View PDF Version
 
DOI: 10.1039/A708814K (Paper) Reference Section for: Analyst, 1998, 123, 1587-1591

Cyclodextrin enhanced fluorimetric method for the determination of tryptamine

(Note: The full text of this document is currently only available in the PDF Version )

Raquel E. Galian, Alicia V. Veglia and Rita H. de Rossi

Abstract

The effect of native cyclodextrins (α-, β- or γ- with six, seven or eight glucose units, respectively), hydroxypropyl-β-cyclodextrin, β-cyclodextrin solubilized in urea, soluble starch and glucose in water solution on the fluorescence behaviour of tryptamine [3-(2-aminoethyl)indole] (T) was determined. In addition, the effect of methanol and propanol with and without β-cyclodextrin or hydroxypropyl-β-cyclodextrin was ascertained. From the fluorescence changes with pH and with β-cyclodextrin or hydroxypropyl-β-cyclodextrin, the values of the pKa of the ground and excited states and the association constants of T and TH [3-(2-ammoniumethyl)indole] with the two hosts were determined. The values are pKa = 9.5 ± 0.2 and pKa* = 8.4 ± 0.2; KAssocTH = (1.6 ± 0.3) × 102 mol–1 dm3 and KAssocT = (2.8 ± 0.3) × 102 mol–1 dm3 with β-cyclodextrin, KAssocTH = (1.8 ± 0.5) × 102 mol–1 dm3 and KAssocT = (4.9 ± 0.9) × 102 mol–1 dm3 with hydroxypropyl-β-cyclodextrin. The ratio of the fluorescence quantum yields for the bound and free substrate (Φb/Φf) were in the range 1.25–1.33. The detection limit for the better conditions where the host–guest interactions produce fluorescence enhancement was 0.454 ± 0.002 ng ml–1 for the complex T–hydroxypropyl-β-cyclodextrin in water. The method is simpler than others reported previously.

References

  1. R. H. De Rossi, M. Barra and E. B. de Vargas, J. Org. Chem., 1986, 51, 2157 CrossRef CAS.
  2. A. V. Veglia and R. H. de Rossi, J. Org. Chem., 1988, 53, 5281 CrossRef CAS.
  3. A. V. Veglia, A. M. Sanchez and R. H. de Rossi, J. Org. Chem., 1990, 55, 4083 CrossRef CAS.
  4. A. V. Veglia and R. H. de Rossi, J. Org. Chem., 1993, 58, 4941 CrossRef CAS.
  5. M. L. Bender and M. Komiyama, in Cyclodextrin Chemistry, ed. Hafner, K., Rees, Ch. W., Trost, B. M., Lehn, J.-M., von Rague Schleyer, P., and Zahradnik, R., Springer, Berlin, 1978 Search PubMed.
  6. P. Bartolus, G. Kohler and S. Monti, Coord. Chem. Rev., 1993, 125, 261 CrossRef; D. F. Eaton, Tetrahedron, 1987, 43, 1551 CrossRef CAS.
  7. K. Kalyanasundaram, Photochemistry in Microheterogeneous Systems, Academic Press, Orlando, FL, 1987, ch. 9 Search PubMed.
  8. V. Balzani and F. Scandola, Supramolecular Photochemistry, ed. Kemp, T. P., Ellis Horwood, Chichester, 1991 Search PubMed.
  9. R. P. Frankewich, K. N. Thimmaiah and W. L. Hinze, Anal. Chem., 1991, 63, 2924 CrossRef CAS.
  10. S. Li and W. C. Purdy, Chem. Rev., 1992, 92, 1457 CrossRef CAS.
  11. Analytical Chemistry: The Working Tools, ed. Strauts, C. R. N., Gilfillan, J. H., and Wilson, H. N., Oxford University Press, London, 1958, vol. I, p. 228 Search PubMed.
  12. CRC Handbook of Chemistry and Physics, ed. Lide, D. R., CRC Press, Boca Raton, FL, 72nd edn., 1991, pp. 8-34–8-36 Search PubMed.
  13. G. Patonay, M. E. Rolie and I. M. Warner, Anal. Chem., 1985, 57, 569 CrossRef CAS.
  14. CRC Handbook of Biochemistry and Molecular Biology, Fasman, G. D., CRC Press, Cleveland, OH, 3rd edn. 1977, vol. 1, p. 305 Search PubMed.
  15. Z. R. Grabowski and W. Rubaszewska, J. Chem. Soc., Faraday Trans. 1, 1977, 73, 11 RSC.
  16. B. Marciniak, H. Kozubek and S. Paszyc, J. Chem. Educ., 1992, 69, 247 CAS.
  17. C. N. Sanramé, R. H. de Rossi and G. A. Argüello, J. Phys. Chem., 1996, 100, 8151 CrossRef CAS.
  18. J. Schang and G. Laustriat, J. Chim. Phys. Phys.-Chim. Biol., 1975, 72, 1291 CAS.
  19. S. Lehrer, J. Am. Chem. Soc., 1970, 92, 3459 CrossRef CAS.
  20. A. White, Biochem. J., 1959, 71, 217 CAS.
  21. L. Styrer, J. Am. Chem. Soc., 1966, 88, 5708 CrossRef.
  22. E. Vander Donckt, Bull. Soc. Chim. Belg., 1969, 78, 69 CAS.
  23. A. Örstan and J. B. A. Ross, J. Phys. Chem., 1987, 91, 2739 CrossRef CAS.
  24. K. A. Connors, Binding Constants, Wiley, New York, 1987 Search PubMed.
  25. F. Cramer, W. Saenger and H. Spatz, J. Am. Chem. Soc., 1967, 89, 1 CrossRef.
  26. A. Muñoz de la Peña, F. Salinas, I. Durán-Merás and M. D. Moreno, Anal. Lett., 1994, 27, 1893.
  27. A. Muñoz de la Peña, T. T. Ndou, J. B. Zung, D. H. Greene, D. H. Live and I. M. Warner, J. Am. Chem. Soc., 1991, 113, 1572 CrossRef.
  28. J. Huang, G. C. Catena and F. V. Bright, Appl. Spectrosc., 1992, 46, 606.
  29. Y. Matsui and K. Mochida, Bull. Chem. Soc. Jpn., 1979, 52, 2808 CAS.
  30. IUPAC, Anal. Chem., 1980, 52, 2242 Search PubMed.
  31. G. L. Long and J. D. Winefordner, Anal. Chem., 1983, 55, 712A CrossRef CAS.
  32. J. M. Lisy and B. C. Gerstein, Anal. Chem., 1973, 45, 1536 CrossRef CAS.
  33. H. Iizuka and T. Yajima, Chem. Pharm. Bull., 1985, 33, 2591 CAS.
  34. H. Nakamura and J. J. Pisano, Arch. Biochem. Biophys., 1976, 172, 98 CrossRef CAS.
  35. T. Hojo, H. Nakamura and Z. Tamura, Chem. Pharm. Bull., 1982, 30, 189 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.