Synthesis, crystal structure, stability studies, DNA/albumin interactions, and antimicrobial activities of two Cu(II) complexes with amino acids and 5-nitro-1,10-phenanthroline

et al. 2019

Self Cite

Three novel water‐soluble copper(II) complexes – {[Cu(phen)(trp)]ClO4·3H2O}n (1), {[Cu(4‐mphen)(trp)]ClO4·3H2O}n (2) and [[Cu(dmphen)(trp)(MeOH)][Cu(dmphen)(trp)(NO3)]]NO3 (3) (phen: 1,10‐phenanthroline; 4‐mphen: 4‐methyl‐1,10‐phenanthroline; dmphen: 4,7‐dimethyl‐1,10‐phenanthroline; trp: l‐tryptophan) – have been synthesized and characterized using various techniques. Complexes 1 and 2 are isostructural, and exist as one‐dimensional coordination polymers. Complex 3 consists of two discrete copper(II) complexes containing [Cu(trp)(dmphen)(MeOH)]+, [Cu(trp)(dmphen)(NO3)] and one nitrate anion. The binding interaction of the complexes with calf thymus DNA (CT‐DNA) was investigated using thermal denaturation, electronic absorption and emission spectroscopic methods, revealing that the complexes could interact with CT‐DNA via a moderate intercalation mode. The binding activity of the complexes to CT‐DNA follows the order: 3 > 2 > 1. The pUC19 DNA cleavage activity of the complexes was investigated in the absence and presence of external agents using the agarose gel electrophoresis method. Especially, in the presence of H2O2 as an activator, the pUC19 DNA cleavage abilities of the complexes are clearly enhanced at low concentration. Addition of hydroxyl radical scavenger dimethylsulfoxide shows a marked inhibition of the pUC19 DNA cleavage activity of the complexes. In vitro cytotoxic effect of the complexes was examined on human tumor cell lines (Caco‐2, A549 and MCF‐7) and healthy cells (BEAS‐2B). The potent cytotoxic effect of complex 3, with IC50 values of 1.04, 1.16 and 1.72 μM, respectively, is greater relative to clinically used cisplatin (IC50 = 22.70, 31.1 and 22.2 μM) against the Caco‐2, A549 and MCF‐7 cell lines.

Section: Introductionmentioning

confidence: 99%

Methyl substituent effect on one‐dimensional copper(II) coordination polymers containing biologically active ligands: Synthesis, characterization, DNA interactions and cytotoxicities

Şenel

et al. 2019

Self Cite

“…Copper(II) complexes have been reported as potential anticancer agents owing to the selective permeability of cancer cell membranes and a number of copper complexes have been found to be active both in vitro and in vivo . The ligands in such Cu(II) complexes, especially planar ligands, considerably influence the anticancer activities, which can intercalate DNA . Especially, phenanthroline (phen) derivatives such as pyrazino[2,3‐f][1,10]phenanthroline, with an extended planar quinoxaline moiety, can act as good bidentate ligands as well as good binders to DNA.…”

Section: Introductionmentioning

confidence: 99%

“…In our previous studies, our group synthesized a series of binary and ternary copper(II) complexes where the ancillary ligand was kept the same (tyrosine or glycine) but the substituted phen intercalating ligand was changed with respect to the number and position of the methyl/nitro groups, and stability of the binary and ternary copper(II) complexes in aqueous solution was determined . From stabilities, DNA/bovine serum albumin (BSA) interactions and cytotoxicity assays, it was found that methyl‐substituted phen complexes were more active than the corresponding unsubstituted phen complexes .…”

Section: Introductionmentioning

confidence: 99%

Newly synthesized Cu(II) pyrazino[2,3‐f][1,10]phenanthroline complexes as potential anticancer candidates

Huriyet

et al. 2018

Self Cite

pyrazino[2,3-f][1,10]phenanthroline; gly: glycine;tyr: tyrosine), have been synthesized and characterized using CHN analysis, electrospray ionization mass spectrometry, Fourier transform infrared spectroscopy and single-crystal X-ray diffraction. Interaction of these complexes with calf thymus DNA has been investigated using absorption spectral titration, ethidium bromide and Hoechst 33258 displacement assay and thermal denaturation measurements. These complexes were found to be efficient cleaving agents and cleavage reactions were mediated by hydrolytic and oxidative pathways. The interaction between these complexes and bovine serum albumin (BSA) was investigated using electronic absorption and fluorescence spectroscopy. The experimental results show that the fluorescence quenching mechanism of these complexes and BSA is a static quenching process. Furthermore, in vitro cytotoxicities of these complexes against tumour cell lines (Caco-2, MCF-7 and A549) and healthy cell line (BEAS-2B) showed that they exhibited anticancer activity with low IC 50 values. These complexes were markedly active against the cell lines and can be good drug candidates that are effective and safe for healthy tissue.

“…In this study stems from our continuous interest in defining and evaluating DNA/protein interactions of copper (II) complexes and also explore the relationship between structure and biological activity. Quite recently, we have reported the synthesis, characterization, DNA/protein interactions and biological activities of some binary and ternary copper (II) complexes . Additionally, we have investigated the stability constants of ternary complexes formed of copper (II) with substituted 1,10‐phenanthrolines and L‐amino acids in aqueous solution .…”

Section: Introductionmentioning

confidence: 99%

“…Quite recently, we have reported the synthesis, characterization, DNA/protein interactions and biological activities of some binary and ternary copper (II) complexes . Additionally, we have investigated the stability constants of ternary complexes formed of copper (II) with substituted 1,10‐phenanthrolines and L‐amino acids in aqueous solution . In this report, our group has focused on the synthesis and property studies (CHN analysis, cyclic voltammetry, ESI‐MS, FTIR and single‐crystal X‐ray diffraction techniques) of ternary copper (II) complexes with methyl substituted 1,10‐phenanthrolines (4‐mphen, 5‐mphen, dmphen and tmphen) and tyrosine (tyr) ligands.…”

Section: Introductionmentioning

confidence: 99%

Cu (II) tyrosinate complexes containing methyl substituted phenanthrolines: Synthesis, X‐ray crystal structures, biomolecular interactions, antioxidant activity, ROS generation and cytotoxicity

Vatan

et al. 2018

Self Cite

In this paper, three new copper (II) complexes, [Cu(4-mphen)(tyr)(H 2 O)] ClO 4 (1), [Cu(5-mphen)(tyr)(H 2 O)]ClO 4 ·1.5H 2 O (2) and [Cu (tmphen)(tyr) (NO 3 )]0.5H 2 O (3) (4-mphen: 4-methyl-1,10-phenanthroline, 5-mphen: 5-methyl-1,10-phenanthroline, tmphen: 3,4,7,8-tetramethyl-1,10-phenanthroline and tyr: L-tyrosine), were synthesized and characterized using elemental analyses, FT-IR, ESI-MS, cyclic voltammetry and single-crystal X-ray diffraction. It was found that the complexes adopt a distorted five-coordinate square pyramidal geometry. The interaction of the three complexes with calf thymus DNA was also investigated using UV-visible absorption spectra, ethidium bromide and Hoechst 33258 displacement assay and thermal denaturation. The DNA cleavage activity of the complexes, monitored using gel electrophoresis, showed significant damage of the pUC19 plasmid DNA. Binding activity of bovine serum albumin (BSA) reveals that these complexes can strongly quench the fluorescence of BSA through a static quenching mechanism. The results suggested that interaction of the complexes with DNA occurred through a partial intercalation into the minor grooves of DNA. In addition, interaction of the complexes with bovine serum albumin quenched the fluorescence emission of the tryptophan residues of the protein binding constants and thermodynamic parameters were obtained from the fluorescence quenching experiments at different temperatures. Free radical scavenging activities of the complexes were determined by various in vitro assays such as 1,1-diphenyl-2-picryl-hydrazyl free radicals (DPPH˙) and H 2 O 2 scavenging methods. In addition, the cytotoxicity of these complexes in vitro on tumor cell lines (Caco-2 and MCF-7) was examined by XTT and showed better antitumor effect on the tested cells. ROS (reactive oxygen species) and comet experiments are consistent with each other and these complexes lead to DNA damage via the production of ROS. The effect of the hydrophobic properties of the synthesized complexes on DNA and BSA binding activities were discussed.