry, Click chemistry, General Materials Science, Photosensitizer, 0210 nano-technology, Mesoporous material, ComputingMilieux_MISCELLANEOUS
Abstract

The synthesis of ethenylene-based periodic mesoporous organosilica nanoparticles for two-photon imaging and photodynamic therapy of breast cancer cells is described. A dedicated two-photon absorbing fluorophore possessing four triethoxysilyl groups and having large two-photon absorption in the near IR region, and azidopropyltriethoxysilane were incorporated into the structure. The mesoporous nanoparticles of 100 nm diameter were further functionalized by means of click chemistry with a propargylated fluorescent bromo-quinoline photosensitizer able to generate singlet oxygen. The photophysical properties and two-photon absorption properties of the nanoparticles were investigated evidencing complementary contribution of the two dyes. Both dyes contribute to the two-photon absorption response of the mesoporous nanoparticles while efficient FRET from the two-photon fluorophore to the quinoline sensitizer is observed. The dual-functionalized nanoparticles were incubated with MCF-7 breast cancer cells. Two-photon confocal imaging demonstrated the endocytosis of the nanoparticles within cancer cells. Moreover, brief two-photon irradiation (3 scans of 1.57 s) at 760 nm at high laser power (3 W) was shown to induce 40% of cancer cell death demonstrating the potential of the dual-functionalized mesoporous organosilica nanoparticles for two-photon photodynamic therapy.

Published
2020

8. Influence of the synthetic method on the properties of two-photon-sensitive mesoporous silica nanoparticles

Author

Marie Maynadier, Laurence Raehm, Clarence Charnay, Michel Wong Chi Man, Vanja Stojanovic, Xavier Cattoën, Magali Gary-Bobo, Olivier Mongin, Jonas G. Croissant, Jean-Olivier Durand, Mireille Blanchard-Desce, Marcel Garcia, Vincent Hugues, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Moléculaires (ISM), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Optique et Matériaux (NEEL - OPTIMA), Institut Néel (NEEL), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), NanoMedSyn (NMS), ANR-10-NANO-0022,MECHANANO,Nanomachines mécanisées pour l'activation à deux photons(2010), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), 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), Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Optique et Matériaux (OPTIMA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), and NanoMedSyn

Subjects
cross-section, Materials science, Mesoporous silica nanoparticles, Biomedical Engineering, Nanoparticle, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Two-photon excitation microscopy, Bromide, Organic chemistry, General Materials Science, Photosensitizer, Porosity, two-photon, Aqueous medium, [CHIM.ORGA]Chemical Sciences/Organic chemistry, imaging, General Chemistry, General Medicine, Mesoporous silica, 021001 nanoscience & nanotechnology, 0104 chemical sciences, chemistry, Chemical engineering, Spatial dispersion, cancer cells, 0210 nano-technology
Abstract

International audience; Herein we report the modulation of the properties of mesoporous silica nanoparticles (NPs) via various synthetic approaches. Three types of elaborations were compared, one in aqueous media at 25 °C, and the other two at 80 °C in water or in a water–ethanol mixture. For all these methods, an alkoxysilylated two-photon photosensitizer (2PS) was co-condensed with tetraethylorthosilicate (TEOS) in the presence of cetyltrimethylammonium bromide (CTAB), leading to five two-photon-sensitive mesoporous silica (M2PS) NPs. The M2PS NP porous structure could be tuned from radial to worm-like and MCM-41 types of organization. Besides, the 2PS precursor spatial dispersion was found to be highly dependent on both the 2PS initial concentration and the elaboration process. As a result, two-photon properties were modulated by the choice of the synthesis, the best results being found in aqueous media at 25 or 80 °C. Finally, the M2PS NPs were used for in vitro two-photon imaging of cancer cells.

Published
2020

9. Preparation and characterization of novel mixed periodic mesoporous organosilica nanoparticles

Author

Hao Li, Clarence Charnay, Roser Pleixats, Laurence Raehm, Jean-Olivier Durand, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), and Universitat Autònoma de Barcelona (UAB)

Subjects
Thermogravimetric analysis, Materials science, Nanoparticle, 02 engineering and technology, 010402 general chemistry, sol-gel process, lcsh:Technology, 01 natural sciences, Article, Nanomaterials, Dynamic light scattering, 5dialkoxybenzoates, [CHIM]Chemical Sciences, General Materials Science, Sol-gel process, lcsh:Microscopy, lcsh:QC120-168.85, Sol-gel, disilylated tert-butyl 3,5-dialkoxybenzoates, lcsh:QH201-278.5, lcsh:T, periodic mesoporous organosilica nanoparticles, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Mesoporous organosilica, Disilylated tert -butyl 3,5-dialkoxybenzoates, lcsh:TA1-2040, disilylated tert-butyl 3, lcsh:Descriptive and experimental mechanics, Nanorod, lcsh:Electrical engineering. Electronics. Nuclear engineering, Periodic mesoporous organosilica nanoparticles, lcsh:Engineering (General). Civil engineering (General), 0210 nano-technology, Mesoporous material, lcsh:TK1-9971, Nuclear chemistry
Abstract

We report herein the preparation of mixed periodic mesoporous organosilica nanoparticles (E-Pn 75/25 and 90/10 PMO NPs) by sol-gel co-condensation of E-1,2-bis(triethoxysilyl)ethylene ((E)-BTSE or E) with previously synthesized disilylated tert-butyl 3,5-dialkoxybenzoates bearing either sulfide (precursor P1) or carbamate (precursor P2) functionalities in the linker. The syntheses were performed with cetyltrimethylammonium bromide (CTAB) as template in the presence of sodium hydroxide in water at 80 &deg, C. The nanomaterials have been characterized by Transmission Electron Microscopy (TEM), nitrogen-sorption measurements (BET), Dynamic Light Scattering (DLS), zeta-potential, Thermogravimetric Analysis (TGA), FTIR, 13C CP MAS NMR and small angle X-ray diffraction (p-XRD). All the nanomaterials were obtained as mesoporous rodlike-shape nanoparticles. Remarkably, E-Pn 90/10 PMO NPs presented high specific surface areas ranging from 700 to 970 m2g-1, comparable or even higher than pure E PMO nanorods. Moreover, XRD analyses showed an organized porosity for E-P1 90/10 PMO NPs typical for a hexagonal 2D symmetry. The other materials showed a worm-like mesoporosity.

Published
2020

10. Gemcitabine Delivery and Photodynamic Therapy in Cancer Cells via Porphyrin-Ethylene-Based Periodic Mesoporous Organosilica Nanoparticles

Author

Jean-Olivier Durand, Sébastien Richeter, Marie Maynadier, Jonas G. Croissant, Laure Lichon, Makhlouf Boufatit, Marcel Garcia, Laurence Raehm, Chiara Mauriello Jimenez, Danielle Laurencin, Dina Aggad, Soraya Dib, Shahad Alsaiari, Magali Gary-Bobo, and Niveen M. Khashab

Subjects
Materials science, Membrane permeability, medicine.medical_treatment, Energy Engineering and Power Technology, Nanotechnology, Photodynamic therapy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Gemcitabine Hydrochloride, Biomaterials, chemistry.chemical_compound, Materials Chemistry, medicine, Photosensitizer, Renewable Energy, Sustainability and the Environment, 021001 nanoscience & nanotechnology, Porphyrin, Gemcitabine, 0104 chemical sciences, Mesoporous organosilica, chemistry, Cancer cell, Cancer research, 0210 nano-technology, medicine.drug
Abstract

Gemcitabine hydrochloride is an FDA-approved chemotherapeutic drug used in the treatment of various cancers. Several drawbacks of gemcitabine including its short in vivo half-life of 8-17 min associated with a rapid excretion by the kidneys and its poor membrane permeability have inspired research on a nanodelivery approach. In this study, we report ethylene-based periodic mesoporous organosilica nanoparticles (PMOs) for photodynamic therapy and the autonomous delivery of gemcitabine in cancer cells. Porphyrins were used as photosensitizers and were localized in the walls of the PMOs while a high loading capacity of gemcitabine was observed in the porous structure. Depending on the nature of the photosensitizer, and its aggregation state, we were able to perform one or two-photon photodynamic therapy. Two-photon excited photodynamic therapy combined with gemcitabine delivery led to a synergy and a very efficient cancer cell killing.

Published
2017

11. Porphyrin- or phthalocyanine-bridged silsesquioxane nanoparticles for two-photon photodynamic therapy or photoacoustic imaging

Author

Vefa Ahsen, Dina Aggad, Jean-Luc Coll, Serkan Alpugan, Michel Wong Chi Man, Marcel Garcia, Marie Maynadier, Laurence Raehm, Deniz Kutlu Tarakci, Philippe Maillard, Fabienne Dumoulin, Clarence Charnay, Jean-Olivier Durand, Maxime Henry, Magali Gary-Bobo, Xavier Cattoën, Véronique Josserand, Chiara Mauriello-Jimenez, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut d'oncologie/développement Albert Bonniot de Grenoble (INSERM U823), Université Joseph Fourier - Grenoble 1 (UJF)-CHU Grenoble-EFS-Institut National de la Santé et de la Recherche Médicale (INSERM), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Optique et Matériaux (OPTIMA ), Institut Néel (NEEL), Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019]), Department of chemistry - Gebze Technical University, Gebze Teknik Üniversitesi [Gebze], Chimie, Modélisation et Imagerie pour la Biologie [Orsay], Institut de Chimie du CNRS (INC)-Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut Curie [Paris], and NanoMedSyn

Subjects
Materials science, [CHIM.ORGA]Chemical Sciences/Organic chemistry, medicine.medical_treatment, Nanoparticle, Photodynamic therapy, [CHIM.MATE]Chemical Sciences/Material chemistry, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, Photochemistry, 01 natural sciences, Porphyrin, Fluorescence, Silsesquioxane, 0104 chemical sciences, 3. Good health, chemistry.chemical_compound, chemistry, Two-photon excitation microscopy, Excited state, Phthalocyanine, medicine, General Materials Science, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract

Porphyrin- or phthalocyanine-bridged silsesquioxane nanoparticles (BSPOR and BSPHT) were prepared. Their endocytosis in MCF-7 cancer cells was shown with two-photon excited fluorescence (TPEF) imaging. With two-photon excited photodynamic therapy (TPE-PDT), BSPOR was more phototoxic than BSPHT, which in contrast displayed a very high signal for photoacoustic imaging in mice.

Published
2017

12. Porphyrin‐based bridged silsesquioxane nanoparticles for targeted two‐photon photodynamic therapy of zebrafish xenografted with human tumor

Author

Magali Gary-Bobo, Denis Durand, Makhlouf Boufatit, Soraya Dib, Jean-Olivier Durand, Ahmed Lakrafi, Alain Morère, Sofia Dominguez Gil, Vincent Chaleix, Dina Aggad, Nadir Bettache, Karim Bouchmella, Michel Wong Chi Man, Vincent Sol, Laurence Raehm, Guillaume Hery, Xavier Cattoën, Khaled El Cheikh, Chiara Mauriello Jimenez, Christophe Nguyen, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), CHU Pontchaillou [Rennes], Laboratoire de Chimie des Substances Naturelles (LCSN), Université de Limoges (UNILIM)-Génomique, Environnement, Immunité, Santé, Thérapeutique (GEIST FR CNRS 3503), Université des Sciences et de la Technologie Houari Boumediene [Alger] (USTHB), Optique et Matériaux (OPTIMA ), Institut Néel (NEEL), and Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Grenoble Alpes [2016-2019] (UGA [2016-2019])

Subjects
Cancer Research, Porphyrins, medicine.medical_treatment, Nanoparticle, Breast Neoplasms, Photodynamic therapy, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 02 engineering and technology, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, 01 natural sciences, Theranostic Nanomedicine, chemistry.chemical_compound, Two-photon excitation microscopy, In vivo, Cell Line, Tumor, medicine, Animals, Humans, Zebrafish, two-photon excitation, Photosensitizing Agents, bridged silsesquioxane nanoparticles, Lasers, human tumor targeting, Original Articles, Silanes, 021001 nanoscience & nanotechnology, Xenograft Model Antitumor Assays, Porphyrin, 3. Good health, 0104 chemical sciences, Microscopy, Fluorescence, Multiphoton, photodynamic therapy, Photochemotherapy, Oncology, chemistry, Injections, Intravenous, Cancer cell, Click chemistry, Biophysics, Nanoparticles, Nanomedicine, Female, 0210 nano-technology
Abstract

International audience; Background: Bridged silsesquioxane nanoparticles (BSNs) recently described represent a new class of nanoparticles exhibiting versatile applications and particularly a strong potential for nanomedicine.Aims: In this work, we describe the synthesis of BSNs from an octasilylated functional porphyrin precursor (PORBSNs) efficiently obtained through a click reaction. These innovative and very small-sized nanoparticles were functionalized with PEG and mannose (PORBSNs-mannose) in order to target breast tumors in vivo. Methods and Results: The structure of these nanoparticles is constituted of porphyrins J aggregates that allow two-photon spatiotemporal excitation of the nanoparticles. The therapeutic potential of such photoactivable nanoparticles was first studied in vitro, in human breast cancer cells in culture and then in vivo on zebrafish embryos bearing human tumors. These animal models were intravenously injected with 5 nL of a solution containing PORBSNs-mannose. An hour and half after the injection of photoactivable and targeted nanoparticles, the tumor areas were excited for few seconds with a two-photon beam induced focused laser. We observed strong tumor size decrease, with the involvement of apoptosis pathway activation.onclusion: We demonstrated the high targeting, imaging, and therapeutic potential of PORBSNs-mannose injected in the blood stream of zebrafish xenografted with human tumors.

Published
2019

13. Nanodiamond–PMO for two-photon PDT and drug delivery

Author

Rabah Boukherroub, Vanja Stojanovic, Yolanda Galàn Rubio, Ouahiba Hocine, Marcel Garcia, Dina Aggad, J.O. Durand, Nikola Knezevic, Chiara Mauriello Jimenez, Magali Gary-Bobo, Florina Teodorescu, Marie Maynadier, Laurence Raehm, Martina Seric, Sabine Szunerits, Jonas G. Croissant, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut d’Électronique, de Microélectronique et de Nanotechnologie - UMR 8520 (IEMN), Centrale Lille-Institut supérieur de l'électronique et du numérique (ISEN)-Université de Valenciennes et du Hainaut-Cambrésis (UVHC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)-Université Polytechnique Hauts-de-France (UPHF), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), NanoMedSyn, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), and NanoMedSyn (NMS)

Subjects
Materials science, Biomedical Engineering, Nanoparticle, Nanotechnology, 02 engineering and technology, 010402 general chemistry, Photochemistry, 01 natural sciences, Two-photon excitation microscopy, medicine, General Materials Science, Doxorubicin, Nanodiamond, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, Reactive oxygen species, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemistry, General Medicine, 021001 nanoscience & nanotechnology, 0104 chemical sciences, 3. Good health, Mesoporous organosilica, chemistry, Drug delivery, Cancer cell, 0210 nano-technology, medicine.drug
Abstract

In this article, we highlight the properties of nanodiamonds (ND), which were encapsulated in periodic mesoporous organosilica nanoparticles (PMO) and were able to generate reactive oxygen species for photodynamic applications upon two-photon excitation (TPE). The ND@PMO nanoparticles were characterized by various techniques and were then loaded with the anti-cancer drug doxorubicin. The release of the drug was pH sensitive and a synergistic cancer cell killing effect was observed when cancer cells were incubated with doxorubicin-loaded ND@PMO and irradiated with two-photon excitation at 800 nm.

Published
2016

14. Cover Feature: Synthesis of Cyclen‐Functionalized Ethenylene‐Based Periodic Mesoporous Organosilica Nanoparticles and Metal‐Ion Adsorption Studies (ChemNanoMat 11/2020)

Author

Laurence Raehm, Roser Pleixats, Jean-Olivier Durand, Hao Li, Gulaim A. Seisenbaeva, Ani Vardanyan, and Clarence Charnay

Subjects
Materials science, Renewable Energy, Sustainability and the Environment, Energy Engineering and Power Technology, Nanoparticle, Metal adsorption, Biomaterials, chemistry.chemical_compound, Mesoporous organosilica, Cyclen, chemistry, Chemical engineering, Metal ion adsorption, Feature synthesis, Materials Chemistry, Cover (algebra)
Published
2020

15. Chick chorioallantoic membrane assay as an in vivo model to study the effect of nanoparticle-based anticancer drugs in ovarian cancer

Author

Jonas G. Croissant, Altagracia Conteras, Laurence Raehm, Tammy Yik, Kotaro Matsumoto, Fuyuhiko Tamanoi, Niveen M. Khashab, Laura E. Ratliff, Tan Le Hoang Doan, Carlotta A. Glackin, Yevhen Fatieiev, Shirleen I. Simargi, Chiara Mauriello Jimenez, Sophia Allaf Shahin, Binh Thanh Vu, Jean-Olivier Durand, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier ( ICGM ICMMM ), Université Montpellier 1 ( UM1 ) -Université Montpellier 2 - Sciences et Techniques ( UM2 ) -Ecole Nationale Supérieure de Chimie de Montpellier ( ENSCM ) -Université de Montpellier ( UM ) -Centre National de la Recherche Scientifique ( CNRS ), Microbiology, Immunology and Molecular Genetics ( UCLA ), University of California at Los Angeles [Los Angeles] ( UCLA ), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Microbiology, Immunology and Molecular Genetics (UCLA), University of California [Los Angeles] (UCLA), and University of California-University of California

Subjects
0301 basic medicine, 02 engineering and technology, Chick Embryo, Chorioallantoic Membrane, Models, Nanotechnology, ComputingMilieux_MISCELLANEOUS, Cancer, Ovarian Neoplasms, Drug Carriers, Multidisciplinary, Tumor, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, 021001 nanoscience & nanotechnology, Ovarian Cancer, 3. Good health, Chorioallantoic membrane, 5.1 Pharmaceuticals, Drug delivery, embryonic structures, Medicine, Biological Assay, Female, Development of treatments and therapeutic interventions, 0210 nano-technology, Biotechnology, medicine.drug, Stromal cell, Science, Bioengineering, Models, Biological, Article, Cell Line, 03 medical and health sciences, Targeted therapies, Rare Diseases, In vivo, [ CHIM.ORGA ] Chemical Sciences/Organic chemistry, Cell Line, Tumor, medicine, Animals, Humans, Doxorubicin, medicine.disease, Biological, Orphan Drug, 030104 developmental biology, Cell culture, Cancer research, Nanoparticles, Ovarian cancer
Abstract

New therapy development is critically needed for ovarian cancer. We used the chicken egg CAM assay to evaluate efficacy of anticancer drug delivery using recently developed biodegradable PMO (periodic mesoporous organosilica) nanoparticles. Human ovarian cancer cells were transplanted onto the CAM membrane of fertilized eggs, resulting in rapid tumor formation. The tumor closely resembles cancer patient tumor and contains extracellular matrix as well as stromal cells and extensive vasculature. PMO nanoparticles loaded with doxorubicin were injected intravenously into the chicken egg resulting in elimination of the tumor. No significant damage to various organs in the chicken embryo occurred. In contrast, injection of free doxorubicin caused widespread organ damage, even when less amount was administered. The lack of toxic effect of nanoparticle loaded doxorubicin was associated with specific delivery of doxorubicin to the tumor. Furthermore, we observed excellent tumor accumulation of the nanoparticles. Lastly, a tumor could be established in the egg using tumor samples from ovarian cancer patients and that our nanoparticles were effective in eliminating the tumor. These results point to the remarkable efficacy of our nanoparticle based drug delivery system and suggests the value of the chicken egg tumor model for testing novel therapies for ovarian cancer., がんの個別化医療を可能にする患者癌由来の鶏卵モデル. 京都大学プレスリリース. 2018-06-06.

Published
2018

16. Synthesis of disulfide-based biodegradable bridged silsesquioxane nanoparticles for two-photon imaging and therapy of cancer cells

Author

Marcel Garcia, Xavier Cattoën, Marie Maynadier, Laurence Raehm, Magali Gary-Bobo, Olivier Mongin, Chiara Mauriello-Jimenez, Jean-Olivier Durand, Michel Wong Chi Man, Jonas G. Croissant, Philippe Maillard, Mireille Blanchard-Desce, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Médicaments Photoactivables - Photochimiothérapie (PHOTOMED), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Optique et Matériaux (OPTIMA), Institut Néel (NEEL), Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS)-Université Joseph Fourier - Grenoble 1 (UJF)-Institut polytechnique de Grenoble - Grenoble Institute of Technology (Grenoble INP )-Centre National de la Recherche Scientifique (CNRS), 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), Institut des Sciences Moléculaires (ISM), Centre National de la Recherche Scientifique (CNRS)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Université Sciences et Technologies - Bordeaux 1-Université Montesquieu - Bordeaux 4-Institut de Chimie du CNRS (INC), Institut Curie [Paris], Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM), Optique et Matériaux (NEEL - OPTIMA), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Montesquieu - Bordeaux 4-Université Sciences et Technologies - Bordeaux 1 (UB)-École Nationale Supérieure de Chimie et de Physique de Bordeaux (ENSCPB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Materials science, Cell Survival, Surface Properties, Dispersity, Nanoparticle, Nanotechnology, Catalysis, Nanomaterials, Structure-Activity Relationship, chemistry.chemical_compound, Two-photon excitation microscopy, Materials Chemistry, Humans, Organosilicon Compounds, Disulfides, Particle Size, ComputingMilieux_MISCELLANEOUS, Photosensitizing Agents, Dose-Response Relationship, Drug, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Metals and Alloys, Disulfide bond, General Chemistry, Silsesquioxane, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Microscopy, Fluorescence, Multiphoton, chemistry, Cancer cell, MCF-7 Cells, Ceramics and Composites, Nanoparticles, Breast cancer cells
Abstract

Biodegradable bridged silsesquioxane (BS) nanomaterials for two-photon-excited (TPE) imaging and therapy of breast cancer cells were described. A versatile synthesis was developed to design monodisperse tetra-alkoxysilylated diamino-diphenylbutadiene or Zn-porphyrin-based nanospheres of 30 to 50 nm.

Published
2015

17. Two-Photon-Excited Silica and Organosilica Nanoparticles for Spatiotemporal Cancer Treatment

Author

Laurence Raehm, Jean-Olivier Durand, Jeffrey I. Zink, Jonas G. Croissant, Chemical and Biological Engineering [Albuquerque], The University of New Mexico [Albuquerque], Center for Micro-Engineered Materials [Albuquerque] (CMEM), Department of Chemistry and Biochemistry, University of California Los Angeles, University of California [Los Angeles] (UCLA), University of California-University of California, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
medicine.medical_treatment, Biomedical Engineering, Pharmaceutical Science, Nanoparticle, Nanotechnology, Photodynamic therapy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Nanomaterials, Biomaterials, chemistry.chemical_compound, Drug Delivery Systems, Two-photon excitation microscopy, Neoplasms, medicine, [CHIM]Chemical Sciences, Humans, Chemistry, Singlet oxygen, Mesoporous silica, 021001 nanoscience & nanotechnology, Silicon Dioxide, 3. Good health, 0104 chemical sciences, Cancer treatment, Photochemotherapy, Drug delivery, Nanoparticles, 0210 nano-technology, Porosity
Abstract

International audience; Coherent two‐photon‐excited (TPE) therapy in the near‐infrared (NIR) provides safer cancer treatments than current therapies lacking spatial and temporal selectivities because it is characterized by a 3D spatial resolution of 1 µm3 and very low scattering. In this review, the principle of TPE and its significance in combination with organosilica nanoparticles (NPs) are introduced and then studies involving the design of pioneering TPE‐NIR organosilica nanomaterials are discussed for bioimaging, drug delivery, and photodynamic therapy. Organosilica nanoparticles and their rich and well‐established chemistry, tunable composition, porosity, size, and morphology provide ideal platforms for minimal side‐effect therapies via TPE‐NIR. Mesoporous silica and organosilica nanoparticles endowed with high surface areas can be functionalized to carry hydrophobic and biologically unstable two‐photon absorbers for drug delivery and diagnosis. Currently, most light‐actuated clinical therapeutic applications with NPs involve photodynamic therapy by singlet oxygen generation, but low photosensitizing efficiencies, tumor resistance, and lack of spatial resolution limit their applicability. On the contrary, higher photosensitizing yields, versatile therapies, and a unique spatial resolution are available with engineered two‐photon‐sensitive organosilica particles that selectively impact tumors while healthy tissues remain untouched. Patients suffering pathologies such as retinoblastoma, breast, and skin cancers will greatly benefit from TPE‐NIR ultrasensitive diagnosis and therapy.

Published
2017

18. Hybrid Particles

Author

Laurence Raehm, Jean-Olivier Durand, and Nikola Ž. Knežević

Subjects
chemistry.chemical_classification, chemistry, Biomolecule, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, 0104 chemical sciences, Nanomaterials
Published
2017

19. Biodegradable Ethylene-Bis(Propyl)Disulfide-Based Periodic Mesoporous Organosilica Nanorods and Nanospheres for Efficient In-Vitro Drug Delivery

Author

Jean-Olivier Durand, Michel Wong Chi Man, Jonas G. Croissant, Audrey Gallud, Philippe Trens, Marie Maynadier, Xavier Cattoën, Laurence Raehm, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), and Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)

Subjects
Nanostructure, Materials science, Ethylene, Cell Survival, Nanoparticle, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Ethylene bis, chemistry.chemical_compound, medicine, Humans, Organic chemistry, General Materials Science, Doxorubicin, Disulfides, Drug Carriers, Antibiotics, Antineoplastic, Nanotubes, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Mechanical Engineering, Ethylenes, Hydrogen-Ion Concentration, Silicon Dioxide, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Mesoporous organosilica, Chemical engineering, chemistry, Mechanics of Materials, Drug delivery, MCF-7 Cells, Nanorod, 0210 nano-technology, Porosity, Nanospheres, medicine.drug
Abstract

International audience; Periodic mesoporous organosilica nanorods and nanospheres are synthesized from 1,4-bis(triethoxysilyl)ethylene and bis(3-ethoxysilylpropyl)disulfide. The nanosystems present the long-range order of the hexagonal nanostructure. They are degraded in simulated physiological conditions. The loading and release of doxorubicin with these nanosystems are both pH dependent. These nanoparticles are endocytosed by breast cancer cells and are very efficient for doxorubicin delivery in these cells.

Published
2014

20. Front Cover: Organosilica Nanoparticles for Gemcitabine Monophosphate Delivery in Cancer Cells (ChemNanoMat 7/2019)

Author

Saher Rahmani, Clarence Charnay, Yannick Guari, Laurence Raehm, Morgane Daurat, Magali Gary-Bobo, Christophe Nguyen, Peter Hesemann, Roza Bouchal, Jelena Budimir, Alia Akrout, Nadir Bettache, Jean-Olivier Durand, Sébastien Richeter, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
Renewable Energy, Sustainability and the Environment, Chemistry, Energy Engineering and Power Technology, Nanoparticle, Cancer, 02 engineering and technology, 010402 general chemistry, 021001 nanoscience & nanotechnology, medicine.disease, 01 natural sciences, Gemcitabine, 0104 chemical sciences, Biomaterials, Front cover, Cancer cell, Drug delivery, Materials Chemistry, Cancer research, medicine, [CHIM]Chemical Sciences, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS, medicine.drug
Abstract

International audience

Published
2019

21. Functionalisation of mesoporous silica nanoparticles with 3-isocynatopropyltrichlorosilane

Author

Wassim El Malti, Laurence Raehm, Jean-Olivier Durand, Mireille Blanchard-Desce, Olivier Mongin, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Chimie et Photonique Moléculaires (CPM), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS)

Subjects
animal structures, [CHIM.ORGA]Chemical Sciences/Organic chemistry, General Chemical Engineering, Nanoparticle, 02 engineering and technology, General Chemistry, Mesoporous silica, 010402 general chemistry, 021001 nanoscience & nanotechnology, Grafting, 01 natural sciences, Isocyanate, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Nucleophile, Covalent bond, Polymer chemistry, Urea, Organic chemistry, Reactivity (chemistry), sense organs, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract

The functionalisation of Mesoporous Silica Nanoparticles (MSN) with the isocyanate group was carried out. The excellent reactivity of 3-isocynanatopropyltrichlorosilane allowed its grafting on the surface of MSN in mild conditions. Further reaction with different nucleophiles bearing primary amino groups led to the formation of a urea linkage and thus the covalent grafting of the nucleophiles to the MSN surface.

Published
2011

22. Photodynamic Therapy: Porous Porphyrin-Based Organosilica Nanoparticles for NIR Two-Photon Photodynamic Therapy and Gene Delivery in Zebrafish (Adv. Funct. Mater. 21/2018)

Author

Marcel Garcia, Nicolas Cubedo, Rachid Sougrat, Vincent Sol, Jean-Olivier Durand, Erwan Oliviero, Magali Gary-Bobo, Vincent Chaleix, Danielle Laurencin, Mireille Rossel, Karen Tresfield, Niveen M. Khashab, Xavier Cattoën, Nadir Bettache, Dorothée Berthomieu, Sébastien Clément, Chiara Mauriello Jimenez, Manuel A. Roldan-Gutierrez, Sébastien Richeter, Dina Aggad, Jonas G. Croissant, Michel Wong Chi Man, Marie Maynadier, Laurence Raehm, Dalaver H. Anjum, Shahad Alsaiari, and Clarence Charnay

Subjects
Materials science, biology, medicine.medical_treatment, Nanoparticle, Photodynamic therapy, 02 engineering and technology, Gene delivery, 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, biology.organism_classification, 01 natural sciences, Porphyrin, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Biomaterials, chemistry.chemical_compound, Two-photon excitation microscopy, chemistry, Electrochemistry, Zebrafish embryo, medicine, Biophysics, 0210 nano-technology, Zebrafish
Published
2018

23. Cancer Treatment: Two-Photon-Excited Silica and Organosilica Nanoparticles for Spatiotemporal Cancer Treatment (Adv. Healthcare Mater. 7/2018)

Author

Jean-Olivier Durand, Jonas G. Croissant, Laurence Raehm, and Jeffrey I. Zink

Subjects
Materials science, medicine.medical_treatment, Biomedical Engineering, Pharmaceutical Science, Nanoparticle, Photodynamic therapy, Nanotechnology, Silsesquioxane, Cancer treatment, Biomaterials, chemistry.chemical_compound, Two-photon excitation microscopy, chemistry, Excited state, Drug delivery, medicine
Published
2018

24. Surface Modifications of Love Acoustic Waves Sensors for Chemical and Biological Detection

Author

Rémi Desmet, Marc Rolland, Corinne Dejous, Dominique Rebière, Oleg Melnyk, Jean Olivier Durand, Marc Cretin, Michel Persin, Laurent Fertier, Laurence Raehm, Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Laboratoire de l'intégration, du matériau au système (IMS), Université Sciences et Technologies - Bordeaux 1-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut de biologie de Lille - IBL (IBLI), Université de Lille, Sciences et Technologies-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille, Droit et Santé, Institut de Biologie, Centre National de la Recherche Scientifique (CNRS), and UMR 8525

Subjects
Materials science, Acoustics, 02 engineering and technology, 01 natural sciences, Surface Functionalization, chemistry.chemical_compound, SELF-ASSEMBLED MONOLAYERS, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, BINDING, 0103 physical sciences, Molecule, Chelation, Electrical and Electronic Engineering, SILICON, ComputingMilieux_MISCELLANEOUS, SH-SAW, AGENT, Thin Films, 010302 applied physics, Semicarbazide, [CHIM.ORGA]Chemical Sciences/Organic chemistry, PEPTIDES, TRANSDUCERS, 021001 nanoscience & nanotechnology, Combinatorial chemistry, Atomic and Molecular Physics, and Optics, ARRAYS, Transducer, chemistry, Thiourea, Covalent bond, Chemisorption, DENSITY, FUNCTIONALIZATION, Surface modification, METAL IONS, 0210 nano-technology
Abstract

The surface functionalization of guided-SH-SAW (Shear Horizontal-Surface Acoustic Wave) transducers was carried out to prepare layers for heavy metals chelation and antibodies recognition. For the preparation of the chemical sensors, a thiourea molecule acting as a chelating agent for heavy metals was grafted on the top-layer of the transducer. This covalent immobilization was obtained by amide bonds through primary amine groups immobilized on the device by the chemisorption of the 3-aminopropyltriethoxysilane (APTES). The thiourea modified transducer was inserted in a microfluidic analysis system to test its sensitivity for cadmium ions in liquid media. In the aim to develop bio-chemical sensors based on antigen/antibody recognition, a functionalization way based on SAMs of semicarbazide functions leading to alpha-oxo-semicarbazone bonds with antigenic peptides is described. The real-time immobilization of the peptide on the surface was observed for the first time and the antibody recognition was successfully monitored. Based on these results, the gravimetric determination by guided-SH-SAW transducers functionalized by the semicarbazide/alpha-oxo-aldehyde chemistry is a promising complementary route for antibodies analysis.

Published
2009

25. Love wave immunosensor for antibody recognition using an innovative semicarbazide surface functionalization

Author

Corinne Dejous, Oleg Melnyk, Jean-Olivier Durand, Laurent Fertier, Céline Zimmermann, Marc Cretin, Rémi Desmet, Laurence Raehm, Dominique Rebière, Marc Rolland, Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Institut de biologie de Lille - IBL (IBLI), Université de Lille, Sciences et Technologies-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP)-Centre National de la Recherche Scientifique (CNRS)-Université de Lille, Droit et Santé, Laboratoire de l'intégration, du matériau au système (IMS), and Université Sciences et Technologies - Bordeaux 1-Institut Polytechnique de Bordeaux-Centre National de la Recherche Scientifique (CNRS)

Subjects
medicine.drug_class, Nanotechnology, 02 engineering and technology, 010402 general chemistry, Monoclonal antibody, 01 natural sciences, chemistry.chemical_compound, Materials Chemistry, Fluorescence microscope, medicine, [SPI.NANO]Engineering Sciences [physics]/Micro and nanotechnologies/Microelectronics, Electrical and Electronic Engineering, Instrumentation, ComputingMilieux_MISCELLANEOUS, Semicarbazide, biology, Atomic force microscopy, Metals and Alloys, Acoustic sensor, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, 3. Good health, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Love wave, chemistry, biology.protein, Surface modification, Antibody, 0210 nano-technology
Abstract

A new novel and easy functionalization route of a Love wave acoustic sensor based on the α-oxo-semicarbazone bond is described. The interest is firstly to observe in real-time the immobilization of the peptide on the semicarbazide surface of the transducer and secondly to monitor the specific binding of antibodies. Site-specific immobilization of antigenic-peptides as well as binding of murine monoclonal antibodies has been shown by gravimetric measurements. A tetramethylrhodamine-labeled goat antibody directed against murine antibodies was used to further characterize the biomolecular interactions by fluorescence microscopy and surface analysis (by AFM). Our data show that the gravimetric monitoring developed from the prepared Love wave immunosensor is a promising alternative route to characterize chemical and biomolecular events.

Published
2009

26. Host-Guest Interactions: Design Strategy and Structure of an Unusual Cobalt Cage That Encapsulates a Tetrafluoroborate Anion

Author

Marie Noelle Rager, Brian E. Mann, Carine Guyard-Duhayon, Hani Amouri, Laurence Raehm, Lamia Mimassi, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), and Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)

Subjects
Tetrafluoroborate, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Supramolecular chemistry, chemistry.chemical_element, General Chemistry, General Medicine, 010402 general chemistry, 01 natural sciences, Catalysis, Ion, 0104 chemical sciences, 3. Good health, Crystallography, chemistry.chemical_compound, chemistry, Cage, Cobalt, ComputingMilieux_MISCELLANEOUS
Abstract

International audience

Published
2005

27. Crucial Role of the Counteranion on the Templation of Metallomacrocycles and a 3D Network: Synthesis, Characterization, and Structural Analysis

Author

Laurence Raehm, Hani Amouri, Carine Guyard-Duhayon, Lamia Mimassi, and Marie Noelle Rager

Subjects
Benzimidazole, Chemistry, Stereochemistry, Supramolecular chemistry, Bridging ligand, Ion, Inorganic Chemistry, chemistry.chemical_compound, Crystallography, Product (mathematics), Physical and Theoretical Chemistry, Benzene, Trifluoromethanesulfonate, Monoclinic crystal system
Abstract

Two novel supramolecular architectures, [[Ag(2)L(1)(2)][X](2)] with X = CF(3)SO(3)(-) (2a) or X = NO(3)(-) (2b) and [[AgL(1)(2)][X]](n) with X = BF(4)(-) (3), were constructed by self-assembly and obtained in quantitative yields, using AgX as a building block and L(1) as the bridging ligand (L(1) = 1,3-bis(benzimidazol-1-ylmethyl)benzene). The X-ray molecular structures of 2a and 3 are reported. Complex 2a was identified as a metallomacrocycle in which one ligating triflate anion is coordinated to each of the two unsaturated Ag(I) ions. 2a crystallizes in monoclinic unit cell P2(1)/n with a = 9.728(6) A, b = 17.303(4) A, c = 13.268(3) A, beta = 92.52(4) degrees, V = 2231(2) A(3), and Z = 2. Remarkably, the X-ray structure of 2a shows a layered network structure consisting of infinite metallomacrocycles held together through pi-pi interactions between benzimidazole rings. In dramatic contrast, the product 3 prepared from AgBF(4) and L(1) lacks metal-counterion bonding, leading to a supramolecular 3D network with the following three outstanding features: (i) in one dimension, metallomacrocycles containing two Ag centers and two bridging ligands form infinite, double-stranded chains; (ii) neighboring chains are arranged by two distinct pi-pi interactions, one between substituted benzene rings and the other between benzimidazole rings, leading to a 3D structure; (iii) cavities within the 3D network contain BF(4)(-) counteranions. 3 crystallizes in monoclinic unit cell C2/c with a = 25.33(3) A, b = 11.655(6) A, c = 18.466(8) A, beta = 123.00(8) degrees, V = 4572(8) A(3), and Z = 4. Interestingly, electrospray mass spectroscopy suggests in either case that the identified elemental subunit [AgL(1)(2)](+) is the key building block which self-assembles and subsequent anion templation provides either the macrocycles 2a, b or the inorganic polymer 3. Remarkably, in dichloromethane solvent ligand-to-metal stoichiometries of 2:1 in 3 and 1:1 in 2a, b are obtained even with excess ligand, showing the power of metal-anion interactions in determining the overall supramolecular structure. Anion metathesis, showing supramolecular structural rearrangements from 2a to 2b and more spectacularly from 3 to 2b, smoothly occurred. The crucial effect and the nature of coordinating counteranions (BF(4)(-), CF(3)SO(3)(-), NO(3)(-)) on the supermolecule design are presented and discussed.

Published
2003

28. Serendipity and Rational Design of One-Dimensional Doubly Stranded Chains with Nanometric Cavities Based on AgI Coordination Chemistry

Author

Hani Amouri, Laurence Raehm, Lamia Mimassi, and Carine Guyard-Duhayon

Subjects
chemistry.chemical_classification, Coordination polymer, Stereochemistry, Supramolecular chemistry, Rational design, Polymer, Triclinic crystal system, Coordination complex, Inorganic Chemistry, Crystallography, chemistry.chemical_compound, chemistry, Self-assembly, Isostructural
Abstract

Spontaneous and cooperative self-assembly processes allowed the preparation of two complexes {[AgL1 2][X]}n [X = CF3SO3, (3a); X = BF4, (3b)] in quantitative yields, identified as 1-D doubly stranded chains. The X-ray molecular structures of 3a,b are reported. Complexes 3a,b are isostructural and crystallize in the triclinic unit cell. The structures of 3a and 3b show the formation of a one-dimensional coordination polymer exhibiting as an outstanding feature the presence of infinite chained metallomacrocycles with nanometric cavit

Published
2002

29. From Kinetic to Thermodynamic Assembly of Catenanes: Error Checking, Supramolecular Protection and Oligocatenanes

Author

Laurence Raehm, Darren G. Hamilton, and Jeremy K. M. Sanders

Subjects
chemistry.chemical_classification, Alkene, Organic Chemistry, Catenane, Supramolecular chemistry, General Medicine, Mechanically interlocked molecular architectures, Kinetic energy, Ring (chemistry), Combinatorial chemistry, chemistry, Computational chemistry, Polycatenane, Organic chemistry, Molecule, Self-assembly, Error checking, Topology (chemistry)
Abstract

Catenanes are molecules comprising at least two mechanically interlocked rings: they cannot be separated, yet do not possess covalent links between ring constituents. Over the last two decades several efficient templatingmechanisms for the assembly of catenanes, and other topologically complex molecules, have been developed and exploited in the synthesis of numerous systems, often with impressive efficiency. Kinetically controlled assembly routes, employing transition metal complexation or amide hydrogen bonding interactions, have proved tremendously successful. A third arena of investigation, and perhaps the most thoroughly explored and exploited, is the utilisation of π-complementary components, principally bipyridinium dications and aromatic ethers. In our work electron deficient bipyridinium dications were replaced with uncharged, yet electron accepting, aromatic diimides. This replacement permitted the use of a variety of ring closing reactions for catenane formation by allowing us to step away from the structurally powerful but ultimately limited chemistry demanded by bipyridinium systems. A total of four ring-closing reactions were employed: acetylenic coupling, Mitsunobu alkylation, Grubbs' alkene metathesis, and zinc(II)-bipyridyl ligation. The first three methods yielded fully covalent interlocked systems, the fourth a catenane containing a metallomacrocycle. The first two methods employed irreversible bond forming reactions in catenane formation, the latter two thermodynamically controlled processes. This flexible system of interacting components, the synthetic chemistry used in their preparation, and the structural flexibility offered by the combination of these factors, is discussed in terms of a series of model systems leading to the proposition of a method for the synthesis of a polycatenane. Such systems, polymeric chains of interlocked rings, are unrealised yet coveted goals of chemists working in the area of supramolecular topology and are predicted to exhibit valuable and unusual material properties.

Published
2002

30. Functionalized mesoporous silica nanoparticles for one and two-photon photodynamic therapy

Author

Marcel Garcia, Alain Morère, Magali Gary-Bobo, J.O. Durand, Mireille Blanchard-Desce, Laurence Raehm, and Ph. Maillard

Subjects
Materials science, medicine.medical_treatment, Biophysics, Nanoparticle, Nanotechnology, Photodynamic therapy, 02 engineering and technology, Dermatology, Mesoporous silica, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Oncology, Two-photon excitation microscopy, medicine, Pharmacology (medical), 0210 nano-technology
Published
2017

31. Improved gene transfer with histidine-functionalized mesoporous silica nanoparticles

Author

David Brevet, Jean-Olivier Durand, Ouahiba Hocine, Anthony Delalande, Chantal Pichon, Laurence Raehm, Patrick Midoux, Clarence Charnay, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Centre de biophysique moléculaire (CBM), and Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
animal structures, media_common.quotation_subject, Genetic Vectors, Pharmaceutical Science, Nanoparticle, Cytomegalovirus, Transfection, Achilles Tendon, Mice, In vivo, Luciferases, Firefly, Animals, Humans, Electrophoretic mobility shift assay, Histidine, Internalization, ComputingMilieux_MISCELLANEOUS, media_common, Drug Carriers, Propylamines, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, Gene Transfer Techniques, DNA, Mesoporous silica, Silanes, Silicon Dioxide, 3. Good health, HEK293 Cells, Biochemistry, Biophysics, Degradation (geology), Nanoparticles, sense organs, Plasmids
Abstract

Mesoporous silica nanoparticles (MSN) were functionalized with aminopropyltriethoxysilane (MSN-NH2) then L-histidine (MSN-His) for pDNA delivery in cells and in vivo. The complexation of pDNA with MSN-NH2 and MSN-His was first studied with gel shift assay. pDNA complexed with MSN-His was better protected from DNase degradation than with MSN-NH2. An improvement of the transfection efficiency in cells was observed with MSN-His/pDNA compared to MSN-NH2/pDNA, which could be explained by a better internalization of MSN-His. The improvement of the transfection efficiency with MSN-His was also observed for gene transfer in Achilles tendons in vivo.

Published
2014

33. Controlled Molecular Motions in Copper-Complexed Rotaxanes: An XAS Study

Author

Pierre-Louis Vidal, Laurence Raehm, Jean-Marc Kern, B. Divisia-Blohorn, and Jean-Pierre Sauvage

Subjects
X-ray absorption spectroscopy, Denticity, Rotaxane, Phenanthroline, chemistry.chemical_element, Photochemistry, Copper, Inorganic Chemistry, Metal, chemistry.chemical_compound, Crystallography, chemistry, visual_art, visual_art.visual_art_medium, Moiety, Physical and Theoretical Chemistry, Terpyridine
Abstract

The environment of the central metal of a molecular machine-like copper rotaxane was observed by XAS experiments. The wheel of the rotaxane is a hetero-bischelating macrocycle containing both bidentate (phenanthroline) and terdentate (terpyridine) moieties. The axle of the assembly contains only a bidentate moiety. Applying an external chemical stimulus-oxidation of the metal-increases the number of coordinating atoms required by the metal template from 4 to 5. This variation is consistent with the oscillation of the wheel around the axle, leading thus to the most stable environment for the metal in the Cu(II) rotaxane.

Published
2000

34. Nanoparticules de silice mésoporeuse optimisées pour la fluorescence à deux photons

Author

Laurence Raehm, Mireille Blanchard-Desce, Jean-Olivier Durand, Nicolas Nerambourg, Monique Smaïhi, Catherine Dubernet, Valérie Lebret, Martinus H. V. Werts, Corine Gérardin, and Delphine Méthy-Gonnod

Subjects
02 engineering and technology, General Medicine, 010402 general chemistry, 021001 nanoscience & nanotechnology, 0210 nano-technology, 01 natural sciences, General Biochemistry, Genetics and Molecular Biology, 0104 chemical sciences
Abstract

Les nanoparticules mesoporeuses ont des proprietes uniques : une grande surface specifique ou une distribution etroite des tailles de pores. Les perspectives d’utilisation sont la creation de nouveaux outils pour le diagnostic precoce. Pour ces potentielles applications biologiques, l’innocuite de ces nanoparticules doit etre etablie.

Published
2009

35. A Transition Metal Containing Rotaxane in Motion: Electrochemically Induced Pirouetting of the Ring on the Threaded Dumbbell

Author

Jean-Marc Kern, Laurence Raehm, and Jean-Pierre Sauvage

Subjects
Bearing (mechanical), Rotaxane, Organic Chemistry, Supramolecular chemistry, chemistry.chemical_element, General Chemistry, Ring (chemistry), Photochemistry, Electrochemistry, Copper, Catalysis, law.invention, Axle, Crystallography, chemistry, law, Dumbbell
Abstract

Fast spinning motion is observed in a copper(I) rotaxane. This “motor-like” molecule consists of an axle, bearing two bulky stoppers at its ends, and a ring containing two differrent coordination sites, each of them corresponding to the preferred situation for copper(I) or copper(II). Thus, using electrochemistry, the axle can be forced to oscillate inside the wheel.

Published
1999

36. Recognition of the dihydrogenophosphate anion on a gold electrode derivatized with an amidoferrocenylalkylthiolate ligand

Author

Laurence Raehm, Jean-Marc Kern, Didier Astruc, Agnès Labande, and Ester Alonso

Subjects
chemistry.chemical_compound, chemistry, Ferrocene, Transition metal, Ligand, Inorganic chemistry, Electrode, General Chemistry, Cyclic voltammetry, Electrochemistry, Combinatorial chemistry, Derivative (chemistry), Ion
Abstract

A dialkyl disulfide derivative with an amidoferrocenyl termini was synthesized and coordinated as an alkylthiolate ligand to the surface of a gold electrode which was shown by cyclic voltammetry. This derivatized electrode behaved as an electrochemical redox sensor allowing the recognition of the dihydrogenophosphate anion.

Published
1999

37. Formation of a copper(I) catenate on an électrode surface via S-Au interactions

Author

Jean-Marc Kern, Jean-Pierre Sauvage, and Laurence Raehm

Subjects
Rotaxane, Inorganic chemistry, Catenane, chemistry.chemical_element, General Chemistry, Copper, chemistry.chemical_compound, Crystallography, Adsorption, chemistry, Electrode, Cyclic voltammetry, Derivative (chemistry), Dichloromethane
Abstract

A bis-thiol derivative of 2,9-diaryi-1,10-phenanthroline was threaded through a coordinating macrocycle using Cu(I) as a templating agent. This rotaxane adsorbs onto a gold surface, leading to a novel type of catenate, where gold atoms are incorporated within one of the two interlocking rings. The adsorption procedure was monitored by cyclic voltammetry.

Published
1999

38. Hyaluronic acid-functionalized mesoporous silica nanoparticles for efficient photodynamic therapy of cancer cells

Author

Magali Gary-Bobo, Marcel Garcia, Philippe Maillard, Nadia Benkirane-Jessel, Laurence Raehm, Jean-Olivier Durand, David Brevet, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Biomatériaux et ingénierie tissulaire, Université Louis Pasteur - Strasbourg I-Institut National de la Santé et de la Recherche Médicale (INSERM), Hôpital Central, Service de Chirurgie Orthopédique (UMR7561 CNRS), Inconnu, Conception, synthèse et vectorisation de biomolécules. (CSVB), Institut Curie-Centre National de la Recherche Scientifique (CNRS)-Université Paris Descartes - Paris 5 (UPD5), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), and Université Paris Descartes - Paris 5 (UPD5)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Curie [Paris]

Subjects
animal structures, medicine.medical_treatment, Biophysics, Photodynamic therapy, Apoptosis, 02 engineering and technology, Dermatology, 010402 general chemistry, Endocytosis, 01 natural sciences, chemistry.chemical_compound, Nanocapsules, Cell Line, Tumor, Hyaluronic acid, medicine, Moiety, Humans, Pharmacology (medical), Hyaluronic Acid, ComputingMilieux_MISCELLANEOUS, biology, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Chemistry, CD44, Mesoporous silica, 021001 nanoscience & nanotechnology, Silicon Dioxide, 0104 chemical sciences, Treatment Outcome, Oncology, Biochemistry, Photochemotherapy, Cell culture, Cancer cell, biology.protein, Cancer research, sense organs, 0210 nano-technology, Colorectal Neoplasms, Porosity
Abstract

Mesoporous silica nanoparticles (MSN) for photodynamic therapy (PDT) were coated with poly-(L-lysine) and hyaluronic acid (HA) by using the layer-by-layer method. HA is able to target cancer cells over-expressing the corresponding CD44 receptor. MSN functionalized with HA (MSN-HA) were more efficient than MSN without the targeting moiety when PDT was performed at low fluence (14 Jcm(-2)) and low dosage of MSN (20 μgmL(-1)) on HCT 116 colorectal cancer cells, known to over-express the CD44 receptor. Incubation of HCT-116 cancer cells with an excess of HA impaired the PDT effect with MSN-HA thus demonstrating that an active endocytosis mechanism was involved in the uptake of MSN-HA by these cells.

Published
2011

40. Nanoparticules mésoporeuses de silice (MSN) et applications biologiques

Author

Jean-Olivier Durand and Laurence Raehm

Abstract

Des nanoparticules mesoporeuses de silice (MSN), c'est-a-dire des particules d'un diametre de l'ordre de 60 a 300 nm, possedant une porosite organisee en reseau hexagonal avec des diametres de pores de 1,5 a 10 nm et de grandes surfaces specifiques de l'ordre de 1000 m2.g-1, ont pu etre synthetisees. Elles possedent des proprietes uniques, notamment une grande surface specifique et une distribution etroite de taille de pores. Elles peuvent etre facilement fonctionnalisees et sont biocompatibles, ce qui en font des candidates ideales pour des applications biologiques. Ainsi, des MSN ont ete utilisees pour le marquage cellulaire, en encapsulant dans leurs pores des fluorophores mono ou biphotoniques. Elles trouvent egalement des utilisations en transfection genetique ou comme agents de contraste en IRM. Enfin, les systemes de delivrance controlee de medicaments en sont une des applications les plus prometteuses pour l'amelioration de la sante humaine.

Published
2009

41. Unexpected coordination chemistry of bisphenanthroline complexes within hybrid materials: a mild way to Eu(2+) containing materials with bright yellow luminescence

Author

Laurence Raehm, Catherine Reyé, Ahmad Mehdi, Claudia Wickleder, Robert J. P. Corriu, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Anorganische Chemie, and Universität Siegen [Siegen]

Subjects
chemistry.chemical_classification, Chemistry, Inorganic chemistry, 02 engineering and technology, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Biochemistry, Catalysis, 0104 chemical sciences, Coordination complex, Ion, Colloid and Surface Chemistry, [CHIM.COOR]Chemical Sciences/Coordination chemistry, 0210 nano-technology, Luminescence, Hybrid material
Abstract

International audience; A hybrid organic-inorganic material containing bisphenanthroline units forming tetrahedral cavities was prepared. We show that these cavities not only allow the incorporation of Cu2+ and Eu3+ ions but also induce the reduction of these ions in Cu+ and Eu2+, respectively. The Eu2+ containing material shows an extremely bright yellow luminescence and might be therefore a candidate for future applications.

Published
2007

42. Electrode-deposited films of polyrotaxanes: electrochemically induced gliding motion

Author

B. Divisia-Blohorn, Ge′rard Bidan, Martial Billon, Jean-Pierre Sauvage, Laurence Raehm, and Jean-Marc Kern

Subjects
chemistry.chemical_compound, chemistry, Stereochemistry, Electrode, Polymer chemistry, Materials Chemistry, chemistry.chemical_element, Chelation, General Chemistry, Ring (chemistry), Copper, Catalysis, Pyrrole
Abstract

Using the three-dimensional template effect of copper(I) or copper(II), a macrocycle incorporating two different chelating units was threaded by a coordinating molecular fragment whose two ends bear pyrrole nuclei; after electropolymerization, an electroactive film was obtained that clearly showed pirouetting of the ring induced by reducing the five-coordinate copper(II) complex to copper(I). The motion is driven by the difference in the stereoelectronic preferences of copper(I) and copper(II). The present system allows motions of the monovalent complex only.

Published
1998

43. Disulfide- and thiol-incorporating copper catenanes: synthesis, deposition onto gold, and surface studies

Author

Jean-Philippe Bourgoin, Jean-Pierre Sauvage, Laurence Raehm, Christine Hamann, Jean-Marc Kern, Serge Palacin, Chimie des métaux de transition et catalyse (CMTC), Université Louis Pasteur - Strasbourg I-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie des Surfaces et Interfaces (LCSI), Commissariat à l'énergie atomique et aux énergies alternatives (CEA), and Laboratoire d'Electronique Moléculaire (LEM)

Subjects
Absorption spectroscopy, Stereochemistry, Organic Chemistry, Catenane, chemistry.chemical_element, Infrared spectroscopy, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, Copper, Catalysis, Metal, Crystallography, chemistry, Oxidation state, visual_art, Monolayer, visual_art.visual_art_medium, Molecule
Abstract

Two new copper-complexed [2]catenanes have been prepared, both of which consist of two different interlocking rings. In both cases, one of the rings incorporates a disulfide bridge. The other ring contains either a single chelate (phen=1,10-phenanthroline, a bidentate ligand) or two different chelates (phen and terpy, 2,2',6',2"-terpyridine, a tridentate chelate). Deposition of these two complexes on a gold electrode surface was carried out by standard procedures, leading to reductive cleavage of the S-S bridge. The adsorbed species can be viewed as [2]catenanes for which the gold atoms of the electrode surface are an integral fragment of one of the two rings. They yield clear electrochemical responses, but no motion is observed for the catenane incorporating a phen unit and a terpy fragment in one of the two rings, regardless of the metal oxidation state. This is at odds with the behavior of the parent compound in solution, which undergoes ring-gliding motions upon electrochemical reduction or oxidation of the copper center. Near-field microscopy was used to study the deposited layers (STM and AFM). STM images suggest that the molecules do not tend to order at long range on the surface. Polarization modulation-infrared reflection absorption spectroscopy (PM-IRRAS) led to promising results: the two catenanes deposited are likely to be oriented perpendicular to the gold surface. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2111/2002/f3636_s.pdf or from the author. 1: Infrared spectra of [Cu.2]+ as a powder (black line, transmission IR spectroscopy) and as a SAM on gold (dotted line, PM-IRRAS). (Spectra offset and scaled for clarity; significant peaks marked with an asterisk.) 2: STM image (819x819 nm2) of a monolayer of [Cu.3]+ on Au(111) on mica.

Published
2002

44. Molecular Machines and Motors Based on Transition Metal-Containing Catenanes and Rotaxanes

Author

Jean-Pierre Sauvage and Laurence Raehm

Subjects
Axle, Chemistry, Catenane, Molecular motor, Order (ring theory), Type (model theory), Ring (chemistry), Translation (geometry), Topology, Molecular machine
Abstract

Molecular motors of various kind (linear, rotary) are very common in biology where they play an essential role. However, the number of synthetic molecular ensembles whose dynamic behavior is reminiscent of biological motors is presently very limited. In order for an object to be regarded as a motor, several basic requirements have to be fulfilled. Even without trying to apply a strict thermodynamic definition, the system will have to convert a certain type of energy into another form of energy, while undergoing some kind of continuous motion. Threaded or interlocked rings are ideally suited to the construction of fully artificial molecular motors. If a ring is threaded onto a rod, it can either rotate around the axle or undergo a translation movement. Similarly, in catenanes, a ring can glide at will within another ring. Several examples of such compounds have been elaborated and studied in recent years, using threaded and interlocked molecules either based on acceptor-donor and hydrogen-bonded complexes or on transition metal complexes.

Published
2001

45. Synthesis of Copper(I) catenanes incorporating a disulfide bridge and their deposition on a gold surface

Author

Christine Hamann, Jean-Pierre Sauvage, Jean-Marc Kern, and Laurence Raehm

Subjects
Organic Chemistry, Catenane, Inorganic chemistry, Disulfide bond, chemistry.chemical_element, Biochemistry, Copper, Adsorption, chemistry, Polymer chemistry, Moiety, Gold surface, Physical and Theoretical Chemistry, Deposition (law)
Abstract

The synthesis of two coordinating catenates with the ability to undergo surface-confined chemistry is described. For each catenate, one of the rings includes a 2,9-diphenyl-1,10-phenanthroline unit as a coordinating moiety and a disulfide bridge, which allows adsorption of the catenate onto a gold surface, thus going from a molecular catenate to a [gold-adsorbed] species in which gold atoms are elements of one of the rings.

Published
2000

46. Functionalized mesoporous silica nanoparticles for two-photon photodynamic therapy

Author

Laurence Raehm, Magali Gary-Bobo, Olivier Mongin, Marie Maynadier, Cédric Rouxel, J.-O. Durand, Ilaria Basile, David Brevet, Youssef Mir, Mireille Blanchard-Desce, M. Garcia, and Alain Morère

Subjects
Materials science, Oncology, Two-photon excitation microscopy, medicine.medical_treatment, Biophysics, medicine, Nanoparticle, Pharmacology (medical), Nanotechnology, Photodynamic therapy, Dermatology, Mesoporous silica
Published
2011

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