Clusters in bis-tridentate tethered domains of an iron chelating drug[hair space]

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William Henderson, Lip L. Koh, John D. Ranford, Ward T. Robinson, Jan O. Svensson, Jagadese J. Vittal, Yu M. Wang and Yan Xu


Abstract

The tridentate metal binding domains of iron chelating agents have been tethered via a variable length methylene (CH2)n linker (n = 1, 2, 4, 6, 8, 10, 14). The single-crystal X-ray structures of monomeric ([Fe(HL8)]·2.5H2O n = 8; H4L8 is 1,10-decanedioyl di(salicylaldehyde hydrazone)) and dimeric ([{Fe(H2PL4)}2]Cl2·2H2O n = 4; H4PL4 is 1,6-hexanedioyl di(pyridoxal hydrazone)) iron(III) complexes have been determined. The complexes exhibit oligomerism: with chain lengths of n ≥ 6 monomers are prevalent whereas for shorter chains this is not possible and a series of clusters exist as shown by ESMS and molecular modelling.


References

  1. M. A. Engle, M. Erlandson and C. H. Smith, Circulation, 1964, 300, 698 Search PubMed.
  2. P. J. Giardina, R. W. Grady, K. H. Ehlers, S. Burstein, J. H. Graziano, A. L. Marjenson and M. W. Hilgertner, Ann. N. Y. Acad. Sci., 1990, 612, 275 CAS.
  3. The Development of Iron Chelators for Clinical Use, eds. R. J. Bergerson and G. M. Brittenham, CRC Press, London, 1994 Search PubMed.
  4. Iron Transport and Storage, eds. P. Ponka, H. M. Schulman and R. C. Woodworth, CRC Press, Boston, 1990 Search PubMed.
  5. Progress in Iron Research: Advances in Experimental Medicine and Biology, eds. C. Hershko, A. M. Konijn and P. Aisen, Plenum, New York, 1994, vol. 356 Search PubMed.
  6. A. Jacobs, Brit. J. Haematol., 1979, 43, 1 CAS; C. Hershko, S. Avramovici-Grisaru, G. Link, L. Gelfand and S. Sarel, J. Lab. Clin. Med., 1981, 98, 99 CAS.
  7. P. Ponka, D. Richardson, E. Baker, H. M. Schulman and J. T. Edward, Biochim. Biophys. Acta, 1988, 967, 122 CrossRef CAS; P. Ponka, J. Borova, J. Neuwirt, O. Fuchs and E. Necas, FEBS Lett., 1979, 97, 317 CrossRef CAS.
  8. P. Ponka, R. W. Grady, A. Wilcznska and H. M. Schulman, Biochim. Biophys. Acta, 1984, 802, 477 CrossRef CAS.
  9. G. M. Brittenham, V. R. Gordeuk, P. Ponka, P. Pootrakul, S. Fucharoen, P. Wasi and C. A. Finch, Workshop on the Development of Oral Iron Chelating Agents, Crete, 1987 Search PubMed; G. M. Brittenham, Semin. Hematol., 1990, 27, 112 Search PubMed.
  10. P. Ponka, J. Borova, J. Neuwirt, O. Fuchs and E. Necas, Biochim. Biophys. Acta, 1979, 586, 278 CrossRef CAS.
  11. D. K. Johnson, M. J. Pippard, T. B. Murphy and N. J. Rose, J. Pharmacol. Exp. Ther., 1982, 221, 339 Search PubMed.
  12. H. A. Offe, W. Siefken and G. Domagk, Z. Naturforsch., Teil B, 1952, 7, 446 Search PubMed.
  13. D. K. Johnson, T. B. Murphy, N. J. Rose, W. H. Goodwin and L. Pickart, Inorg. Chim. Acta, 1982, 67, 159 CrossRef CAS; L. Pickart, W. H. Goodwin, W. Burgua, T. B. Murphy and D. K. Johnson, Biochem. Pharmacol., 1983, 32, 3868 CrossRef CAS; E. W. Ainscough, A. M. Brodie, W. A. Denny, G. J. Finlay, S. A. Gothe, J. D. Ranford and J. M. Waters, J. Inorg. Biochem., in the press Search PubMed.
  14. O. V. Arapov, O. F. Alferva, E. I. Levocheskaya and I. Krasil'nikov, Radiobiol., 1987, 27, 843 Search PubMed.
  15. L. L. Koh, O. L. Kon, K. W. Loh, Y. C. Long, J. D. Ranford, A. L. C. Tan and Y. Y. Tjan, J. Inorg. Biochem., 1998, 72, 155 CrossRef CAS.
  16. T. B. Murphy, D. K. Johnson, N. J. Rose, A. Aruffo and V. Schomaker, Inorg. Chim. Acta, 1982, 66, L67 CrossRef CAS; T. B. Murphy, N. J. Rose, V. Schomaker and A. Aruffo, Inorg. Chim. Acta, 1985, 108, 183 CrossRef CAS; T. B. Murphy, D. K. Johnson, N. J. Rose, A. Aruffo and V. Schomaker, Inorg. Chim. Acta, 1982, 66, L67 CrossRef CAS; S. C. Chan, L. L. Koh, P.-H. Leung, J. D. Ranford and K. Y. Sim, Inorg. Chim. Acta, 1995, 236, 101 CrossRef CAS; E. W. Ainscough, A. M. Brodie, A. Dobbs, J. D. Ranford and J. M. Waters, Inorg. Chim. Acta, 1998, 267, 27 CrossRef CAS.
  17. Progress in Iron Research: Advances in Experimental Medicine and Biology, eds. C. Hershko, A. M. Konijn and P. Aisen, Plenum, New York, 1994, vol. 356, p. 343 Search PubMed.
  18. J. D. Ranford, J. J. Vittal and Y. M. Wang, Inorg. Chem., 1998, 37, 1226 CrossRef CAS.
  19. B. B. Umarov, K. S. Khusenov, M. M. Ishankhodzhaeva, N. A. Parpiev and K. S. Gaibullaev, Zh. Org. Khim., 1996, 32, 93 CAS; R. C. Aggarawal and B. Singh, Curr. Sci., 1978, 47, 679 Search PubMed; K. K. Narang and R. A. Lal, Transition Met. Chem., 1977, 2, 100 CAS; X.-M. Zhang and X.-Z. You, Polyhedron, 1996, 15, 1793 CrossRef CAS; L. Sacconi, J. Chem. Soc., 1954, 1326 Search PubMed; X. Wang, X. M. Zhang and H. X. Liu, Polyhedron, 1994, 13, 2611 CrossRef CAS; X. Wang, X. M. Zhang and H. X. Liu, Acta Crystallogr., Sect. C, 1994, 50, 1878 CrossRef; R. A. Lal, S. Das and R. K. Thapa, Inorg. Chim. Acta, 1987, 132, 129 CrossRef CAS; S. Das and R. A. Lal, Indian J. Chem., Sect. A, 1988, 27, 225; M. Husain, S. S. Bhattacharjee, K. B. Singh and R. A. Lal, Polyhedron, 1991, 10, 779 CrossRef CAS; K. K. Narang and R. A. Lal, Curr. Sci., 1977, 46, 401 Search PubMed; R. A. Lal, K. N. Srivastava and S. Das, Synth. React. Inorg. Met.-Org. Chem., 1988, 18, 837 CAS.
  20. See e.g. D. L. Caulder and K. N. Raymond, J. Chem. Soc., Dalton Trans., 1999, 1185 Search PubMed and refs. therein.
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