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Water‐Soluble Triarylborane Chromophores for One‐ and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells
Authors:Stefanie Griesbeck  Dr. Zuolun Zhang  Marcus Gutmann  Dr. Tessa Lühmann  Dr. Robert M. Edkins  Guillaume Clermont  Dr. Adina N. Lazar  Dr. Martin Haehnel  Dr. Katharina Edkins  Antonius Eichhorn  Dr. Mireille Blanchard‐Desce  Prof. Dr. Lorenz Meinel  Prof. Dr. Todd B. Marder
Affiliation:1. Institut für Anorganische Chemie, Julius-Maximilians-Universit?t Würzburg, Würzburg, Germany;2. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, P.R. China;3. Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universit?t Würzburg, Würzburg, Germany;4. Chemistry Research Laboratory, University of Oxford, Oxford, UK;5. Institut des Sciences Moléculaires, Univ. Bordeaux, ISM (CNRS UMR5255), Batiment A12, 351 cours de la libération, TALENCE cedex, France;6. School of Medicine, Pharmacy and Health, Durham University, University Boulevard, Stockton-on-Tees, UK
Abstract:Three water‐soluble tetracationic quadrupolar chromophores comprising two three‐coordinate boron π‐acceptor groups bridged by thiophene‐containing moieties were synthesised for biological imaging applications. Compound 3 containing the bulkier 5‐(3,5‐Me2C6H2)‐2,2′‐(C4H2S)2‐5′‐(3,5‐Me2C6H2) bridge is stable over a long period of time, exhibits a high fluorescence quantum yield and strong one‐ and two‐photon absorption (TPA), and has a TPA cross section of 268 GM at 800 nm in water. Confocal laser scanning fluorescence microscopy studies in live cells indicated localisation of the chromophore at the mitochondria; moreover, cytotoxicity measurements proved biocompatibility. Thus, chromophore 3 has excellent potential for one‐ and two‐photon‐excited fluorescence imaging of mitochondrial function in cells.
Keywords:boron  fluorescence  fluorescent probes  imaging agents  nonlinear optics
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