A water-soluble Pd(<scp>ii</scp>) complex with a terpyridine ligand: experimental and molecular modeling studies of the interaction with DNA and BSA; and in vitro cytotoxicity investigations against five human cancer cell lines

Darabi, Farivash; Hadadzadeh, Hassan; Simpson, Jim; Shahpiri, Azar

doi:10.1039/c6nj01880g

Cited by 58 publications

(30 citation statements)

References 119 publications

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“…Some transition metal complexes of terpyridines have redox, magnetic and optical properties, photovoltaic applications and catalytic properties . Some terpyridine ligands and their complexes bind to RNA and DNA and have been investigated for antitumour activity against various human cell lines …”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Njogu

Martincigh

Omondi

et al. 2018

Applied Organom Chemis

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Six new silver(I) complexes, [(AgL1) 2 ](ClO 4 ) 2 (1), [(AgOTfL1) 2 ] (2), [(AgO 2 CF 3 L1) 2 ] (3), [AgL2](ClO 4 ) 2 (4), [(AgOTfL2) 2 ] (5) and [(AgO 2 CF 3 L2) 2 ] (6), were synthesized by reaction of 4′-(2-thienyl)-2,2′;6′,2″-terpyridine (L1)or 4′-(2-furyl)-2,2′;6′,2″-terpyridine (L2) with the respective silver salts, i.e. AgClO 4 , AgOTf or AgTFA. The complexes are dinuclear of the type Ag 2 L 2 in which the two ligands utilize the pyridinyl N atoms from the central rings and one of the peripheral rings to coordinate to one of the silver(I) centres while the remaining pyridinyl N atoms coordinate to the second silver(I) centre. Complexes 2 and 5 have the trifluoromethanesulfonate anion remotely coordinating via a single O atom while complex 3 has the trifluoroacetate anion coordinating to a single silver(I) centre in a bidentate mode. The perchlorate anion in complex 4 is excluded from the silver(I) coordination sphere.All complexes demonstrate moderate to high antimicrobial activity against the Gram-negative bacteria Escherichia coli and Salmonella typhimirium and the fungus Candida albicans. Complexes 1-6 interact strongly with salmon testes DNA as indicated by the steady increase in the relative viscosity of DNA solutions with increasing concentration of the silver(I) complexes and the relatively large intrinsic binding constants measured. There was substantial hyperchromism and hypsochromism recorded in solutions of complexes 1-6 with increasing concentration of salmon testes DNA. Complexes 1-6 interact with DNA via intercalation, and groove and external binding.

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Njogu

Martincigh

Omondi

et al. 2018

Applied Organom Chemis

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“…The binding constants were calculated to be 1.25 × 10 5 , 1.56 × 10 5 , 5.61 × 10 5 and 1.47 × 10 5 m −1 for 4 – 7 , respectively. Comparing these values with the literature suggests that the interactions of compounds with CT‐DNA are significant . The binding constants indicate that 6 has significantly higher affinity to DNA.…”

Section: Resultsmentioning

confidence: 67%

Bis‐aroylhydrazone based on 2,2′‐bis substituted diphenylamine for synthesis of new binuclear organotin (IV) complexes: Spectroscopic characterization, crystal structures, in vitro DNA‐binding, plasmid DNA cleavage, PCR and cytotoxicity against MCF7 cell line

Yousefi

Sedaghat

Shafiei

2019

Applied Organom Chemis

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have been synthesized from reaction of R 2 SnCl 2 (R = Me, Ph and Bu) with a 2,2′-bis-substituted diphenylamine arοylidene hydrazone, H 4 L. The synthesized compounds were investigated by elemental analysis and infrared, 1 H-NMR and 119 Sn-NMR spectroscopy. The structures of H 4 L, Me 4 Sn 2 L and Bu 4 Sn 2 L were also confirmed by X-ray crystallography. H 4 L molecules adopt (E)-configuration and keto-tautomeric form in the solid state. In all complexes, the bis-hydrazone acts as a tetra-anionic ligand with two contiguous ONO tridentate domains that coordinate the two R 2 Sn moieties in the enolate form.The coordination environments of both tin centers are five-coordinate. DNAbinding studies were performed by UV-Vis spectroscopy, and the results indicate that the synthesized compounds significantly interact with calf thymus-DNA in the intercalative mode. The results of polymerase chain reaction assay show that all the compounds affect on amplification of DNA, and complexes are more effective than ligands. The in vitro cytotoxicity against the human breast cancer line (MCF7) was determined using the MTT assay, and H 4 L and the dibutytin complex showed higher activity.

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“…The fluorescence activity of BSA comes from three of its amino acid residues tyrosine, tryptophan and phenylalanine . The major contribution in intrinsic fluorescence property of different proteins has been shown by tryptophan where the corresponding emission intensity depends on the extent of exposure of the tryptophan side chains 134 and 212 to polar solvent like water. Figure points to the quenching of BSA in presence of complex C1 while the quenching activity of other complexes C2 ‐ C6 has been shown in Figure S31 in the supporting information.…”

Section: Resultsmentioning

confidence: 99%

In Vitro DNA/BSA Binding, Anticancer and Normal Cell Activity of Pd(II) Complexes: Substitution Behaviour and Computational Study

et al. 2018

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In the aspect of an effective palladium based anticancer drug design, Pd(II) complexes [Pd(MAMP)Cl2], C1; [Pd(MAMP)(H2O)2]x2, C2; [Pd(MAMP)(L‐cys)]x, C3; [Pd(MAMP)(N‐ac‐L‐cys)], C4; [Pd(MAMP)(DL‐meth)]x2, C5; and [Pd(MAMP)(DL‐pen)]x, C6 (where x=ClO4−/NO3−) have been synthesised and characterised where 2‐[(methylamino)methyl]pyridine (MAMP) has been considered as carrier ligand and chloride, aqua, L‐cysteine (L‐cys), N‐acetyl‐L‐cysteine (N‐ac‐L‐cys), DL‐methionine (DL‐meth) and DL‐penicillamine (DL‐pen) are selected as leaving group. DNA as well as protein binding ability of the complexes has been investigated with CT‐DNA and BSA and the related binding parameters have been evaluated. Kinetic investigation for the reactions of Pd(II)‐diaqua complex C2 with four selected sulfur containing bio‐molecules have been carried out under pseudo first order condition. In addition, theoretical investigation has also been considered for structural optimisation, frontier molecular orbital mapping, TD‐DFT and NBO analysis. To get an insight into the cytotoxicity, the complexes have been treated on three different cancer cell lines (A549, HeLa, Hep G2) which reveal comparable anticancer activity of the reported complexes with the clinically acquainted anticancer drug Cisplatin. Very less complex initiated reactive oxygen species (ROS) with low degree of cell death in two different non‐tumour cell lines (L6 myotubes and HEK 293) indicate minimum normal cell toxicity of the complexes.

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A water-soluble Pd(ii) complex with a terpyridine ligand: experimental and molecular modeling studies of the interaction with DNA and BSA; and in vitro cytotoxicity investigations against five human cancer cell lines

Abstract: [Pd(4-OHPh-tpy)Cl]Cl was prepared. The complex interacts with DNA via a combination of covalent, intercalation, and hydrogen bonding interactions.

Cited by 58 publications

References 119 publications

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Synthesis, characterization, antimicrobial screening and DNA binding of novel silver(I)–thienylterpyridine and silver(I)–furylterpyridine complexes

Bis‐aroylhydrazone based on 2,2′‐bis substituted diphenylamine for synthesis of new binuclear organotin (IV) complexes: Spectroscopic characterization, crystal structures, in vitro DNA‐binding, plasmid DNA cleavage, PCR and cytotoxicity against MCF7 cell line

In Vitro DNA/BSA Binding, Anticancer and Normal Cell Activity of Pd(II) Complexes: Substitution Behaviour and Computational Study

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