Bioinorganic Chemistry and Applications
Volume 2009 (2009), Article ID 542979, 12 pages
doi:10.1155/2009/542979
Research Article

Synthesis, Characterization, and Biological Studies of Organotin(IV) Derivatives with o- or p-hydroxybenzoic Acids

Mohamed A. Abdellah,1,2 Sotiris K. Hadjikakou,1 Nick Hadjiliadis,1 Maciej Kubicki,3 Thomas Bakas,4 Nikolaos Kourkoumelis,4,5 Yannis V. Simos,6 Spyros Karkabounas,6 Mirela M. Barsan,7 and Ian S. Butler7

1Section of Inorganic and Analytical Chemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
2Department of Chemistry, Qena Faculty of Science, South Valley University, Qena 83523, Egypt
3Faculty of Chemistry, Adam Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznan, Poland
4Physics of Material Laboratory, Department of Physics, University of Ioannina, 45110 Ioannina, Greece
5Medical Physics Laboratory, Medical School, University of Ioannina, 45110 Ioannina, Greece
6Department of Experimental Physiology, Medical School, University of Ioannina, 45110 Ioannina, Greece
7Department of Chemistry, McGill University, 801 Sherbrooke, Montreal QC, H2A 2K6, Canada

Received 6 November 2008; Accepted 14 January 2009

Academic Editor: Lorenzo Pellerito

Copyright © 2009 Mohamed A. Abdellah et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. A. G. Davis, Organotin Chemistry, VCH, Weinheim, Germany, 1997.
  2. P. J. Smith, Chemistry of Tin, Blackie Academic & Professional, London, UK, 1998.
  3. W. T. Piver, “Organotin compounds: industrial applications and biological investigation,” Environmental Health Perspectives, vol. 4, pp. 61–79, 1973. View at Publisher · View at Google Scholar
  4. G. J. M. van de Kerk, “Organotin chemistry: past, present and future,” in Organotin Compounds: New Chemistry and Applications, J. J. Zuckerman, Ed., vol. 1, pp. 204–226, American Chemical Society, Washington, DC, USA, 1976.
  5. G. J. M. van der Kerk and J. G. A. Luijten, “The biocidal properties of organo-tin compounds,” Journal of Applied Chemistry, vol. 4, no. 6, pp. 314–319, 1954.
  6. G. J. M. van der Kerk and J. G. A. Luijten, “Investigations on organo-tin compounds. V. The preparation and antifungal properties of unsymmetrical tri-n-alkyltin acetates,” Journal of Applied Chemistry, vol. 6, no. 2, pp. 56–60, 1956. View at Publisher · View at Google Scholar
  7. B. D. James, S. Gioskos, S. Chandra, R. J. Magee, and J. D. Cashion, “Some triphenyltin(IV) complexes containing potentially bidentate, biologically active anionic groups,” Journal of Organometallic Chemistry, vol. 436, no. 2, pp. 155–167, 1992. View at Publisher · View at Google Scholar
  8. S. Chandra, S. Gioskos, B. D. James, B. J. Macauley, and R. J. Magee, “Studies on the fungicidal properties of some triphenyltin(IV) compounds,” Journal of Chemical Technology and Biotechnology, vol. 56, no. 1, pp. 41–44, 1993.
  9. B. D. James, L. M. Kivlighon, B. W. Skelton, and A. H. White, “Triphenyltin(IV) compounds with biologically active anionic groups: crystal and molecular structures of the p-ethoxybenzoic acid, acetylsalicylic acid, phthalic acid and salicylaldehyde derivatives,” Applied Organometallic Chemistry, vol. 12, no. 1, pp. 13–23, 1998. View at Publisher · View at Google Scholar
  10. S. K. Hadjikakou and N. Hadjiliadis, “Antiproliferative and anti-tumor activity of organotin compounds,” Coordination Chemistry Reviews, vol. 253, no. 1-2, pp. 235–249, 2009. View at Publisher · View at Google Scholar
  11. C.-L. Ma, Y.-W. Han, and R.-F. Zhang, “Syntheses and crystal structures of di- and triorganotin(IV) derivatives with 2,4,5-trifluoro-3-methoxybenzoic acid,” Polyhedron, vol. 25, no. 17, pp. 3405–3412, 2006. View at Publisher · View at Google Scholar
  12. A. K. Saxena and F. Huber, “Organotin compounds and cancer chemotherapy,” Coordination Chemistry Reviews, vol. 95, no. 1, pp. 109–123, 1989. View at Publisher · View at Google Scholar
  13. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Synthesis and characterization of a new chloro-di-phenyltin(IV) complex with 2-mercapto-nicotinic acid: study of its influence upon the catalytic oxidation of linoleic acid to hydroperoxylinoleic acid by the enzyme lipoxygenase,” Journal of Organometallic Chemistry, vol. 691, no. 8, pp. 1780–1789, 2006. View at Publisher · View at Google Scholar
  14. V. I. Balas, S. K. Hadjikakou, N. Hadjiliadis, et al., “Crystal structure and antitumor activity of the novel zwitterionic complex of tri-n-butyltin(IV) with 2-thiobarbituric acid,” Bioinorganic Chemistry and Applications, vol. 2008, Article ID 654137, 5 pages, 2008. View at Publisher · View at Google Scholar · View at PubMed
  15. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Biological studies of new organotin(IV) complexes of thioamide ligands,” European Journal of Medicinal Chemistry, vol. 43, no. 2, pp. 327–335, 2008. View at Publisher · View at Google Scholar · View at PubMed
  16. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Biological studies of organotin(IV) complexes with 2-mercaptopyrimidine,” Russian Chemical Bulletin, vol. 56, no. 4, pp. 767–773, 2007. View at Publisher · View at Google Scholar
  17. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Communication: synthesis of a novel triphenyltin(IV) derivative of 2- mercaptonicotinic acid with potent cytotoxicity in vitro,” Bioinorganic Chemistry and Applications, vol. 1, no. 3-4, pp. 227–231, 2004. View at Publisher · View at Google Scholar · View at PubMed
  18. M. Gielen and E. R. T. Tiekink, “S50n tin compounds and their therapeutic potential,” in Metallotherapeutic Drugs & Metal-Based Diagnostic Agents: The Use of Metals in Medicine, M. Gielen and E. R. T. Tiekink, Eds., pp. 421–439, John Wiley & Sons, Chichester, UK, 2005. View at Publisher · View at Google Scholar
  19. A. Jancsó, L. Nagy, E. Moldrheim, and E. Sletten, “Potentiometric and spectroscopic evidence for co-ordination of dimethyltin(IV) to phosphate groups of DNA fragments and related ligands,” Journal of the Chemical Society, Dalton Transactions, no. 10, pp. 1587–1594, 1999. View at Publisher · View at Google Scholar
  20. A. Casini, L. Messori, P. Orioli, M. Gielen, M. Kemmer, and R. Willem, “Interactions of two cytotoxic organotin(IV) compounds with calf thymus DNA,” Journal of Inorganic Biochemistry, vol. 85, no. 4, pp. 297–300, 2001. View at Publisher · View at Google Scholar
  21. L. Ghys, M. Biesemans, M. Gielen, et al., “Multinuclear 1D and 2D NMR investigations on the interaction between the pyrimidic nucleotides 5′-CMP, 5′-dCMP, and 5′-UMP and diethyltin dichloride in aqueous medium,” European Journal of Inorganic Chemistry, vol. 2000, no. 3, pp. 513–522, 2000. View at Publisher · View at Google Scholar
  22. Z. Yang, T. Bakas, A. Sanchez-Diaz, C. Charalampopoulos, J. Tsangaris, and N. Hadjiliadis, “Interaction of Et2SnCl2 with 5′-IMP and 5′-GMP,” Journal of Inorganic Biochemistry, vol. 72, no. 3-4, pp. 133–140, 1998. View at Publisher · View at Google Scholar
  23. S. P. Narula, S. K. Bharadwaj, Y. Sharda, R. Day, L. Howe, and R. R. Holmes, “Dimeric structures of di-n-butyltin(IV) ortho-substituted dibenzoates,” Organometallics, vol. 11, no. 6, pp. 2206–2211, 1992. View at Publisher · View at Google Scholar
  24. T. S. Basu Baul and E. R. T. Tiekink, “Bis(2-hydroxybenzoato-O,O′)dimethyltin,” Acta Crystallographica Section C, vol. 52, part 8, pp. 1959–1961, 1996. View at Publisher · View at Google Scholar
  25. M. K. Rauf, M. A. Saeed, Imtiaz-ud-Din, M. Bolte, A. Badshah, and B. Mirza, “Synthesis, characterization and biological activities of some new organotin(IV) derivatives: crystal structure of [(SnPh3)(OOCC6H4OH)] and [(SnMe3)2(OOC)2C6Cl4(DMSO)2],” Journal of Organometallic Chemistry, vol. 693, no. 18, pp. 3043–3048, 2008. View at Publisher · View at Google Scholar
  26. G. E. Dunn and R. S. McDonal, “Infrared spectra of aqueous sodium benzoates and salicylates in the carboxyl-stretching region: chelation in aqueous sodium salicylates,” Canadian Journal of Chemistry, vol. 47, no. 24, pp. 4577–4588, 1969. View at Publisher · View at Google Scholar
  27. C. H. Specht and F. H. Frimmel, “An in situ ATR-FTIR study on the adsorption of dicarboxylic acids onto kaolinite in aqueous suspensions,” Physical Chemistry Chemical Physics, vol. 3, no. 24, pp. 5444–5449, 2001. View at Publisher · View at Google Scholar
  28. N. Hadjiliadis and T. Theophanides, “Infrared studies on complexes of platinum with adenosine and derivatives,” Canadian Journal of Spectroscopy, vol. 16, p. 134, 1971.
  29. N. Hadjiliadis, A. Yannopoulos, and R. Bau, “Complexes of mercury(II) with thiamine,” Inorganica Chimica Acta, vol. 69, pp. 109–115, 1983. View at Publisher · View at Google Scholar
  30. A. Szorcsik, L. Nagy, J. Sletten, et al., “Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids,” Journal of Organometallic Chemistry, vol. 689, no. 7, pp. 1145–1154, 2004. View at Publisher · View at Google Scholar
  31. T. K. Sham and G. M. Bancroft, “Tin-119 Mössbauer quadrupole splittings for distorted dimethyltin(IV) structures,” Inorganic Chemistry, vol. 14, no. 9, pp. 2281–2283, 1975. View at Publisher · View at Google Scholar
  32. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Synthesis, structural characterization and in vitro cytotoxicity of organotin(IV) derivatives of heterocyclic thioamides, 2-mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, 3-methyl-2-mercaptobenzothiazole and 2-mercaptonicotinic acid,” Journal of Inorganic Biochemistry, vol. 96, no. 2-3, pp. 425–434, 2003. View at Publisher · View at Google Scholar
  33. M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, et al., “Synthesis, structural characterization, and biological studies of six- and five-coordinate organotin(IV) complexes with the thioamides 2- mercaptobenzothiazole, 5-chloro-2-mercaptobenzothiazole, and 2 -mercaptobenzoxazole,” Inorganic Chemistry, vol. 46, no. 4, pp. 1187–1195, 2007. View at Publisher · View at Google Scholar · View at PubMed
  34. M. Bouâlam, R. Willem, M. Biesemans, and M. Gielen, “Synthesis, characterization and in vitro antitumor activity of dimethyl-, diethyl, and di-t-butyl-tin(IV) derivatives of substituted salicylic acids,” Applied Organometallic Chemistry, vol. 5, no. 6, pp. 497–506, 1991. View at Publisher · View at Google Scholar
  35. S.-G. Teoh, S.-H. Ang, and J.-P. Declercq, “Synthesis and characterization of di-n-butylbis(2,4-dihydroxybenzoato)tin(IV),” Polyhedron, vol. 16, no. 21, pp. 3729–3733, 1997. View at Publisher · View at Google Scholar
  36. S. S. Batsanov, “Van der Waals radii of elements,” Inorganic Materials, vol. 37, no. 9, pp. 871–885, 2001. View at Publisher · View at Google Scholar
  37. KUMA KM-4CCD user manual, “KUMA Diffraction,” Wroclaw, Poland, 1999.
  38. CRYSALIS, “Program for Reduction of the Data from KUMA CCD Diffractometer,” KUMA Diffraction, Wroclaw, Poland, 1999.
  39. R. H. Blessing, “DREADD—data reduction and error analysis for single-crystal diffractometer data,” Journal of Applied Crystallography, vol. 22, part 4, pp. 396–397, 1989. View at Publisher · View at Google Scholar
  40. G. M. Sheldrick, “Phase annealing in SHELX-90: direct methods for larger structures,” Acta Crystallographica Section A, vol. 46, part 6, pp. 467–473, 1990. View at Publisher · View at Google Scholar
  41. G. M. Sheldrick, “SHELXL-97, Program for the Refinement of Crystal Structures,” University of Göttingen, Göttingen, Germany, 1997.