213
Views
11
CrossRef citations to date
0
Altmetric
Research Articles

Copper(II), cobalt(II) and nickel(II) complexes of lapachol: synthesis, DNA interaction, and cytotoxicity

, &
Pages 3330-3341 | Received 31 Aug 2016, Accepted 20 Oct 2016, Published online: 26 Dec 2016

References

  • Barton, J. K., Goldberg, J. M., Kumar, C. V., & Turro, N. J. (1986). Binding modes and base specificity of tris(phenanthroline) ruthenium(II) enantiomers with nucleic acids: Tuning the stereoselectivity. Journal of the American Chemical Society, 108, 2081–2088. doi:10.1021/ja00268a057.
  • Bustamante, F. L. S., Miranda, F. S., Castro, F. A. V., Resende, J. A. L. C., Pereira, M. D., & Lanznaster, M. (2014). A study on the properties and reactivity of naphthoquinone-cobalt(III) prototypes for bioreductive prodrugs. Journal of Inorganic Biochemistry, 132, 37–44. doi:10.1016/j.jinorgbio.2013.11.007.
  • Carter, M. T., Rodriguez, M., & Bard, A. J. (1989). Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2′-bipyridine. Journal of the American Chemical Society, 111, 8901–8911. doi:10.1021/ja00206a020
  • Chattopadhyay, T., Mukherjee, M., Mondal, A., Maiti, P., Banerjee, A., Banu, K. S., … Das, D. (2010). A unique Nickel system having versatile catalytic activity of biological significance. Inorganic Chemistry, 49, 3121–3129. doi:10.1021/ic901546t
  • Dimiza, F., Fountoulaki, S., Papadopoulos, A. N., Kontogiorgis, C. A., Tangoulis, V., Raptopoulou, C. P., … Psomas, G. (2011). Non-steroidal antiinflammatory drug–copper(II) complexes: Structure and biological perspectives. Dalton Transactions, 40, 8555–8568. doi:10.1039/C1DT10714C
  • Dimiza, F., Papadopoulos, A. N., Tangoulis, V., Psycharis, V., Raptopoulou, C. P., Kessissoglou, D. P., & Psomas, G. (2012). Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen. Journal of Inorganic Biochemistry, 107, 54–64. doi:10.1016/j.jinorgbio.2011.10.014
  • Efthimiadou, E. K., Karaliota, A., & Psomas, G. (2008). Structure, antimicrobial activity and DNA-binding properties of the cobalt(II)-sparfloxacin complex. Bioorganic & Medicinal Chemistry Letters, 18, 4033–4037. doi:10.1016/j.bmcl.2008.05.115.
  • El-Hendawy, A. M. (1991). Complexes of lawsone with uranium, molybdenum, ruthenium and osmium, and their use as organic oxidants. Polyhedron, 10, 2511–2518. doi:10.1016/S0277-5387(00)86217-8
  • Erkkila, K. E., Odom, D. T., & Barton, J. K. (1999). Recognition and reaction of metallointercalators with DNA. Chemical Reviews, 99, 2777–2796. doi:10.1021/cr9804341
  • Finney, L., Vogt, S., Fukai, T., & Glesne, D. (2009). Copper and angiogenesis: Unravelling a relationship key to cancer progression. Clinical and Experimental Pharmacology and Physiology, 36, 88–94. doi:10.1111/j.1440-1681.2008.04969.x
  • Frezza, M., Hindo, S. S., Tomco, D., Allard, M. M., Cui, Q. C., Heeg, M. J., … Verani, C. N. (2009). Comparative activities of nickel(II) and zinc(II) complexes of asymmetric [NN’O] ligands as 26S proteasome inhibitors. Inorganic Chemistry, 48, 5928–5937. doi:10.1021/ic900276g
  • Friedman, A. E., Kumar, C. V., Turro, N. J., & Barton, J. K. (1991). Luminescence of ruthenium(II) polypyridyls: Evidence for intercalative binding to Z-DNA. Nucleic Acids Research, 19, 2595–2602.
  • Garge, P., Padhye, S., & Tauchagues, J. P. (1989). Iron(II) complexes of ortho-functionalized para-naphthoquinones. 1. Synthesis, characterization, electronic structure and magnetic properties. Inorganica Chimica Acta, 157, 239–249. doi:10.1016/S0020-1693(00)80548-4
  • Gokhale, N. H., Shirisha, K., Padhye, S. B., Croft, S. L., Kendrick, H. D., Davies, W., … Powell, A. K. (2003). Transition metal complexes of buparvaquone as potent new antimalarial agents. 1. Synthesis, X-ray crystal-structures, electrochemistry and antimalarial activity against Plasmodium falciparum. Journal of Inorganic Biochemistry, 95, 249–258. doi:10.1016/S0162-0134(03)00134-X.
  • Gokhale, N. H., Shirisha, K., Padhye, S. B., Croft, S. L., Kendrick, H. D., & Mckee, V. (2006). Metalloantimalarials: Synthesis, X-ray crystal structure of potent antimalarial copper (II) complex of arylazo-4-hydroxy-1,2-naphthoquinone. Bioorganic & Medicinal Chemistry Letters, 16, 430–432. doi:10.1016/j.bmcl.2005.09.061
  • Goswami, T. K., Chakravarthi, B. V., Roy, M., Karande, A. A., & Chakravarty, A. R. (2011). Ferrocene-conjugated l-tryptophan copper(II) complexes of phenanthroline bases showing DNA photocleavage activity and cytotoxicity. Inorganic Chemistry, 50, 8452–8464. doi:10.1021/ic201028e
  • Goswami, T. K., Roy, M., Nethaji, M., & Chakravarty, A. R. (2009). Photoinduced DNA and protein cleavage activity of ferrocene-appended l-methionine reduced schiff base copper(II) complexes of phenanthroline bases. Organometallics, 28, 1992–1994. doi:10.1021/om900012b
  • Guerrero, J. S., Sanchez, P. C., Perez, E. R., Garcia, F. V., Gomez, M. E. B., & Azuara, L. R. (2011). Genotoxicity of the copper antineoplastic coordination complexes casiopeinas®. Toxicology in Vitro, 25, 1376–1384. doi:10.1016/j.tiv.2011.05.008
  • Hadjiliadis, N., & Sletten, E. (Eds.). (2009). Metal complex-DNA interactions. Hoboken, NJ: Wiley.
  • Hernandez-Molina, R., Kalinina, I., Esparza, P., Sokolov, M., Gonzalez-Platas, J., Estevez-Braun, A., & Perez-Sacau, E. (2007). Complexes of Co(II), Ni(II) and Cu(II) with lapachol. Polyhedron, 26, 4860–4864. doi:10.1016/j.poly.2007.06.022
  • Hill, J. M., & Sper, R. J. (1981). Organo-platinum complexes as antitumor agents. Anticancer Research, 2, 173–186
  • Jahani, S., Khorasani-Motlagh, M., & Noroozifar, M. (2016). DNA interaction of europium(III) complex containing 2,2′-bipyridine and its antimicrobial activity. Journal of Biomolecular Structure and Dynamics, 34, 612–624. doi:10.1080/07391102.2015.1048481
  • Kandioller, W., Balsano, E., Meier, S. M., Jungwirth, U., Goschl, S., Roller, A., … Hartinger, C. G. (2013). Organometallic anticancer complexes of lapachol: Metal center-dependent formation of reactive oxygen species and correlation with cytotoxicity. Chemical Communications, 49, 3348–3350. doi:10.1039/c3cc40432c
  • Kandioller, W., Kurzwernhart, A., Hanif, M., Henke, H., Keppler, B. K., Meier, S. M., & Hartinger, C. G. (2011). Pyrone derivatives and metals: From natural products to metal-based drugs. Journal of Organometallic Chemistry, 696, 999–1010. doi:10.1016/j.jorganchem.2010.11.010
  • Kelly, T. M., Tossi, A. B., McConnell, D. J., & Strekas, T. C. (1985). A study of the interactions of some polypyridylruthenium (II) complexes with DNA using fluorescence spectroscopy, topoisomerisation and thermal denaturation. Nucleic Acids Research, 13, 6017–6034.
  • Lakowicz, J. R., & Weber, G. (1973). Quenching of fluorescence by oxygen. Probe for structural fluctuations in macromolecules. Biochemistry, 12, 4161–4170. doi:10.1021/bi00745a020
  • Lakshmipraba, J., Arunachalam, S., Solomon, R. V., Venuvanalingam, P., Riyasdeen, A., Dhivya, R., & Akbarsha, M. A. (2015). Surfactant–copper(II) Schiff base complexes: Synthesis, structural investigation, DNA interaction, docking studies, and cytotoxic activity. Journal of Biomolecular Structure & Dynamics, 33, 877–891. doi:10.1080/07391102.2014.918523
  • Lincoln, P., Tuite, E., & Norden, B. (1997). Short-circuiting the molecular wire: cooperative binding of Δ-[Ru(phen)2d ppz]2+ and Δ-[Rh(phi)2bipy]3+ to DNA. Journal of the American Chemical Society, 119, 1454–1455. doi:10.1021/ja9631965
  • Liu, Y., Chao, H., Tan, L., Yuan, Y., Wei, W., & Ji, L. (2005). Interaction of polypyridyl ruthenium (II) complex containing asymmetric ligand with DNA. Journal of Inorganic Biochemistry, 99, 530–537. doi:10.1016/j.jinorgbio.2004.10.030
  • Liu, Y.-H., Li, A., Shao, J., Xie, C.-Z., Song, X.-Q., Bao, W.-G., & Xu, J.-Y. (2016). Four Cu(II) complexes based on antitumor chelators: Synthesis, structure, DNA binding/damage, HSA interaction and enhanced cytotoxicity. Dalton Transactions, 45, 8036–8049. doi:10.1039/C6DT00451B
  • Liu, J. G., Zhang, Q. L., Shi, X. F., & Ji, L. N. (2001). Interaction of [Ru(dmp)2(dppz)]2+ and [Ru(dmb)2(dppz)]2+with DNA: Effects of the ancillary ligands on the DNA-binding behaviors. Inorganic Chemistry, 40, 5045–5050. doi:10.1021/ic001124f
  • Lopez-Sandoval, H., Londono-Lemos, M. E., Garza-Velasco, R., Poblano-Melendez, I., Granada-Macias, P., Gracia-Mora, I., & Barba-Behrens, N. (2008). Synthesis, structure and biological activities of cobalt(II) and zinc(II) coordination compounds with 2-benzimidazole derivatives. Journal of Inorganic Biochemistry, 102, 1267–1276. doi:10.1016/j.jinorgbio.2008.01.016
  • Lv, J., Liu, T., Cai, S., Wang, X., Liu, L., & Wang, Y. (2006). Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived schiff bases. Journal of Inorganic Biochemistry, 100, 1888–1896. doi:10.1016/j.jinorgbio.2006.07.014
  • Mahendiran, D., Gurumoorthy, P., Gunasekaran, K., Kumar, R. S., & Rahiman, A. K. (2015). Structural modeling, in vitro antiproliferative activity, and the effect of substituents on the DNA fastening and scission actions of heteroleptic copper(II) complexes with terpyridines and naproxen. New Journal of Chemistry, 39, 7895–7911. doi:10.1039/C5NJ01059D
  • Mahendiran, D., Kumar, R. S., Viswanathan, V., Devadasan Velmuruganc, D., & Rahiman, A. K. (2016). Targeting of DNA molecules, BSA/c-Met tyrosine kinase receptors and anti-proliferative activity of bis(terpyridine)copper(II) complexes. Dalton Transactions, 45, 7794–7814. doi:10.1039/C5DT03831F
  • Martin-Navarro, C. M., Lopez-Arencibia, A., Lorenzo-Morales, J., Oramas-Royo, S., Hernández-Molina, R., Estévez-Braun, A., … Castellanii Neff, A. (2010). In vitro activity against the trophozoite stage of a natural sesquiterpene and a synthetic cobalt(II)–lapachol complex. Experimental Parasitology, 126, 106–108. doi:10.1016/j.exppara.2009.12.015
  • McGhee, J. D., & von Hippel, P. H. (1974). Theoretical aspects of DNA-protein interactions: Co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. Journal of Molecular Biology, 86, 469–489. doi:10.1016/0022-2836(74)90031-X
  • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55–63. doi:10.1016/0022-1759(83)90303-4
  • Nehru, S., Arunachalam, S., Arun, R., & Premkumar, K. (2014). Polymer–cobalt(III) complexes: Structural analysis of metal chelates on DNA interaction and comparative cytotoxic activity. Journal of Biomolecular Structure and Dynamics, 32, 1876–1888. doi:10.1080/07391102.2013.836460
  • Neves, A. P., Barbosa, C. C., Greco, S. J., Vargas, M. D., Visentin, L. C., Pinheiro, C. B., … da Costa, G. L. (2009). Novel aminonaphthoquinone Mannich bases derived from lawsone and their copper (II) complexes: Synthesis, characterization and antibacterial activity. Journal of the Brazilian Chemical Society, 20, 712–727. doi:10.1590/S0103-50532009000400015
  • Oramas-Royo, S., Torrejon, C., Cuadrado, I., Hernandez-Molina, R., Hortelano, S., Estevez-Braun, A., & de las Heras, B. (2013). Synthesis and cytotoxic activity of metallic complexes of lawsone. Bioorganic & Medicinal Chemistry, 21, 2471–2477. doi:10.1016/j.bmc.2013.03.002
  • Parrilha, G., Vieira, R., Campos, P., Silva, G., Duarte, L., Andrade, S., & Beraldo, H. (2012). Coordination of lapachol to bismuth(III) improves its anti-inflammatory and anti-angiogenic activities. BioMetals, 25, 55–62. doi:10.1007/s10534-011-9481-y
  • Pelosi, G. (2010). Thiosemicarbazone metal complexes: From structure to activity. Open Crystallography Journal, 3, 16–28.
  • Pizarro, A. M., & Sadler, P. J. (2009). Unusual DNA binding modes for metal anticancer complexes. Biochimie, 91, 1198–1211. doi:10.1016/j.biochi.2009.03.017
  • Polonik, S. G., Prokofeva, N. G., Agafonova, I. G., & Uvarova, N. I. (2003). Antitumor and immunostimulating activity of 5-hydroxy-1, 4-naphthoquinone (juglone) O-and S-acetylglycosides. Pharmaceutical Chemistry Journal, 37, 397–398.
  • Pyle, A. M., Morri, T., & Barton, J. K. (1990). Probing microstructures in double-helical DNA with chiral metal complexes: Recognition of changes in base-pair propeller twisting in solution. Journal of the American Chemical Society, 112, 9432–9434. doi:10.1021/ja00181a077
  • Ravelo, A. G., Estevez-Braun, A., Chavez-Orellana, H., Perez-Sacau, E., & Mesa-Siverio, D. (2004). Recent studies on natural products as anticancer agents. Current Topics in Medicinal Chemistry, 4, 241–265.
  • Reichmann, M. E., Rice, S. A., & Thomas, P. (1954). A further examination of the molecular weight and size of desoxypentose nucleic acid. Journal of the American Chemical Society, 76, 3047–3053. doi:10.1021/ja01640a06
  • Ribeiro, M. A., Lanznaster, M., Silva, M. M. P., Resende, J. A. L. C., Pinheiro, M. V. B., Krambrock, K., … Pinheiro, C. B. (2013). Cobalt lawsone complexes: Searching for new valence tautomers. Dalton Transactions, 42, 5462–5470. doi:10.1039/c3dt32968b
  • Rodrigues de Almeida, E. (2009). Preclinical and clinical studies of lapachol and beta-lapachone. Open Natural Products Journal, 2, 42–47. doi:10.2174/1874848100902010042
  • Rosenberg, B. (1977). Noble metal complexes in cancer chemotherapy. Advances in Experimental Medicine and Biology, 91, 129–150.
  • Saha, S., Majumdar, R., Roy, M., Dighe, R. R., & Chakravarty, A. R. (2009). An iron complex of dipyridophenazine as a potent photocytotoxic agent in visible light. Inorganic Chemistry, 48, 2652–2663. doi:10.1021/ic8022612
  • Shahabadi, N., Kashanian, S., Khosravi, M., & Mahdavi, M. (2010). Multispectroscopic DNA interaction studies of a water-soluble nickel(II) complex containing different dinitrogen aromatic ligands. Transition Metal Chemistry, 35, 699–705. doi:10.1007/s11243-010-9382-x
  • Silva, T. F. S., Martins, L. M. D. R. S., da Silva, M. F. C. G., Fernandes, A. R., Silva, A., Borralho, P. M., … Pombeiro, A. J. L. (2012). Cobalt complexes bearing scorpionate ligands: Synthesis, characterization, cytotoxicity and DNA cleavage. Dalton Transactions, 41, 12888–12897. doi:10.1039/C2DT11577H
  • Tabrizi, L., & Chiniforoshan, H. (2016). Ruthenium(II) p-cymene complexes of naphthoquinone derivatives as antitumor agents: A structureactivity relationship study. Journal of Organometallic Chemistry, 822, 211–220. doi:10.1016/j.jorganchem.2016.09.003
  • Takeuchi, T., Bottcher, A., Quezada, C. M., Meade, T. J., & Gray, H. B. (1999). Inhibition of thermolysin and human α-thrombin by cobalt(III) Schiff base complexes. Bioorganic & Medicinal Chemistry, 7, 815–819. doi:10.1016/S0968-0896(98)00272-7
  • Thirumurugan, R. S., Kavimani, S., & Srivastava, R. S. (2000). Antitumour activity of rhinacanthone against Dalton’s ascitic lymphoma. Biological & Pharmaceutical Bulletin, 23, 1438–1440. doi:10.1248/bpb.23.1438
  • Tiwari, S. B., Pai, R. M., & Udupa, N. (2002). Temperature sensitive liposomes of plumbagin: Characterization and in vivo evaluation in mice bearing melanoma B16F1. Journal of Drug Targeting, 10, 585–591. doi:10.1080/1061186021000054924
  • Trawick, B. N., Danihe, A. T., & Bashkin, J. K. (1998). Inorganic mimics of ribonucleases and ribozymes: From random cleavage to sequence-specific chemistry to catalytic antisense drugs. Chemical Reviews, 98, 939–960. doi:10.1021/cr960422k
  • Tysoe, S. A., Morgan, R. J., Baker, A. D., & Strekas, T. C. (1993). Spectroscopic investigation of differential binding modes of Δ- and Λ-Ru(bpy)2(ppz)2+ with calf thymus DNA. Journal of Physical Chemistry, 97, 1707–1711. doi:10.1021/j100110a038
  • Vijayalakshmi, R., Kanthimathi, M., Parthsarathi, R., & Nair, B. U. (2006). Interaction of chromium(III) complex of chiral binaphthyl tetradentate ligand with DNA. Bioorganic & Medicinal Chemistry, 14, 3300–3306. doi:10.1016/j.bmc.2005.12.049
  • Vijayalakshmi, R., Subramanian, V., Nair, B. U., & Sarma, R. H. (2002). A study of the interaction of Cr(III) complexes and their selective binding with B-DNA: A molecular modeling approach. Journal of Biomolecular Structure and Dynamics, 19, 1063–1071. doi:10.1080/07391102.2002.10506809
  • Yin, H. D., Liu, H., & Hong, M. (2012). Synthesis, structural characterization and DNA-binding properties of organotin(IV) complexes based on Schiff base ligands derived from 2-hydroxy-1-naphthaldy and 3- or 4-aminobenzoic acid. Journal of Organometallic Chemistry, 713, 11–19. doi:10.1016/j.jorganchem.2012.03.027
  • Zhang, G.-W., Guo, J.-B., Pan, J.-H., Chen, X.-X., & Wang, J.-J. (2009). Spectroscopic studies on the interaction of morin–Eu(III) complex with calf thymus DNA. Journal of Molecular Structure, 923, 114–119. doi:10.1016/j.molstruc.2009.02.011

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.