title: A biphenyl type two-photon fluorescence probe for monitoring the mitochondrial membrane potential.
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) cm(4) 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.
authors.affiliation: Graduate School of Medicine, Yamaguchi University.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moritomo
authors.forename: Kengo
authors.initials: K
authors.lastname: Yamada
authors.forename: Yuki
authors.initials: Y
authors.lastname: Kojima
authors.forename: Yasutaka
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Seiji
authors.initials: S
authors.lastname: Tani
authors.forename: Hazuki
authors.initials: H
authors.lastname: Kinoshita
authors.forename: Akira
authors.initials: A
authors.lastname: Sasaki
authors.forename: Shintaro
authors.initials: S
authors.lastname: Mikuni
authors.forename: Masataka
authors.initials: M
authors.lastname: Kinjo
authors.forename: Jun
authors.initials: J
authors.lastname: Kawamata
mesh_terms: D001713:Biphenyl Compounds / Q000737:chemistry* / Q000378:metabolism; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D057809:HEK293 Cells; D006367:HeLa Cells; D006801:Humans; D053078:Membrane Potential, Mitochondrial; D008856:Microscopy, Fluorescence; D048488:Paramecium caudatum / Q000166:cytology; D017785:Photons; D011726:Pyridinium Compounds / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013194:Staining and Labeling
chemical_list: D001713:Biphenyl Compounds; D005456:Fluorescent Dyes; C000596169:N,N'-dimethyl-4,4'-(biphenyl-2,1-ethenediyl)dipyridinium; D011726:Pyridinium Compounds