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

Stefanie  Griesbeck; Evripidis Michail; Florian Rauch; Hiroaki Ogasawara; Chenguang Wang; Yoshikatsu Sato; Robert Edkins; Zuolun Zhang; Masayasu Taki; Christoph Lambert; Shigehiro Yamaguchi; Todd B. Marder

doi:10.1002/chem.201902461

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

Stefanie Griesbeck, Evripidis Michail, Florian Rauch, Hiroaki Ogasawara, Chenguang Wang, Yoshikatsu Sato, Robert Edkins, Zuolun Zhang, Masayasu Taki, Christoph Lambert, Shigehiro Yamaguchi, Todd B. Marder

Pure And Applied Chemistry

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Abstract

Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and non-linear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.

Original language	English
Pages (from-to)	13164-13175
Number of pages	12
Journal	Chemistry - A European Journal
Volume	25
Issue number	57
Early online date	19 Jul 2019
DOIs	https://doi.org/10.1002/chem.201902461
Publication status	Published - 11 Oct 2019

Keywords

borane
fluorescence
two-photon excited fluorescence
cell imaging
lysosome

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10.1002/chem.201902461Licence: CC BY 4.0

Griesbeck-etal-CEJ-2019-The-effect-of-branching-on-the-one-and-two-photon-absorption-cell-viability-and-localizationFinal published version, 1.71 MBLicence: CC BY 4.0

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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. (2019). 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. Chemistry - A European Journal, 25(57), 13164-13175. https://doi.org/10.1002/chem.201902461

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title = "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",

abstract = "Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and non-linear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.",

keywords = "borane, fluorescence, two-photon excited fluorescence, cell imaging, lysosome",

author = "Stefanie Griesbeck and Evripidis Michail and Florian Rauch and Hiroaki Ogasawara and Chenguang Wang and Yoshikatsu Sato and Robert Edkins and Zuolun Zhang and Masayasu Taki and Christoph Lambert and Shigehiro Yamaguchi and Marder, {Todd B.}",

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doi = "10.1002/chem.201902461",

language = "English",

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journal = "Chemistry - A European Journal",

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Griesbeck, S, Michail, E, Rauch, F, Ogasawara, H, Wang, C, Sato, Y, Edkins, R, Zhang, Z, Taki, M, Lambert, C, Yamaguchi, S & Marder, TB 2019, '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', Chemistry - A European Journal, vol. 25, no. 57, pp. 13164-13175. https://doi.org/10.1002/chem.201902461

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, Stefanie; Michail, Evripidis; Rauch, Florian et al.
In: Chemistry - A European Journal, Vol. 25, No. 57, 11.10.2019, p. 13164-13175.

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

TY - JOUR

T1 - 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

AU - Griesbeck, Stefanie

AU - Michail, Evripidis

AU - Rauch, Florian

AU - Ogasawara, Hiroaki

AU - Wang, Chenguang

AU - Sato, Yoshikatsu

AU - Edkins, Robert

AU - Zhang, Zuolun

AU - Taki, Masayasu

AU - Lambert, Christoph

AU - Yamaguchi, Shigehiro

AU - Marder, Todd B.

PY - 2019/10/11

Y1 - 2019/10/11

N2 - Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and non-linear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.

AB - Two different chromophores, namely a dipolar and an octupolar system, were prepared and their linear and non-linear optical properties as well as their bioimaging capabilities were compared. Both contain triphenylamine as the donor and a triarylborane as the acceptor, the latter modified with cationic trimethylammonio groups to provide solubility in aqueous media. The octupolar system exhibits a much higher two-photon brightness, and also better cell viability and enhanced selectivity for lysosomes compared with the dipolar chromophore. Furthermore, both dyes were applied in two-photon excited fluorescence (TPEF) live-cell imaging.

KW - borane

KW - fluorescence

KW - two-photon excited fluorescence

KW - cell imaging

KW - lysosome

UR - https://onlinelibrary.wiley.com/journal/15213765

U2 - 10.1002/chem.201902461

DO - 10.1002/chem.201902461

M3 - Article

SN - 0947-6539

VL - 25

SP - 13164

EP - 13175

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 57

ER -

Griesbeck S, Michail E, Rauch F, Ogasawara H, Wang C, Sato Y et al. 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. Chemistry - A European Journal. 2019 Oct 11;25(57):13164-13175. Epub 2019 Jul 19. doi: 10.1002/chem.201902461

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

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