Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: The novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage

Selvakumar, Balaraman; Rajendiran, Venugopal; Maheswari, Palanisamy Uma; Stœckli-Evans, Helen; Palaniandavar, Mallayan

doi:10.1016/j.jinorgbio.2005.11.018

Cited by 285 publications

(146 citation statements)

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“…The CD spectrum of CT DNA consists of a positive band at 275 nm a negative band at 245 nm, characteristic of DNA in right handed B form. 34) When 2 is incubated with CT DNA at Rϭ3 which is enough to produce the absorption change (Fig. 5b), the CD spectrum of DNA undergoes the small red shift in the positive band at 275 nm and the reduction in the negative band at 245 nm.…”

Section: Resultsmentioning

confidence: 99%

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)

Yodoshi

Okabe

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Following the discovery of cis-diamminedichloroplatinum(II) (cisplatin) as the successful antitumor drug, 1) the research of the design and synthesis of novel platinum(II) complexes, having more favorable antitumor activities as compared with cisplatin, has been continued. [2][3][4][5] Palladium(II) complexes have been also investigated for developing the new antitumor agents, [6][7][8][9][10][11][12] because palladium(II) has a similar coordination mode and chemical properties to platinum(II).12) As the result, several novel palladium(II) complexes having antitumor citotoxic activities against MCF-7, TK-10 and UACC-62 human tumor cell lines, 13) and P388 lymphocytic leukemia cells have been found. [14][15][16][17] In these complexes, the ternary palladium(II) complexes with a heterocyclic ligand and L-glycine one, [Pd(Gly)(X)] (where X is a heterocyclic ligand; 2,2Ј-bipyridylamine(bpa), 15) 1,10-phenanthroline (phen) 16) and 2,2Ј-bipyridine(bpy) 17) ) have the antitumor activity against P388 lymphocytic leukemia cells. At the present time, the structures of these complexes are not yet clear, although they are important for clarifying the mechanism of their antitumor activity. By these circumstances, in this study, our aim was to determine the structures of three ternary Pd(II) complexes, [Pd(Gly)(bpy)], and evaluate the interaction with DNA, which is one of targets in the chemotherapy of tumor. 18) ExperimentalMaterials Analytical grade of 2,2Ј-bipyridine (bpy), 1,10-phenanthroline (phen), and 2,2Ј-bipyridylamine (bpa), L-glycine Methods The X-ray measurements were performed on a Rigaku R-AXIS RAPID diffractometer with a graphite monochromatized MoKa radiation (lϭ0.71069 Å) using the w scan mode at 123.1 K.Fluorescence measurements were performed with a Hitachi 850 spectrofluorometer. UV measurements were made on a Shimazu Pharma Spec UV-1700 Spectrophotometer and CD measurements on a JASCO J-710 CD spectrophotometer. The agarose gel electrophoresis was performed using a COSMO BIO Mupid-2. Elemental analysis was done by using a YANACO CHN Coder MT-3.Preparation of the Complexes The complex 1, 2 and 3 were prepared according to the analogous method described previously. 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. Each precipitate was dried under a vacuum and assumed as [Pd(bpy)Cl 2 ], [Pd(phen)Cl 2 ] and [Pd(bpa)Cl 2 ]. Then, 0.015 mmol of the precipitate was reacted with equal moles of Gly and NaHCO 3 in 5 ml of water solution for about 1 h at 333-343 K, until the volume of the reaction mixture was concentrated to ca. 1 ml. The concentrated solution was allowed to stand at room temperature for slow evaporation. Two weeks later, the light yellow needle crystals of the complex 1 and 3 suitable for X-ray diffraction studies were obtained from the mother liquid, and three months later the brown needle crystal of the complex 2 was obt...

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Section: Resultsmentioning

confidence: 99%

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)

Yodoshi

Okabe

2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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confidence: 99%

“…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.…”

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confidence: 99%

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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“…Thus the type of changes in the CD spectra reflect base stacking interactions through intercalation of compound 1. [30] A slight increase in negativity of the band at 211 nm can be due to a partial B to C-DNA conformational transition of compound 1-DNA adduct as recently reported by Marty et al [31] VISCOSITY STUDIES In classical intercalation the DNA helix lengthens as the base pairs are separated to accommodate the bound ligand leading to increased DNA viscosity. Whereas, a partial, nonclassical ligand intercalation causes a bend in DNA helix reducing its effective length and thereby its viscosity.…”

Section: Circular Dichroism (Cd) Studiesmentioning

confidence: 81%

Synthesis, Crystal Structure and in vitro DNA Binding Studies of Combretastatin A-4 Analogue

Rizvi¹,

Dangat²,

Yaseen³

et al. 2015

Croat. Chem. Acta

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Synthesis of a novel Combretastatin A-4 analogue using Schiff's reaction of benzil and 4-aminoantipyrine has been achieved under solvent free conditions. The structure of compound was examined spectroscopically and confirmed from single crystal diffraction studies. The synthesized Combretastatin A-4 analogue was investigated for its DNA binding ability as the plausible mechanism for its antitumor activity. The binding propensity of the synthesized compound with calf-thymus (CT) DNA was monitored with absorption and emission spectrophotometric titrations. The calculations predict a binding constant of 7.24 × 10 4 for the complex of the synthesized compound with CT DNA which is comparable in magnitude to that of DNA binding of bactericidal drug enoxacin and typical intercalation indicator ethidium bromide (EB). Competitive binding studies of the synthesized compound with EB using fluorescence titration reveal that it displaces the DNA-bound EB and binds in intercalative mode which was further supported by circular dichroism (CD) spectroscopy. The probable site and binding energy of the compound with DNA was further theoretically investigated by molecular docking studies. The significant DNA binding ability of the synthesized Combretastatin A4 analogue as revealed from this study could be related to the anticancer activity of the Combretastatin A4.

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Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: The novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage

Cited by 285 publications

References 73 publications

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)

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)

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

Synthesis, Crystal Structure and in vitro DNA Binding Studies of Combretastatin A-4 Analogue

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Structures, spectra, and DNA-binding properties of mixed ligand copper(II) complexes of iminodiacetic acid: The novel role of diimine co-ligands on DNA conformation and hydrolytic and oxidative double strand DNA cleavage

Cited by 285 publications

References 73 publications

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

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

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

Synthesis, Crystal Structure and in vitro DNA Binding Studies of Combretastatin A-4 Analogue

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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)

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)