Selective complexation and sensitive analysis of charge diffuse cationic species using lipophilic cyclodextrins

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David Parker and Ritu Kataky


Abstract

Lipophilic peralkylated cyclodextrins are useful ionophores for the selective binding of a variety of size-matched charge-diffuse cationic species. Chiral potentiometric sensors may be devised using plasticised membrane electrodes, while voltammetric sensors may be fabricated that allow sub-nanomolar levels of detection of electron-rich aromatic cations. The observation of the binding of size-matched tetraalkylammonium ions has led to the development of sensitive methods of detection for species such as acetylcholine. When lipophilic cyclodextrins are coupled to enzymes in a disposable biosensor, a highly specific method of analysis is achieved giving sub-picomolar levels of detection.


References

  1. Perspectives in Coordination Chemistry, ed. A. F. Williams, C. Floriani and A. E. Merbach, VCH, Basel, 1992 Search PubMed.
  2. S. C. Peacock and D. J. Cram, J. Chem. Soc., Chem. Commun., 1976, 282 RSC; W. Bussmann, J.-M. Lehn, U. Oesch, P. Plumère and W. Simon, Helv. Chim. Acta., 1981, 64, 557.
  3. D. A. Dougherty, P. C. Kearney, L. S. Mizoire, R. A. Kumpf, J. E. Forman and A. McCurdy, in Computational Approaches in Supramolecular Chemistry, ed. G. Wipff, NATO ASI Series C, vol. 426, Kluwer, London, 1994, pp. 301–309 Search PubMed; P. C. Kearney, L. S. Mizoire, R. A. Kumpf, J. E. Forman, A. McCurdy and D. A. Dougherty, J. Am. Chem. Soc., 1993, 115, 9907 Search PubMed.
  4. M. Harel, D. M. Quinn, H. K. Nair, I. Silman and J. L. Sussman, J. Am. Chem. Soc., 1996, 118, 2340 CrossRef CAS; J. L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Tolker and I. Silman, Science, 1991, 253, 872 CrossRef CAS.
  5. C. A. Deakyne and M. Meot-Ner, J. Am. Chem. Soc., 1985, 107, 474 CrossRef CAS; M. Meot-Ner and C. A. Deakyne, J. Am. Chem. Soc., 1985, 107, 469 CrossRef.
  6. O. Kennard, Supramol. Chem., 1993, 1, 277 CAS; T. Steiner and W. Saenger, J. Am. Chem. Soc., 1992, 114, 10 146 CrossRef CAS.
  7. W. A. Konig, R. Krebber and G. Wenz, J. High Resolut. Chromatogr., 1989, 12, 641.
  8. S. Li and W. C. Purdy, Chem. Rev., 1992, 92, 1457 CrossRef CAS.
  9. P. S. Bates, R. Kataky and D. Parker, J. Chem. Soc., Chem. Commun., 1992, 153 RSC; P. S. Bates, B. N. Green and D. Parker, J. Chem. Soc., Chem. Commun., 1993, 693 RSC; P. S. Bates, D. Parker and A. F. Patti, J. Chem. Soc., Perkin Trans. 2, 1994, 657 RSC.
  10. P. S. Bates, R. Kataky and D. Parker, Analyst (London), 1992, 117, 1313 RSC; P. S. Bates, R. Kataky and D. Parker, J. Chem. Soc., Perkin Trans. 2, 1994, 669 RSC; R. Kataky, D. Parker and P. M. Kelly, Scand. J. Clin. Lab. Invest., 1995, 55, 409 CrossRef CAS.
  11. P. M. Kelly, R. Kataky, D. Parker and A. F. Patti, J. Chem. Soc., Perkin Trans. 2, 1995, 1955 RSC.
  12. Y. Cohen, S. Palmer and D. Parker, unpublished results: for PGSE NMR methods in assessing complexation, see O. Mayzel and Y. Cohen, J. Chem. Soc., Chem. Commun., 1994, 901 Search PubMed; O. Mayzel, O. Aleksiuk, F. Grynszpan, S. Biali and Y. Cohen, J. Chem. Soc., Chem. Commun., 1995, 1183 Search PubMed.
  13. K. B. Lipkowitz, S. Raghothama and D. Young, J. Am. Chem. Soc., 1992, 114, 1554 CrossRef CAS.
  14. G. C. Best and P. B. Dervan, J. Am. Chem. Soc., 1995, 117, 1187 CrossRef CAS.
  15. P. S. Bates, R. Kataky and D. Parker, J. Chem. Soc., Chem. Commun., 1993, 691 RSC.
  16. P. S. Bates, R. Kataky and D. Parker, Analyst (London), 1994, 117, 181 RSC; increases in the rate of relaxation of the 2H nucleus in C12N(CD3)3+ were observed following addition of 1b or 2b; P. M. Kelly and D. Parker, unpublished observations.
  17. F. Cramer, W. Saenger and H.-C. Spatz, J. Am. Chem. Soc., 1967, 89, 14 CrossRef CAS.
  18. M. H. Greenhall, P. Lukes, R. Kataky, N. E. Agbor, J. P. S. Badyal, J. Yarwood, D. Parker and M. C. Petty, Langmuir, 1995, 11, 3997 CrossRef CAS.
  19. R. Kataky, P. M. Kelly, D. Parker and A. F. Patti, J. Chem. Soc., Perkin Trans. 2, 1994, 2381 RSC.
  20. D. Parker, R. Kataky, P. M. Kelly and S. Palmer, Pure Appl. Chem., 1996, 68, 1219 CAS.
  21. W. J. Albery, M. G. Boutelle, S. L. T. Durrant, M. Fillenz, A. R. Hopkins and B. P. Mangold, Phil. Trans. R. Soc. London A, 1990, 333, 49 Search PubMed.
  22. L. E. Webb and R. C. Johnston, Clin. Biochem., 1986, 19, 212 CAS.
  23. A. Guerrieri, G. E. De Benedetto, F. Palmisano and P. G. Zambonin, Analyst (London), 1995, 120, 2731 RSC.
  24. A. Harada and S. Takahaslin, J. Chem. Soc., Chem. Commun., 1984, 645 RSC.
  25. R. Kataky and D. Parker, Br. Pat. Appl., 9611499.6 Search PubMed; R. Kataky and D. Parker, Analyst (London), 1996, 1829 Search PubMed.
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