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Bioinorganic Chemistry and Applications
Volume 2014, Article ID 354138, 9 pages
http://dx.doi.org/10.1155/2014/354138
Research Article

Synthesis, Characterization, DNA Interaction, and Antitumor Activities of La (III) Complex with Schiff Base Ligand Derived from Kaempferol and Diethylenetriamine

1Rongchang Campus, Southwest University, Chongqing 402460, China
2Pharmacy College, Ningxia Medical University, Yinchuan 750004, China
3School of Chemistry and Material Science, Guizhou Normal University, Guiyang 550001, China

Received 14 May 2014; Revised 2 August 2014; Accepted 4 August 2014; Published 12 October 2014

Academic Editor: Nick Katsaros

Copyright © 2014 Qin Wang 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. H. Junicke and C. Bruhn, “Carbohydrates coordinated to platinum(IV) through hydroxyl groups: a new class of platinum complexes with bioactive ligands,” Angewandte Chemie International Edition, vol. 36, no. 23, pp. 2686–2688, 1997. View at Google Scholar
  2. Z. J. Guo and P. J. Sadler, “Metals in medicine,” Angewandte Chemie International Edition, vol. 38, no. 11, pp. 1512–1531, 1999. View at Google Scholar
  3. S. P. Fricker, “The therapeutic application of lanthanides,” Chemical Society Reviews, vol. 35, no. 6, pp. 524–533, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. F. Biba, M. Groessl, A. Egger, A. Roller, C. G. Hartinger, and B. K. Keppler, “New insights into the chemistry of the antineoplastic lanthanum complex tris(1,10-phenanthroline)tris(thiocyanato-κN)lanthanum(III) (KP772) and its interaction with biomolecules,” European Journal of Inorganic Chemistry, vol. 2009, no. 28, pp. 4282–4287, 2009. View at Publisher · View at Google Scholar
  5. 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 Scopus
  6. I. Kostova and G. Momekov, “New cerium(III) complexes of coumarins—synthesis, characterization and cytotoxicity evaluation,” European Journal of Medicinal Chemistry, vol. 43, no. 1, pp. 178–188, 2008. View at Publisher · View at Google Scholar · View at Scopus
  7. A. Kulkarni, S. A. Patil, and P. S. Badami, “Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La(III), Th(IV) and VO(IV) complexes with Schiff bases of coumarin derivatives,” European Journal of Medicinal Chemistry, vol. 44, no. 7, pp. 2904–2912, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. J. G. Chen, X. Qiao, Y. C. Gao et al., “Synthesis, DNA binding, photo-induced DNA cleavage and cell cytotoxicity studies of a family of light rare earth complexes,” Journal of Inorganic Biochemistry, vol. 109, pp. 90–96, 2012. View at Publisher · View at Google Scholar
  9. F.-Z. Chen, X.-M. Tan, C.-Y. Liu et al., “Synthesis, characterization and preliminary cytotoxicity evaluation of five Lanthanide(III)-Plumbagin complexes,” Journal of Inorganic Biochemistry, vol. 105, no. 3, pp. 426–434, 2011. View at Publisher · View at Google Scholar
  10. Z.-F. Chen and H. Liang, “Progresses in TCM metal-based antitumour agents,” Anti-Cancer Agents in Medicinal Chemistry, vol. 10, no. 5, pp. 412–423, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. C. D. Kanakis, A. P. Tarantilis, and M. G. Polissiou, “An overview of DNA and RNA bindings to antioxidant flavonoids,” Cell Biochemistry and Biophysics, vol. 49, pp. 29–36, 2007. View at Publisher · View at Google Scholar
  12. R. J. Nijveldt, E. van Nood, D. E. C. van Hoorn, P. G. Boelens, K. van Norren, and P. A. M. van Leeuwen, “Flavonoids: a review of probable mechanisms of action and potential applications,” The American Journal of Clinical Nutrition, vol. 74, no. 4, pp. 418–425, 2001. View at Google Scholar · View at Scopus
  13. J. A. Dugas, J. Castaneda-Acosta, and G. C. J. Bonin, “Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships,” Journal of Natural Products, vol. 63, pp. 327–331, 2000. View at Publisher · View at Google Scholar
  14. G. Dehghan, A. Shafiee, M. H. Ghahremani, S. K. Ardestani, and M. Abdollahi, “Antioxidant potential of various extracts from Ferula szovitsiana in relation to their phenolic content,” Pharmaceutical Biology, vol. 45, no. 9, pp. 691–699, 2007. View at Publisher · View at Google Scholar · View at Scopus
  15. M. Thapa, Y. Kim, J. Desper, K.-O. Chang, and D. H. Hua, “Synthesis and antiviral activity of substituted quercetins,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 1, pp. 353–356, 2012. View at Publisher · View at Google Scholar · View at Scopus
  16. J. Zhou, F. L. Wang, Y. J. Wang, and N. Tang, “Synthesis, characterization, antioxidative and antitumor activities of solid quercetin rare earth(III) complexes,” Journal of Inorganic Biochemistry, vol. 83, pp. 41–48, 2001. View at Publisher · View at Google Scholar
  17. J. Tan, C. B. Wang, and L. C. Zhu, “DNA binding, cytotoxicity, apoptotic inducing activity, and molecular modeling study of quercetin zinc (II) complex,” Bioorganic & Medicinal Chemistry, vol. 17, no. 2, pp. 614–620, 2009. View at Google Scholar
  18. G. Dehghan and Z. Khoshkam, “Tin(II)-quercetin complex: synthesis, spectral characterisation and antioxidant activity,” Food Chemistry, vol. 131, no. 2, pp. 422–426, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. M. Kopacz, E. Woznicka, and J. Gruszecka, “Antibacterial activity of morin and its complexes with La (III), Gd (III) and Lu (III) ions,” Acta Potoniae Pharmaceutica-Drug Research, vol. 62, no. 1, pp. 65–67, 2005. View at Google Scholar
  20. B. D. Wang, Z. Y. Yang, Q. Wang, T. K. Cai, and P. Crewdsonc, “Synthesis, characterization, cytotoxic activities, and DNA-binding properties of the La(III) complex with Naringenin Schiff-base,” Bioorganic & Medicinal Chemistry, vol. 14, no. 6, pp. 1880–1888, 2006. View at Google Scholar
  21. Y. Li, Y. Z. Yang, and M. F. Wang, “Synthesis, characterization, DNA binding properties and antioxidant activity of Ln(III) complexes with hesperetin-4-one-(benzoyl) hydrazone,” European Journal of Medicinal Chemistry, vol. 44, pp. 4585–4595, 2009. View at Publisher · View at Google Scholar
  22. C. S. Bestwick, L. Milne, L. Pirie, and S. J. Duthie, “The effect of short-term kaempferol exposure on reactive oxygen levels and integrity of human (HL-60) leukaemic cells,” Biochimica et Biophysica Acta: Molecular Basis of Disease, vol. 1740, no. 3, pp. 340–349, 2005. View at Publisher · View at Google Scholar · View at Scopus
  23. C. S. Bestwick, L. Milne, and S. J. Duthie, “Kaempferol induced inhibition of HL-60 cell growth results from a heterogeneous response, dominated by cell cycle alterations,” Chemico-Biological Interactions, vol. 170, no. 2, pp. 76–85, 2007. View at Publisher · View at Google Scholar · View at Scopus
  24. G. W. Zhang, J. B. Guo, N. Zhao, and J. R. Wang, “Study of interaction between kaempferol-Eu3+ complex and DNA with the use of the Neutral Red dye as a fluorescence probe,” Sensors and Actuators B: Chemical, vol. 144, no. 1, pp. 239–246, 2010. View at Publisher · View at Google Scholar
  25. X. B. Yang, Q. Wang, Y. Huang, P. H. Fu, S. J. Zhang, and R. Q. Zeng, “Synthesis, DNA interaction and antimicrobial activities of copper (II) complexes with Schiff base ligands derived from kaempferol and polyamines,” Inorganic Chemistry Communications, vol. 25, pp. 55–59, 2012. View at Google Scholar
  26. I. Manolova, I. Kostovab, S. Konstantinovc, and M. Karaivanovac, “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 Google Scholar
  27. J. Kang, Y. Liu, X. M. Xie, S. Li, M. Jiang, and Y. D. Wang, “Interactions of human serum albumin with chlorogenic acid and ferulic acid,” Biochimica et Biophysica Acta, vol. 1674, pp. 205–214, 2004. View at Publisher · View at Google Scholar
  28. S. B. Bukhari, S. Memon, M. Mahroof-Tahir, and M. I. Bhanger, “Synthesis, characterization and antioxidant activity copper-quercetin complex,” Spectrochimica Acta A, vol. 71, no. 5, pp. 1901–1906, 2009. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Kuwabara, C. Yoon, T. Goyne, T. Thederahn, and D. S. Sigman, “Nuclease activity of 1,10-phenanthroline-copper ion: reaction with CGCGAATTCGCG and its complexes with netropsin and EcoRI,” Biochemistry, vol. 25, no. 23, pp. 7401–7408, 1986. View at Publisher · View at Google Scholar · View at Scopus
  30. T. Thederahn, A. Spassky, and M. D. Kuwabara, “Chemical nuclease activity of 5-phenyl-1,10-phenanthroline-copper ion detects intermediates in transcription initiation by E. Coli RNA polymerase,” Biochemical and Biophysical Research Communications, vol. 168, pp. 756–762, 1990. View at Publisher · View at Google Scholar
  31. M. R. Eftink and C. A. Ghiron, “Fluorescence quenching studies with proteins,” Analytical Biochemistry, vol. 114, no. 2, pp. 199–227, 1981. View at Publisher · View at Google Scholar · View at Scopus
  32. J. R. Lakowicz and G. Weber, “Quenching of fluorescence by oxygen: a probe for structural fluctuations in macromolecules,” Biochemistry, vol. 12, no. 21, pp. 4161–4170, 1973. View at Publisher · View at Google Scholar · View at Scopus
  33. D. Silva, C. M. Cortez, and S. R. W. Louro, “Chlorpromazine interactions to sera albumins: a study by the quenching of fluorescence,” Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy, vol. 60, no. 5, pp. 1215–1223, 2004. View at Publisher · View at Google Scholar · View at Scopus
  34. M. Jiang, X. M. Xie, D. Zheng, Y. Liu, Y. X. Li, and X. J. Chen, “Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin,” Journal of Molecular Structure, vol. 692, pp. 71–80, 2004. View at Publisher · View at Google Scholar
  35. S. Geng, G. Liu, W. Li, and F. Cui, “Molecular interaction of ctDNA and HSA with sulfadiazine sodium by multispectroscopic methods and molecular modeling,” Luminescence, vol. 28, no. 5, pp. 785–792, 2013. View at Publisher · View at Google Scholar · View at Scopus
  36. J. G. Collins, T. P. Shields, and J. K. Barton, “1H-NMR of Rh(NH3)4phi3+ bound to d(TGGCCA)2: classical intercalation by a nonclassical octahedral metallointercalator,” Journal of the American Chemical Society, vol. 116, no. 22, pp. 9840–9846, 1994. View at Publisher · View at Google Scholar · View at Scopus
  37. B. Norden and F. Tjerneld, “Structure of methylene blue-DNA complexes studied by linear and circular dichroism spectroscopy,” Biopolymers, vol. 21, no. 9, pp. 1713–1734, 1982. View at Publisher · View at Google Scholar · View at Scopus
  38. M. Tabatabaee, M. Bordbar, M. Ghassemzadeh et al., “Two new neutral copper(II) complexes with dipicolinic acid and 3-amino-1H-1,2,4-triazole formed under different reaction conditions: Synthesis, characterization, molecular structures and DNA-binding studies,” European Journal of Medicinal Chemistry, vol. 70, pp. 364–371, 2013. View at Publisher · View at Google Scholar · View at Scopus
  39. L. S. Lerman, “Structural considerations in the interaction of DNA and acridines,” Journal of Molecular Biology, vol. 3, pp. 18–30, 1961. View at Publisher · View at Google Scholar
  40. S. Satyanarayana, C. J. Dabrowiak, and J. B. Chairs, “Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: Mode and specificity of binding,” Biochemistry, vol. 32, no. 10, pp. 2573–2583, 1993. View at Publisher · View at Google Scholar