Skip to main content

Advertisement

Log in

Energy-transfer-based wavelength-shifting DNA probes with “clickable” cyanine dyes

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

Abstract

The insertion of cyanine dye azides as energy donor dyes via postsynthetic “click”-type cycloaddition chemistry with e.g. a new thiazole orange azide combined with thiazole red yields dual emitting DNA probes with good fluorescence readout properties.

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

Access this article

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

Instant access to the full article PDF.

Notes and references

  1. A. A. Marti, S. Jockusch, N. Stevens, J. Ju, N. J. Turro, iAcc. Chem. Res., 2007, 40, 402–409

    Article  CAS  Google Scholar 

  2. K. Wang, Z. Tang, J. Y. Chaoyong, Y. Kim, X. Fang, W. Li, Y. Wu, C. D. Medley, Z. Cao, J. Li, P. Colon, H. Lin, W. Tan, iAngew. Chem., Int. Ed., 2009, 48, 856–870

    Article  CAS  Google Scholar 

  3. J. Stambasky, M. Hocek, P. Kocovsky, iChem. Rev., 2009, 109, 6729–6764

    CAS  Google Scholar 

  4. V. L. Malinowski, D. Wenger, R. Häner, iChem. Soc. Rev., 2010, 39, 410–422

    Article  Google Scholar 

  5. R. W. Sinkeldam, N. J. Greco, Y. Tor, iChem. Rev., 2010, 110, 2579–2619

    Article  CAS  Google Scholar 

  6. F. Wojciechowski, C. J. Leumann, iChem. Soc. Rev., 2011, 40, 5669–5679

    Article  CAS  Google Scholar 

  7. Y. N. Teo, E. T. Kool, iChem. Rev., 2012, 112, 4221–4245.

    Article  CAS  Google Scholar 

  8. S. Preis, L. M. Wilhelmsson, iChemBioChem, 2012, 13, 1990–2001.

    Article  Google Scholar 

  9. F. Hövelmann, L. Bethge, O. Seitz, iChemBioChem, 2012, 13, 2072–2081.

    Article  Google Scholar 

  10. H. Kobayashi, M. Ogawa, R. Alford, P. L. Choydke, Y. Urano, iChem. Rev., 2010, 110, 2620–2640

    Article  CAS  Google Scholar 

  11. M. Y. Berezin, S. Achilefu, iChem. Rev., 2010, 110, 2641–2684.

    Article  CAS  Google Scholar 

  12. G. Patterson, M. Davidson, S. Manley, J. Lippincott-Schwartz, iAnnu. Rev. Phys. Chem., 2010, 61, 345–367.

    Article  CAS  Google Scholar 

  13. A. Okamoto, iChem. Soc. Rev., 2011, 40, 5815–5828.

    Article  CAS  Google Scholar 

  14. C. Holzhauser, H.-A. Wagenknecht, iAngew. Chem., Int. Ed., 2011, 50, 7268–7272

    Article  CAS  Google Scholar 

  15. C. Holzhauser, H.-A. Wagenknecht, iChemBioChem, 2012, 13, 1136–1138.

    Article  CAS  Google Scholar 

  16. C. Holzhauser, S. Berndl, F. Menacher, M. Breunig, A. Göpferich, H.-A. Wagenknecht, iEur. J. Org. Chem., 2010, 1239–1248.

    Google Scholar 

  17. R. Huisgen, iAngew. Chem., Int. Ed. Engl, 1962, 2, 565–598

    Article  Google Scholar 

  18. Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, iJ. Am. Chem. Soc., 2003, 125, 3192–3193

    Article  CAS  Google Scholar 

  19. M. Meldal, C. W. Tornoe, iChem. Rev., 2008, 108, 2952–3015.

    Article  CAS  Google Scholar 

  20. P. M. Gramlich, C. T. Wirges, A. Manetto, T. Carell, iAngew. Chem., Int. Ed., 2008, 47, 8350–8358

    Article  CAS  Google Scholar 

  21. M. Grotli, M. Douglas, R. Eritja, B. S. Sproat, iTetrahedron, 1998, 54, 5899–5914

    Article  CAS  Google Scholar 

  22. A. H. El-Sagheer, T. Brown, iChem. Soc. Rev., 2010, 39, 1388–1405.

    Article  Google Scholar 

  23. S. Berndl, N. Herzig, P. Kele, D. Lachmann, X. Li, O. S. Wolfbeis, H.-A. Wagenknecht, iBioconjugate Chem., 2009, 20, 558–564.

    Article  CAS  Google Scholar 

  24. M. M. Rubner, C. Holzhauser, P. R. Bohländer, H.-A. Wagenknecht, iChem.–Eur. J., 2012, 18, 1299–1302.

    Article  CAS  Google Scholar 

  25. T. Ehrenschwender, B. R. Varga, P. Kele, H.-A. Wagenknecht, iChem.–Asian J., 2010, 5, 1761–1764.

    Article  CAS  Google Scholar 

  26. A. L. Stadler, J. O. D. Santos, E. S. Stensrud, A. Dembska, G. L. Silva, S. Liu, N. I. Shank, E. Kunttas-Tatli, C. J. Sobers, P. M. E. Gramlich, T. Carell, L. A. Peteanu, B. M. McCartney, B. A. Armitage, iBioconjugate Chem., 2011, 22, 1491–1502.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hans-Achim Wagenknecht.

Additional information

Electronic supplementary information (ESI) available: Synthetic procedures for the TO azide and postsynthetic modifications, images of NMR and MS analyses

Rights and permissions

Reprints and permissions

About this article

Cite this article

Holzhauser, C., Rubner, M.M. & Wagenknecht, HA. Energy-transfer-based wavelength-shifting DNA probes with “clickable” cyanine dyes. Photochem Photobiol Sci 12, 722–724 (2013). https://doi.org/10.1039/c2pp25366f

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1039/c2pp25366f

Navigation