Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells

Stephanie Griesbeck; Zuolun Zhang; Marcus Gutmann; Tessa Luehmann; Robert M. Edkins; Guillaume Clermont; Adina N. Lazar; Martin Haehnel; Katharina Edkins; Antonius Eichhorn; Mireille Blanchard-Desce; Lorenz Meinel; Todd B. Marder

doi:10.1002/chem.201602639

Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells

Stephanie Griesbeck
, Zuolun Zhang
, Marcus Gutmann
, Tessa Luehmann
, Robert M. Edkins
, Guillaume Clermont
, Adina N. Lazar
, Martin Haehnel
, Katharina Edkins
, Antonius Eichhorn
, Mireille Blanchard-Desce
, Lorenz Meinel
, Todd B. Marder

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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.

Original language	English
Pages (from-to)	14701-14706
Number of pages	6
Journal	Chemistry - A European Journal
Volume	22
Issue number	41
Early online date	15 Sept 2016
DOIs	https://doi.org/10.1002/chem.201602639
Publication status	Published - 04 Oct 2016

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Water-Soluble Triarylborane Chromophores for One- and TwoPhoton Excited Fluorescence Imaging of Mitochondria in Cells
Copyright 2016 Wiley-VCH Verlag GmbH &Co. KGaA. This work is made available online in accordance with the publisher’s policies. Please refer to any applicable terms of use of the publisher.
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Griesbeck, S., Zhang, Z., Gutmann, M., Luehmann, T., Edkins, R. M., Clermont, G., Lazar, A. N., Haehnel, M., Edkins, K., Eichhorn, A., Blanchard-Desce, M., Meinel, L., & Marder, T. B. (2016). Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells. Chemistry - A European Journal, 22(41), 14701-14706. https://doi.org/10.1002/chem.201602639

@article{350872fb72d64ae1b082826c94777faa,

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-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.",

author = "Stephanie Griesbeck and Zuolun Zhang and Marcus Gutmann and Tessa Luehmann and Edkins, \{Robert M.\} and Guillaume Clermont and Lazar, \{Adina N.\} and Martin Haehnel and Katharina Edkins and Antonius Eichhorn and Mireille Blanchard-Desce and Lorenz Meinel and Marder, \{Todd B.\}",

year = "2016",

month = oct,

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doi = "10.1002/chem.201602639",

language = "English",

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pages = "14701--14706",

journal = "Chemistry - A European Journal",

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Griesbeck, S, Zhang, Z, Gutmann, M, Luehmann, T, Edkins, RM, Clermont, G, Lazar, AN, Haehnel, M, Edkins, K, Eichhorn, A, Blanchard-Desce, M, Meinel, L & Marder, TB 2016, 'Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells', Chemistry - A European Journal, vol. 22, no. 41, pp. 14701-14706. https://doi.org/10.1002/chem.201602639

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T1 - Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells

AU - Griesbeck, Stephanie

AU - Zhang, Zuolun

AU - Gutmann, Marcus

AU - Luehmann, Tessa

AU - Edkins, Robert M.

AU - Clermont, Guillaume

AU - Lazar, Adina N.

AU - Haehnel, Martin

AU - Edkins, Katharina

AU - Eichhorn, Antonius

AU - Blanchard-Desce, Mireille

AU - Meinel, Lorenz

AU - Marder, Todd B.

PY - 2016/10/4

Y1 - 2016/10/4

N2 - 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.

AB - 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.

U2 - 10.1002/chem.201602639

DO - 10.1002/chem.201602639

M3 - Article

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JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 41

ER -

Water‐Soluble Triarylborane Chromophores for One‐and Two‐Photon Excited Fluorescence Imaging of Mitochondria in Cells

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