A Biphenyl Type Two-Photon Fluorescence Probe for Monitoring the Mitochondrial Membrane Potential

Hiroki Moritomo; Kengo Yamada; Yuki Kojima; Yasutaka Suzuki; Seiji Tani; Hazuki Kinoshita; Akira Sasaki; Shintaro Mikuni; Masataka Kinjo; Jun Kawamata

doi:10.1247/csf.14006

A Biphenyl Type Two-Photon Fluorescence Probe for Monitoring the Mitochondrial Membrane Potential

Hiroki Moritomo, Kengo Yamada, Yuki Kojima, Yasutaka Suzuki, Seiji Tani, Hazuki Kinoshita, Akira Sasaki, Shintaro Mikuni, Masataka Kinjo, Jun Kawamata

Author information

Hiroki Moritomo
Graduate School of Medicine, Yamaguchi University
Kengo Yamada
Graduate School of Science and Engineering, Yamaguchi University
Yuki Kojima
Department of Chemistry, Faculty of Science, Yamaguchi University
Yasutaka Suzuki
Graduate School of Medicine, Yamaguchi University
Department of Chemistry, Faculty of Science, Yamaguchi University
Seiji Tani
Graduate School of Science and Engineering, Yamaguchi University
Department of Chemistry, Faculty of Science, Yamaguchi University
Hazuki Kinoshita
Laboratory of Molecular Cell Dynamics, Faculty of Advanced Life Science, Hokkaido University
Akira Sasaki
Laboratory for Nano-Bio Probes, Quantitative Biology Center
Shintaro Mikuni
Laboratory of Molecular Cell Dynamics, Faculty of Advanced Life Science, Hokkaido University
Masataka Kinjo
Laboratory of Molecular Cell Dynamics, Faculty of Advanced Life Science, Hokkaido University
Jun Kawamata
Graduate School of Medicine, Yamaguchi University
Department of Chemistry, Faculty of Science, Yamaguchi University

Keywords: Two-photon fluorescence, fluorescence probe, mitochondrial membrane potential, biphenyl derivative

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2014 Volume 39 Issue 2 Pages 125-133

DOI https://doi.org/10.1247/csf.14006

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Abstract

Here we describe the design and synthesis of a bifunctional two-photon fluorescence probe, N,N'-‍dimethyl-4,4'-(biphenyl-2,1-ethenediyl)dipyridinium hexafluorophosphate (BP6). HeLa, Hek293, and Paramecium caudatum cells were stained with BP6. BP6 accumulated on the mitochondria of all three cell types when the mitochondrial membrane potential was high. As the mitochondrial membrane potential decreased following the addition of carbonyl cyanide m-chlorophenyl hydrazine, BP6 moved from the mitochondria to the nucleus in a reversible manner, depending on the mitochondrial membrane potential status. The maximum value of the two-photon absorption cross-section of BP6 is 250 GM (1 GM=1×10^–50 cm⁴ s molecules^–1 photon^–1). This value is 3 and 30 times larger, respectively, than that of the conventional mitochondria selective probes, rhodamine 123 and green fluorescence protein. These results suggest that BP6 should be useful for monitoring mitochondrial membrane potential by two-photon excitation.

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