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Contemporary Materials I−2 (2010)

Contemporary Materials I−2 (2010)     Page 133 of 137

UDK 616−006.04−084

ANTICANCER ACTIVITY OF NEW COPPER(II) COMPLEXES INCORPORATING A PYRIDOXAL-SEMICARBAZONE LIGAND

V. Jevtović1,*, S. Ivković2, S. Kaisarević3, R. Kovačević3

1University of Novi Sad, Faculty of Sciences, Department of Chemistry, 21000 Novi Sad, Trg D. Obradovića 3, Serbia
2University EDUCONS, Faculty of Environmental Protection, 21202 Sremska Kamenica, Vojvode Putnika bb, Serbia
3University of Novi Sad, Faculty of Science, Department of Biology and Ecology, 21000 Novi Sad, Trg D. Obradovića 3, Serbia

Ab­stract:

Three newly synthe­si­zed cop­per com­ple­xes with pyri­do­xal se­mi­car­ba­zo­ne (PLSC), as li­gand, af­ter be­ing su­bjec­ted to bi­o­lo­gi­cal tests, sho­wed an­ti­can­cer ac­ti­vity. As li­gand  PLSC is bi­o­lo­gi­cally ac­ti­ve, the re­sults of bi­o­lo­gi­cal ac­ti­vity are as ex­pec­ted. Spe­ci­fi­cally, an ac­ti­vity was de­mon­stra­ted in bre­ast can­cer cells (MCF7 and MDA MB 231) and pro­li­fe­ra­ti­ve cells (MCF7).

Keywords:  Cu(II) com­plex, bi­o­lo­gi­cal in­ve­sti­ga­ti­on, an­ti­can­cer ac­ti­vity.

References

[1] B. Lippert, Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, Wiley Inter-science 1999.
[2] A. S. Abu-Surrah, M. Kettunen, Platinum Group Antitumor Chemistry: Design and deve-lopment of New Anticancer Drugs Complementary to Cisplatin, Curr. Med. Chem. 13 (2006) 1337. PMid:16712474
[3] C. S. Allardyce, P. J. Dyson, Ruthenium in Medicine: Current Clinical Uses and Future Prospects, Platinum Met. Rev. 45 (2001) 62.
[4] I. Ott, R. Gust, Non Platinum Metal Complexes as Anti-cancer Drugs, Arch. Pharm. Chem. Life 340 (2007) 117.
PMid:17315259
[5] M. A. Jakupec, M. Galanski, V. B. Arion, C. G. Hartinger, B. K. Keppler, Antitumour metal compounds: more than theme and variations, Dalton Trans. (2008) 183.
PMid:18097483
[7] S. K. Hadjikakou, N. Hadjiliadis, Antipro-liferative and anti-tumor activity of organotin compounds, Coord. Chem. Rev. 253 (2009) 235.

[8] K. Strohfeldt, M. Tacke, Bioorganometallic fulvene-derived titanocene anti-cancer drugs, Chem. Soc. Rev. 37 (2008) 1174.
PMid:18497930
[9] P. M. Abeysinghe, M. M. Harding, Antitumour bis(cyclopentadienyl) metal complexes: titanocene and molybdocene dichloride and derivatives, Dalton Trans. (2007) 3474.
PMid:17680034
[10] R. Gust, D. Posselt, K. Sommer, Development of Cobalt(3,4-diarylsalen) Complexes as Tumor Therapeutics, J. Med. Chem. 47 (2004) 5837.
PMid:15537341
[11] C. G. Hartinger, P. J. Dyson, Bioorgano-metallic chemistry from teaching paradigms to medicinal applications, Chem. Soc. Rev. 38 (2009) 391.
PMid:19169456
[12] M. B. Ferrari, F. Biscegliea, G. G. Favaa, G. Pelosia, P. Tarasconi, R. Albertini, S. Pinelli, Synthesis, characterization and biological activity of two new polymeric copper(II) complexes with aketo-glutaric acid thiosemicarbazone, J. Inorg. Biochem. 89 (2002) 36.

[13] M. B. Ferrari, F. Biscegliea, G. Pelosi, P. Tarasconia, R. Albertini, A. Bonati, P. Lunghi, S. Pinelli, Synthesis, characterisation, X-ray structure and biological activity of three new 5-formyluracil thiosemicarbazone complexes, J. Inorg. Biochem. 83 (2001) 169.

[14] M. R. Arguelles, M. B. Ferrari, F. Bisce-gli, C. Pelizzi, G. Pelosi, S. Pinelli, M. Sassi, Synthesis, characterization and biological activity of Ni, Cu and Zn complexes of isatin hydrazones, J. Inorg. Biochem. 98 (2004) 313.

[15] M. B. Ferraria, F. Bisceglie, A. Buschini, S. Franzoni, G. Pelosi, S. Pinelli, P. Tarasconi, M. Tavone, Synthesis, structural characterization and antiproliferative and toxic bio-activities of copper(II) and nickel(II) citronellal N4-ethylmorpholine thiosemicarbazonates, J. Inorg. Bi-ochem. 104 (2010) 199.
PMid:19962763
[16] V. Jevtovic, G. Pelosi, S. Ianelli, R. Kovacevic, S. Kaisarevic, Synthesis, Structural Studies and Biological Activity of a Dioxovanadium(V) Complex with Pyridoxal Semicarbazon, Acta Chim. Slo., 57, 2 (2010) 363−369.
[17] M. Ferrari Beliccchi, G. Fava Gasparri, E. Leporati, C. Pelizzi, P. Tarasconi, G. Tosi, Thiosemicarbazones as coordinating agents. Solution chemistry and X-ray structure of pyridoxal thio-semicarbazone trihydrate and spectroscopic properties of its metal complexes, J. Chem. Soc. Dalton Trans. (1986) 2455−2461.

[18] M. Ferrari Beliccchi, G. Fava Gasparri, C. Pelizzi, P. Tarasconi, G. Tosi, Thiosemicarbazones as coordinating agents. Part 2. Synthesis, spectroscopic characterization, and X-ray structure of aquachloro(pyridoxal thiosemicarbazone)manganese(II) chloride and aqua(pyridoxal thiosemicarbazonato)-copper(II) chloride monohydrate. J. Chem. Soc. Dalton Trans. (1987) 227.

[19] M. Belicchi Ferrari, G. Fava Gasparri, P. Tarasconi, R. Albertini, S. Pinelli, R. Starcich, Synthesis, spectroscopic and structural characterization, and biological activity of aquachloro(pyrido-xal thiosemicarbazone) copper(II) chloride, J. Inorg. Biochem. 53 (1994) 13.

[20] M. Belicchi Ferrari, G. Fava Gasparri, G. Pelosi, G. Rodriguez-Argulles, P. Tarasconi, Cobalt(III) complexes with thiosemicarbazones as co-ordinating agents. Spontaneous resolution by crystallization and absolute configuration, J. Chem. Soc. Dalton Trans. (1995) 3035.

[21] M. Belicchi Ferrari, G. Fava Gasparri, G. Pelizzi, G. Pelosi, P. Tarasconi, Synthetic, spectroscopic and X-ray crystallographic studies on copper(II) complexes with pyruvic acid and pyridoxal thiosemicarbazones, Inorg. Chim. Acta, (1998) 297.

[22] J. S. Casas, M. C. Rodrigues-Arguleles, U. Russo, A. Sanchez, J. Sordo, A. Vazques- Lopez, S. Pinelli, P. Lunghi, A. Bonati, R. Albertini, Diorganotin(IV) complexes of pyridoxal thiosemi-carbazone: Synthesis, spectroscopic properties and biological activity, J. Inorg. Biochem. 69 (1998) 283.

[23] D. Poleti, Lj. Karanovic, V.Leovac, V. Jevtovic, Dibromo (pyridoxal semicarbazone-κ3N1,O3,O3′)copper(II), Acta Cryst. C-59 (2003) m73.

[24] N. Knezevic, V. Leovac, V. Jevtovic, S.Grguric-Sipka,T. Sabo, Platinum(IV) complex with pyridoxal semicarbazone, Inorg. Chem. Communications. 6 (2003) 561.

[25] V. Leovac, Lj. Jovanovic, V.Divjakovic, A. Pevec, I. Leban, T. Armbruster, Transition metal complexes with thiosemicarbazide-based ligands. Part LIV. Nickel(II) complexes with pyridoxal semi- (PLSC) and thiosemicarbazone (PLTSC). Crystal and molecular structure of [Ni(PLSC)(H2O)3](NO3)2 and [Ni(PLTSC-H)py]NO3, Polyhedron 26 (2007) 49.

[26] V. Leovac, Lj. Jovanovic, V. Jevtovic, G. Pelosi, F. Bisceglie, Transition metal complexes with thiosemicarbazide-based ligand – Part LV: Synthesis and X-ray structural study of novel Ni(II) complexes with pyridoxal semicarbazone and pyridoxal thiosemicarbazone, Polyhedron 26 (2007) 2971.

[27] V. Leovac, S. Markovic, V. Divjakovic, K. Mesaros-Secenji, M. Joksovic, I. Leban, Structural and DFT Studies on Molecular Structure of Ni(II) Chloride Complex with Pyridoxal Semicarbazone (PLSC). Unusual Coordination Mode of PLSC, Acta Chim. Slov. 55 (2008) 850.
[28] Z. Jacimovic, V. Leovac, G. Geister, Z.Tomic, K.Secenji-Mesaros, Structural and thermal characterization of Fe(III) and Fe(II) complexes with tridentate ONO pyridoxal semicarbazone, J. Therm. Anal. and Calo. 90 (2007) 2 549.
[29] V. Leovac, V. S. Jevtovic, Lj. Jovanovic, G.A.Bogdanovic, Metal complexes with Schiff-base ligands - pyridoxal and semicarbazide-based derivatives, J. Serb. Chem. Soc.70 (3) (2005) 393.

[30] V. S. Jevtovic, Ph. D. Thesis, Faculty of Science, University of Novi Sad, 2002.
[31] N. C. Kasuga, K. Sekino, C. Kuomo, N. Shimada, M. Ishikawa, K. Nomiya, Synthesis, structural characterization and antimicrobial activities of 4- and 6-coordinate nickel(II) complexes with three thiosemicarbazones and semicarbazone ligands, J. Inorg. Biochem. 84 (2001) 55.

[32] P. F. Lee, C. T. Yang, D. Fan, J. J. Vittal, J. D. Ranford, Synthesis, characterization and physiccochemical properties of copper(II) complexes containing salicylaldehyde semicarbazone, Polyhedron 22 (2003) 2781.

[33] J. Patole, S. Dutta, S. Padhey, E. Sinn, Tuning up superoxide dismutase activity of copper complex of salicylaldehyde semicarbazone by heterocyclic bases pyridine and N-methyl imidazole, Inorg. Chim. Acta 318 (2001) 207.

[34] K. H. Reddy, P. S. Reddy, P. R. Babu, Synthesis, spectral studies and nuclease activity of mixed ligand copper(II) complexes of heteroaromatic semicarbazones/thiosemicarbazones and pyridine, J. Inorg. Biochem. 77 (1999) 169.

[35] R. Sharma, S. K. Agarwal, S. Rawat, M. Nagar, Synthesis, Characterization and Antibacterial Activity of Some Transition Metal cis-3,7-dimet-hyl-2,6-octadiensemicarbazone Complexes, Trans. Met. Chem. 31 (2006) 201.

[36] Z. Afrasiabi, E. Sinn, W. Lin, Y. Ma, C. Campana, S. Padhye, Nickel (II) complexes of naph-thaquinone thiosemicarbazone and semicarbazone:Synthesis, structure, spectroscopy, and biological activity, J. Inorg. Biochem. 9 (2005)1526.

PMid:15927263
[37] V. Jevtovic, Monograph, Synthesis, physical-chemical characterisation, structure and biological activity of Cu(II), Fe(III), Ni(II), and V(V) complex with pyridoxal semi-, thiosemi- and isothio-semicarbazones, LAP Academic Publishing, Germany, 2010.
[38] N. V. Gerbeleu, Koordinatsionie soedineniya perekhodnikh elpolidentatnimi ligandami na osnove tio- i selenosemikarbazida, PhD Thesis, MGU, Moskva, 1972.
[39] V. M. Leovac, Sinteza i ispitivanje koordinacionih jedinjenja 3d-elemenata sa Smetiltiose-mikarbazidom i S-metiltiosemikarbazonima, Doktorska disertacija, Prirodno-matematički fakultet, Novi Sad, 1978.
[40] M. Ferrari Belicchi, F. Bisceglie, G. Pelosi, P. Tarasconi, R. Albertini, P.P. Dall’Aglio, S. Pinelli, A. Bergamo, G. Sava, Synthesis, characterization and biological activity of copper complexes with pyridoxal thiosemicarbazone derivatives. X-ray crystal structure of three dimeric complexes, J. of Inorg. Biochem. 98 (2004) 301.