Antioxidant, pro-oxidant effect of the thiosemicarbazone derivative Schiff base (4-(1-phenylmethylcyclobutane-3-yl)-2-(2-hydroxybenzylidenehydrazino) thiazole) and its metal complexes on rats

Cell Biochemistry and Function

Volumn 24, Issue 6, 2006, Pages 547-554

  Karatepe, Mustafa ^a   Karatas, Fikret ^a  

^a FIRAT UNIVERSITY   (Turkey)

Author keywords

Antioxidant vitamins; Cyclobutane; GSH Px, malondialdehyde; Rat; Schiff base; Thiosemicarbazone

Indexed keywords

4 (1 PHENYLMETHYLCYCLOBUTANE 3 YL) 2 (2 HYDROXYBENZYLIDENEHYDRAZINO)THIAZOLE; ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; COPPER COMPLEX; GLUTATHIONE; MALONALDEHYDE; METAL COMPLEX; RETINOL; SCHIFF BASE; SELENIUM; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; MORPHOLOGICAL ADAPTATION; NONHUMAN; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT; VITAMIN BLOOD LEVEL;

ANIMALS; ANTIOXIDANTS; COPPER; KIDNEY; LIVER; MALE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDANTS; OXIDATION-REDUCTION; RATS; RATS, WISTAR; SCHIFF BASES; THIOSEMICARBAZONES; ZINC;

ANIMALIA;

EID: 33751189349     PISSN: 02636484     EISSN: 10990844     Source Type: Journal    
DOI: 10.1002/cbf.1266     Document Type: Article

References (61)

1. Liberta AE, West DX. Antifungal and antitumour activity of heterocyclic thiosemicarbazones and their metal complexes. Biometals 1992; 5: 121-126.
2. Wang LF, Zhu Y, Yang ZY, Wu JG, Wang Q. Manganase(II) complex of a hydrazone ligand derived from pyruvic acid and 4-pyridine carboxylic acid hydrazide-synthesis and crystal structure. Polyhedron 1991; 10: 2477-2481.
3. Padhy S, Kauffman GB. Transition metal complexes of semicarbazones and thiosemicarbazones. Coord Chem Rev 1985; 63: 127-160.
4. Cory JG, Chiba P (eds). Combination chemotheraphy directed at the components of nucleoside diphosphate reductase. In Inhibitors of Ribonucleoside Diphosphate Reductase Activity. Pergamon Press: Oxford, 1989; 245-264.
5. Cory JG, Cory AH, Rappa G, et al. Inhibitors of ribonucleotide reductase, comparative effects of amino and hydroxy-substituted pyridine-2-carboxyaldehyde thiosemicarbazones. Biochem Pharm 1994; 48: 335-344.
6. Cory JG, Carter GL, Bacon PE, T'ang A, Lien EJ. Inhibition of ribonucleotide reductase and L1210 cell growth by N-hydroxy-N′- aminoguadine derivatives. Biochem Pharm 1985; 34: 2645-2650.
7. Blanco JM, Caamano O, Fernandez F, et al. Synthesis and antiviral and antineoplastic activities of some novel carbocyclic guanosine analogues with a cyclobutane ring. Chem Pharm Bull 1999; 47: 1314-1317.
8. Christophe SG, Caubere CK, Renard P, et al. Synthesis and antiproliferative activity of benzocyclobutacarbazol derivatives. A new class of potential antitumor agents. Bioorgan Med Chem Let 2000; 10: 2589-2591.
9. Dehmlow EV, Schmidt SS. Synthesis of stereoisomeric 3-substituted cyclobutanecarboxylic acid-derivatives. Liebigs Ann Chem 1990; 5: 411-414.
10. Agrawal KC, Mooney PD, Sartorelli AC. Potential antitumor agents' 4-methyl-5-amino-1-formylisoquinolme thiosemicarbazone. J Med Chem 1976; 19: 970-972.
11. Rodriguez-Argüelles MC, Ferrari MB, Fava GG, et al. Acenaphthenequinone thiosemicarbazone and its transition metal complexes: synthesis, structure, and biological activity. J Inorg Kochem 1997; 66: 7-17.
12. Perez JM, Matesanz AI, Martin-Ambite A, Novarro P, Alonso C, Savza P. Synthesis and characterization of complexes of p-isopropyl benzaldehyde and methyl-2-pyridyl ketone thiosemicarbazones with Zn(II) and Cd(II), metallic centers, cytotoxic activity and induction of apoptosis in pam-ras cells. J Inorg Biochem 1999; 75: 255-261.
13. Demertzi DK, Domopoulou A, Demertzis MA, Valle G, Papageorgiou A. Palladium(II) complexes of 2-acetylpyridine N(4)-methyl, N(4)-ethyl and N(4)-phenyl-thiosemicarbazones. Crystal structure of chloro (2-acetylpyridine N(4)-methylthiosemicarbazonato) alladium(II). Synthesis, spectral studies, in vitro and in vivo antitumour activity. J Inorg Biochem 1997; 68: 147-155.
14. Demertzi DK, Demertzis MA, Voragi V, et al. Antineoplastic and cytogenetic effects of platinum(II) and palladium(II) complexes with pyridine-2-carboxaldehyde thiosemicarbazone. Chemotheraphy 1998; 44: 421-426.
15. Novelli EL, Silva AM, Novellif JL, Curi PR. Reactive oxygen generation by azomethine H: a new antimalarial drug. Can J Physiol Pharma 1995; 73: 1189-1194.
16. Novelli EL, Silva AM, Monteiro JP, Sacomani LB, Novellif JL. Free radical production by azomethine H: effects on pancreatic and hepatic tissues. Free Radic Res 1997; 26: 319-324.
17. Oner H, Karatepe M, Karatas F, Öner J, Yilmaz I, Cukurovali A. Effects on the rat testes of thiosemicarbazone derivative schiff base (4-(1-phenyl-methylcyclobutane-3-yl)-2-(2-hydroxybenzylidenehydrazino) thiazole) and its cadmium (II) complex. Cell Biochem. Funct. 2005; 22: 1-7. DOI: 10.1027/cbf.1169
18. Byrnes RW, Mohan M, Antholine WE, Xu RX, Petering DH. Oxidative stress induced by a copper thiosemicarbazones complex. Biochemistry 1990; 29: 7046-7053.
19. Durackova Z, Mendiola MA, Sevilla MT, Valent A. Thiohydrazone copper (II) complexes. The relationship between redox properties and superoxide dismutase mimetic activity. Bioelectrochem Bioenerg 1999; 48: 109-116.
20. Hrnciarova M, Carsky J, Jakus V, Zlatos L, Kucharska J, Gvozdjakova A. Inhibition of lipid peroxidation in erythrocytes by aminoguanidine, resorcylidine aminoquanidine and their oxygen and sulfur analogs in diabetic rats. Bratisl Lek Listy 1998; 99: 364-367.
21. Kaur S, AH B. Membrane stabilization and inhibition of lipid peroxidation by anti -inflammatory indoles. Pharmacology 1982; 25: 210-213.
22. Amlacher R, Baumgart J, Weber H, Kuhnel HJ, Schulze W, Hoffman H. Influence of age on antileukemic action, subacute toxicity and tissue distrubition of ambazone in B6D2F1 mice. Arch Geschwulstforsch 1990; 60: 11-18.
23. 14C-ambazone in rats. Pharmazie 1988; 43: 197-199.
24. Lober G, Hoffmann H. Ambazone as a membrane active antitumor drug. Biophy Chem 1990; 35: 287-300.
25. Cukurovali A, Yilmaz I. Synthesis and characterization of a new cyclobutane substituted Schiff base ligand and its Cd(II), Co(II), Ni(II) and Zn(II) complexes. Polish J Chem 2000; 74: 147-151.
26. Yilmaz I. Synthesis of some Schiff bases and their metal complexes, determination of their protonation and stability constants by potentiometric titration method. Firat University, Graduate School of Natural and Applied Sciencies, Department of Chemistry, Elazig, Turkey. PhD Thesis, 2002.
27. Stubbe J, Kozarich JW. Mechanism of bleomycin-induced DNA degradation. Chem Rev 1987; 87: 1107-1136.
28. Aust SD, Morehouse LA, Thomas CE. Role of metals in oxygen radicals reactions. J Free Rad Biol Med 1985; 1: 3-25.
29. Geran RI, Greenberg NH, Macdonald MM, Schumacher AM, Abbott BD. Protocols for screening chemical agents and natural products against animal tumors and other biological systems (3rd ed.), Cancer Chemother Rep (Part 3) 1972; 3: 1-103.
30. Anisimov VN, Khavinson V, Morozof VG. Carcinogenesis and aging. IV. Effect of low molecular weight factors of thymus, pineal gland and anterior hypothalamus on immunity, tumor incidence and life span of C3H/Sn mice. Mech Aging Dev 1982; 19: 245-258.
31. Kato T, Sato K, Kakinuma H, Matsuda Y. Enhanced suppression of tumor growth by combination of angiogenesis inhibitor o-(chloroacetyl-carbamoyl) fumagillol (TNP-470) and cytotoxic agents in mice. Cancer Res 1994; 54: 5143-5147.
32. Papageorgiou Z, Iakovidou DM, Mioglou E, et al. Antineoplastic and cytogenetic effects of complexes of Pd(II) with 4N-substituted derivatives of 2-acetyl-pyridine-thiosemicarbazone. Anticancer Res 1997; 17: 247-252.
33. Kumamoto T, Toyooka K, Nishida M, et al. Effect of 2,4-dihydro-3H-1,2,4- triazole-3-thiones and thiosemicarbazones on iodide uptake by the mouse thyroid; the relationship between their structure and antithyroid activity. Chem Pharm Bull 1990; 38: 2595-2596.
34. Catignani GL. Simultaneous determination of retinol and α-tocopherol in serum of plazma by liquid chromatography. Clin Chem 1983; 2914: 708-712.
35. Arain MA, Khuhawar MY, Bhanger MI. Liquid chromatographic determination of selenium in vegetables and tea leaves as 2,1,3-benzoselenadiazole. J Chem Soc Pak 1999; 21: 137-140.
36. Cerhata D, Bauerova A, Ginter E. Determination of ascorbic acid in blood serum using high-performance liquid chromatography and its correlation with spectrophotometric. Caska-Slov-Farm 1994; 43: 166-168.
37. Karatas F, Karatepe M, Baysar A. Determination of free malondialdehyde in human serum by high performance liquid chromatography. Anal Biochem 2002; 311: 76-79.
38. Paglia DE, Valentine WN. Studies on the quantitative and qualitative properties of erythrocyte glutathione peroxidase. J Lab Clin Med 1967; 70: 158-168.
39. Luna LG (ed.). Manual of Histologic Staining Methods of the Armed Forces Institute of pathology (3rd edn). McGraw-Hill Book Company: New York, 1968.
40. Romine MT, Kessel D. Intracellular glutation as a determinant of responsiveness to antitumor drugs. Biochem Pharm 1986; 35: 3323-3326.
41. Nordberg J, Arner ESJ. Reactive oxygen species, antioxidants, and the mammalian thioredoxin system. J Free Rod Biol Med 2001; 31: 1287-1312.
42. Maccarrone M, Catani MV, Iraci S, Melino G, Agro AF. A survey of reactive oxygen species and their role in dermatology. J Eu Acad Derm Venreol 1997; 8: 185-202.
43. Morrow JD. The isoprostanes: their quantification as an index of oxidant stress status in vivo. Drug Metab Rev 2000; 32: 377-385.
44. Liu CM, Lin TS, Sartorelli AC. Synthesis and antitumor activity of amino derivatives of pyridine-2-carboxoldehyde thiosemicarbazone. J Med Chem 1992; 35: 3672-3677.
45. Vallee BL, Falchuk KH. The biochemical basis of zinc physiology. Physiol Rev 1993; 73: 79-118.
46. Hultberg B, Andersson A, Lsaksson A. Copper ions differ from other thiol reactive metal ions in their effects on the concentrations and redox status of thiols in HeLa cell cultures. Toxicology 1997; 117: 89-97.
47. Shen SG, Lia H, Zhao YY, Zhang QY, Sun HW. The distribution patterns of trace elements in the blood and organs in a rabbit experimental model of copper pollution and study of haematology and biochemistry parameters. Environ Toxicol Pharm 2005; 19: 379-384.
48. Sokol RJ, Devereaux MW, Traber MG, Shikes RH. Copper toxicity and lipid peroxidation in isolated rat hepatocytes: effect of vitamin E. Pediatric Res 1989; 25: 55-62.
49. Santos MLP, Alario AF, Mangrich AS, Ferreira AMC. Antioxidant and pro-oxidant properties of some di-Schiff base copper(II) complexes. J Inorg Biochem 1998; 71: 71-78.
50. Offing OE, Martelli S. Antibacterial activity of metal complexes of benzil and benzoin thiosemicarbazones. Il Farmaco 1994; 49: 513-518.
51. Ferrari BM, Capacchi S, Pelosi G, et al. Synthesis, structural characterization and biological activity of helicin thiosemicarbazone monohydrate and a copper(II) complex of salicylaldehyde thiosemicarbazone. Inorganica Chimica Acta 1999; 286: 134-141.
52. 4 substituted thiosemicarbazone. J Inorg Biochem 1989; 36: 107-113.
53. Rohde W, Shafer R, Idriss T, Levinson W. Binding of N-methyl isatin beta-thiosemicarbazone-copper complexes to proteins and nucleic acids. J Inorganic Biochem 1979; 10: 183-194.
54. Bamhart BA, Gren MA. The effect of glutathione depletion on the biodistribution of Cu(PTSM) in rats. Int J Rad Appl Instrum B 1991; 18: 865-869.
55. Urena FH, Chamorro ALP, Carretero MNM, Amigo JM, Estave V, Debaerdemaeker T. Synthesis and spectroscopic studies, on metal complexes with the neutral O,N,O tridentate Schiff base 6-amino-5-formyl-1,3-dimethyl-perchlorate copper(II) complex. Polyhedron 1999; 18: 2205-2210.
56. Stemkuhler C, Pedersen JZ, Weser U, Potilio G. Oxidative stress induced by a di-Schiff base copper complex is both mediated and modulated by glutathione. Biochem Pharm 1991; 42: 1821-1827.
57. Nagele A, Felix K, Lengfelder E. Induction of oxidative stress and protection against hydrogen peroxide-mediated cytotoxicity by the superoxide dismutase-mimetic complex copper-putrescine-pyridine. Biochem Pharm 1994; 47: 555-562.
58. Rockcliffe DA, Martel AE. Stoichiometric and catalytic oxidations by dinuclear copper(I) and copper(II) complexes of a Schiff base ligand derived from the 2:2 condensation of pyridine 2,6-dicarboxyaldahyde and 1,5,9-triazanonane. J Mol Catal A: Chem 1995; 106: 211-221.
59. Spodine E, Manzur J. Oxygen insertion in organic substrates catalyzed by copper compounds. Coord Chem Rev 1992; 119: 171-198.
60. 2 superoxide dismutase. Inorg Chim Acta 1987; 138: 163-166.
61. Yaping T, Yunzhong F, Qinhui L, Meng chang S, Qin L, Wenmei S. The inhibitory effects of 21 mimics of Superoxide dismutase on luminal-mediated chemiluminescence emitted from PMA-stimulated polymorphonuclear leukocyte. Free Rad Biol Med 1992; 13: 533-541.