Ternary rhenium (i) complexes: from fluorescent reporters to interesting scaffolds for dual-imaging heterobimetallic probes

Authors

  • Louise Marty Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; CNRS; Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, France
  • Alison François Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; CNRS; Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, France
  • Tetiana Krachko Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; Kyiv National University n. Taras Shevchenko, Ukraine
  • Chantal Galaup Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; CNRS; Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, France
  • Claude Picard Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; CNRS; Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, France
  • V. M. Amirkhanov Kyiv National University n. Taras Shevchenko, Ukraine
  • Eric Benoist Université de Toulouse, UPS, Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique; CNRS; Laboratoire de Synthèse et Physico-Chimie de Molécules d’Intérêt Biologique, France

DOI:

https://doi.org/10.24959/ophcj.13.773

Keywords:

Click chemistry, ternary complexes, tricarbonylrhenium(I), fluorescence

Abstract

In this paper, five new ternary tricarbonylrhenium(I) complexes based on a pyridinetriazole moiety, the so-called pyta, have been investigated. These cationic complexes of the general formula [Re(CO)3(pyta-COOMe)L] (L = substituted pyridine derivatives) combine a carboxylate functionalization, for further biomolecule conjugation, with a metal chelating site – a pyta-based tricarbonylrhenium moiety – which can act as a fluorescent reporter. The complexes have been prepared using a two-steps pathway involved the activation of [Re(CO)3Cl(bipy)] with triflate silver salts in the presence of acetonitrile followed by the thermally activated substitution of the acetonitrile adduct by commercially available substituted pyridine derivatives. They have been prepared from modest to good yields, fully characterized by means of NMR, IR and mass spectrometry, and their photophysical properties have been investigated. Upon excitation into the MLCT band of each complex (absorption band at ca. 300 nm), three of them exhibit a bright green luminescence centered at c.a. 494 nm, with a quantum yield of 0.60% in acetonitrile. These interesting photophysical features make them potential fluorescent cellular imaging agents. Moreover, thank to their ancillary ligand, they could be also considered as interesting scaffolds for the preparation of dual-imaging heterobimetallic species.

Downloads

Download data is not yet available.

References

  1. Fernandez-Moreira V., Thorp-Greenwood F.L., Coogan M.P. // Chem. Commun. – 2010. – Vol. 46. – P. 186-202.
  2. Coleman A., Brennan C., Vos J.G. et al. // Coord. Chem. Rev. – 2008. – Vol. 252. – P. 2585-2595.
  3. Balasingham R.G., Coogan M.P., Thorp-Greenwood F.L. // Dalton Trans. – 2011. –Vol. 40. – P. 11663-11674.
  4. Boulay A., Seridi A., Zedde C. et al. // Eur. J. Inorg. Chem. – 2010. – P. 5058-5062.
  5. Wolff M., Munoz L., François A. et al. // Dalton Trans. – 2013. – Vol. 42. – P. 7019-7031.
  6. Kolb H.C., Finn M.G., Sharpless K.B. // Angew. Chem. Int. Ed. – 2001. – Vol. 40. – P. 2004-2021.
  7. Rostovtsev V.V., Green L.G., Fokin V.V. et al. // Angew. Chem. Int. Ed. – 2002. – Vol. 41. – P. 2596-2599.
  8. Meldal M., Tornøe C.W. // Chem. Rev. – 2008. – Vol. 108. – P. 2952-3015.
  9. François A., Auzanneau C., Le Morvan V. et al. // Dalton Trans. – 2013. – accepted.
  10. François A., Marty L., Picard C. et al. // Acta Cryst. E. – 2012. – Vol. E68. – P. o3162.
  11. Amoroso A.J., Arthur R.J., Coogan M.P. et al. // New J. Chem. – 2008. – Vol. 32. – P. 1097-1102.
  12. Ishida H., Tobita S., Hasegawa Y. et al. // Coord. Chem. Rev. – 2010. – Vol. 254. – P. 2449-2458.

Downloads

Published

2013-12-02

How to Cite

(1)
Marty, L.; François, A.; Krachko, T.; Galaup, C.; Picard, C.; Amirkhanov, V. M.; Benoist, E. Ternary Rhenium (i) Complexes: From Fluorescent Reporters to Interesting Scaffolds for Dual-Imaging Heterobimetallic Probes. J. Org. Pharm. Chem. 2013, 11, 67-71.

Issue

Vol. 11 No. 4(44) (2013)

Section

Original Researches

License

Copyright (c) 2013 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:

1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.

3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).