Synthesis, crystal structure, spectroscopic properties and potential biological activities of salicylate?neocuproine ternary copper(II) complexes

Molecules

Volumn 20, Issue 2, 2015, Pages 2115-2137

  Kucková, Lenka ^a   Jomová, Klaudia ^b   Švorcová, Andrea ^b   Valko, Marián ^a   Segl'A, Peter ^a   Moncol', Ján ^a   Kožíšek, Jozef ^a  

^a SLOVAK UNIVERSITY OF TECHNOLOGY   (Slovakia)

^b The Philosopher University in Nitra Geoinformatics and Regional Development   (Slovakia)

Author keywords

Biological activity; Crystal structure; Ternary copper complexes

Indexed keywords

COORDINATION COMPOUND; COPPER; HYDROGEN PEROXIDE; INTERCALATING AGENT; PHENANTHROLINE DERIVATIVE; SALICYLIC ACID DERIVATIVE;

CHEMISTRY; CONFORMATION; DNA CLEAVAGE; HYDROGEN BOND; OXIDATION REDUCTION REACTION; PLASMID; X RAY CRYSTALLOGRAPHY;

COORDINATION COMPLEXES; COPPER; CRYSTALLOGRAPHY, X-RAY; DNA CLEAVAGE; HYDROGEN BONDING; HYDROGEN PEROXIDE; INTERCALATING AGENTS; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PHENANTHROLINES; PLASMIDS; SALICYLATES;

EID: 84921917085     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules20022115     Document Type: Article

References (52)

1. Neville, S.N.; Leverett, P.; Hibbs, D.E.; Yang, Q.; Bulanadi, C.; Wu, M.J.; Aldrich-Wright, J.R. The antimicrobial properties of some copper(II) and platinum(II) 1,10-phenanthroline complexes. Dalton Trans. 2013, 42, 3196-3209.
2. Alanis, A.J. Resistance to antibiotics: Are we in the post-antibiotic era? Arch. Med. Res. 2005, 36, 697-705.
3. Zimmermann, N.; Weber, A.-A.; Hohlfeld, T. Aspirin "Resistance". Herz 2008, 33, 270-278.
4. Marzano, C.; Pellei, M.; Tisato, F.; Santini, C. Copper complexes as anticancer agents. Anti-Cancer Agents Med. Chem. 2009, 9, 185-211.
5. Veitía, M.S.-I.; Dumas, F.; Morgant, G.; Sorenson, J.R.J.; Frapart, Y.; Tomas, A. Synthesis, structural analysis and anticonvulsant activity of a ternary Cu(II) mononuclear complex containing 1,10-phenanthroline and the leading antiepileptic drug valproic acid. Biochimie 2009, 9, 1286-1293.
6. Kannan, D.; Arumugham, M.N. Synthesis, characterisation, DNA-binding studies and antimicrobial activity of copper(II) complex with 1,10-phenanthroline, L-tyrosine and urea as ligands. Int. J. Inorg. Bioinorg. Chem. 2013, 3, 8-15.
7. Bales, B.C.; Kodama, T.; Weledji, Y.N.; Pitié, M.; Meunier, B.; Greenberg, M.M. Mechanistic studies on DNA damage by minor groove binding copper-phenanthroline conjugates. Nucleic Acids Res. 2005, 33, 5371-5379.
8. Fernandes, C.; Parrilha, G.L.; Lessa, J.A.; Santiago, L.J.M.; Kanashiro, M.M.; Boniolo, F.S.; Bortoluzzi, A.J.; Vugman, N.V.; Herbst, M.H.; Horn, A., Jr. Synthesis, crystal structure, nuclease and in vitro antitumor activities of a new mononuclear copper(II) complex containing a tripodal N3O ligand. Inorg. Chim. Acta 2006, 359, 3167-3176.
9. Adelaide, O.M.; James, O.O. Antimicrobial, DNA cleavage and antitumoral properties of some transition metal complexes of 1,10-phenanthroline and 2,2'-bipyridine: A review. Int. J. Res. Pharm. Biomed. Sci. 2013, 4, 1160-1171.
10. Zoroddu, M.A.; Zanetti, S.; Pogni, R.; Basosi, R. An electron spin resonance study and antimicrobial activit of copper(II)-phenanthroline complexes. J. Inorg. Biochem. 1996, 63, 291-300.
11. Sigman, D.S.; Graham, D.R.; D'Aurora, V.; Stern, A.M. Oxygen-dependent cleavage of DNA by the 1,10-phenanthroline cuprous complex. J. Biol. Chem. 1979, 254, 12269-12272.
12. Francois, J.C.; Faria, M.; Perrin, D.; Giovannangeli, C. DNA and RNA cleavage mediated by phenanthroline-cuprous oligonucleotides: From properties to applications. In Nucleic Acids and Molecular Biology; Zenkova, M.A., Ed.; Springer Verlag: Berlin/Heidelberg, Germany, 2004; Volume 13, pp. 223-242.
13. Chikira, M.; Tomizawa, Y.; Fukita, D.; Sugizaki, T.; Sugawara, N.; Yamazaki, T.; Sasano, A.; Shindo, H.; Palaniandavar, M.; Antholine, W.E. DNA-fiber EPR study of the orientation of Cu(II) complex es of 1,10-phenanthroline and its derivatives bound to DNA: Mono(phenanthroline)-copper(II) and its ternary complexes with amino acids. J. Inorg. Biochem. 2002, 89, 163-173.
14. Kowol, C.R.; Heffeter, P.; Miklos, W.; Gille, L.; Trondl, R.; Cappellacci, L.; Berger, W.; Keppler, B.K. Mechanisms underlying reductant-induced reactive oxygen species formation by anticancer copper(II) compounds. J. Biol. Inorg. Chem. 2012, 17, 409-423.
15. Jungwirth, U.; Kowol, C.R.; Keppler, B.K.; Hartinger, C.G.; Berger, W.; Heffeter, P. Anticancer activity of metal complexes: Involvement of redox processes. Antiox. Redox. Signal. 2011, 15, 1085-1127.
16. Tardito, S.; Marchió, L. Copper compounds in anticancer strategies. Curr. Med. Chem. 2009, 16, 1325-1348.
17. Kumar, R.S.; Arunachalam, S.; Periasamy, V.S.; Preethy, C.P.; Riyasdeen, A.; Akbarsha, M.A. DNA binding and biological studies of some novel water-soluble polymer-copper(II)-phenanthroline complexes. Eur. J. Med. Chem. 2008, 43, 2082-2091.
18. D'Angelo, J.; Morgant, G.; Ghermani, N.E.; Desmaele, D.; Fraisse, B.; Bonhomme, F.; Dichi, E.; Sghaier, M.; Li, Y.; Journaux, Y.; et al. Crystal structures and physico-chemical properties of Zn(II) and Co(II) tetraaqua(3-nitro-4-hydroxybenzoato) complexes: Their anticonvulsant activities as well as related (5-nitrosalicylato)-metal complexes. Polyhedron 2008, 27, 537-546.
19. Abuhijleh, A.L. Mononuclear copper(II) aspirinate or salicylate complexes with methylimidazoles as biomimetic catalysts for oxidative dealkylation of a hindered phenol, oxidation of catechol and their superoxide scavenging activities. Inorg. Chem. Commun. 2011, 14, 759-762.
20. Tong, Y.-P.; Lin, Y.-W. Synthesis, crystal structure, electronic structure, bonding, photoluminescence and spectroscopic property investigations of a mononuclear 1,10-phenanthroline and 5-bromo-salicylate ternary indium(III) complex. Inorg. Chim. Acta 2009, 362, 4791-4796.
21. Mackowiak, P.A. Brief history of antipyretic therapy. Clin. Infect. Dis. 2000, 31, 154-156.
22. Rizzotto, M. Metal complexes as antimicrobial agents. In A Search for Antibacterial Agents; Bobbarala, V., Ed.; InTech: Rijeka, Croatia, 2012; pp. 73-88.
23. Abuhujleh, A.L. Synthesis and characterization of copper-ibuprofenate complexes with 2,2'-bipyridine and 1,10-phenanthrolines and their hydrolytic activities in phosphate diester cleavage. Polyhedron 1997, 16, 733-740.
24. Ranford, J.D.; Sadler, P.J.; Tocher, D.A. Cytotoxicity and antiviral activity of transition-metal salicylato complexes and crystal structure of bis(diisopropylsalicylato)(1,10-phenanthroline)copper(II). J. Chem. Soc. Dalton Trans. 1993, 3393-3399.
25. Jakab, N.I.; Vasková, Z.; Moncol, J.; Gyurcsik, B.; Šima, J.; Koman, M.; Valigura, D. Ternary complex formation of copper(II) with 5-fluorosalicylate and 3-pyridylmethanol in aqueous solutions and solid state. Polyhedron 2010, 29, 2262-2268.
26. Palanisami, N.; Prabusankar, G.; Murugavel, R. A novel dimeric copper salicylate with an undissociated COOH group: Synthesis and crystal structure of [Cu2(HSal)(Sal)(2,2'-bpy)2](ClO4). Inorg. Chem. Commun. 2006, 9, 1002-1006.
27. Lemoine, P.; Viossat, B.; Dung, N.H.; Tomas, A.; Morgant, G.; Greenaway, F.T.; Sorenson, J.R.J. Synthesis, crystal structures, and anti-convulsant activities of ternary [ZnII(3,5-diisopropylsalicylate)2], [ZnII(salicylate)2] and [ZnII(aspirinate)2] complexes. J. Inorg. Biochem. 2004, 98, 1734-1749.
28. Zhai, C.; Yan, F.-M.; Zhao, P.-Z. (2,9-Dimethyl-1,10-phenanthroline-2N,N')bis(2-hydroxybenzoato-O)-copper(II). Acta Crystallogr. Sect. E 2008, 64, m1526-m1527.
29. Moncol, J.; Jomová, K.; Porubská, M. Two centrosymmetric dinuclear phenanthroline-copper(II) complexes with 3,5-dichloro-2-hydroxybenzoic acid and 5-chloro-2-hydroxybenzoic acid. Acta Crystallogr. Sect. C 2012, 68, m85-m89.
30. Addison, A.; Rao, T.N.; Reedijk, J.; van Rijn, J.; Verschoor, G.C. Synthesis, structure, and spectroscopic properties of copper(II) compounds containing nitrogen-sulphur donor ligands; the crystal and molecular structure of aqua[1,7-bis(N-methylbenzimidazol-2'-yl)-2,6-dithiaheptane]copper(II) perchlorate. J. Chem. Soc. Dalton Trans. 1984, 1349-1356.
31. Lin, J.-L.; Xu, W.; Xie, H.-Z. A second polymorph of aqua(2,9-dimethyl-1,10-phenanthroline-2N,N')-bis(formato-O)copper(II). Acta Crystallogr. Sect. E 2008, 64, m1062.
32. Yu, Z.-W.; Chang, L.; Song, P.; He, M.H. Aqua(3-formyl-2-oxidobenzoato-2O1,O2)(1,10-phenanthroline-2N,N')-copper(II) dimethylformamide solvate. Acta Crystallogr. Sect. E 2009, 65, m485.
33. Zhang, W.; Cui, Q.; Chang, L.; Yu, Z. Aqua(3-formyl-2-oxidobenzoato-2O1,O2)(1,10-phenanthroline-2N,N')-copper(II) methanol solvate. Acta Crystallogr. Sect. E 2008, 64, m294.
34. Fan, S.-R.; Zhu, L.-G. Secondary synthesis of two cobalt complexes by the use of 5-sulfosalicylate and 1,10-phenanthroline and their crystal structures. Chin. J. Chem. 2005, 23, 1292-1296.
35. Nie, J.-J.; Li, J.-H.; Xu, D.-J. Bis(μ-4-chloro-2-oxidobenzoato)-bis[(1,10-phenanthroline)copper(II)] dihydrate. Acta Crystallogr. Sect. E 2010, 66, m387-m388.
36. Humbert, B.; Alnot, M.; Quiles, F. Infrared and raman spectroscopical studies of salicylic and salicylate derivatives in aqueous-solution. Spectrochim. Acta Part A 1998, 54, 465-476.
37. Lalia-Kantouri, M.; Papadopoulos, C.D.; Hatzidimitriou, A.G.; Sigalas, M.P.; Quiros, M.; Stavroula, S. Different geometries of novel cobalt(II) compounds with 2-hydroxy-benzophenones and neocuproine: Crystal and molecular structures of [Co(2-hydroxy-benzophenone)2(neoc)], [Co(2-hydroxy-4-methoxybenzophenone)(neoc)Br] and [Co(neoc)Br-2]·CH3OH·H2O. Polyhedron 2013, 52, 1306-1316.
38. Yost, E.C.; Tejedor-Tejedor, M.I.; Anderson, M.A. In situ CIR-FTIR characterization of salicylate complexes at the goethite/aqueous solution interface. Environ. Sci. Technol. 1990, 24, 822-828.
39. Nakamoto, K. Complexes of amino acids, EDTA, and related ligands. In Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, 5th ed.; Wiley: New York, NY, USA, 1997; pp. 64-67.
40. Lever, A.B.P. Electronic spectra of dn ions. In Inorganic Electronic Spectroscopy, 2nd ed.; Elsevier: Amsterdam, The Netherlands, 1984; p. 480.
41. Peisach, J.; Blumberg, W.E. Structural implications derived from the analysis of electron paramagnetic resonance spectra of natural and artificial copper proteins. Arch. Biochem. Biophys. 1974, 165, 691-708.
42. Valko, M.; Morris, H.; Mazur, M.; Telser, J.; McInnes, F.; Mabbs, F. High affinity binding site for copper(II) in human and dog serum albumins (an EPR study). J. Phys. Chem. B 1999, 103, 5591-5597.
43. Maheswari, P.U.; Roy, S.; den Dulk, H.; Barends, S.; van Wezel, G.; Kozlevcar, B.; Gamez, P.; Reedijk, J. The square-planar cytotoxic [Cu(II)(pyrimol)Cl] complex acts as an efficient DNA cleaver without reductant. J. Am. Chem. Soc. 2006, 128, 710-711.
44. O'Connor, M.; Kellett, A.; McCann, M.; Rosair, G.; McNamara, M.; Howe, O.; Creaven, B.S.; McClean, S.; Foltyn-Arfa Kia, A.; O'Shea, D.; et al. Copper(II) complexes of salicylic acid combining superoxide dismutase mimetic properties with DNA binding and cleaving capabilities display promising chemotherapeutic potential with fast acting in vitro cytotoxicity against cisplatin sensitive and resistant cancer cell lines. J. Med. Chem. 2012, 55, 1957-1968.
45. Starosta, R.; Florek, M.; Król, J.; Puchalska, M.; Kochel, A. Cooper(I) iodide complexes containing new aliphatic aminophosphine ligands and diimines-luminescent properties and antibacterial activity. New. J. Chem. 2010, 34, 1441-1449.
46. Patel, M.N.; Patel, C.R.; Joshi, H.N. Metal-based biologically active compounds: Synthesis, characterization, DNA interaction, antibacterial, cytotoxic and SOD mimic activities. Appl. Biochem. Biotechnol. 2013, 169, 1329-1345.
47. Milne, L.; Nicotera, P.; Orrenius, S.; Burkitt, M.J. Effects of glutathione and chelating agents on copper-mediated DNA oxidation: Pro-oxidant and antioxidant properties of glutathione. Arch. Biochem. Biophys. 1993, 304, 102-109.
48. Haas, K.L.; Franz, K.J. Application of metal coordination chemistry to explore and manipulate cell biology. Chem. Rev. 2009, 109, 4921-4960.
49. CrysAlis RED, CrysAlis CCD, Version 1.171.36.32; Oxford Diffraction Ltd.: Abingdon, Oxfordshire, UK, 2013.
50. Sheldrick, G.M. A short history of SHELX. Acta Crystallogr. Sect. A 2008, 64, 112-122.
51. Sheldrick, G.M. Crystal structure refinement with SHELXL. Acta Crystallogr. Sect. C 2015, 71, 3-8.
52. Brandenburg, K. Diamond; Visual Information System for Crystal Structures: Bonn, Germany, 2009.