New ternary copper(II) complexes of l-alanine and heterocyclic bases: DNA binding and oxidative DNA cleavage activity

Chetana, P.R.; Rao, R. Nagaraja; Roy, Mithun; Patra, Ashis K.

doi:10.1016/j.ica.2009.06.024

Cited by 36 publications

(26 citation statements)

References 49 publications

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“…A 1 cm pathlength quartz cuvette was used to conduct the measurements. The concentration of DNA used for the binding experiments was determined by measuring the absorption intensity at 260 nm with a molar extinction coefficient value of 6600 M -1 cm -1 [14]. , the y-intercept is equal to 1/ (Δεap × K), whereas the slope is equal to 1/ Δεap.…”

Section: Dna Binding Experiments: Uv-vis Titration Studymentioning

confidence: 99%

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Synthesis and Characterization of 6,6’-Bis(2-Hydroxyphenyl)-2,2’-Bipyridyl Ligand and Its Platinum Complex for the Interaction With Ct-Dna

Selamat¹,

Heng²,

Hassan³

et al. 2016

MJAS

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A tetradentate ligand with four donor atoms OONN and its platinum metal complex were synthesized. Bis(phenoxy)bipyridine ligand was prepared by Suzuki coupling reaction between 6,6'-dibromo-2,2'-bipyridyl and 2-hydroxyphenylboronic acid with the presence of palladium (II) acetate. The formation of platinum complex was done by introducing the ligand with platinum (II) chloride in benzonitrile. Both ligand and complex structures were confirmed by 1 H, 2D cosy and 13 C NMR spectroscopy, ESI-MS spectrometry and FTIR spectroscopy. Binding studies of small molecules with DNA are useful to understand the reaction mechanism and to provide guidance for the application and design of new and more efficient drugs or sensors targeted on DNA. In this study, the binding interaction between the synthesized ligand and complex with calf thymus DNA (CT-DNA) has been investigated using UV-Visible and emission DNA titration. From the UV-Visible DNA study, it showed that platinum (II) bipyridine complex had higher affinity towards CT-DNA with binding constant K b =(3.1 ± 0.02 x 10 5 ) ± 0.02 M -1 compared to that of bis(phenoxy) bipyridine ligand with binding constant (K b ) = (1.19 ± 0.08) × 10 3 M -1 . These findings will be valuable for the potential use of platinum (II) bipyridine complex as a phosphorescent probe in optical sensor DNA.Keyword: bis(phenoxy)bipyridine, intercalating ligand, calf thymus-DNA, DNA interaction Abstrak Ligan tetradentat dengan empat atom penderma OONN dan kompleks platinumnya telah disintesis. Ligan bis(fenoksi)bipiridin disediakan melalui tindak balas pengkupelan Suzuki antara 6,6'-dibromo-2,2'-bipiridil dan asid 2-hidroksifenilboronik dengan kehadiran palladium(II) asetat. Pembentukan kompleks platinum dilakukan dengan menambahkan platinum(II) klorida terhadap ligan di dalam benzonitril. Kedua-dua struktur ligan dan kompleks dibuktikan dengan spekroskopi 1 H, 2D dan 13 C RMN, spektrometri ESI-MS dan spektroskopi FTIR. Kajian pengikatan terhadap molekul kecil dengan DNA sangat berguna untuk memahami mekanisme tindak balas dan untuk panduan bagi aplikasi dan reka bentuk dadah yang baharu dan berkesan atau sensor target kepada DNA. Dalam kajian ini, interaksi ikatan antara ligan dan kompleks terhadap DNA timus anak lembu (CT-DNA) dilakukan dengan kajian titratan ultra lembayung boleh Nampak dan titratan pendaflour. Kaedah tersebut membuktikan bahawa kompleks platinum (II) bipiridin mempunyai ikatan yang lebih kuat terhadap CT-DNA berbanding dengan ligan iaitu sebanyak K b =(3.1 ± 0.02 x 10 5 ) ± 0.02 M -1 berbanding K b =(1.19 ± 0.08) x 10 3 M -1 . Penemuan ini sangat bernilai dan berpotensi dalam menjadikan kompleks platinum (II) bipiridin sebagai prob fosforesen dalam sensor DNA optik.Kata kunci: bis(fenoksi)bipiridin, ligan berinterkalasi, DNA timus, interaksi DNA

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Section: Dna Binding Experiments: Uv-vis Titration Studymentioning

confidence: 99%

“…This means that the complex binds better than the ligand due to its planar aromatic rings structure. Square planar geometry can make the molecule planar, hence increases its intercalation properties [14].…”

Section: Uv-vis Dna Titrationmentioning

confidence: 99%

Synthesis and Characterization of 6,6’-Bis(2-Hydroxyphenyl)-2,2’-Bipyridyl Ligand and Its Platinum Complex for the Interaction With Ct-Dna

Selamat¹,

Heng²,

Hassan³

et al. 2016

MJAS

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“…The UV absorbance of CT-DNA solution at wavelength 260 and 280 nm gave a ratio of (1.9:1) which is more than 1.8, indicating that DNA was sufficiently free from protein [5]. The concentration of DNA was calculated from its absorption intensity at 260 nm with known molar absorption coefficient value of 6600 M -1 cm -1 [7]. For emission DNA titration studies, excitation and emission wavelengths of 380 nm and 400 nm were used respectively.…”

Section: Dna Binding Experimentsmentioning

confidence: 99%

Synthesis and characterisation of platinum (II) salphen complex and its interaction with calf thymus DNA

Sukri

Heng

Karim

2014

AIP Conference Proceedings

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“…The strong binding affinity of the copper bis phen complex and the redox behavior of the copper center play an important role in inducing oxidative DNA cleavage. Chakravarty and co-workers recently explored amino acid transition metal based chemistry towards cleavage of DNA under physiological conditions by oxidative as well as photochemical means on charge transfer or d-d band excitation [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39]. The copper complex of L-lysine structure is closely resembles the copper-ornithine structure, which shows efficient chemical nuclease activity [25].…”

Section: Introductionmentioning

confidence: 99%

Oxidative DNA cleavage, cytotoxicity and antimicrobial studies of l-ornithine copper (II) complexes

et al. 2012

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a b s t r a c tNew ternary copper (II) complexes, [Cu(L-orn)(B)(Cl)](ClÁ2H 2 O) (1-2) where L-orn is L-ornithine, B is an N,N-donor heterocyclic base, viz. 2,2 0 -bipyridine (bpy, 1) and 1,10-phenanthroline (phen, 2), were synthesized and characterized by various spectroscopic techniques. Complex 2 is characterized by the X-ray single crystallographic method. The complex shows a distorted square-pyramidal (4 + 1) CuN 3 OCl coordination sphere. Binding interactions of the complexes with calf thymus DNA (CT-DNA) were investigated by UV-Vis absorption titration, ethidium bromide displacement assay, viscometric titration experiment and DNA melting studies. Complex 2 shows appreciable chemical nuclease activity in the presence of 3-mercaptopropionic acid (MPA). The complexes were subjected to in vitro cytotoxicity studies against carcinomic human alveolar basal epithelial cells (A-549) and human epithelial (HEp-2) cells. The IC 50 values of 1 and 2 are less than that of cisplatin against HEp-2 cell lines. MIC values for 1 against the bacterial strains Streptococcus mutans and Pseudomonas aeruginosa are 0.5 mM.

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New ternary copper(II) complexes of l-alanine and heterocyclic bases: DNA binding and oxidative DNA cleavage activity

Abstract: Crystal structure DNA binding Chemical nuclease activity Hydroxyl radical a b s t r a c t

Cited by 36 publications

References 49 publications

Synthesis and Characterization of 6,6’-Bis(2-Hydroxyphenyl)-2,2’-Bipyridyl Ligand and Its Platinum Complex for the Interaction With Ct-Dna

Synthesis and Characterization of 6,6’-Bis(2-Hydroxyphenyl)-2,2’-Bipyridyl Ligand and Its Platinum Complex for the Interaction With Ct-Dna

Synthesis and characterisation of platinum (II) salphen complex and its interaction with calf thymus DNA

Oxidative DNA cleavage, cytotoxicity and antimicrobial studies of l-ornithine copper (II) complexes

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