Table of Contents
Metal-Based Drugs
Volume 2007 (2007), Article ID 15925, 8 pages
http://dx.doi.org/10.1155/2007/15925
Research Article

New Samarium(III), Gadolinium(III), and Dysprosium(III) Complexes of Coumarin-3-Carboxylic Acid as Antiproliferative Agents

1Department of Chemistry, Faculty of Pharmacy, Medical University, 2 Dunav Street, Sofia 1000, Bulgaria
2Department of Pharmacology and Toxicology, Faculty of Pharmacy, Medical University, 2 Dunav Street, Sofia 1000, Bulgaria
3Department of Inorganic Chemistry, University of Sofia, Sofia 1000, Bulgaria

Received 31 August 2006; Revised 16 November 2006; Accepted 27 December 2006

Academic Editor: Domenico Osella

Copyright © 2007 Irena Kostova 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. D. Egan, R. O'Kennedy, E. Moran, D. Cox, E. Prosser, and R. D. Thornes, “The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds,” Drug Metabolism Reviews, vol. 22, no. 5, pp. 503–529, 1990.
  2. J. R. S. Hoult and M. Payá, “Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential,” General Pharmacology, vol. 27, no. 4, pp. 713–722, 1996. View at Publisher · View at Google Scholar
  3. P. Laurin, D. Ferroud, and M. Klich et al., “Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B,” Bioorganic and Medicinal Chemistry Letters, vol. 9, no. 14, pp. 2079–2084, 1999. View at Publisher · View at Google Scholar
  4. A. Matsumoto and P. C. Hanawalt, “Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts,” Cancer Research, vol. 60, no. 14, pp. 3921–3926, 2000.
  5. V. P. Kelly, E. M. Ellis, and M. M. Manson et al., “Chemoprevention of aflatoxin B1 hepatocarcinogenesis by coumarin, a natural benzopyrone that is a potent inducer of aflatoxin B1-aldehyde reductase, the glutathione S-transferase A5 and P1 subunits, and NAD(P)H: quinone oxidoreductase in rat liver,” Cancer Research, vol. 60, no. 4, pp. 957–969, 2000.
  6. S. Kirkiacharian, D. T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire, “Structure-activity relationships of some 3-substituted-4-hydroxycoumarins as HIV-1 protease inhibitors,” Il Farmaco, vol. 57, no. 9, pp. 703–708, 2002. View at Publisher · View at Google Scholar
  7. D. Yu, M. Suzuki, L. Xie, S. L. Morris-Natschke, and K.-H. Lee, “Recent progress in the development of coumarin derivatives as potent anti-HIV agents,” Medicinal Research Reviews, vol. 23, no. 3, pp. 322–345, 2003. View at Publisher · View at Google Scholar · View at PubMed
  8. E. M. Marshall, M. Ryles, K. Butler, and L. Weiss, “Treatment of advanced renal cell carcinoma (RCC) with coumarin and cimetidine: longterm follow-up of patients treated on a phase I trial,” Journal of Cancer Research and Clinical Oncology, vol. 120, pp. 535–538, 1994.
  9. D. Conley and E. M. Marshall, “Effects of coumarin on human tumour cell growth and cell cycle analysis in vitro,” Proceedings of the American Association for Cancer Research, vol. 28, p. 63, 1987.
  10. R. D. Thornes, L. Daly, and G. Lynch et al., “Treatment with coumarin to prevent or delay recurrence of malignant melanoma,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S32–S34, 1994. View at Publisher · View at Google Scholar
  11. M. E. Marshall, J. L. Mohler, and K. Edmonds et al., “An updated review of the clinical development of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S39–S42, 1994. View at Publisher · View at Google Scholar
  12. J. L. Mohler, B. T. Williams, I. M. Thompson, and M. E. Marshall, “Coumarin (1,2-benzopyrone) for the treatment of prostatic carcinoma,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S35–S38, 1994. View at Publisher · View at Google Scholar
  13. E. von Angerer, M. Kager, and A. Maucher, “Antitumour activity of coumarin in prostate and mammary cancer models,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S14–S16, 1994. View at Publisher · View at Google Scholar
  14. B. G. Lake, “Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment,” Food and Chemical Toxicology, vol. 37, no. 4, pp. 423–453, 1999. View at Publisher · View at Google Scholar
  15. M. E. Marshall, K. Butler, and A. Fried, “Phase I evaluation of coumarin (1,2-benzopyrone) and cimetidine in patients with advanced malignancies,” Molecular Biotherapy, vol. 3, no. 3, pp. 170–178, 1991.
  16. M. E. Marshall, K. Kervin, and C. Benefield et al., “Growth-inhibitory effects of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin on human malignant cell lines in vitro,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S3–S10, 1994. View at Publisher · View at Google Scholar
  17. R. B. Myers, M. Parker, and W. E. Grizzle, “The effects of coumarin and suramin on the growth of malignant renal and prostatic cell lines,” Journal of Cancer Research and Clinical Oncology, vol. 120, supplement 1, pp. S11–S13, 1994. View at Publisher · View at Google Scholar
  18. S. Kawaii, Y. Tomono, K. Ogawa, M. Sugiura, M. Yano, and Y. Yoshizawa, “The antiproliferative effect of coumarins on several cancer cell lines,” Anticancer Research, vol. 21, no. 2A, pp. 917–923, 2001.
  19. I. Kostova, I. Manolov, I. Nicolova, S. Konstantinov, and M. Karaivanova, “New lanthanide complexes of 4-methyl-7-hydroxycoumarin and their pharmacological activity,” European Journal of Medicinal Chemistry, vol. 36, no. 4, pp. 339–347, 2001. View at Publisher · View at Google Scholar
  20. I. Kostova, I. Manolov, S. Konstantinov, and M. Karaivanova, “Synthesis, physicochemical characterisation and cytotoxic screening of new complexes of cerium, lanthanum and neodymium with Warfarin and Coumachlor sodium salts,” European Journal of Medicinal Chemistry, vol. 34, no. 1, pp. 63–68, 1999. View at Publisher · View at Google Scholar
  21. I. Manolov, I. Kostova, S. Konstantinov, and M. Karaivanova, “Synthesis, physicochemical characterization and cytotoxic screening of new complexes of cerium, lanthanum and neodymium with Niffcoumar sodium salt,” European Journal of Medicinal Chemistry, vol. 34, no. 10, pp. 853–858, 1999. View at Publisher · View at Google Scholar
  22. I. Manolov, I. Kostova, T. Netzeva, S. Konstantinov, and M. Karaivanova, “Cytotoxic activity of cerium complexes with coumarin derivatives. Molecular modeling of the ligands,” Archiv der Pharmazie: Pharmaceutical and Medicinal Chemistry, vol. 333, no. 4, pp. 93–98, 2000. View at Publisher · View at Google Scholar
  23. I. Kostova, I. Manolov, I. Nicolova, and N. D. Danchev, “New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity,” Il Farmaco, vol. 56, no. 9, pp. 707–713, 2001. View at Publisher · View at Google Scholar
  24. I. Kostova, I. Manolov, and M. Karaivanova, “Synthesis, physicochemical characterization, and cytotoxic screening of new zirconium complexes with coumarin derivatives,” Archiv der Pharmazie: Pharmaceutical and Medicinal Chemistry, vol. 334, no. 5, pp. 157–162, 2001. View at Publisher · View at Google Scholar
  25. I. Kostova, I. Manolov, and G. Momekov, “Cytotoxic activity of new neodymium (III) complexes of bis-coumarins,” European Journal of Medicinal Chemistry, vol. 39, no. 9, pp. 765–775, 2004. View at Publisher · View at Google Scholar · View at PubMed
  26. I. Kostova, N. Trendafilova, and G. Momekov, “Theoretical and spectroscopic evidence for coordination ability of 3,3-benzylidenedi-4-hydroxycoumarin. New neodymium (III) complex and its cytotoxic effect,” Journal of Inorganic Biochemistry, vol. 99, no. 2, pp. 477–487, 2005. View at Publisher · View at Google Scholar · View at PubMed
  27. I. Kostova, G. Momekov, M. Zaharieva, and M. Karaivanova, “Cytotoxic activity of new lanthanum (III) complexes of bis-coumarins,” European Journal of Medicinal Chemistry, vol. 40, no. 6, pp. 542–551, 2005. View at Publisher · View at Google Scholar · View at PubMed
  28. I. Kostova, N. Trendafilova, and T. Mihaylov, “Theoretical and spectroscopic studies of pyridyl substituted bis-coumarins and their new neodymium (III) complexes,” Chemical Physics, vol. 314, no. 1–3, pp. 73–84, 2005. View at Publisher · View at Google Scholar
  29. I. Kostova, I. Manolov, G. Momekov, T. Tzanova, S. Konstantinov, and M. Karaivanova, “Cytotoxic activity of new cerium (III) complexes of bis-coumarins,” European Journal of Medicinal Chemistry, vol. 40, no. 12, pp. 1246–1254, 2005. View at Publisher · View at Google Scholar · View at PubMed
  30. H. G. Drexler, R. A. F. MacLeod, and C. C. Uphoff, “Leukemia cell lines: in vitro models for the study of Philadelphia chromosome-positive leukemia,” Leukemia Research, vol. 23, no. 3, pp. 207–215, 1999. View at Publisher · View at Google Scholar
  31. Tz. Mihaylov, N. Trendafilova, I. Kostova, I. Georgieva, and G. Bauer, “DFT modeling and spectroscopic study of metal-ligand bonding in La(III) complex of coumarin-3-carboxylic acid,” Chemical Physics, vol. 327, no. 2-3, pp. 209–219, 2006. View at Publisher · View at Google Scholar
  32. I. Georgieva, N. Trendafilova, W. Kiefer, V. K. Rastogi, and I. Kostova, “Vibrational and theoretical study of coumarin-3-carboxylic acid binding mode in Ce(III) and Nd(III) complexes,” to appear in Vibrational Spectroscopy.