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DOI: 10.1039/A802183J (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1573-1580

Synthesis and spectroscopic characterisation of fluorescent indicators for Na+ and K+

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Els Cielen, Abdellah Tahri, Katja Ver Heyen, Georges J. Hoornaert, Frans C. De Schryver and Noël Boens

Abstract

The synthesis and the spectral and cation binding properties of new fluorescent indicators for Na+, dicaesium 5-[5-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)-2-thienyl]isophthalate (Benzos), and for K+, dicaesium 5-[5-(2,3,5,6,8,9,11,12,14,15-decahydro-1,4,7,10,13,16-benzohexaoxacyclooctadecin-18-yl)-2-thienyl]isophthalate (Benzop), are reported. Both indicators consist of a benzocrown ether with an appropriate cavity for the sodium and the potassium cation, respectively, linked to an aryl thiophene fluorophore. In aqueous solution, the indicators have an absorption maximum at 340 nm and an emission maximum at 430 nm. The chelating abilities of Benzos and Benzop with Na+, K+, Li+, Cs+, Mg2+ and Ca2+ were studied by means of their fluorescence properties. Upon cation binding, a change in the fluorescence intensity is observed, whereas the spectral distribution remains unaltered. While Benzos cannot discriminate between Na+ and other monovalent cations, Benzop shows a three-fold selectivity for K+ over Na+.

References

  1. R. Y. Tsien, Am. J. Physiol. (Cell. Physiol. 32), 1992, 263, C723 Search PubMed; A. W. Czarnik, Fluorescent Chemosensors for Ion and Molecule Recognition, ed. A. W. Czarnik, ACS Symposium Series, Washington, 1993, p. 538 Search PubMed.
  2. J. Darnell, H. Lodish and D. Baltimore, Molecular Cell Biology, Freeman, New York, 1986 Search PubMed; M. N. Hughes, The Inorganic Chemistry of Biological Processes, Wiley, London, 1972, p. 256 Search PubMed.
  3. I. P. Romanov, Lab. Delo, 1974, 7, 438 Search PubMed.
  4. E. Dufau, H. Acker and D. Sylvester, Med. Prog. Technol., 1980, 7, 35 Search PubMed.
  5. R. V. Smith and M. A. Nessen, J. Pharm. Sci., 1971, 60, 907 CAS.
  6. D. Burstein and E. T. Fossel, Am. J. Physiol., 1987, 252, HI 138 Search PubMed.
  7. R. Y. Tsien, Annu. Rev. Neurosci., 1991, 12, 227 CrossRef CAS; A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, Chem. Rev., 1997, 97, 1515 CrossRef.
  8. J. R. Blinks, W. Wier, P. Hess and F. G. Prendergast, Prog. Biophys. Mol. Biol., 1982, 40, 1 CrossRef CAS.
  9. G. Grynkiewicz, M. Poenie and R. Y. Tsien, J. Biol. Chem., 1989, 264, 19 449.
  10. A. T. Harootunian, J. Kao, B. Eckert and R. Y. Tsien, J. Biol. Chem., 1989, 32, 19 485.
  11. J. D. Lamb, R. M. Izatt, C. S. Swain and J. J. Christensen, J. Am. Chem. Soc., 1980, 102, 475 CrossRef CAS.
  12. J.-M. Lehn, M. R. Truter, R. M. Izatt, D. Eatough and J. J. Christensen, Alkali Metal Complexes with Organic Ligands, Structure and Bonding 16, Springer Verlag, Berlin, Heidelberg, New York, 1973 Search PubMed.
  13. R. M. Izatt, R. E. Terry, B. L. Haymore, L. D. Hansen, N. K. Dalley, A. G. Avondet and J. J. Christensen, J. Am. Chem. Soc., 1976, 98, 7620 CrossRef CAS.
  14. R. P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, ed. M. T. Z. Spence, Molecular Probes, Eugene, OR, USA, 6th edn., 1996, p. 572 Search PubMed.
  15. G. Kirsch and D. Prim, J. Heterocycl. Chem., 1994, 31, 1005 CAS.
  16. A. Kowalczyk, N. Boens, V. Van den Bergh and F. C. De Schryver, J. Phys. Chem., 1994, 98, 8585 CrossRef CAS.
  17. J. K. Stille, Angew. Chem., 1986, 98, 504 CAS; Angew. Chem., Int. Ed. Engl., 1986, 25, 508 Search PubMed; T. N. Mitchell, Synthesis, 1992, 803 Search PubMed; C. Amatore, E. Carré, A. Jutand, H. Tanaka, Q. Ren and S. Torii, Chem. Eur. J., 1996, 2, 957 CrossRef CAS.
  18. G. A. Delzenne and U. Laridon, J. Polym. Sci., Part C, 1969, 22, 1149 Search PubMed.
  19. A. Grahl, Chem. Ber., 1895, 28, 84 Search PubMed.
  20. R. J. Sundberg and R. W. Heintzelman, J. Org. Chem., 1974, 39, 2547.
  21. N. A. Bumagin and I. G. Bumagina, Dokl. Akad. Nauk SSSR, 1983, 274, 39 Search PubMed.
  22. N. Gjøs and S. Gronowitz, Acta Chem. Scand., 1972, 26, 1851.
  23. D. Azarian, S. S. Dua, C. Eaborn and D. R. M. Walton, J. Organomet. Chem., 1976, 117, C55 CrossRef CAS; H. Azizian, C. Eaborn and A. Pidcock, J. Organomet. Chem., 1981, 215, 49 CrossRef CAS.
  24. R. A. Olofson and C. M. Dougherty, J. Am. Chem. Soc., 1973, 95, 581 CrossRef CAS.
  25. E. D. Laganis and B. L. Chenard, Tetrahedron Lett., 1984, 25, 5831 CrossRef CAS.
  26. A. Minta and R. Y. Tsien, J. Biol. Chem., 1989, 264, 8171 CAS.
  27. R. M. Izatt, R. E. Terry, D. P. Welson, Y. Chan, D. J. Eatough, J. S. Bradshaw, L. D. Hansen and J. J. Christensen, J. Am. Chem. Soc., 1976, 98, 7626 CrossRef CAS.
  28. D. F. Eaton, Handbook of Organic Photochemistry, ed. J. C. Scaiano, CRC Press, Boca Raton, FL, 1989, p. 231 Search PubMed.
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