A rigid, cyclohexane-based polyamino-polyalcohol as a versatile building block for tailored chelating agents

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Kaspar Hegetschweiler


Abstract

Selective, tailored chelators are of importance in medicine for the treatment of metal intoxication, or to stabilise metal cations in diagnostic radiopharmaceuticals and paramagnetic contrast agents. In this report, the co-ordination chemistry of polyamines, polyalcohols, and polyamino-polyalcohols is examined and some general prerequisites for a successful design of tailored chelators are summarised. The metal binding properties of 1,3,5-triamino-1,3,5-trideoxy-cis-inositol (taci), a rigid, cyclohexane-based polyamino-polyalcohol, are reviewed. Concepts for the design of selective chelators which are based on the taci structure are presented, and the potential of such ligands for medical applications is briefly discussed.


References

  1. A. E. Martell and R. D. Hancock, Metal Complexes in Aqueous Solutions, Plenum Press, New York, 1996 Search PubMed.
  2. R. G. Pearson, Chemical Hardness, Wiley-VCH, Weinheim, Germany, 1997 Search PubMed.
  3. J. N. Butler and D. R. Cogley, Ionic Equilibrium—Solubility and pH Calculations, Wiley, New York, NY, 1998 Search PubMed.
  4. P. Comba and T. W. Hambley, Molecular Modeling of Inorganic Compounds, VCH, Weinheim, Germany, 1995 Search PubMed.
  5. G. A. Lawrance, M. Maeder and E. N. Wilkes, Rev. Inorg. Chem., 1993, 13, 199 Search PubMed and references therein.
  6. D. A. House, Comprehensive Coordination Chemistry, G. Wilkinson, ed., Vol. 2, Pergamon Press, Oxford, UK, 1987, pp. 23–72 Search PubMed.
  7. P. Paoletti, R. Walser, A. Vacca and G. Schwarzenbach, Helv. Chim. Acta, 1971, 54, 243 CAS and references therein.
  8. A. Bianchi, M. Micheloni and P. Paoletti, Coord. Chem. Rev., 1991, 110, 17 CrossRef CAS.
  9. K. Burger and L. Nagy, in Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems, K. Burger, ed., Ellis Horwood, Chichester, 1990, pp. 236–283 Search PubMed.
  10. J.-F. Verchère, S. Chapelle, F. Xin and D. C. Crans, Prog. Inorg. Chem., 1998, 47, 837 CAS.
  11. S. Yano, Coord. Chem. Rev., 1988, 92, 113 CrossRef CAS.
  12. M. Allan and C. J. Willis, J. Am. Chem. Soc., 1968, 90, 5343 CrossRef CAS.
  13. P. Goldschmidt, E. Weingardt and W. Bachmann, Kolloid-Z., 1929, 47, 49 Search PubMed.
  14. J. Burger, C. Gack and P. Klüfers, Angew. Chem., 1995, 107, 2950 (Angew. Chem., Int. Ed. Engl., 1995, 34, 2647).
  15. K. Hegetschweiler, L. Hausherr-Primo, W. H. Koppenol, V. Gramlich, L. Odier, W. Meyer, H. Winkler and A. X. Trautwein, Angew. Chem., 1995, 107, 2421 (Angew. Chem., Int. Ed. Engl., 1995, 34, 2242).
  16. D. A. House, V. McKee and P. J. Steel, Inorg. Chem., 1986, 25, 4884 CrossRef CAS.
  17. W. Plass, Eur. J. Inorg. Chem., 1998, 799 CrossRef CAS and references therein.
  18. K. Hegetschweiler, I. Erni, W. Schneider and H. Schmalle, Helv. Chim. Acta, 1990, 73, 97 CrossRef CAS.
  19. K. Hegetschweiler, T. Kradolfer, V. Gramlich and R. D. Hancock, Chem. Eur. J., 1995, 1, 74 CAS.
  20. K. Hegetschweiler, T. Raber, G. J. Reiß, W. Frank, M. Wörle, A. Currao, R. Nesper and T. Kradolfer, Angew. Chem., 1997, 109, 2052 (Angew. Chem., Int. Ed. Engl., 1997, 36, 1964).
  21. M. C. Ghisletta, Thesis, Diss. No. 10891, ETH-Zürich, Switzerland, 1994 Search PubMed.
  22. K. Hegetschweiler, M. Wörle, M. D. Meienberger, R. Nesper, H. W. Schmalle and R. D. Hancock, Inorg. Chim. Acta, 1996, 250, 35 CrossRef CAS.
  23. M. Ghisletta, L. Hausherr-Primo, K. Gajda-Schrantz, G. Machula, L. Nagy, H. W. Schmalle, G. Rihs, F. Endres and K. Hegetschweiler, Inorg. Chem., 1998, 37, 997 CrossRef CAS and references therein.
  24. K. Hegetschweiler, R. D. Hancock, M. Ghisletta, T. Kradolfer, V. Gramlich and H. W. Schmalle, Inorg. Chem., 1993, 32, 5273 CrossRef CAS.
  25. K. Hegetschweiler, M. Ghisletta and V. Gramlich, Inorg. Chem., 1993, 32, 2699 CrossRef CAS.
  26. R. Hedinger, M. Ghisletta, K. Hegetschweiler, É. Tóth, A. E. Merbach, R. Sessoli, D. Gatteschi and V. Gramlich, Inorg. Chem., 1998, 37, 6698 CrossRef CAS.
  27. A. Egli, Thesis, Diss. No. 10936, ETH-Zürich, Switzerland, 1994 Search PubMed.
  28. R. Hedinger, Thesis, Diss. No. 12611, ETH-Zürich, Switzerland, 1998 Search PubMed.
  29. M. Weber, D. Kuppert, K. Hegetschweiler and V. Gramlich, Inorg. Chem., 1999, 38, 859 CrossRef CAS.
  30. K. Hegetschweiler, M. Weber, V. Huch, M. Veith, H. W. Schmalle, A. Linden, R. J. Geue, P. Osvath, A. M. Sargeson, A. C. Willis and W. Angst, Inorg. Chem., 1997, 36, 4121 CrossRef CAS.
  31. K. Hegetschweiler, A. Egli, R. Alberto and H. W. Schmalle, Inorg. Chem., 1992, 31, 4027 CrossRef CAS.
  32. K. Hegetschweiler, M. Weber, V. Huch, R. J. Geue, A. D. Rae, A. C. Willis and A. M. Sargeson, Inorg. Chem., 1998, 37, 6136 CrossRef CAS.
  33. R. Hedinger, T. Kradolfer, K. Hegetschweiler, M. Wörle and K.-H. Dahmen, Chem. Vap. Deposition, 1999, 5, 29 CrossRef CAS.
  34. A. Kramer, R. Alberto, A. Egli, I. Novak-Hofer, K. Hegetschweiler, U. Abram, P. V. Bernhard and P. A. Schubiger, Bioconjugate Chem., 1998, 9, 691 CrossRef CAS.
  35. S. Singh, Chem. Ind., 1994, 452 Search PubMed.
  36. W. Schneider, I. Erni and K. Hegetschweiler, all-cis-1,3,5-Triamino-2,4,6-cyclohexanetriol derivatives, their use, processes for their preparation and pharmaceutical applications containing them, European Patent EP 0 190 676 B1, 1988.
  37. A. Wong, M. J. Pippard, K. Pattanapanyasat, B. Faller and H. P. Schnebli, In Vivo Distribution of Iron Chelator Complexes and Routes of Iron Excretion, Novartis Pharma AG, Internal Report, 1995 Search PubMed.
  38. S. Aime, M. Botta, M. Fasano and E. Terreno, Chem. Soc. Rev., 1998, 27, 19 RSC and references therein.
  39. É. Tóth, L. Helm, A. E. Merbach, R. Hedinger, K. Hegetschweiler and A. Jánossy, Inorg. Chem., 1998, 37, 4104 CrossRef CAS.
  40. J. R. Dilworth and S. J. Parrott, Chem. Soc. Rev., 1998, 27, 43 RSC and references therein.
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