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

Pure And Applied Chemistry

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

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

Keywords

boron
fluorescence
fluorescent probes
imaging agents
nonlinear optics

Access to Document

10.1002/chem.201602639

Link to publication in Scopus

48 Citations
1 Article

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
Griesbeck, S., Michail, E., Rauch, F., Ogasawara, H., Wang, C., Sato, Y., Edkins, R., Zhang, Z., Taki, M., Lambert, C., Yamaguchi, S. & Marder, T. B., 11 Oct 2019, In: Chemistry - A European Journal. 25, 57, p. 13164-13175 12 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
24 Citations (Scopus)

7 Downloads (Pure)

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

Griesbeck, Stefanie ; Zhang, Zuolun ; Gutmann, Marcus ; Lühmann, Tessa ; Edkins, Robert M. ; Clermont, Guillaume ; Lazar, Adina N. ; Haehnel, Martin ; Edkins, Katharina ; Eichhorn, Antonius ; Blanchard-Desce, Mireille ; Meinel, Lorenz ; Marder, Todd B. / Water-soluble triarylborane chromophores for one- and two-photon excited fluorescence imaging of mitochondria in cells. In: Chemistry - A European Journal . 2016 ; Vol. 22, No. 41. pp. 14701-14706.

@article{4d7ec697131d406d9dfdba163e6e2760,

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.",

keywords = "boron, fluorescence, fluorescent probes, imaging agents, nonlinear optics",

author = "Stefanie Griesbeck and Zuolun Zhang and Marcus Gutmann and Tessa L{\"u}hmann 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,

day = "4",

doi = "10.1002/chem.201602639",

language = "English",

volume = "22",

pages = "14701--14706",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

number = "41",

}

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

Water-soluble triarylborane chromophores for one- and two-photon excited fluorescence imaging of mitochondria in cells. / Griesbeck, Stefanie; Zhang, Zuolun; Gutmann, Marcus; Lühmann, Tessa; Edkins, Robert M.; Clermont, Guillaume; Lazar, Adina N.; Haehnel, Martin; Edkins, Katharina; Eichhorn, Antonius; Blanchard-Desce, Mireille; Meinel, Lorenz; Marder, Todd B.

In: Chemistry - A European Journal , Vol. 22, No. 41, 04.10.2016, p. 14701-14706.

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

TY - JOUR

T1 - Water-soluble triarylborane chromophores for one- and two-photon excited fluorescence imaging of mitochondria in cells

AU - Griesbeck, Stefanie

AU - Zhang, Zuolun

AU - Gutmann, Marcus

AU - Lühmann, 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.

KW - boron

KW - fluorescence

KW - fluorescent probes

KW - imaging agents

KW - nonlinear optics

UR - http://www.scopus.com/inward/record.url?scp=84987735852&partnerID=8YFLogxK

U2 - 10.1002/chem.201602639

DO - 10.1002/chem.201602639

M3 - Article

C2 - 27627995

AN - SCOPUS:84987735852

VL - 22

SP - 14701

EP - 14706

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 41

ER -

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

Abstract

Keywords

Access to Document

Fingerprint

Research output

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

Cite this