Synthesis, Photophysical Properties, and Living Cell Imaging of Theranostic Half-Sandwich Iridium-4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) Dyads
| Autor: | Blaise Gatin-Fraudet, Kevin Passador, Damian Plażuk, Claude-Marie Bachelet, Lise-Marie Chamoreau, Serge Thorimbert, Michèle Salmain, Jeremy M. Zimbron, Candice Botuha |
|---|---|
| Přispěvatelé: | Institut Parisien de Chimie Moléculaire (IPCM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut du Cerveau et de la Moëlle Epinière = Brain and Spine Institute (ICM), Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-CHU Pitié-Salpêtrière [AP-HP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU), University of Lódź, Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut National de la Santé et de la Recherche Médicale (INSERM)-CHU Pitié-Salpêtrière [AP-HP], Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Assistance publique - Hôpitaux de Paris (AP-HP) (AP-HP)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), HAL-UPMC, Gestionnaire |
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Fluorescence-lifetime imaging microscopy
010405 organic chemistry Stereochemistry Ligand [CHIM.THER] Chemical Sciences/Medicinal Chemistry Organic Chemistry chemistry.chemical_element [CHIM.THER]Chemical Sciences/Medicinal Chemistry [CHIM.COOR] Chemical Sciences/Coordination chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences Inorganic Chemistry Turn (biochemistry) chemistry.chemical_compound chemistry Lipophilicity Molecule [CHIM.COOR]Chemical Sciences/Coordination chemistry Iridium Physical and Theoretical Chemistry BODIPY Cytotoxicity |
| Zdroj: | Organometallics Organometallics, American Chemical Society, 2017, 36 (18), pp.3435-3442. ⟨10.1021/acs.organomet.7b00250⟩ Organometallics, 2017, 36 (18), pp.3435-3442. ⟨10.1021/acs.organomet.7b00250⟩ |
| ISSN: | 0276-7333 1520-6041 |
| Popis: | International audience; We report the synthesis, characterization, and photophysical properties of two new cyclometalated half-sandwich iridium(III) complexes having the general formula [(η5-Cp*)Ir(ppy)Z]PF6 where η5-Cp* = pentamethylcyclopentadienyl and ppy = 2-phenyl-pyridine as C∧N-chelating ligand and Z = 3- or 4-pyridyl-BODIPY (BODIPY = 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene dye containing a 3- or 4-pyridyl group at the meso position). The molecular structure of both complexes has been determined by X-ray crystallography. The photophysical properties of the dyads were investigated and compared to the pyridyl-BODIPY precursors. Antiproliferative studies demonstrated that one of the compounds was highly active with submicromolar IC50 on a panel of cancer cell lines. The replacement of the chlorido ligand by the pyridyl-BODIPY increased the lipophilicity of the complexes and slowed down the hydrolysis rate, which in turn increased the cytotoxicity of the metallodrug candidate. For the first time, cell uptake of one of the dyads was monitored by living cell fluorescence imaging. Interestingly, extremely fast internalization was observed the rate of which was temperature-dependent. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|