Water-soluble triarylborane chromophores for one- and two-photon excited fluorescence imaging of mitochondria in cells

Stefanie Griesbeck; Zuolun Zhang; Marcus Gutmann; Tessa Lühmann; 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

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

75 Citations (Scopus)

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 - 4 Oct 2016

Funding

T.B.M. is grateful for generous financial support from the Bavarian State Ministry of Science, Research, and the Arts for the Collaborative Research Network ?Solar Technologies go Hybrid?. Z.Z. and R.M.E. thank the Alexander von Humboldt Foundation for Postdoctoral Research Fellowships. R.M.E also thanks The Royal Commission for the Exhibition of 1851 for a research fellowship. M.B.D. is grateful for generous funding from the R?gion Aquitaine (chair of excellence). This study has also been carried out with financial support from the French State, managed by the French National Research Agency (ANR) in the frame of ?the Investments for the future? Programme IdEx Bordeaux - LAPHIA (ANR-10-IDEX-03-02). The two-photon microscopy was carried out at the Bordeaux Imaging Center, a service unit of the CNRS-INSERM and Bordeaux University, a member of the national infrastructure France BioImaging. Financial support by Deutsche Forschungsgemeinschaft (DFG; ME-3820/3-1) is gratefully acknowledged by L.M.

Keywords

boron
fluorescence
fluorescent probes
imaging agents
nonlinear optics

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10.1002/chem.201602639

Cite this

Griesbeck, S., Zhang, Z., Gutmann, M., Lühmann, 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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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.",

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Griesbeck, S, Zhang, Z, Gutmann, M, Lühmann, 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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AU - Zhang, Zuolun

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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.

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Water-soluble triarylborane chromophores for one- and two-photon excited fluorescence imaging of mitochondria in cells

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The effect of branching on the one- and two-photon absorption, cell viability and localization of cationic triarylborane chromophores with dipolar vs. octupolar charge distributions for cellular imaging

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