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DOI: 10.1039/A608212B (Paper) Reference Section for: J. Chem. Soc., Dalton Trans., 1997, 1765-1772

Rhenium complexes with phosphine-containing peptides. Synthesis and characterization of oxorhenium(V) complexes with N-{N -[3-(diphenylphosphino)propionyl]glycyl}-L-S -benzylcysteine and its methyl ester

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Monica Santimaria, Ulderico Mazzi, Stefano Gatto, Alessandro Dolmella, Giuliano Bandoli and Marino Nicolini

Abstract

The co-ordination of dipeptides modified with a phosphine group to the Re[double bond, length as m-dash]O3+ core has been studied, and the new donor sets PN2X (X = O or S) achieved. N-{N-[3-(Diphenylphosphino)propionyl]glycyl }-L-S-benzylcysteine (H3L2) and its methyl ester derivative (H2L1) have been used for preparing six-co-ordinated oxorhenium(V) complexes, providing a new chelating system for targeting 186/188Re to protein bioactive molecules. The complexes have been characterized by means of UV/VIS, IR, FAB and 1H NMR spectroscopy. The crystal structures of [ReO(L2)(OH2)]·H2O·MeOH and [ReO(L1)Cl] have been established. In both the complexes the co-ordination geometry is distorted octahedral. The ligands are tetradentate, co-ordinating the Re[double bond, length as m-dash]O3+ moiety through the phosphine phosphorus, the two deprotonated amide nitrogens and the O or S atom from the carboxylate or thioether groups. When the cysteine carboxylic moiety is free, it can replace, in organic solvents, the thioether sulfur to give a stable complex, the fourth donor atom in the equatorial plane being a carboxylate oxygen. In basic medium [ReO(L1)Cl] underwent substitution of Cl- by OH-, evidence for the high stability of the PN2S donor set.

References

  1. E. John, M. L. Thakur, J. De Fulvio, M. R. McDevitt and I. Dajanov, J. Nucl. Med., 1993, 34, 260 Search PubMed.
  2. P. L. Beaumier, P. Wenkatesan, J.-L. Vanderheiden, W. D. Burgua, L. Kunz, A. R. Fritzberg, P. G. Abrams and A. C. Morgan, jun., Cancer Res., 1991, 51, 676 CAS.
  3. W. C. Eckelman, Eur. J. Nucl. Med., 1995, 22, 249 CAS.
  4. A. R. Fritzberg, P. G. Abrams and P. L. Beaumier, Proc. Natl. Acad. Sci. USA, 1988, 5, 4025.
  5. S. Kazina, T. N. Rao and A. Srinivasan, J. Nucl. Med., 1992, 32, 1445 Search PubMed.
  6. K. E. Baidoo, U. Scheffel and S. Z. Lever, Cancer Res. (Suppl.), 1990, 150, 799s Search PubMed.
  7. R. T. Dean, R. Weber, K. Pak, R. Boutin, R. Buttram, M. Nedelmann and J. Lister-James, Technetium and Rhenium in Chemistry and Nuclear Medicine 3, eds. M. Nicolini, G. Bandoli and U. Mazzi, Cortina International, Verona, 1990, p. 581 Search PubMed.
  8. H. R. Maecke, P. Smith-Jones, Th. Maina, B. Stolz, R. Albert, B. Burns and H. Reist, Horm. Metab. Res. Suppl., 1993, 27, 12 CAS.
  9. W. A. Volkert, Technetium in Chemistry and Nuclear Medicine 4, eds. M. Nicolini, G. Bandoli and U. Mazzi, SGE Editorials, Padova, 1995, p. 17 Search PubMed.
  10. U. Mazzi and F. Lunghi, Eur. Pat., 94 120 079.2, 1994 Search PubMed.
  11. J. Chatt and G. A. Rowe, J. Chem. Soc., 1962, 4019 RSC.
  12. M. Santimaria, Th. Maina, U. Mazzi and M. Nicolini, Inorg. Chim. Acta, 1995, 240, 291 CrossRef CAS.
  13. G. M. Sheldrick, SHELXTL PLUS, Release 4.2, University of Göttingen, 1990.
  14. C. K. Johnson, ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN, 1976.
  15. H. J. Banbery, W. Hussain, T. A. Hamor, C. J. Jones and J. A. McCleverty, J. Chem. Soc., Dalton Trans., 1987, 657 RSC; F. Tisato, F. Refosco, U. Mazzi, G. Bandoli and M. Nicolini, Inorg. Chim. Acta, 1991, 189, 97 CrossRef CAS; H. Luo, I. Setyawati, S. J. Retting and C. Orvig, Inorg. Chem., 1995, 34, 2287 CrossRef CAS; J. P. O'Neil, S. R. Wilson and J. A. Katzenellenbogen, Inorg. Chem., 1994, 33, 319 CrossRef; B. Winckler Tsang, J. Reibenspies and A. E. Martell, Inorg. Chem., 1993, 32, 1988; L. G. Marzilli, M. G. Banaszczyk, L. Hansen, Z. Kuklenyik, R. Cini and A. Taylor, jun., Inorg. Chem., 1994, 33, 4850 CrossRef CAS.
  16. A. G. Orpen, L. Brammer, F. H. Allen, O. Kennard, D. G. Watson and R. Taylor, J. Chem. Soc., Dalton Trans., 1989, S1 RSC.
  17. F. Refosco, F. Tisato, G. Bandoli, C. Bolzati, A. Dolmella, A. Moresco and M. Nicolini, J. Chem. Soc., Dalton Trans., 1993, 605 RSC.
  18. C. Bolzati, F. Tisato, F. Refosco, G. Bandoli and A. Dolmella, Inorg. Chem., 1996, 35, 6221 CrossRef CAS.
  19. F. Tisato, F. Refosco, A. Moresco, G. Bandoli, A. Dolmella and C. Bolzati, Inorg. Chem., 1995, 34, 1779 CrossRef CAS.
  20. T. N. Nicholson and J. Zubieta, Inorg. Chem., 1987, 26, 2094 CrossRef CAS.
  21. S. C. Nyburg, Acta Crystallogr., Sect. B, 1974, 30, 251 CrossRef CAS.
  22. F. Tisato, F. Refosco, A. Moresco, G. Bandoli and C. Bolzati, Inorg. Chem., 1995, 34, 1779 CrossRef CAS.
  23. T. Rao, D. Adhikesavalu, A. Camerman and A. R. Fritzberg, Inorg. Chem. Acta, 1991, 180, 63 CrossRef CAS.
  24. A. Duatti and U. Mazzi, unpublished work.
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