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1. A Porphyrin Dimer–GdDOTA Conjugate as a Theranostic Agent for One- and Two-Photon Photodynamic Therapy and MRI

Author

Sébastien Jenni, Barbara Ventura, Célia S. Bonnet, Éva Tóth, Angélique Sour, Frédéric Bolze, Valérie Heitz, Agnès Pallier, Julie Schmitt, Institut de Chimie de Strasbourg, Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Conception et application de molécules bioactives (CAMB), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre de biophysique moléculaire (CBM), 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), Istituto per la Sintesi Organica e la Fotoreattività (ISOF-CNR), Consiglio Nazionale delle Ricerche (CNR), Université de Strasbourg (UNISTRA), ISOF-CNR, Alma Mater Studiorum Università di Bologna [Bologna] (UNIBO), Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and LEGOUPIL, Laëtitia

Subjects
Porphyrins, [SDV]Life Sciences [q-bio], medicine.medical_treatment, MRI contrast agent, Dimer, Biomedical Engineering, Pharmaceutical Science, Bioengineering, Photodynamic therapy, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Theranostic Nanomedicine, HeLa, chemistry.chemical_compound, Nuclear magnetic resonance, Two-photon excitation microscopy, Heterocyclic Compounds, Theranostic agent, Neoplasms, Organometallic Compounds, medicine, Humans, [CHIM.COOR]Chemical Sciences/Coordination chemistry, ComputingMilieux_MISCELLANEOUS, Pharmacology, Photons, Photosensitizing Agents, Singlet Oxygen, biology, Singlet oxygen, Organic Chemistry, 021001 nanoscience & nanotechnology, biology.organism_classification, Magnetic Resonance Imaging, Porphyrin, 0104 chemical sciences, 3. Good health, [SDV] Life Sciences [q-bio], Photochemotherapy, chemistry, Porphyrin dimer, 0210 nano-technology, Dimerization, MRI, HeLa Cells, Biotechnology, Conjugate
Abstract

International audience; A molecular theranostic agent designed for photodynamic therapy (PDT) treatment in the near-infrared and for imaging tissue tumors with magnetic resonance imaging (MRI) is reported. It consists of a linear pi-conjugated Zn(II) porphyrin dimer linked at each extremity to a GdDOTA-type complex. This agent has shown very promising potential for PDT applications with good singlet oxygen generation in DMSO and high linear absorption in the near- infrared (lambda(max) = 746 nm, epsilon approximate to 10(5) M-1 cm(-1)). Moreover, this molecule has a propensity for two-photon excited PDT with high two-photon cross sections (similar to 8000 GM in 880-930 nm range), which should allow for deeper tumor treatments and higher spatial precision as compared to conventional one-photon PDT. Regarding the MRI contrast agent properties, the molecule has shown superior relaxivity (14.4 mM(-1) s(-1) at 40 MHz, 298 K) in comparison to clinical contrast agents and the ability to be internalized in cells, thanks to its amphiphilic character. Irradiation of HeLa cells using either one-photon (740 nm) or two-photon excitation (910 nm) has led in both cases to important cell death.

Published
2018
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2. Dinuclear Copper(I) Complexes Combining Bis(diphenylphosphanyl)acetylene with 1,10-Phenanthroline Ligands

Author

Michel Holler, Enrico Leoni, Filippo Monti, Alix Sournia-Saquet, Nicola Armaroli, Béatrice Delavaux-Nicot, Jean-François Nierengarten, Iwona Nierengarten, Laboratoire de chimie moléculaire (LCM), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratorio Tecnologie dei Materiali Faenza, ENEA, Agenzia Nazionale per le nuove Tecnologie, l’energia e lo sviluppo economico sostenibile (ENEA), Istituto per la Sintesi Organica e la Fotoreattività (ISOF-CNR), Consiglio Nazionale delle Ricerche (CNR), Institut de Chimie de Toulouse (ICT), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Université de Toulouse (UT)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université de Toulouse (UT)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université de Toulouse (UT)-Centre National de la Recherche Scientifique (CNRS), Agenzia Nazionale per le nuove Tecnologie, l’energia e lo sviluppo economico sostenibile = Italian National Agency for New Technologies, Energy and Sustainable Economic Development (ENEA), National Research Council of Italy | Consiglio Nazionale delle Ricerche (CNR), International Center for Frontier Research in Chemistry, LabEx 'Chimie des Systèmes Complexes', CNR (PHEEL), Nierengarten, J. -F., Nierengarten, I., Holler, M., Sournia-Saquet, A., Delavaux-Nicot, B., Leoni, E., Monti, F., and Armaroli, N.

Subjects
Luminescence, Dinuclear complexes, Phenanthroline, Substituent, chemistry.chemical_element, Phosphanes, 02 engineering and technology, Crystal structure, 010402 general chemistry, 01 natural sciences, Inorganic Chemistry, Neocuproine, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Homoleptic, Copper, 030304 developmental biology, 0303 health sciences, Ligand, Metallacycle, 021001 nanoscience & nanotechnology, 3. Good health, 0104 chemical sciences, Dinuclear complexe, Crystallography, chemistry, 030220 oncology & carcinogenesis, 0210 nano-technology
Abstract

Dinuclear copper(I) complexes have been prepared starting from bis(diphenylphosphanyl)acetylene (dppa), [Cu(CH3CN)(4)](BF4) and various 1,10-phenanthroline ligands (NN), namely 1,10-phenanthroline (phen), neocuproine (dmp), bathophenanthroline (Bphen), bathocuproine (Bdmp) and 2-phenyl-1,10-phenanthroline (mpp). The resulting [Cu-2(mu-dppa)(2)(NN)(2)](BF4)(2) complexes have been thus obtained in excellent yields (88 to 94 %). X-ray crystal structure analysis of four complexes revealed that the 10-membered dimetallacycle adopts a chair-like conformation in the solid state. Detailed variable temperature NMR investigations have evidenced dynamic coordination/decoordination of the NN ligands as well as ligand exchange reactions. At high temperature (100 degrees C), entropic effects tend to destabilize the dinuclear heteroleptic complexes. As a result, homoleptic mononuclear complexes, i.e. [Cu(NN)(2)](+) and undefined dppa copper(I) complexes, start to appear in solution. In contrast, the heteroleptic coordination scenario is almost exclusively favored at lower temperatures. For most of the dinuclear complexes, the 10-membered dimetallacycle remains flexible and chair-to-chair interconversion occurs faster than the NMR timescale even at -70 degrees C. In the particular case of the mpp derivative, the bulky phenyl substituent prevents the isomerization of the metallacycle and thus contributes to rigidify the structure. This rigidification has a dramatic effect on the emission properties of this particular compound. The emission quantum yield of [Cu-2(mu-dppa)(2)(mpp)(2)](BF4)(2) is effectively one order of magnitude higher when compared to all the other complexes in this series (20 % vs. 0.3-1.7 % in the solid state).

Published
2019
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3. Ester-substituted cyclometallated rhodium and iridium coordination assemblies with π-bonded dioxolene ligand: synthesis, structures and luminescent properties

Author

Maria Pia Gullo, Hugo Sesolis, Marie Noelle Rager, Hani Amouri, Andrea Barbieri, Aurélie Damas, Lise Marie Chamoreau, Institut Parisien de Chimie Moléculaire (IPCM), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie du CNRS (INC), Istituto per la Sintesi Organica e la Fotoreattività (ISOF-CNR), Consiglio Nazionale delle Ricerche (CNR), Architectures Moléculaires (A.R.C), Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), National Research Council of Italy | Consiglio Nazionale delle Ricerche (CNR), and Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Chemistry, Ligand, General Chemical Engineering, Supramolecular chemistry, Stacking, chemistry.chemical_element, General Chemistry, Photochemistry, 3. Good health, Rhodium, Excited state, Polymer chemistry, [CHIM]Chemical Sciences, Iridium, Luminescence, ComputingMilieux_MISCELLANEOUS
Abstract

A series of functionalized cyclometallated rhodium and iridium coordination assemblies 2-7 displaying a pi-bonded dioxolene ligand is described. The X-ray molecular structures of two of the above compounds showed the formation of a 1D supramolecular chain mediated by pi-pi interactions among individual units. The luminescent properties of these compounds are presented and discussed. These results show that the stacking interactions are retained also in solution and emission from excited dimeric species is observed.

Published
2014
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