Synthesis and Characterization of a New Macrocyclic Ligand and Its Copper (II), Cadmium (II), and Lead (II) Complexes: Genotoxic Activity of These Complexes in Cultured Human Lymphocytes

REFERENCES

• Abou-Eisha A. Evaluation of cytogenetic and DNA damage induced by the antibacterial drug, trimethoprim. Toxicol. in Vitro 2006; 20: 601–607
   PubMed Web of Science ®Google Scholar
• Adams R., Miyano S. Condensation reactions of picoline 1-oxides. J. Am. Chem. Soc. 1954; 76: 3168–3171
   Web of Science ®Google Scholar
• Adatia T., Beynek N., Murphy B. P. Helical group 12 co-ordination. The x-ray crystal structure of a five co-ordinate zinc(II) complex. Polyhedron 1995; 14: 335–338
   Web of Science ®Google Scholar
• Bertin G., Averbeck D. Cadmium: cellular effects, modifications of biomolecules, modulation of DNA repair and genotoxic consequences (a review). Biochimie, Facets of Environmental Nuclear Toxicology 2006; 88(11)1549–1559
   Google Scholar
• Beynek N., Partlin M. Mc., Murphy B. P., Scowen I. J. Ligand control of molecular helicity in the coordination of toxic heavy metal ions: crystal structure of a monohelical cadmium(II) complex. Polyhedron 1998; 17: 2137–2140
   Web of Science ®Google Scholar
• Dendrinou-Samara C., George P., Raptopoulou C. P., Kessissoglou D. P. Copper(II) complexes with phenoxyalkanoic acids and nitrogen donor heterocyclic ligands: structure and bioactivity. J. Inorg. Biochem. 2001; 83: 7–16
   PubMed Web of Science ®Google Scholar
• Easmon J., Pürstinger G., Heinisch G., Roth T., Fiebig H. H., Holzer W., Jäger W., Jenny M., Hofmann J. Synthesis, cytotoxicity, and antitumor activity of copper(II) and iron(II) complexes of 4N-azabicyclo[3.2.2]nonane thiosemicarbazones derived from acyl diazines. J. Med. Chem. 2001; 44(13)2164–2171
   PubMed Web of Science ®Google Scholar
• Fabian R. H., Klasses D. M., Sonntag R. W. Synthesis and spectroscopic characterization of ruthenium and osmium complexes with sterically hindering ligands. 3. Tris complexes with methyl-substituted and dimethyl-substituted 2,2′-bipyridine and 1,10-phenanthroline. Inorg. Chem. 1980; 19: 1977–1982
   Web of Science ®Google Scholar
• Fenech M. The in vitro micronucleus technique. Mutat. Res. 2000; 455: 81–95
   PubMed Web of Science ®Google Scholar
• Fenech M., Chang W. P., Kirsch-Volders M., Holland N., Bonassi S., Zeiger E. HUMN project: detailed description of the scoring criteria for the cytokinesis-block micronucleus assay using isolated human lymphocyte cultures. Mutat. Res. 2003; 534: 65–75
   PubMed Web of Science ®Google Scholar
• Fimognari C., Berti F., Iori R., Cantelli-Forti G., Hrelia P. Micronucleus formation and induction of apoptosis by different isothiocyanates and a mixture of isothiocyanates in human lymphocyte cultures. Mutat. Res. 2005; 582: 1–10
   PubMed Web of Science ®Google Scholar
• Franke S. I. R., Prá D., Giulian R., Dias J. F., Yoneama M. L., da Silva J., Erdtmann B., Henriques J. A. P. Influence of orange juice in the levels and in the genotoxicity of iron and copper. Food Chem. Toxicol. 2006; 44(3)425–435
   PubMed Web of Science ®Google Scholar
• Giuliani R., Bettoni F., Leali D., Morandini F., Apostoli P., Grigolato P., Cesana B. M., Aleo M. F. Focal adhesion molecules as potential target of lead toxicity in NRK-52E cell line. FEBS Lett. 2005; 579: 6251–6258
   PubMed Web of Science ®Google Scholar
• Iyoda M., Otsuka H., Sato K., Nisato N., Oda M. Homocoupling of aryl halide using nickel(II) complex and zinc in the presence of Et4NI an efficient method for the synthesis of biaryls and bipyridines. Bull. Chem. Soc. Jpn. 1990; 63: 80–87
   Web of Science ®Google Scholar
• Jacobi H., Eicke B., Witte I. DANN strand break induction and enhanced cytotoxicity of propyl gallate in the presence of copper(II). Free Radic. Biol. Medi. 1998; 24(6)972–978
   PubMed Web of Science ®Google Scholar
• Kirsch-Volders M., Elhajouji A. The in vitro micronucleus test: A multi-endpoint test for the detection of apoptosis, chromosome breakage, chromosome loss and non-disjunction. Mutation Research Fundamental and Molecular Mechanisms of Mutagenesis 1997; 379(11001)134
   Google Scholar
• Lerda D., Biaggi B. M., Peralta N., Ychari S., Vazquez M., Bosio G. Fumonisins in foods from Cordoba (Argentina), presence, and genotoxicity. Food Chem. Toxicol. 2005; 43: 691–698
   PubMed Web of Science ®Google Scholar
• Lukevics E., Shestakova I., Domracheva I., Nesterova A., Ashaks J., Zaruma D. Synthesis of complex compounds of methyl derivatives of 8-quinolineselenol with metals and their cytotoxic activity. Chemistry of Heterocyclic Compounds 2006; 42(1)53–59
   Google Scholar
• Michailova P., Petrova N., Ilkova J., Bovero S., Brunetti S., White K., Sella G. Genotoxic effect of copper on salivary gland polytene chromosomes of Chironomus riparius Meigen 1804 (Diptera, Chironomidae). Environmental Pollution 2006; 144(2)647–654
   PubMed Web of Science ®Google Scholar
• Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds3rd. John Wiley, New York 1972
   Google Scholar
• Nersesyan A., Perrone E., Roggieri P., Bolognesi C. Genotoxic action of cycloplatam, a new platinum antitumor drug, on mammalian cells in vivo and in vitro. Chemotherapy 2003; 49(3)132–137
   PubMed Web of Science ®Google Scholar
• Noel S., Kasinathan M., Rath S. K. Evaluation of apigenin using in vitro cytochalasin blocked micronucleus assay. Toxicol. in Vitro 2006; 20: 1168–1172
   PubMed Web of Science ®Google Scholar
• Patra M., Bhowmik N., Bandopadhyay B., Sharma A. Comparison of mercury, lead and arsenic with respect to genotoxic effects on plant systems and the development of genetic tolerance. Environ. Exp. Botany 2006; 52(3)199–223
   Web of Science ®Google Scholar
• Pérez J. M., Cerrillo V., Matesanz A. I., Millán J. M., Navarro P., Alonso C., Souza P. DNA interstrand cross-linking efficiency and cytotoxic activity of novel cadmium(II) – thiocarbodiazone complexes. Chem. Biochem. 2001; 2: 119–123
   Google Scholar
• Psomas G., Raptopoulou C. P., Iordanidis L., Dendrinou-Samara C., Tangoulis V., Kessissoglou D. P. Structurally diverse copper(II)-carboxylato complexes: neutral and ionic mononuclear structures and a novel binuclear structure. Inorg. Chem. 2000; 39: 3042–3048
   PubMed Web of Science ®Google Scholar
• Rodriguez-Ubis J. C., Alpha B., Plancherel D., Lehn J-M. Photoactive cryptands. synthesis of the sodium cryptates of macrobicyclic ligands containing bipyridine and phenanthroline groups. Helv. Chim. Acta. 1984; 67: 2264–2269
   Web of Science ®Google Scholar
• Tang W., Xie J., Shaikh Z. A. Protection of renal tubular cells against the cytotoxicity of cadmium by glycine. Toxicology 2006; 223: 202–208
   PubMed Web of Science ®Google Scholar
• Tarafder Md. T. H., Saravanan N., Crouse K. A., Ali A. M. B. Coordination chemistry and biological activity of nickel(II) and copper(II) ion complexes with nitrogen–sulphur donor ligands derived from S-benzyldithiocarbazate (SBDTC). Transition Metal Chem. 2001; 26(6)613–618
   Web of Science ®Google Scholar
• Vogel A. Textbook of Practical Organic Chemistry4th. William Clowes Limited, London 1987; 613
   Google Scholar
• Williams D. H., Fleming I. Spectroscopic Methods in Organic Chemistry4th. McGraw Hill, London 1989
   Google Scholar
• Yang Z. S., Yu J. S., Chen H. Y. Studies on the interaction of 1,10-phenanthroline Cd2+ with DNA. Chin. J. Inorg. Chem. 2002; 18: 373–377
   Web of Science ®Google Scholar
• Zhang J., Ke X., Tu C., Lin J., Ding J., Lin L., Fun H-K., You X., Guo Z. Novel Cu(II)-quinoline carboxamide complexes: Structural characterization, cytotoxicity and reactivity towards 5′-GMP. BioMetals 2003; 16(3)485–496
   PubMed Web of Science ®Google Scholar