Table of Contents Author Guidelines Submit a Manuscript
The Scientific World Journal
Volume 2014, Article ID 540463, 12 pages
http://dx.doi.org/10.1155/2014/540463
Research Article

A Schiff Base-Derived Copper (II) Complex Is a Potent Inducer of Apoptosis in Colon Cancer Cells by Activating the Intrinsic Pathway

1Department of Biomedical Science, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
2Faculty of Science, Institute of Biological Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
3Department of Pharmacology, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
4Department of Chemistry, University of Malaya, University of Malaya, 50603 Kuala Lumpur, Malaysia

Received 15 November 2013; Accepted 16 January 2014; Published 5 March 2014

Academic Editors: M. W. Jann and F. M. Mahomoodally

Copyright © 2014 Maryam Hajrezaie 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. S. E. Atawodi, “Nigerian foodstuffs with prostate cancer chemopreventive polyphenols,” Infectious Agents and Cancer, vol. 6, supplement 2, article S9, 2011. View at Publisher · View at Google Scholar · View at Scopus
  2. R. Siegel, C. DeSantis, K. Virgo et al., “Cancer treatment and survivorship statistics, 2012,” CA: A Cancer Journal for Clinicians, vol. 62, no. 4, pp. 220–241, 2012. View at Publisher · View at Google Scholar
  3. H. Li, W. K. K. Wu, Z. Zheng et al., “2,3′,4,4′,5′-pentamethoxy-trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting microtubules,” Biochemical Pharmacology, vol. 78, no. 9, pp. 1224–1232, 2009. View at Publisher · View at Google Scholar · View at Scopus
  4. D. Kranz and M. Dobbelstein, “A killer promoting survival: p53 as a selective means to avoid side effects of chemotherapy,” Cell Cycle, vol. 11, no. 11, pp. 2053–2054, 2012. View at Publisher · View at Google Scholar
  5. D. Hanahan and R. A. Weinberg, “The hallmarks of Cancer,” Cell, vol. 100, no. 1, pp. 57–70, 2000. View at Publisher · View at Google Scholar · View at Scopus
  6. X. Hao, M. Du, A. E. Bishop, and I. Talbot, “Imbalance between proliferation and apoptosis in the development of colorectal carcinoma,” Virchows Archiv, vol. 433, no. 6, pp. 523–527, 1998. View at Publisher · View at Google Scholar · View at Scopus
  7. J. F. Whitfield, “Calcium, calcium-sensing receptor and colon cancer,” Cancer Letters, vol. 275, no. 1, pp. 9–16, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. C. K. Chan, B. H. Goh, M. N. A. Kamarudin, and H. A. Kadir, “Aqueous fraction of Nephelium ramboutan-ake rind induces mitochondrial-mediated apoptosis in HT-29 human colorectal adenocarcinoma cells,” Molecules, vol. 17, no. 6, pp. 6633–6657, 2012. View at Publisher · View at Google Scholar
  9. I. Kostova, “Gold coordination complexes as anticancer agents,” Anti-Cancer Agents in Medicinal Chemistry, vol. 6, no. 1, pp. 19–32, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. V. Milacic, D. Chen, L. Ronconi, K. R. Landis-Piwowar, D. Fregona, and Q. P. Dou, “A novel anticancer gold(III) dithiocarbamate compound inhibits the activity of a purified 20S proteasome and 26S proteasome in human breast cancer cell cultures and xenografts,” Cancer Research, vol. 66, no. 21, pp. 10478–10486, 2006. View at Publisher · View at Google Scholar · View at Scopus
  11. H. Dollwet and J. Sorenson, “Historic uses of copper compounds in medicine,” Trace Elements in Medicine, vol. 2, no. 2, pp. 80–87, 1985. View at Google Scholar · View at Scopus
  12. A. W. Tai, E. J. Lien, M. M. Lai, and T. A. Khwaja, “Novel N-hydroxyguanidine derivatives as anticancer and antiviral agents,” Journal of Medicinal Chemistry, vol. 27, no. 2, pp. 236–238, 1984. View at Google Scholar · View at Scopus
  13. P. H. Wang, J. G. Keck, E. J. Lien, and M. M. Lai, “Design, synthesis, testing, and quantitative structure-activity relationship analysis of substituted salicylaldehyde Schiff bases of 1-amino-3-hydroxyguanidine tosylate as new antiviral agents against coronavirus,” Journal of Medicinal Chemistry, vol. 33, no. 2, pp. 608–614, 1990. View at Google Scholar · View at Scopus
  14. J. Sorensen, “Copper complexes offer a physiological approach to treatment of chronic leases,” Progress in Medicinal Chemistry, vol. 26, pp. 437–568, 1989. View at Google Scholar
  15. C. Bolos, G. S. Nikolov, L. Ekateriniadou, A. Kortsaris, and D. Kyriakidis, “Structure-activity relationships for some diamine, triamine and Schiff base derivatives and their copper(II) complexes,” Metal-Based Drugs, vol. 5, no. 6, pp. 323–332, 1998. View at Publisher · View at Google Scholar · View at Scopus
  16. A. T. Chaviara, P. Cox, K. Repana et al., “The unexpected formation of biologically active Cu(II) Schiff mono-base complexes with 2-thiophene-carboxaldehyde and dipropylenetriamine: crystal and molecular structure of CudptaSCl2,” Journal of Inorganic Biochemistry, vol. 99, no. 2, pp. 467–476, 2005. View at Publisher · View at Google Scholar · View at Scopus
  17. A. T. Chaviara, P. Cox, K. Repana et al., “Copper(II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5-methyl-thiazole: synthesis, characterization, antiproliferative and antibacterial studies. Crystal structure of CudienOOCl2,” Journal of Inorganic Biochemistry, vol. 98, no. 8, pp. 1271–1283, 2004. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Hajrezaie, S. Golbabapour, P. Hassandarvish et al., “Acute toxicity and gastroprotection studies of a new Schiff base derived copper (II) complex against ethanol-induced acute gastric lesions in rats,” PloS ONE, vol. 7, no. 12, Article ID e51537, 2012. View at Publisher · View at Google Scholar
  19. M. J. Thomson, Y. Paydar, L. Wong et al., “Antibacterial, antioxidant activity and phytochemical studies of Crossandra infundibuliformis leaf extracts,” Pakistan Journal of Biological Sciences, vol. 16, pp. 1212–1215, 2013. View at Google Scholar
  20. S.-C. Cheah, D. R. Appleton, S.-T. Lee, M.-L. Lam, A. H. A. Hadi, and M. R. Mustafa, “Panduratin a inhibits the growth of A549 cells through induction of apoptosis and inhibition of NF-KappaB translocation,” Molecules, vol. 16, no. 3, pp. 2583–2598, 2011. View at Publisher · View at Google Scholar · View at Scopus
  21. M. R. Patel, G. J. Dehmer, J. W. Hirshfeld, P. K. Smith, and J. A. Spertus, “ACCF/SCAI/STS/AATS/AHA/ASNC 2009 appropriateness criteria for coronary revascularization : a report by the American College of Cardiology Foundation Appropriateness Criteria Task Force, Society for Cardiovascular Angiography and Interventions, Society of Thoracic Surgeons, American Association for Thoracic Surgery, American Heart Association, and the American Society of Nuclear Cardiology Endorsed by the American Society of Echocardiography, the Heart Failure Society of America, and the Society of Cardiovascular Computed Tomography,” Journal of the American College of Cardiology, vol. 53, no. 6, pp. 530–553, 2009. View at Publisher · View at Google Scholar · View at Scopus
  22. R. Scatena, “Mitochondria and cancer: a growing role in apoptosis, cancer cell metabolism and dedifferentiation,” in Advances in Mitochondrial Medicine, vol. 942 of Advances in Experimental Medicine and Biology, pp. 287–308, Springer, Amsterdam, The Netherlands, 2012. View at Publisher · View at Google Scholar
  23. T. Verfaillie, A. D. Garg, and P. Agostinis, “Targeting ER stress induced apoptosis and inflammation in cancer,” Cancer Letters, vol. 332, no. 2, pp. 249–264, 2013. View at Publisher · View at Google Scholar · View at Scopus
  24. M. J. Lee, A. S. Ye, A. K. Gardino et al., “Sequential application of anticancer drugs enhances cell death by rewiring apoptotic signaling networks,” Cell, vol. 149, no. 4, pp. 780–794, 2012. View at Google Scholar
  25. A. Chakraborty, P. Kumar, K. Ghosh, and P. Roy, “Evaluation of a Schiff base copper complex compound as potent anticancer molecule with multiple targets of action,” European Journal of Pharmacology, vol. 647, no. 1–3, pp. 1–12, 2010. View at Publisher · View at Google Scholar · View at Scopus
  26. N. A. Rey, A. Neves, P. P. Silva et al., “A synthetic dinuclear copper(II) hydrolase and its potential as antitumoral: cytotoxicity, cellular uptake, and DNA cleavage,” Journal of Inorganic Biochemistry, vol. 103, no. 10, pp. 1323–1330, 2009. View at Publisher · View at Google Scholar · View at Scopus
  27. R. Suzuki, Y. Yasui, H. Kohno et al., “Catalpa seed oil rich in 9t,11t,13c-conjugated linolenic acid suppresses the development of colonic aberrant crypt foci induced by azoxymethane in rats,” Oncology Reports, vol. 16, no. 5, pp. 989–996, 2006. View at Google Scholar · View at Scopus
  28. T.-I. Jeon, C.-H. Jung, J.-Y. Cho, D. K. Park, and J.-H. Moon, “Identification of an anticancer compound against HT-29 cells from Phellinus linteus grown on germinated brown rice,” Asian Pacific Journal of Tropical Biomedicine, vol. 3, no. 10, pp. 785–789, 2013. View at Google Scholar
  29. S. Asciutti, E. Camaioni, P. Mong et al., “Tu1898 therapeutic potential of a novel poly(ADP-ribose) polymerase inhibitor, hydamtiq, in human pancreatic and colon cancers,” Gastroenterology, vol. 144, no. 5, supplement 1, p. 875, 2013. View at Google Scholar
  30. R. A. Schneider, K. G. Eckles, V. C. Kelty et al., “Celecoxib induces apoptosis by the intrinsic pathway in HT-29 colon carcinoma and A375 melanoma cells,” The Faseb Journal, vol. 27, pp. 20814–23998, 2013. View at Google Scholar
  31. E. J. Choi, J. I. Lee, and G.-H. Kim, “Evaluation of the anticancer activities of thioflavanone and thioflavone in human breast cancer cell lines,” International Journal of Molecular Medicine, vol. 29, no. 2, pp. 252–256, 2012. View at Publisher · View at Google Scholar · View at Scopus
  32. J. Ly, D. Grubb, and A. Lawen, “The mitochondrial membrane potential (Δψm) in apoptosis; an update,” Apoptosis, vol. 8, no. 2, pp. 115–128, 2003. View at Publisher · View at Google Scholar · View at Scopus
  33. W. Hu and J. J. Kavanagh, “Anticancer therapy targeting the apoptotic pathway,” The Lancet Oncology, vol. 4, no. 12, pp. 721–729, 2003. View at Publisher · View at Google Scholar · View at Scopus
  34. M. Aarts, R. Sharpe, I. Garcia-Murillas et al., “Forced mitotic entry of S-phase cells as a therapeutic strategy induced by inhibition of WEE1,” Cancer Discovery, vol. 2, no. 6, pp. 524–539, 2012. View at Google Scholar
  35. L. Wang, Y. Xu, L. Fu, and L. Lou, “(5R)-5-hydroxytriptolide (LLDT-8), a novel immunosuppressant in clinical trials, exhibits potent antitumor activity via transcription inhibition,” Cancer Letters, vol. 324, no. 1, pp. 75–82, 2012. View at Google Scholar
  36. A. R. Tentner, M. J. Lee, G. J. Ostheimer, L. D. Samson, D. A. Lauffenburger, and M. B. Yaffe, “Combined experimental and computational analysis of DNA damage signaling reveals context-dependent roles for Erk in apoptosis and G1/S arrest after genotoxic stress,” Molecular Systems Biology, vol. 8, no. 1, article 568, 2012. View at Publisher · View at Google Scholar · View at Scopus
  37. F. Gasparri, P. Cappella, and A. Galvani, “Multiparametric cell cycle analysis by automated microscopy,” Journal of Biomolecular Screening, vol. 11, no. 6, pp. 586–598, 2006. View at Publisher · View at Google Scholar · View at Scopus
  38. W. L. See, J. P. Miller, M. Squatrito, E. Holland, M. D. Resh, and A. Koff, “Defective DNA double-strand break repair underlies enhanced tumorigenesis and chromosomal instability in p27-deficient mice with growth factor-induced oligodendrogliomas,” Oncogene, vol. 29, no. 12, pp. 1720–1731, 2010. View at Publisher · View at Google Scholar · View at Scopus
  39. Y.-J. Liu, Z.-H. Liang, X.-L. Hong, Z.-Z. Li, J.-H. Yao, and H.-L. Huang, “Synthesis, characterization, cytotoxicity, apoptotic inducing activity, cellular uptake, interaction of DNA binding and antioxidant activity studies of ruthenium(II) complexes,” Inorganica Chimica Acta, vol. 387, pp. 117–124, 2012. View at Publisher · View at Google Scholar · View at Scopus
  40. F. Chen, V. Vallyathan, V. Castranova, and X. Shi, “Cell apoptosis induced by carcinogenic metals,” Molecular and Cellular Biochemistry, vol. 222, no. 1-2, pp. 183–188, 2001. View at Publisher · View at Google Scholar · View at Scopus
  41. Y. Zhang, X. Wang, W. Fang et al., “Synthesis and in vitro antitumor activity of two mixed-ligand oxovanadium (IV) complexes of Schiff base and phenanthroline,” Bioinorganic Chemistry and Applications, vol. 2013, Article ID 437134, 14 pages, 2013. View at Publisher · View at Google Scholar
  42. A. Bishayee and A. S. Darvesh, “Pomegranate-derived constituents as inducers of cell death: implications in cancer prevention and therapy,” in Natural Compounds as Inducers of Cell Death, vol. 1, pp. 33–47, Springer, Amesterdam, The Netherlands, 2012. View at Publisher · View at Google Scholar
  43. L. Y. Li, X. Luo, and X. Wang, “Endonuclease G is an apoptotic DNase when released from mitochondria,” Nature, vol. 412, pp. 95–99, 2001. View at Publisher · View at Google Scholar · View at Scopus
  44. R. El-Ghany, N. Sharaf, L. Kassem, L. Mahran, and O. Heikal, “Thymoquinone triggers anti-apoptotic signaling targeting death ligand and apoptotic regulators in a model of hepatic ischemia reperfusion injury,” Drug Discoveries & Therapeutics, vol. 3, no. 6, pp. 296–306, 2009. View at Google Scholar
  45. M. Hyer, R. Shi, M. Krajewska et al., “Apoptotic activity and mechanism of 2-cyano-3,12-dioxoolean-1,9-dien-28- oic-acid and related synthetic triterpenoids in prostate cancer,” Cancer Research, vol. 68, no. 8, pp. 2927–2933, 2008. View at Publisher · View at Google Scholar · View at Scopus
  46. F. Qi, A. Li, Y. Inagaki et al., “Induction of apoptosis by cinobufacini preparation through mitochondria- and Fas-mediated caspase-dependent pathways in human hepatocellular carcinoma cells,” Food and Chemical Toxicology, vol. 50, no. 2, pp. 295–302, 2012. View at Publisher · View at Google Scholar · View at Scopus