Structures and DNA-Binding and Cleavage Properties of Ternary Copper(II) Complexes of Glycine with Phenanthroline, Bipyridine, and Bipyridylamine

Abstract

Recently, the interaction of Cu(II) complexes with nucleic acid has attracted attention due to the study of mutation of genes and therapeutic approaches, [2][3][4][5][6] because DNA is thought to be the target of the chemotherapy in the treatment of tumors.7) Some ternary complexes of Cu(II) of 1,10-phenanthroline(phen) have antitumor activity. 8) Various novel Cu(II) complexes with different ligand species have been designed and synthesized, 3,9) and the interaction of complexes with DNA has been characterized. Several groups 1,3,[10][11][12][13] showed that some Cu(II) complexes with phen bind to DNA noncovalently in the minor groove and the free hydroxyl radicals formed due to the reaction of reduced Cu(II) complex with H 2 O 2 lead to strand scission of DNA. Chikira and coworkers 9) investigated the orientation of Cu(II) complexes of phen or the ternary Cu(II) complexes with amino acids on DNA using electron paramagnetic reasonance method and suggested that the complexes bind to DNA with several different binding modes, such as non intercalative binding in the minor groove of DNA and/or intercalative binding. In addition to studies characterizing the interaction of Cu(II) complexes with DNA, there were a few studies on the crystal structures of ternary Cu(II) complexes of amino acids with heterocyclic ligands, such as glutamic acid and phen, 2,2Ј-bipyridine(bpy), 4,14) aspartic acid and bpy, 15) serine and phen, 16) proline and phen, 17) or glycine and phen. 18,19) We aimed to synthesize and determine three ternary Cu(II) complexes containing an amino acid, glycine ligand, and different heterocyclic ligands, phen, bpy, and 2,2Ј-bipyridylamine (bpa) and evaluate the ability the complexes to cleave DNA. The following three complexes (Fig. 1) were prepared and the structures, DNA binding, and DNA cleavage were examined. The three complexes are designated as [Cu(Gly)(bpy)Cl] · 2H 2 O (1), [Cu(Gly)(phen)Cl] 2 · 7H 2 O (2), and [Cu(bpa)(phen)(H 2 O)Cl] (3). We had previously determined the structure of (1), 1) and the structures of (2) and (3) were determined in this study. The structural features of (1) were calculated using the previous coordination data 1) and cited together with those of (2) and (3)

Characterization and cytotoxic effect of aqua-(2,2′,2′′-nitrilotriacetato)-oxo-vanadium salts on human osteosarcoma cells

“…The high anti-proliferative activity of [phenH][VO(nta)(H 2 O)](H 2 O) 0.5 can be assigned to the intercalating properties of the phen derivative that interacts more strongly with DNA than the bpy derivative. A similar relationship in the reactivity towards DNA has also been found for other phen and bpy metal coordination compounds (Yodoshi et al 2007; Chakravarty 2006).

Fig.

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“…3) revealed that the DNA cleavages caused by VO(oda)(bpy) and VO(oda) were similar, while VO(oda)(phen) showed a stronger effect. VO(oda)(phen) presented the most potent antitumor action in human osteosarcoma cells followed by VO(oda)(bpy) and then by VO(oda) according to the number of intercalating heterocyclic moieties (Yodoshi et al 2007). …”

Structures and Interaction with DNA of Ternary Palladium(II) Complexes: [Pd(Gly)(X)] (Gly=Glycine; X=2,2′-Bipyridine, 1,10-Phenanthroline and 2,2′-Bi-pyridylamine)

“…15,19) 0.76 mmol of bpy, phen or bpa were mixed with 0.76 mmol of PdCl 2 · 2NaCl · 3H 2 O in 5 ml of 80% (v/v) methanol-water solution for about 5 min at room temperature. The precipitates appeared after adding palladium salt.…”

Structure, Physicochemical and Biological Properties of an Aqua (2,2′,2′′‐Nitrilotriacetato)‐oxidovanadium(IV) Salt with 4‐Methylpyridinium Cation

“…Oxidovanadium(IV) complexes are the subject of interest to many research groups since it has been found that they reveal an interesting biological activity. Much attention has been focused on studies of their insulin‐mimetic (‐enhancing) properties, the anticancer properties as well as the cytoprotective activity against an oxidative damage . However, the main challenge in designing new oxidovanadium(IV) complexes for the future use in medicine is the selection of the appropriate type of ligands in order to overcome the balance existing between the therapeutic action and adverse effects exerted by vanadium compounds by shifting this balance toward the beneficial side.…”