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	1 Oct 2016
DOIs	https://doi.org/10.1002/chem.201602639
Publication status	Published - 4 Oct 2016

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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

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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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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

TY - JOUR

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

SN - 0947-6539

VL - 22

SP - 14701

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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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