Synthesis, antioxidant properties and antiproliferative activities of tetrameric copper and copper-zinc metal complexes of catecholamine schiff base ligand

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 35, Issue 1, 2005, Pages 3-10

  Dutta, Sabari ^a   Bendre, Ratnamala ^a   Padhye, Subhash ^a,b   Ahmed, Fakhara ^b   Sarkar, Fazlul ^b  

^a UNIVERSITY OF PUNE   (India)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antiproliferative activity; Copper tetramer; Copper zinc mixed metal complex; Schiff base complexes; SOD activity

Indexed keywords

3 [[2' (2'' PYRIDYLETHYL)IMINOETHYL]BENZENE 1,2 DIOL]; ANDROGEN; ANTIOXIDANT; CATECHOLAMINE; COPPER COMPLEX; COPPER ZINC COMPLEX; ESTROGEN; METAL COMPLEX; SCHIFF BASE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; ELECTROCHEMISTRY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; IC 50; MAGNETISM; OXIDATIVE STRESS; PROSTATE CANCER; SPECTROSCOPY;

EID: 18244367637     PISSN: 15533174     EISSN: None     Source Type: Journal    
DOI: 10.1081/SIM-200047494     Document Type: Article

References (50)

1. Armstrong, J. S.; Steinauer, K. K.; Hornung, B.; Irish, J. M.; Lecane, P.; Birrell, G. W.; Peehl, D. M.; Knox, S. J. Role of Glutathione Depletion and Reactive Oxygen Species Generation in Apoptotic Signaling in a Human B Lymphoma Cell Line. Cell Death Differ. 2002, 9, 252-63.
2. 4 and its Adducts with Nitrogen and Oxygen Donors. Inorg. Chim. Acta 1990, 173, 121-125.
3. Bodini, M. E.; Copia, G.; Robinson, R.; Sawyer, D. T. Redox Chemistry of Metal-Catechol Complexes in Aprotic Media. 5. 3,5-Di-tert-butylcatecholato and 3,5-di-tert-butyl-o-benzosemiquinonato Complexes of zinc(II). Inorg. Chem. 1983, 22, 126-129.
4. Bodini, M. E.; Arancibia, V. Polyhedron. Manganese complexes with 2-hydroxy-3(3-methyl-2-butenyl)-1,4-naphthoquinone (Lapachol). Redox Chemistry and Spectroscopy in Dimethylsulphoxide 1989, 8, 1407-1412.
5. Boveris, A.; Chance, B. The Mitochondrial Generation of Hydrogen Peroxide. Biochem J 1973, 134, 707-716.
6. Bu, X. H.; Du, M.; Shang, Z. L.; Zhang, R. H.; Liao, D. Z.; Shionoya, M.; Clifford, T. Varying Coordination Modes and Magnetic Properties of Copper(II) Complexes with Diazamesocyclic Ligands by Altering Additional Donor Pendants on 1,5-diazacyclooctane. Inorg. Chem. 2000, 39, 4190-4199.
7. Buchanan, R. M.; Wilson, C.; Blumenberg, C.; Larsen, S. K.; Greene, D. L.; Pierpont, C. G. Counter Ligand Dependence of Charge Distribution in Copper-Quinone Complexes. Structural and Magnetic Properties of (3,5-di-tert-butylcatecholato)(bipyridine)copper(II). Inorg. Chem. 1986, 25, 3070-3076.
8. Chen, J. S. K.; Konopleva, M.; Andreeff, M.; Multani, A.; Pathak, S.; Mehta, K. Drug-resistant breast carcinoma (MCF-7) cells are paradoxically. J. Cell Physiology 2004, 200, 223.
9. Christou, G.; Perlepes, S. P.; Libby, E.; Folting, K.; Huffman, J. C.; Webbs, R. J.; Hendrickson, D. N. Preparation and Properties of the Triply Bridged. Ferromagnetically Coupled Dinuclear Copper(II) Complexes [Cu2(OAc)3(bpy)2)(ClO4) and [Cu2(OH)(H2O)(OAc)(bpy)2](ClO4)2. Inorg Chem. 1990, 29, 3657-3666
10. Correa, P. The Role of Antioxidants in Gastric Carcinogenesis. Crit. Rev. Food. Sci. Nutr. 1995, 35, 59-64.
11. Coughlin, P. K.; Martin, A. E.; Dewan, J. C.; Watanabe, E.; Bulkowski, J. E.; Lehn, J.-M.; Lippard, S. J. Synthesis and Structure of the Imidazolate-bridged Dicopper(II) Ion in Two Binucleating Macrocycles. Inorg. Chem. 1984, 23, 1004.
12. Dillon, C. T.; Hambley, T. W.; Kennedy, B. J.; Lay, P. A.; Zhou, Q.; Davies, N. M.; Biffin, J. R.; Regtop, H. L. Gastrointestinal Toxicity, Antiinflammatory Activity, and Superoxide Dismutase Activity of Copper and Zinc Complexes of the Antiinflammatory Drug Indomethacin. Chem Res Toxicol. 2003, 16, 28-37.
13. Domenicotti, C.; Paola, D.; Vitali, A.; Nitti, M.; D'Abramo, C.; Cottalasso, D.; Maloberti, G.; Biasi, F.; Poli, G.; Chiarpotto, E.; Marinari, U. M.; Pronzato, M. A. Glutathione Depletion Induces Apoptosis of Rat Hepatocytes through Activation of Protein Kinase C Novel Isoforms and Dependent Increase in AP-1 Nuclear Binding. Free Rad Biol. Med. 2000, 29, 1280-1290.
14. Fridovich, I. Superoxide Radical and Superoxide Dismutases. Annu Rev Biochem. 1995, 64, 97-112.
15. Gojon, E.; Greaves, S. J.; Latour, J. M.; Povey, D. C.; Smith, G. W. X-ray Structural Characterization and Magnetic Properties of a Novel Tetranuclear Copper Catecholate. Inorg. Chem. 1987, 26, 1457.
16. Goodson, P. A.; Oki, A. R.; Glerup, J.; Hodgson, D. J. Design, Synthesis, and Characterization of Bis(mu.-oxo)Dimanganese(III,III) Complexes. Steric and Electronic Control of Redox Potentials. J. Am. Chem. Soc. 1990, 112, 6248-6254.
17. Green, D. R.; Reed, J. C. Mitochondria and Apoptosis. Science 1998, 281, 1309-1312.
18. Halliwell, B.; Gutteridge, J. Free Radicals in Biology and Medicine. 3rd Ed., Oxford University Press: New York, 1999.
19. Halvarson, K. E.; Grigereit, T.; Willet, R. D. Magnetic Properties and Structural Characterizations of Bis(tetramethylammonium) Decachlorotetracuprate(II) and Bis(4-methyl-2-aminopyridinium) Decachlorotetracuprate(II). Inorg. Chem. 1987, 26, 1716-1720.
20. Hathway, B. J. Struct. Bonding. 1984, 57, 55 and references therein.
21. Hileman, E. O.; Liu, J.; Albitar, M.; Keating, M. J.; Huang, P. Intrinsic Oxidative Stress in Cancer Cells: A Biochemical Basis for Therapeutic Selectivity. Cancer Chemother Pharmacol. 2004, 53, 209-219.
22. Hug, H.; Strand, S.; Grambihler, A.; Galle, J.; Hack, V.; Stremmel, W.; Krammer, P. H.; Galle, P. R. Reactive Oxygen Intermediates Are Involved in the Induction of CD95 Ligand mRNA Expression by Cytostatic Drugs in Hepatoma Cells. J. Biol. Chem. 1997, 272, 28191-28193.
23. Kulkarni, P.; Padhye, S.; Sinn, E. Neutral Metal Complex in an Ionic Pocket: Synthesis, Physicochemical Properties and X-ray Structure of a Copper(II) Complex Containing Neutral as well as Cationic Dafone Ligands and Dafonium Perchlorate. Inorg. Chim. Acta, 2001, 321, 193-199.
24. 4 Schiff Base Ligand Modeling CuZn Superoxide Dismutase: Structural and Spectroscopic Characterization and Kinetics of Electron Transfer. Inorg. Chem. 2000, 39, 3342-3349.
25. Li, D.; Li, S.; Yang, D.; Yu, J.; Huang, J.; Li, Y.; Tang, W. Syntheses, Structures, and Properties of Imidazolate-Bridged Cu(II)-Cu(II) and Cu(II)-Zn(II) Dinuclear Complexes of a Single Macrocyclic Ligand with Two Hydroxyethyl Pendants. Inorg. Chem. 2003, 42, 6071-6080.
26. Lintvedt, R. L.; Rupp, K. A.; Heeg, M. J. Synthesis and Spectroscopic and Redox Properties of Binuclear Copper(II) Ketimine Schiff-base Complexes. Further Studies of a Novel Class of pi-Molecular Complexes Derived from Binuclear Copper(II) complexes. Inorg. Chem. 1988, 27, 331-339.
27. Lu, Y.; Gralla, E. B.; Roe, J. A.; Valentine, J. S. The Redesign of a Type 2 into a Type 1 Copper Protein: Construction and Characterization of Yeast Cu-Zn Superoxide Dismutase Mutants. J. Am. Chem. Soc. 1992, 114, 3560-3562.
28. McCord, J. M. Superoxide Radical: Controversies, Contradictions, and Paradoxes. Proc Soc Exp Biol Med. 1995, 209, 112-117.
29. Mckee, V.; Zvagulis, M.; Dagdigian, J. V.; Patch, M. G.; Reed, C. J. Hemocyanin Models: Synthesis, Structure, and Magnetic Properties of a Binucleating Copper(II) System. J. Am. Chem. Soc. 1984, 106, 4765-4772.
30. Miyajima, A.; Nakashima, J.; Yoshioka, K.; Tachibana, M.; Tazaki, H.; Murai, M. Role of Reactive Oxygen Species in Cis-dichlorodiammineplatinum- inducing Cytotoxicity on Bladder Cancer Cells. Br J Cancer, 1997, 76, 206-210.
31. Murrell, G. A.; Francis, M. J.; Bromley, L. Modulation of Fibroblast Proliferation by Oxygen Free Radicals. Biochem. J. 1990, 265, 659-665.
32. Murugkar, A.; Padhye, S.; Guha-Roy, S.; Wagh, U. Metal Complexes of Taxol Precursor: 1. Synthesis, Characterization and Antitumor Activity of the Copper Complex of 10-deacetylbaccatin Thiosemicarbazone. Inorg. Chem. Comm. 1999, 2, 545.
33. Nicotera, T. M.; Privalle, C.; Wang, T. C.; Oshimura, M.; Barrett, J. C. Differential Proliferative Responses in Syrian Hamster Embryo Fibroblasts to Paraquat-Generated Superoxide Radicals Depending on Tumor Suppressor Gene Function. Cancer Res. 1994, 54, 3884-3888.
34. Ohse, T.; Nagaoka, S.; Arakawa, Y.; Kawakami, H.; Nakamura, K. J. Cell Death by Reactive Oxygen Species Generated from Water-Soluble Cationic Metalloporphyrins as Superoxide Dismutase Mimics. Inorg. Biochem. 2001, 85, 201-208.
35. II Model of Superoxide Dismutase. Angew. Chem., Int. Ed. Engl. 2000, 39, 4537-4539.
36. Ohtsu, H.; Shimazaki, Y.; Adnani, A.; Yamauchi, O.; Mori, W.; Itoh, S.; Fukuzumi, S. Synthesis and Characterization of Imidazolate-Bridged Dinuclear Complexes as Active Site Models of Cu, Zn-SOD J. Am. Chem. Soc. 2000, 122, 5733-5741.
37. Perrin, D.; Armargo, W. L. F.; Perrin, D. R. Method for purification of classes of compounds. In Purification of Laboratory Chemicals; Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R.; Eds; Pergamon Press: London, 1966; 549-562.
38. Pierre, J. L.; Chautemps, P.; Refaif, S.; Beguin, C.; Marzouki, A. E.; Serratice, G.; Saint-Aman, E.; Rey, P. Imidazolate-Bridged Dicopper(II) and Copper-Zinc Complexes of a Macrobicyclic Ligand (cryptand). A Possible Model for the Chemistry of Cu-Zn Superoxide Dismutase. J. Am. Chem. Soc. 1995, 117, 1965-1973 and references cited therein.
39. Preeta, R.; Nair, R. R. Stimulation of Cardiac Fibroblast Proliferation by Cerium: A Superoxide Anion-Mediated Response. J Mol Cell Cardiol. 1999, 31, 1573-1580.
40. Raha, S.; Robinson, B. H. Mitochondria, Oxygen Free Radicals, and Apoptosis. Am J Med Genet. 2001, 106, 62-70.
41. n(dien = diethylenetriamine), and its Properties in Dimethyl Sulphoxide Solution. J. Chem. Soc. Dalton Trans. 1986, 1949-1953.
42. Saybasili, H.; Yuksel, M.; Haklar, G.; Yalcin, A. S. Effect of Mitochondrial Electron Transport Chain Inhibitors on Superoxide Radical Generation in Rat Hippocampal and Striatal Slices. Antioxid Redox Signal. 2001, 3, 1099-1104.
43. Serrano, J.; Palmeira, C. M.; Kuehl, D. W.; Wallace, K. B. Cardioselective and Cumulative Oxidation of Mitochondrial DNA Following Subchronic Doxorubicin Administration ochim. Biophys Acta. 1999, 1411, 201-205.
44. Stallings, M. D.; Morrison, M. M.; Sawyer, D. T. Redox Chemistry of Metal-Catechol Complexes in Aprotic Media. 1. Electrochemistry of Substituted Catechols and their Oxidation Product. Inorg. Chem. 1981, 20, 2655-2660.
45. Staniek, K.; Gille, L.; Kozlov, A. V.; Nohl, H. Mitochondrial Superoxide Radical Formation is Controlled by Electron Bifurcation to the High and Low Potential Pathways. Free Radic Res. 2002, 36, 381-387.
46. Strothkamp, K. G.; Lippard, S. J. Chemistry of the Imidazole-bridge Bimetallic Center in the Cu-Zn SOD and its Model Compounds. Acc. Chem. Res. 1982, 15, 318.
47. Suzuki, S.; Higuchi, M.; Proske, R. J.; Oridate, N.; Hong, W. K. Implication of Mitochondria-Derived Reactive Oxygen Species, Cytochrome C and Caspase-3 in N940hydroxyphenyl)retinamide Induced Apoptosis in Cervical Carcinoma Cells. Oncogene 1999, 18, 6380.
48. Tabbi, G.; Driessen, W. L.; Reedijk, J.; Bonoma, R. P.; Veldman, N.; Spek, A. L. High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set. Inorg. Chem. 1997, 36, 1168.
49. Tandon, S. S.; Mandal, S. K.; Thompson, L. K.; Hynes, R. C. Copper Coordination Chemistry of Novel Octadentate, Tetranucleating, Bis(diazine) Ligands. Structural and Magnetic Properties of Tetranuclear Complexes Involving a Rectangular Array of Copper(II) Centers. Inorg. Chem. 1992, 31, 2215-2222.
50. Theil, S.; Yerande, R.; Chikate, R.; Dahan, F.; Bousseksou, A.; Padhye, S.; Tuchagues, J.-P. Synthesis, Structure and Magnetic and Redox Properties of Linear Bis-Dinuclear Complexes Afforded by Schiff Base Ligandscontaining Catecholate and Pyridine or Imidazole Groups. Inorg. Chem. 1997, 36, 6279-6286.