Structure and biological properties of the copper(II) complex with the quinolone antibacterial drug N-propyl-norfloxacin and 2,2′-bipyridine

Efthimiadou, Eleni K.; Thomadaki, Hellinida; Sanakis, Yiannis; Raptopoulou, Catherine P.; Katsaros, Nikos; Scorilas, Andreas; Karaliota, Alexandra; Psomas, George

doi:10.1016/j.jinorgbio.2006.07.019

Cited by 151 publications

(109 citation statements)

References 55 publications

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“…3a) are maintained in aqueous solution, although the dimeric units of the Cu(II) ternary complex with bpy and N-propyl-norfloxacin in the crystal structure occurs as a mixture of dimeric and monomeric species in aqueous solution. 34) Therefore we can conclude safely that complexes 1, 2 and 3 interact with DNA, and but cannot suggest the exact binding mode of each complex. The precise explanation of the binding modes of the complexes will be confirmed in further studies.…”

Section: Resultsmentioning

confidence: 86%

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

Yodoshi

Odoko

Okabe

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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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)

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Section: Resultsmentioning

confidence: 86%

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

Yodoshi

Odoko

Okabe

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The results of the minimum inhibitory concentration (MIC) 43 expressed in µg•mL -1 are listed in Table 3.…”

Section: Antibacterial Activity-minimum Inhibitory Concentrationmentioning

confidence: 99%

Antibacterial Activities and Nuclease Properties of Two New Ternary Copper(II) Complexes with 2‐(4′‐Thiazolyl)‐benzimidazole and 2,2′‐Bipyridine/1,10‐phenanthroline

Ren

Chen

2011

Chin. J. Chem.

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The complexes showed good antibacterial activities against the microorganisms. The interaction between the complexes and calf thymus DNA in aqueous solution was investigated adopting electronic absorption spectroscopy, fluorescence spectroscopy, viscosity measurements and cyclic voltammetry. Results suggest that the two complexes can bind to DNA by intercalative mode. In addition, the result of agarose gel electrophoresis suggested that the complexes can cleave the plasmid DNA at physiological pH and room temperature. Mechanistic studies with different inhibiting reagents reveal that hydroxyl radicals, and a singlet oxygen-like copper-oxo species are all involved in the DNA scission process mediated by the complexes.

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“…Cu II Complexes with linear [14] or simple histidine [15] ligands also show good nuclease activity. The recently described complex formed from copper(II), the quinolone antibacterial drug N-propyl-norfloxacin, and 2,2'-bipyridine [16] was reported to bind to calf-thymus DNA (CT-DNA) by the intercalative mode, and exhibited increased antiproliferative and necrotic effects on both HL-60 and K562 human leukemia cells in comparison to free N-propyl-norfloxacin. Further, salen-based Cu II [17] and Schiff-base Cu II [18] complexes were reported to interact with or modify DNA.…”

mentioning

confidence: 99%

Copper(II) Complexes of Salicylaldehyde Hydrazones: Synthesis, Structure, and DNA Interaction

Teng

et al. 2007

Chemistry & Biodiversity

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Three hydrazone ligands, H2L1-H2L3, made from salicylaldehyde and ibuprofen- or naproxen-derived hydrazides, were prepared and transformed into the corresponding copper(II) complexes [Cu(II)L1] x H2O, [Cu(II)L2], and [(Cu(II))2(L3)2] x H2O x DMF (Scheme). The X-ray crystal structure of the last-mentioned complex was solved (Fig. 1), showing a square-planar complexation geometry, and the single units were found to form a one-dimensional chain structure (Fig. 2). The interactions of these complexes with CT-DNA were studied by different techniques, indicating that they all bind to DNA by classical and/or non-classical intercalation modes.

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Structure and biological properties of the copper(II) complex with the quinolone antibacterial drug N-propyl-norfloxacin and 2,2′-bipyridine

Cited by 151 publications

References 55 publications

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

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

Antibacterial Activities and Nuclease Properties of Two New Ternary Copper(II) Complexes with 2‐(4′‐Thiazolyl)‐benzimidazole and 2,2′‐Bipyridine/1,10‐phenanthroline

Copper(II) Complexes of Salicylaldehyde Hydrazones: Synthesis, Structure, and DNA Interaction

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