Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Organic Photonics and Photovoltaics

Editor-in-Chief: Facchetti, Antonio

Ed. by Ponomarenko, Sergei

1 Issue per year


Emerging Science

Open Access
Online
ISSN
2299-3177
See all formats and pricing
More options …

Bis-pyridinium quadrupolar derivatives. High Stokes shift selective probes for bio-imaging

Patrizio Salice
  • Department of Materials Science and INSTM, University of Milano-Bicocca, Via Cozzi 53, I-20125,Milano, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Silvia Versari / Silvia Bradamante / Francesco Meinardi
  • Department of Materials Science and INSTM, University of Milano-Bicocca, Via Cozzi 53, I-20125,Milano, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Giorgio Macchi
  • Department of Materials Science and INSTM, University of Milano-Bicocca, Via Cozzi 53, I-20125,Milano, Italy
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Giorgio A. Pagani / Luca Beverina
Published Online: 2013-11-05 | DOI: https://doi.org/10.2478/oph-2013-0005

Abstract

We describe the design, synthesis and characterization of five high Stokes shift quadrupolar heteroaryl compounds suitable as fluorescent probes in bio-imaging. In particular, we characterize the photophysical properties and the intracellular localization in Human Umbilical Vein Endothelial Cells (HUVEC) and Human Mesenchymal Stem Cells (HMSCs) for each dye. We show that, amongst all of the investigated derivatives, the 2,5-bis[1-(4-N-methylpyridinium)ethen-2-yl)]- N-methylpyrrole salt is the best candidates as selective mitochondrial tracker. Finally, we recorded the full emission spectrum of the most performing - exclusively mitochondrial selective - fluorescent probe directly from HUVEC stained cells. The emission spectrum collected from the stained mitochondria shows a remarkably more pronounced vibronic structure with respect to the emission of the free fluorophore in solution.

Keywords: fluorescent probes; imaging; mitochondria; heterocycles; high Stokes Shift

  • [1] J. Zhang, R. E. Campbell, A. Y. Ting, R. Y. Tsien, Nat Rev Mol Cell Biol, 3, 906-918 (2002) Google Scholar

  • [2] H. M. Kim, B. R. Cho, Accounts Chem. Res., 42, 863- 872 (2009) Google Scholar

  • [3] E. W. Miller, S. X. Bian, C. J. Chang, J. Am. Chem. Soc., 129, 3458-3459 (2007) Google Scholar

  • [4] A. P. Demchenko, Y. Mély, G. Duportail, A. S. Klymchenko, Biophys J., 96, 3461-3470 (2009) Google Scholar

  • [5] P. J. Santangelo, B. Nix, A. Tsourkas, G. Bao, Nucl. Acids Res., 32, e57 (2004) Google Scholar

  • [6] J. A. N. Fisher et al., J. Neurophysiol., 99, 1545-1553 (2008) Google Scholar

  • [7] W. He, H. Wang, L. C. Hartmann, J.-X. Cheng, P. S. Low, P. Natl. Acad. Sci., 104, 11760-11765 (2007) Google Scholar

  • [8] R. Tsien, Annu. Rev. Biochem., 67, 509-544 (1998) Google Scholar

  • [9] M. Heilemann, S. van de Linde, M. Schüttpelz, R. Kasper, B. Seefeldt, A. Mukherjee, P. Tinnefeld, M. Sauer, Angew. Chem. Int. Ed, 47, 6172-6176 (2008) Google Scholar

  • [10] S. Trapp, R. Horobin, Eur. Biophys. J., 34, 959-966 (2005) Google Scholar

  • [11] R. Horobin, S. Trapp, V. Weissig, J. Control. Release, 121, 125-136 (2007) and ref. therein. Google Scholar

  • [12] A. Leo, C. Hansch, D. Elkins, Chem. Rev., 71, 525-616 (1971) Google Scholar

  • [13] S. Versari, A. M. Villa, A. Villa, S. M. Doglia, G. A. Pagani, S. Bradamante, J. Biomed. Opt., 11, 034014- 4 (2006) Google Scholar

  • [14] A. Abbotto, L. Beverina, R. Bozio, A. Facchetti, C. Ferrante, G. Pagani, D. Pedron, R. Signorini, Org. Lett, 4, 1495-1498 (2002) Google Scholar

  • [15] V. Lebret et al., Chem. Mater., 20, 2174-2183 (2008) Google Scholar

  • [16] Y. Suzuki, Y. Tenma, Y. Nishioka, K. Kamada, K. Ohta, J. Kawamata, J. Phys. Chem. C, 115, 20653-20661 (2011) Google Scholar

  • [17] X. Liu et al. Org. Biomol. Chem., 9, 3615 (2011) Google Scholar

  • [18] A. Baran, A. Plotniece, A. Sobolev, B. Vigante, M. Gosteva, V. Olkhovik, Chem. Heterocyc. Compd., 48, 287-295 (2012) Google Scholar

  • [19] A. Abbotto, L. Beverina, G. A. Pagani, M. Collini, G. Chirico, L. D’Alfonso, G. Baldini, SPIE Proc., 5139, 223-230 (2003) Google Scholar

  • [20] X. J. F. Po et al., Org. Lett., 12, 2194-2197 (2010) Google Scholar

  • [21] J. R. Lakowicz, Principles of fluorescence spectroscopy, 3nd ed., (2008)Google Scholar

About the article


Received: 2013-06-15

Accepted: 2013-07-17

Published Online: 2013-11-05


Citation Information: Organic Photonics and Photovoltaics, ISSN (Online) 2299-3177, DOI: https://doi.org/10.2478/oph-2013-0005.

Export Citation

©2013 Versita Sp. z o.o.. This content is open access.

Comments (0)

Please log in or register to comment.
Log in