Hostname: page-component-848d4c4894-8bljj Total loading time: 0 Render date: 2024-06-19T22:03:58.105Z Has data issue: false hasContentIssue false
  • English
  • Français

Mitochondrion-selective hemicyanine dyes suitable for fiber laser excitation two-photon microscopy

Published online by Cambridge University Press:  03 September 2018

H. Moritomo ,
S. Onishi ,
N. Asamura ,
K. Matsumoto ,
Y. Suzuki  and
J. Kawamata
H. Moritomo
Affiliation:
Department of Integrated Science and Technology, National Institute of Technology Tsuyama College, 624-1 Numa, Tsuyama, Okayama 708-8509, Japan
S. Onishi
Affiliation:
Graduate School of Sciences and Technology for Innovation, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
N. Asamura
Affiliation:
Department of Biology and Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
K. Matsumoto
Affiliation:
Department of Biology and Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
Y. Suzuki
Affiliation:
Graduate School of Sciences and Technology for Innovation, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan Department of Biology and Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
J. Kawamata*
Affiliation:
Graduate School of Sciences and Technology for Innovation, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan Department of Biology and Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan
*
Address all correspondence to J. Kawamata at j_kawa@yamaguchi-u.ac.jp
Get access

Abstract

We investigate the two-photon absorption characteristics of hemicyanine dyes that exhibit a one-photon absorption at around 500 nm. The dyes exhibited two-photon-induced fluorescence upon irradiation with an Yb-doped femtosecond fiber laser operating at 1030 nm. Among the dyes, 4-[4-[4-(dimethylamino)phenyl]-1,3-butadienyl]-1-ethyl-pyridinium perchlorate exhibited the most efficient two-photon-induced fluorescence at 1030 nm. Since these dyes possess cationic moiety, the dyes accumulated in the mitochondria of a living cell. Two-photon images of mitochondria were obtained by staining living HEK293 cells with these dyes. When 4-[4-[4-(dimethylamino)phenyl]-1,3-butadienyl]-1-ethyl-pyridinium perchlorate was employed, a two-photon-induced fluorescence image could be obtained even when a 3 mW fiber laser beam was used as the excitation source.

Type
Research Letters
Information
MRS Communications , Volume 8 , Issue 3 , September 2018 , pp. 1064 - 1069
Check for updates
Copyright
Copyright © Materials Research Society 2018 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

1.Ricaud, S., Jaffres, A., Wentsch, K., Suganuma, A., Viana, B., Loiseau, P., Weichelt, B., Abdou-Ahmed, M., Voss, A., Graf, T., Rytz, D., Hönninger, C., Mottay, E., Georges, P., and Druon, F.: Femtosecond Yb:CaGdAlO4 thin-disk oscillator. Opt. Lett. 37, 3984 (2012).Google Scholar
2.Moritomo, H., Fujii, A., Suzuki, Y., Yoshihara, T., Tobita, S., and Kawamata, J.: Biological oxygen sensing via two-photon absorption by an Ir(III) complex using a femtosecond fiber laser. Jpn. J. Appl. Phys. 55, 092401 (2016).Google Scholar
3.Perillo, E. P., McCracken, J. E., Fernée, D. C., Goldak, J. R., Medina, F. A., Miller, D. R., Yeh, H.-C., and Dunn, A. K.: Deep in vivo two-photon microscopy with a low cost custom built mode-locked 1060 nm fiber laser. Biomed. Opt. Express. 7, 324 (2016).Google Scholar
4.Doan, H., Castillo, M., Bejjani, M., Nurekeyev, Z., Dzyuba, S. V., Gryczynski, I., Gryczynski, Z., and Raut, S.: Solvatochromic dye LDS 798 as microviscosity and pH probe. Phys. Chem. Chem. Phys. 19, 29934 (2017).Google Scholar
5.Moritomo, H., Yamada, K., Kojima, Y., Suzuki, Y., Tani, S., Kinoshita, H., Sasaki, A., Mikuni, S., Kinjo, M., and Kawamata, J.: A biphenyl type two-photon fluorescence probe for monitoring the mitochondrial membrane potential. Cell Struct. Funct. 39, 125 (2014).Google Scholar
6.Niko, Y., Moritomo, H., Sugihara, H., Suzuki, Y., Kawamata, J., and Konishi, G.-I.: A novel pyrene-based two-photon active fluorescent dye efficiently excited and emitting in the “tissue optical window (650–1100 nm)”. J. Mater. Chem. B 3, 184 (2014).Google Scholar
7.Tominaga, M., Mochida, S., Sugihara, H., Satomi, K., Moritomo, H., Fuji, A., Tomoyuki, A., Suzuki, Y., and Kawamata, J.: A red fluorescence two-photon absorption probe for sensitive imaging of live mitochondria. Chem. Lett. 43, 1490 (2014).Google Scholar
8.Li, X., Tian, M., Zhang, G., Zhang, R., Feng, R., Guo, L., Yu, X., Zhao, N., and He, X.: Spatial-dependent fluorescent probe for detecting different situations of mitochondrial membrane potential conveniently and efficiently. Anal. Chem. 89, 3335 (2017).Google Scholar
9.Zhang, G., Sun, Y., He, X., Zhang, W., Tian, M., Feng, R., Zhang, R., Li, X., Guo, L., Yu, X., and Zhang, S.: Red-emitting mitochondrial probe with ultrahigh signal-to-noise ratio enables high-fidelity fluorescent images in two-photon microscopy. Anal. Chem. 87, 12088 (2015).Google Scholar
10.Xu, C. and Webb, W. W.: Measurement of two-photon excitation cross sections of molecular fluorophores with data from 690 to 1050 nm. J. Opt. Soc. Am. B 13, 481 (1996).Google Scholar
11.Makarov, N. S., Campo, J., Hales, J. M., and Perry, J. W.: Rapid, broadband two-photon-excited fluorescence spectroscopy and its application to red-emitting secondary reference compounds. Opt. Mater. Express. 1, 551 (2011).Google Scholar
12.Eisenthal, K. B.: Intermolecular and intramolecular excited state charge transfer. Laser Chem. 3, 145 (1983).Google Scholar
13.Dickey, J. B., Towne, E. B., Bloom, M. S., Moore, W. H., Smith, B. H. Jr., and Hedberg, D. G.: Azo dyes from substituted 2-aminothiophens. J. Soc. Dyers Colour 74, 123 (2008).Google Scholar
14.Peticolas, W. L.: Multiphoton spectroscopy. Annu. Rev. Phys. Chem. 18, 233 (1967).Google Scholar
15.Rumi, M., Ehrlich, J. E., Heikal, A. A., Perry, J. W., Barlow, S., Hu, Z., McCord-Maughon, D., Parker, T. C., Röckel, H., Thayumanavan, S., Marder, S. R., Beljonne, D., and Brédas, J.-L.: Structure–property relationships for two-photon absorbing chromophores: bis-donor diphenylpolyene and bis(styryl)benzene derivatives. J. Am. Chem. Soc. 122, 9500 (2000).Google Scholar
16.Ohta, K., Antonov, L., Yamada, S., and Kamada, K.: Theoretical study of the two-photon absorption properties of several asymmetrically substituted stilbenoid molecules. J. Chem. Phys. 127, 084504 (2007).Google Scholar
17.Hirakawa, S., Kawamata, J., Suzuki, Y., Tani, S., Murafuji, T., Kasatani, K., Kamada, K., Ohta, K., and Antonov, L.: Two-photon absorption properties of azulenyl compounds having a conjugated ketone backbone. J. Phys. Chem. A 112, 5198 (2008).Google Scholar
18.Moritomo, H., Nakagawa, K., Sugihara, H., Suzuki, Y., and Kawamata, J.: Two-photon absorption (TPA) spectra of tris(4,7-diphenyl-1,10-phenanthroline)metal(II) perchlorate: drastic effects of central metal(II) ions on TPA cross section. Chem. Lett. 43, 441 (2014).Google Scholar
19.Onishi, S., Asamura, N., Seki, H., Niko, Y., Tani, S., Kawamata, J., and Suzuki, Y.: Mitochondrial Membrane Potential Sensitive Red-Green-Blue Fluorescent Probes for Multi-Photon Microscope, presented at the 2018 MRS SPRING MEETING EXHIBIT. RP03.01.04, 3 Aip. 2018. to be published elsewhere soon.Google Scholar
20.Icha, J., Weber, M., Waters, J. C., and Norden, C.: Phototoxicity in live fluorescence microscopy, and how to avoid it. BioEssays 39, 1700003 (2017).Google Scholar
21.Weissleder, R.: A clearer vision for in vivo imaging. Nat. Biotechnol. 19, 316 (2001).Google Scholar
Supplementary material: File

Moritomo et al. supplementary material

Figure S1

Download Moritomo et al. supplementary material(File)
File 258.5 KB