Table of Contents
Journal of Inorganic Chemistry
Volume 2013 (2013), Article ID 498598, 8 pages
http://dx.doi.org/10.1155/2013/498598
Research Article

Synthesis and Characterisation of First Generation Luminescent Lanthanide Complexes Suitable for Being Adapted for Uptake via the Mannose Receptor

Mechanisms in Cell Biology and Disease Research Group, University of South Australia, Reid Building, Frome Road, Adelaide, SA 5000, Australia

Received 19 August 2013; Accepted 23 September 2013

Academic Editor: Arturo Espinosa

Copyright © 2013 Robert Brooks et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. C. Penas, E. Pazos, J. L. Mascareñas, and M. E. Vázquez, “A folding-based approach for the luminescent detection of a short rna hairpin,” Journal of the American Chemical Society, vol. 135, no. 10, pp. 3812–3814, 2013. View at Google Scholar
  2. J.-C. G. Bünzli and C. Piguet, “Taking advantage of luminescent lanthanide ions,” Chemical Society Reviews, vol. 34, no. 12, pp. 1048–1077, 2005. View at Publisher · View at Google Scholar · View at Scopus
  3. J. S. Josan, C. R. de Silva, B. Yoo et al., “Fluorescent and lanthanide labeling for ligand screens, assays, and imaging,” Methods in Molecular Biology, vol. 716, pp. 89–126, 2011. View at Publisher · View at Google Scholar · View at Scopus
  4. J. Reifernberger, P. Ge, and P. Selvin, “Progress in lanthanides as luminescent probes,” in Reviews in Fluorescence 2005, C. Geddes and J. Lakowicz, Eds., pp. 399–431, Springer, New York, NY, USA, 2005. View at Google Scholar
  5. J.-C. G. Bünzli, “Lanthanide luminescence for biomedical analyses and imaging,” Chemical Reviews, vol. 110, no. 5, pp. 2729–2755, 2010. View at Publisher · View at Google Scholar · View at Scopus
  6. J. M. Irache, H. H. Salman, C. Gamazo, and S. Espuelas, “Mannose-targeted systems for the delivery of therapeutics,” Expert Opinion on Drug Delivery, vol. 5, no. 6, pp. 703–724, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. H. Du, M. Levine, C. Ganesa, D. P. Witte, E. S. Cole, and G. A. Grabowski, “The role of mannosylated enzyme and the mannose receptor in enzyme replacement therapy,” American Journal of Human Genetics, vol. 77, no. 6, pp. 1061–1074, 2005. View at Publisher · View at Google Scholar · View at Scopus
  8. S. M. van Patten, H. Hughes, M. R. Huff et al., “Effect of mannose chain length on targeting of glucocerebrosidase for enzyme replacement therapy of Gaucher disease,” Glycobiology, vol. 17, no. 5, pp. 467–478, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. S. A. Linehan, “The mannose receptor is expressed by subsets of APC in non-lymphoid organs,” BMC Immunology, vol. 6, no. 1, article 4, 2005. View at Publisher · View at Google Scholar · View at Scopus
  10. M. A. Brimble, R. Kowalczyk, P. W. R. Harris, P. R. Dunbar, and V. J. Muir, “Synthesis of fluorescein-labelled O-mannosylated peptides as components for synthetic vaccines: comparison of two synthetic strategies,” Organic and Biomolecular Chemistry, vol. 6, no. 1, pp. 112–121, 2008. View at Publisher · View at Google Scholar · View at Scopus
  11. V. le Cabec, L. J. Emorine, I. Toesca, C. Cougoule, and I. Maridonneau-Parini, “The human macrophage mannose receptor is not a professional phagocytic receptor,” Journal of Leukocyte Biology, vol. 77, no. 6, pp. 934–943, 2005. View at Publisher · View at Google Scholar · View at Scopus
  12. E. A. L. Biessen, F. Noorman, M. E. Van Teijlingen et al., “Lysine-based cluster mannosides that inhibit ligand binding to the human mannose receptor at nanomolar concentration,” The Journal of Biological Chemistry, vol. 271, no. 45, pp. 28024–28030, 1996. View at Publisher · View at Google Scholar · View at Scopus
  13. B. G. Davis and M. A. Robinson, “Drug delivery systems based on sugar-macromolecule conjugates,” Current Opinion in Drug Discovery and Development, vol. 5, no. 2, pp. 279–288, 2002. View at Google Scholar · View at Scopus
  14. D. A. Moore, “Selective trialkylation of cyclen with tert-butyl bromoacetate [1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid, tri-tert-butyl ester hydrobromide],” Organic Syntheses, vol. 85, pp. 10–14, 2008. View at Google Scholar · View at Scopus
  15. P. Antoni, M. Malkoch, G. Vamvounis et al., “Europium confined cyclen dendrimers with photophysically active triazoles,” Journal of Materials Chemistry, vol. 18, no. 22, pp. 2545–2554, 2008. View at Publisher · View at Google Scholar · View at Scopus
  16. T. M. Tagmose and M. Bols, “Synthesis of the 2-deoxyisomaltose analogue of acarbose by an improved route to chiral valieneamines,” Chemistry—A European Journal, vol. 3, no. 3, pp. 453–462, 1997. View at Google Scholar · View at Scopus
  17. W. Hayes, H. M. I. Osborn, S. D. Osborne, R. A. Rastall, and B. Romagnoli, “One-pot synthesis of multivalent arrays of mannose mono- and disaccharides,” Tetrahedron, vol. 59, no. 40, pp. 7983–7996, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. A. Y. Chernyak, G. V. M. Sharma, L. O. Kononov et al., “2-azidoethyl glycosides: glycosides potentially useful for the preparation of neoglycoconjugates,” Carbohydrate Research, vol. 223, pp. 303–309, 1992. View at Publisher · View at Google Scholar · View at Scopus
  19. P. Lebduková, P. Hermann, L. Helm et al., “Gadolinium(iii) complexes of mono- and diethyl esters of monophosphonic acid analogue of DOTA as potential MRI contrast agents: solution structures and relaxometric studies,” Dalton Transactions, no. 4, pp. 493–501, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. R. S. Dickins, D. Parker, J. I. Bruce, and D. J. Tozer, “Correlation of optical and NMR spectral information with coordination variation for axially symmetric macrocyclic Eu(III) and Yb(III) complexes: axial donor polarisability determines Iigand field and cation donor preference,” Dalton Transactions, no. 7, pp. 1264–1271, 2003. View at Publisher · View at Google Scholar · View at Scopus
  21. D. Chen, Y. Wang, and M. Hong, “Lanthanide nanomaterials with photon management characteristics for photovoltaic application,” Nano Energy, vol. 1, no. 1, pp. 73–90, 2012. View at Publisher · View at Google Scholar · View at Scopus
  22. J. J. Freeman and G. A. Crosby, “Spectra and decay times of the luminescences observed from chelated rare earth ions,” The Journal of Physical Chemistry, vol. 67, no. 12, pp. 2717–2723, 1963. View at Google Scholar
  23. J. Georges and J. M. Mermet, “Simultaneous time-resolved fluorescence and thermal lens measurements: application to energy transfer studies in europium chelates,” Spectrochimica Acta A, vol. 49, no. 3, pp. 397–404, 1993. View at Google Scholar · View at Scopus
  24. M. Iwamura, Y. Kimura, R. Miyamoto, and K. Nozaki, “Chiral sensing using an achiral europium(III) complex by induced circularly polarized luminescence,” Inorganic Chemistry, vol. 51, no. 7, pp. 4094–4098, 2012. View at Publisher · View at Google Scholar · View at Scopus
  25. S. E. Plush, N. A. Clear, J. P. Leonard, A.-M. Fanning, and T. Gunnlaugsson, “The effect on the lanthanide luminescence of structurally simple Eu(III) cyclen complexes upon deprotonation of metal bound water molecules and amide based pendant arms,” Dalton Transactions, vol. 39, no. 15, pp. 3644–3652, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. A. J. L. Villaraza, A. Bumb, and M. W. Brechbiel, “Macromolecules, dendrimers, and nanomaterials in magnetic resonance imaging: the interplay between size, function, and pharmacokinetics,” Chemical Reviews, vol. 110, no. 5, pp. 2921–2959, 2010. View at Publisher · View at Google Scholar · View at Scopus
  27. J. N. Kemsley, K. L. Zaleski, M. S. Chow et al., “Spectroscopic studies of the interaction of ferrous bleomycin with DNA,” Journal of the American Chemical Society, vol. 125, no. 36, pp. 10810–10821, 2003. View at Publisher · View at Google Scholar · View at Scopus
  28. H. Feinberg, S. Park-Snyder, A. R. Kolatkar, C. T. Heise, M. E. Taylor, and W. I. Weis, “Structure of a C-type carbohydrate recognition domain from the macrophage mannose receptor,” The Journal of Biological Chemistry, vol. 275, no. 28, pp. 21539–21548, 2000. View at Publisher · View at Google Scholar · View at Scopus
  29. N. P. Mullin, P. G. Hitchen, and M. E. Taylor, “Mechanism of Ca2+ and monosaccharide binding to a C-type carbohydrate- recognition domain of the macrophage mannose receptor,” The Journal of Biological Chemistry, vol. 272, no. 9, pp. 5668–5681, 1997. View at Publisher · View at Google Scholar · View at Scopus