Siderophore analogues: a new macrocyclic tetraamine tris(hydroxamate) ligand; synthesis and solution chemistry of the iron(III), aluminium(III) and copper(II) complexes[hair space]

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Margarida Gaspar, Raquel Grazina, Andrea Bodor, Etelka Farkas and M. Amélia Santos


Abstract

A new siderophore analogue TETMAHA (1,4,8,11-tetraazacyclotetradecane-N,N[hair space]′,N″-tris(N-methylacetohydroxamic acid), a ligand with three hydroxamic acid groups bonded to the macrocycle CYCLAM, has been synthesized and characterized. Its acid–base and chelating properties towards iron(III), aluminium(III) and copper(II) have been studied by potentiometric and spectroscopic techniques. This ligand forms quite stable complexes with those metal ions and the formation constants have been determined. The mechanism of the electron transfer of the iron complexes, thought to be important in the biological activity shown by this ligand, has also been studied by cyclic voltammetry.


References

  1. J. B. Neilands, Biochem. Biophys., 1993, 302, 1 Search PubMed.
  2. R. A. Jokel, J. Toxicol. Environ. Health, 1994, 41, 131 CAS.
  3. K. N. Raymond, Coord. Chem. Rev., 1990, 105, 135 CrossRef CAS.
  4. J. D. Hu and M. J. Miller, J. Am. Chem. Soc., 1997, 119, 3426.
  5. Y. Hara and M. Akiyama, Inorg. Chem., 1996, 35, 5173 CrossRef CAS.
  6. Y. Sun, R. J. Motekaitis and A. E. Martell, Inorg. Chim. Acta, 1998, 281, 60 CrossRef CAS.
  7. M. A. Esteves, M. C. T. Vaz, M. L. S. Simões Gonçalves, E. Farkas and M. A. Santos, J. Chem. Soc., Dalton Trans., 1995, 2565 RSC.
  8. M. A. Santos, M. A. Esteves, M. C. T. Vaz and M. L. S. Simões Gonçalves, Inorg. Chim. Acta, 1993, 214, 47 CrossRef CAS.
  9. M. A. Santos, M. A. Esteves, M. C. T. Vaz and M. L. S. Simões Gonçalves, J. Chem. Soc., Dalton Trans., 1993, 927 RSC.
  10. M. A. Santos, M. Gaspar, M. L. S. Simões Gonçalves and M. T. Amorim, Inorg. Chim. Acta, 1998, 278, 51 CrossRef CAS.
  11. P. Gans, A. Sabatini and A. Vacca, J. Chem. Soc., Dalton Trans., 1985, 1195 RSC.
  12. M. Micheloni and A. Sabatini, J. Chem. Soc., Perkin Trans. 2, 1978, 828 RSC; B. S. Nakami, J. J. B. Welsh and R. D. Hancock, Inorg. Chem., 1983, 22, 2956 CrossRef CAS.
  13. L. Hertli and T. A. Kaden, Helv. Chim. Acta, 1974, 57, 1328 CrossRef CAS; E. K. Barfield and F. Wagner, Inorg. Chem., 1973, 12, 1435 CrossRef.
  14. K. Myoshi, H. Tanaka, E. Kimura, S. Tsuboyama, S. Murata, H. Shimizu and K. Ishizu, Inorg. Chim. Acta, 1983, 78, 23 CrossRef CAS.
  15. G. Anderegg, F. L'Eplattenier and G. Schwarzenbach, Helv. Chim. Acta, 1963, 156, 1409 CrossRef.
  16. E. Farkas, H. Csóka, G. Micera and A. Dessi, J. Inorg. Biochem., 1997, 282.
  17. G. Anderegg, F. L'Eplattenier and G. Schwarzenbach, Helv. Chim. Acta, 1963, 156, 1400 CrossRef CAS.
  18. E. Leporati, J. Chem. Soc., Dalton Trans., 1987, 1409 RSC.
  19. L. H. Martin, L. DeHayes, L. J. Zompa and D. H. Busch, J. Am. Chem. Soc., 1974, 96, 4046 CrossRef CAS.
  20. R. Buxtorf and T. A. Kaden, Helv. Chim. Acta, 1974, 57, 1035 CrossRef.
  21. B. Kurzak, H. Kozlowski and E. Farkas, Coordination Chem. Rev., 1992, 114, 169 Search PubMed.
  22. B. Kurzak, L. Nakoniczna, G. Rusek, H. Kozlowski and E. Farkas, J. Coord. Chem., 1993, 28, 17 CAS.
  23. E. Farkas, J. Szõke, T. Kiss, H. Kozlowski and W. Bal, J. Chem. Soc., Dalton Trans., 1989, 2247 RSC.
  24. B. Kurzak, E. Farkas, T. Glowiak and H. Kozlowski, J. Chem. Soc., Dalton Trans., 1991, 163 RSC.
  25. M. C. Styka, R. C. Smierciak, E. L. Beinn, R. E. Desimone and J. V. Passariello, Inorg. Chem., 1978, 17, 82 CrossRef CAS.
  26. M. J. Maroney and N. J. Rose, Inorg. Chem., 1984, 23, 2252 CrossRef CAS.
  27. D. A. Brown, D. Makeith and W. K. Glass, Inorg. Chim. Acta, 1979, 35, 5 CrossRef CAS.
  28. F. Chaubet, K. N. Van Duong, J. Courtieu, A. Gaudemer, A. Gref, A. L. Crumbliss and M. T. Caudle, Can. J. Chem., 1984, 72, 2361.
  29. W. C. Vorburgh and G. R. Cooper, J. Am. Chem. Soc., 1941, 63, 437 CrossRef CAS.
  30. M. A. Esteves, Ph.D. Thesis, Instituto Superior Técnico, Universidade Técnica de Lisboa, Lisboa, 1995.
  31. E. Farkas, E. Kozma, T. Kiss, I. Tóth and B. Kurzak, J. Chem. Soc., Dalton Trans., 1995, 477 RSC.
  32. L. Zékány and I. Nagypál, in Computational Methods for the Determination of Stability Constants, ed. D. Legget, Plenum, New York, 1985 Search PubMed.
  33. G. H. Khoe, P. L. Brown, R. N. Sylva and R. G. Robins, J. Chem. Soc., Dalton Trans., 1986, 1901 RSC.
  34. R. S. Nicholson and I. Shain, Anal. Chem., 1964, 36, 706 CrossRef CAS.
  35. K. N. Raymond and C. J. Carrano, Acc. Chem. Res., 1979, 12, 183 CrossRef CAS.
  36. D. J. Brockway, K. S. Murray and P. J. Newman, J. Chem. Soc., Dalton Trans., 1980, 1112 RSC.
  37. J. Leong and J. B. Neilands, J. Bacteriol., 1976, 126, 823 CAS.
  38. M. Gaspar, M. A. Santos, K. Krauter and G. Winkelmann, Biometals, 1999, in the press Search PubMed.
  39. L. O. Öhman and W. Forsling, Acta Chem. Scand., Ser. A, 1981, 35, 795.
  40. A. Evens, R. D. Hancock, A. E. Martell and R. J. Motekaitis, Inorg. Chem., 1989, 28, 2289.
  41. D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd edn., Pergamon, Oxford, 1988, p. 391 Search PubMed.
  42. G. Gran, Analyst (London), 1952, 77, 661 RSC.
  43. A. E. Martell and R. J. Motekaitis, Determination and Use of Stability Constants, VCH, New York, 1988 Search PubMed.
  44. EPR, A Modelling Approach, version 1.0, Frank Neese, Ph.D. Thesis, University of Konstanz, 1993.
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