title: Water-Soluble Triarylborane Chromophores for One- and Two-Photon Excited Fluorescence Imaging of Mitochondria in Cells.
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-Me2 C6 H2 )-2,2'-(C4 H2 S)2 -5'-(3,5-Me2 C6 H2 ) 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.
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Stefanie
authors.initials: S
authors.lastname: Griesbeck
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.|State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, P.R. China.
authors.forename: Zuolun
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Marcus
authors.initials: M
authors.lastname: Gutmann
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Tessa
authors.initials: T
authors.lastname: Lühmann
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.|Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Robert M
authors.initials: RM
authors.lastname: Edkins
authors.affiliation: Institut des Sciences Moléculaires, Univ. Bordeaux, ISM (CNRS UMR5255), Bâtiment A12, 351 cours de la libération, 33405, TALENCE cedex, France.
authors.forename: Guillaume
authors.initials: G
authors.lastname: Clermont
authors.affiliation: Institut des Sciences Moléculaires, Univ. Bordeaux, ISM (CNRS UMR5255), Bâtiment A12, 351 cours de la libération, 33405, TALENCE cedex, France.
authors.forename: Adina N
authors.initials: AN
authors.lastname: Lazar
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Haehnel
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.|School of Medicine, Pharmacy and Health, Durham University, University Boulevard, Stockton-on-Tees, TS17 6BH, UK.
authors.forename: Katharina
authors.initials: K
authors.lastname: Edkins
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany.
authors.forename: Antonius
authors.initials: A
authors.lastname: Eichhorn
authors.affiliation: Institut des Sciences Moléculaires, Univ. Bordeaux, ISM (CNRS UMR5255), Bâtiment A12, 351 cours de la libération, 33405, TALENCE cedex, France. mireille.blanchard-desce@u-bordeaux.fr.
authors.forename: Mireille
authors.initials: M
authors.lastname: Blanchard-Desce
authors.affiliation: Institut für Pharmazie und Lebensmittelchemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany. lorenz.meinel@uni-wuerzburg.de.
authors.forename: Lorenz
authors.initials: L
authors.lastname: Meinel
authors.affiliation: Institut für Anorganische Chemie, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074, Würzburg, Germany. todd.marder@uni-wuerzburg.de.
authors.forename: Todd B
authors.identifier: http://orcid.org/0000-0002-9990-0169
authors.initials: TB
authors.lastname: Marder
mesh_terms: D001880:Boranes / Q000138:chemical synthesis*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D057809:HEK293 Cells; D056945:Hep G2 Cells; D006801:Humans; D008856:Microscopy, Fluorescence; D008928:Mitochondria / Q000378:metabolism*; D057054:Molecular Imaging / Q000379:methods; D015394:Molecular Structure; D061848:Optical Imaging; D012995:Solubility; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000737:chemistry; D014867:Water
chemical_list: D001880:Boranes; D005456:Fluorescent Dyes; D013876:Thiophenes; D014867:Water
keywords: boron; fluorescence; fluorescent probes; imaging agents; nonlinear optics