Skip to main content
SpringerLink
Log in

Synthesis and characterization of water-soluble two-photon excited blue fluorescent chromophores for bioimaging

  • Paper
  • Published:
Photochemical & Photobiological Sciences Aims and scope Submit manuscript

Abstract

We report here the synthesis and characterization of a new type of non-ionic blue fluorescent water-soluble chromophores specifically designed for two-photon absorption microscopy. The water solubility is induced by introduction of short oligo(ethylene glycol) monomethyl ether moieties. This work has led to low molecular weight dyes with efficient two-photon absorption cross sections and high fluorescence quantum yield in organic solvents as well as in aqueous solutions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Y. Morel, A. Irimia, P. Najechalski, Y. Kervella, O. Stephan, P. L. Baldeck and C. Andraud, Two-photon absorption and optical power limiting of bifluorene molecule, J. Chem. Phys., 2001, 114, 5391–5396.

    Article  CAS  Google Scholar 

  2. J. E. Ehrlich, X. L. Wu, I. Y. S. Lee, Z. Y. Hu, H. Rockel, S. R. Marder and J. W. Perry, Two-photon absorption and broadband optical limiting with bis-donor stilbenes, Opt. Lett., 1997, 22, 1843–1845.

    Article  CAS  Google Scholar 

  3. S. Kawata, H. B. Sun, T. Tanaka and K. Takada, Finer features for functional microdevices - Micromachines can be created with higher resolution using two-photon absorption, Nature, 2001, 412, 697–698.

    Article  CAS  Google Scholar 

  4. K. D. Belfield, K. J. Schafer, Y. U. Liu, J. Liu, X. B. Ren and E. W. Van Stryland, Multiphoton-absorbing organic materials for microfabrication, emerging optical applications and non-destructive three-dimensional imaging, J. Phys. Org. Chem., 2000, 13, 837–849.

    Article  CAS  Google Scholar 

  5. J. Liu, Y. W. Zhao, J. Q. Zhao, A. D. Xia, L. J. Jiang, S. Wu, L. Ma, Y. Q. Dong and Y. H. Gu, Two-photon excitation studies of hypocrellins for photodynamic therapy, J. Photochem. Photobiol. B, 2002, 68, 156–164.

    Article  CAS  Google Scholar 

  6. F. Q. Meng, E. Nickel, M. Drobizhev, M. Kruk, A. Karotki, Y. Dzenis, A. Rebane and C. W. Spanger, Porphyrins with greatly enhanced two-photon absorption for photodynamic therapy, Abstr. Pap. Am. Chem. Soc., 2003, 226, U503–U504.

    Google Scholar 

  7. J. D. Bhawalkar, A. Shih, S. J. Pan, W. S. Liou, J. Swiatkiewicz, B. A. Reinhardt, P. N. Prasad and P. C. Cheng, two-photon laser scanning fluorescence microscopy from a fluorophore and specimen perspective, Bioimaging, 1996, 4, 168–178.

    Article  CAS  Google Scholar 

  8. W. R. Zipfel, R. M. Williams and W. W. Webb, Nonlinear magic: multiphoton microscopy in the biosciences, Nat. Biotechnol., 2003, 21, 1368–1376.

    Article  Google Scholar 

  9. C. Xu and W. W. Webb, Measurement of two-photon excitation cross sections of molecular fluorophores with data from 960 to 1050 nm, J. Opt. Soc. Am. B, 1996, 13, 481–491.

    Article  CAS  Google Scholar 

  10. M. Rumi, J. E. Ehrich, A. A. Heikal, J. W. Perry, S. Barlow, Z. Hu, D. McCord-Maughon, T. C. Parker, H. Röckel, S. Thayumananvan, S. R. Marder, D. Beljonne and J.-L. Brédas, Structure-property relationships for two-photon absorbing chromophores: Bis-donor diphenylpolyene and bis(styryl)benzene derivatives, J. Am. Chem. Soc., 2000, 122, 9500–9510.

    Article  CAS  Google Scholar 

  11. Y. Morel, PhD Thesis, Grenoble, 2001.

  12. F. Lincker, P. Masson, J.-F. Nicoud, P. Didier, L. Guidoni and J.-Y. Bigot, Synthesis and characterization of efficient two-photon absorption chromophores with increased dimensionality, J. Nonlinear Opt. Phys. Mater., 2005, in press.

    Google Scholar 

  13. G. A. Crosby and J. N. Demas, Measurement of photoluminescence quantum yields, J. Phys. Chem., 1971, 75, 991–1024.

    Article  CAS  Google Scholar 

  14. C. Lottner, K. C. Bart, G. Bernhardt and H. Brunner, Soluble tetraarylporphyrin-platinum conjugates as cytotoxic and phototoxic antitumor agents, J. Med. Chem., 2002, 45, 2079–2089.

    Article  CAS  Google Scholar 

  15. P. Pengo, S. Polizzi, M. Battagliarin, L. Pasquato and P. Scrimin, Synthesis, characterization and properties of water-soluble gold nanoparticles with tunable core size, J. Mater. Chem., 2003, 13, 2471–2478.

    Article  CAS  Google Scholar 

  16. A. Simeonov, M. Matsushita, E. A. Juban, E. H. Thompson, T. Z. Hoffman, A. E. t. Beuscher, M. J. Taylor, P. Wirsching, W. Rettig, J. K. McCusker, R. C. Stevens, D. P. Millar;, P. G. Schultz, R. A. Lerner and K. D. Janda, Blue-fluorescent antibodies, Science, 2000, 290, 307–313.

    Article  CAS  Google Scholar 

  17. S. Zalipsky, Functionalized poly(ethylene glycols) for preparation of biologically relevant conjugates, Bioconjugate Chem., 1995, 6, 150–165.

    Article  CAS  Google Scholar 

  18. R. B. Greenwald, J. Yang;, H. Zhao, C. D. Conover, S. Lee and D. Filpula, Controlled release of proteins from their poly(ethylene glycol) conjugates: Drug delivery systems employing 1,6-elimination, Bioconjugate Chem., 2003, 14, 395–403.

    Article  CAS  Google Scholar 

  19. A. Margineanu, J. Hofkens, M. Cotlet, S. Habuchi, A. Stefan, J. Q. Qu, C. Kohl, K. Mullen, J. Vercammen, Y. Engelborghs, T. Gensch and F. C. De Schryver, Photophysics of a water-soluble rylene dye: Comparison with other fluorescent molecules for biological applications, J. Phys. Chem. B, 2004, 108, 12242–12251.

    Article  CAS  Google Scholar 

  20. M. W. P. L. Baars, R. Kleppinger, M. H. J. Koch, S. L. Yeu and E. W. Meijer, The localization of guests in water-soluble oligoethyleneoxy-modified poly(propylene imine) dendrimers, Angew. Chem., Int. Ed., 2000, 39, 1285–1288.

    Article  CAS  Google Scholar 

  21. P. Jonkheijm, M. Fransen, A. P. H. J. Schenning and E. W. Meijer, Supramolecular organisation of oligo(p-phenylenevinylene) at the air-water interface and in water, J. Chem. Soc., Perkin Trans. 2, 2001, 1280–1286.

    Google Scholar 

  22. J. Gruber and R. W. C. Li, Electrochemical synthesis of poly(4,4′-biphenylene ethylene)s, Eur. Polym. J., 2000, 36, 923–928.

    Article  CAS  Google Scholar 

  23. M. J. Plater and T. Jackson, Polyaromatic amines. Part 3: Synthesis of poly(diarylamino)styrenes and related compounds, Tetrahedron, 2003, 59, 4673–4685.

    Article  CAS  Google Scholar 

  24. J.-K. Lee, R. R. Schrock, D. R. Baignet and R. H. Friend, A new type of blue light emitting electroluminescent polymer, Macromolecules, 1995, 28, 1966–1971.

    Article  CAS  Google Scholar 

  25. M. S. Wong, Z. H. Li, Y. Tao and M. D’Iorio, Synthesis and functional properties of donor-acceptor pi-conjugated oligomers, Chem. Mater., 2003, 15, 1198–1203.

    Article  CAS  Google Scholar 

  26. J. F. Eckert, J.-F. Nicoud, J.-F. Nierengarten, S. G. Liu, L. Echegoyen, F. Barigelletti, N. Armaroli, L. Ouali, V. Krasnikov and G. Hadziioannou, Fullerene-oligophenylenevinylene hybrids: Synthesis, electronic properties, and incorporation in photovoltaic devices, J. Am. Chem. Soc., 2000, 122, 7467–7479.

    Article  CAS  Google Scholar 

  27. A. Avdeef and B. Testa, Physicochemical profiling in drug research: a brief survey of the state-of-the-art of experimental techniques, Cell. Mol. Life Sci., 2002, 59, 1681–1689.

    Article  CAS  Google Scholar 

  28. European Chemical Bureau, Institute for health and consumer recommendations.

  29. B. Testa, V. Pliskaand and H. Van de Waterbeend, Lipophilicity in Drug Design Action and Toxicology, VCH, 1995; vol. 4.

  30. P. Kaatz and D. P. Shelton, Two-photon fluorescence cross-section measurements calibrated with hyper-Rayleigh scattering, J. Opt. Soc. Am. B, 1999, 16, 998–1006.

    Article  CAS  Google Scholar 

  31. D. A. Oulianov, I. V. Tomov, A. S. Dvornikov and P. M. Rentzepis, Observations on the measurement of two-photon absorption cross-section, Opt. Commun., 2001, 191, 235–243.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Groupe des Matériaux Organiques, Institut de Physique et Chimie des Matériaux de Strasbourg, CNRS (UMR 7504), 23 rue du Loess, F-67034, Strasbourg, France

    Ali Hayek, Frédéric Bolze & Jean-François Nicoud

  2. Laboratoire de Spectrométrie Physique, Université Joseph Fourier, CNRS (UMR 5588), BP 87, 38402, Saint Martin d’Hères, France

    Patrice L. Baldeck

  3. Pharmacologie et Physico-chimie des Interactions Cellulaires et Moléculaires, CNRS (UMR 7034), Faculté de Pharmacie, 74, route du Rhin, BP 60024, 67401, Illkirch-Graffenstaden, France

    Yves Mély

Authors
  1. Ali Hayek
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Frédéric Bolze
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jean-François Nicoud
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Patrice L. Baldeck
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yves Mély
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jean-François Nicoud.

Additional information

Electronic supplementary information (ESI) available: Synthesis and characterization of compounds 1-11. See DOI: 10.1039/b509843b

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hayek, A., Bolze, F., Nicoud, JF. et al. Synthesis and characterization of water-soluble two-photon excited blue fluorescent chromophores for bioimaging. Photochem Photobiol Sci 5, 102–106 (2006). https://doi.org/10.1039/b509843b

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/b509843b

Search

Navigation