Copper(II) and cobalt(III) pyridoxal thiosemicarbazone complexes with nitroprusside as counterion: Syntheses, electronic properties, and antileukemic activity

Journal of Medicinal Chemistry

Volumn 48, Issue 5, 2005, Pages 1671-1675

  Belicchi Ferrari, Marisa ^a   Bisceglie, Franco ^a   Casoli, Claudio ^a   Durot, Stéphanie ^b   Morgenstern Badarau, Irène ^b   Pelosi, Giorgio ^a   Pilotti, Elisabetta ^a   Pinelli, Silvana ^a   Tarasconi, Pieralberto ^a  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

NITRIC OXIDE; NITROPRUSSIDE SODIUM; PYRIDOXAL THIOSEMICARBAZONE NITROPRUSSIDE COBALT COMPLEX; PYRIDOXAL THIOSEMICARBAZONE NITROPRUSSIDE COPPER COMPLEX; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG SYNTHESIS; ELECTRONICS; ENZYME RELEASE; HUMAN; HUMAN CELL; MAGNETISM; SPECTROSCOPY; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; COBALT; COPPER; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; NITROPRUSSIDE; ORGANOMETALLIC COMPOUNDS; PYRIDOXAL; THIOSEMICARBAZONES;

EID: 14944340015     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049529n     Document Type: Article

References (22)

1. Richardson, D. R. Iron chelators as therapeutic agents for the treatment of cancer. Crit. Rev. Oncol./Hematol. 2002, 42, 267-281.
2. Lovejoy, D. B.; Richardson, D. R. Novel "hybrid" iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells. Blood 2002, 100, 666-676.
3. Jütten, P.; Schumann, W.; Härtl, A.; Heinisch, L.; Gräfe, U.; Werner, W.; Ulbricht, H. A novel type of nonsteroidal estrone sulfatase inhibitors. Bioorg. Med. Chem. Lett. 2002, 12, 1339-1342.
4. Richardson, D. R.; Milnes, K. The Potential of Iron Chelators of the Pyridoxal Isonicotinoyl Hydrazone Class as Effective Anti-proliferative Agents II: The Mechanism of Action of Ligands Derived From Salicylaldehyde Benzoyl Hydrazone and 2-Hydroxy-1-Naphthylaldehyde Benzoyl Hydrazone. Blood 1997, 89, 3025-3038.
5. West, D. X.; Liberia, A.; Padhye, S. B.; Chikate, R. C.; Sonawane, P. B.; Kumbhar, A. S.; Yerande, R. G. Thiosemicarbazone complexes of copper(II): structural and biological studies. Coord. Chem. Rev. 1993, 123, 49-71.
6. Byrnes, R. W.; Mohan, M.; Antholine, W. E.; Xu, R. X.; Petering, D. H. Oxidative stress induced by a copper-thiosemicarbazone complex. Biochemistry 1990, 29, 7046-7053.
7. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Tarasconi, P.; Albertini, R.; Pinelli, S.; Starcich, R. Synthesis, spectroscopic and structural characterization, and biological activity of aquachloro-(pyridoxal thiosemicarbazone) copper(II) chloride. J. Inorg. Biochem. 1994, 53, 13-25.
8. Cory, J. G.; Cory, A. H.; Rappa, G.; Lorico, A.; Liu, M.-C.; Lin, T.-S.; Sartorelli, A. C. Inhibitors of ribonucleotide reductase: Comparative effects of amino- and hydroxy-substituted pyridine-2-carboxaldehydethiosemicarbazones. Biochem. Pharmacol. 1994, 48, 335-344.
9. Kovala-Demertzi, D.; Nath Yadav, P.; Demertzis, M. A.; Coluccia, M. Synthesis, crystal structure, spectral properties and cytotoxic activity of platinum(II) complexes of 2-acetyl pyridine and pyridine-2-carbaldehyde N(4)-ethyl-thiosemicarbazones. J. Inorg. Biochem. 2000, 78, 347-354.
10. Lakovidou, Z.; Papageorgiou, A.; Demertzis, M. A.; Mioglou, E.; Mourelatos, D.; Kotsis, A.; Yadav, P. N.; Kovala-Demertzi, D. Platinum(II) and palladium(II) complexes with 2-acetylpyridine thiosemicarbazone: cytogenetic and antineoplastic effects. Anticancer Drugs 2001, 12, 65-70.
11. Belicchi-Ferrari, M.; Bisceglie, F.; Leporati, E.; Pelosi, G.; Tarasconi, P. Synthesis, Solution Chemistry, X-ray Structure and Biological Activity of Novel Pyridoxal Thiosemicarbazone Derivatives. Bull. Chem. Soc. Jpn. 2002, 75, 781-788.
12. Casas, J. S.; Rodríguez-Argüelles, M. C.; Russo, U.; Sànchez, A.; Sordo, J.; Vàzquez-Lòpez, A.; Pinelli, S.; Lunghi, P.; Bonati, A.; Albertini, R. Diorganotin(IV) complexes of pyridoxal thiosemicarbazone: Synthesis, spectroscopic properties and biological activity. J. Inorg. Biochem. 1998, 69, 283-292.
13. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Pelizzi, C.; Tarasconi, P.; Tosi, G. 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, 227-233.
14. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Pelosi, G.; Rodríguez- Argüelles, M. C.; Tarasconi, P. Cobalt(III) complexes with thiosemicarbazones as coordinating agents. Spontaneous resolution by crystallization and absolute configuration. J. Chem. Soc., Dalton Trans. 1985, 3035-3040.
15. Belicchi-Ferrari, M.; Bisceglie, F.; Pelosi, G.; Tarasconi, P.; Pinelli, S.; Bergamo, A.; Sava, G. Synthesis, characterization and biological activity of copper complexes with pyridoxal thiosemicarbazone derivatives. X-ray crystal structure of three dimeric complexes. J. Inorg. Biochem. 2004, 98, 301-312.
16. Butler, A. R.; Megson, I. L. Non-Heme Iron Nitrosyls in Biology. Chem. Rev. 2002, 102, 1155-1165.
17. Kim, P. K. M.; Zamora, R.; Petrosko, P.; Billiar, T. R. The regulatory role of nitric oxide in apoptosis. Int. Immunopharmacol. 2001, 1, 1421-1441.
18. Terwel, D.; Nieland, L. J. M.; Schutte, B.; Reutelingsperger, C. P. M.; Ramaekers, F. C. S.; Steinbusch, H. W. M. S-nitroso-N-acetylpenicillamine and nitroprusside induce apoptosis in a neuronal cell line by the production of different reactive molecules. Eur. J. Pharmacol. 2000, 400, 19-33.
19. Chen, Z. N.; Wang, J. L.; Qiu, J.; Miao, F. M.; Tang, W. X. Crystal Structure and Magnetic Properties of a 2D Sheetlike.mu.-Cyanido-and.mu.- Oxamidato-Bridged Fe(III)-Cu(II) Bimetallic Complex. Inorg. Chem. 1995, 34, 2255-2262.
20. 2O. Inorg. Chim. Acta 1997, 258, 81-86.
21. Belicchi-Ferrari, M.; Gasparri-Fava, G.; Leporati, E.; Pelizzi, C.; Tarasconi, P.; Tosi, G. Thiosemicarbazones as coordinating agents. Solution chemistry and X-ray structure of pyridoxal thiosemicarbazone trihydrate and spectroscopic properties of its metal complexes. J. Chem. Soc., Dalton Trans. 1986, 2455-2461.
22. Kim, N. W.; Piatyszek, M. A.; Prowse, K. R.; Harley, C. B.; West, M. D.; Ho, P. L.; Coviello, G. M.; Wright, W. E.; Weinrich, S. L.; Shay, J. W. Specific association of human telomerase with immortal cells and cancer. Science 1994, 266, 2011-2015.