The effect of potential supramolecular-bond promoters on the DNA-interacting abilities of copper–terpyridine compounds

Abstract

Three copper(ii) coordination compounds have been prepared from three different 2,2':6',2''-terpyridine-based ligands, which have been selected to investigate the potential role of supramolecular interactions on the DNA-interacting and cytotoxicity properties of the corresponding metal complexes. Hence, the ligands 4'-((naphthalen-2-yl)methoxy)-2,2':6',2''-terpyridine () and 4'-((1H-benzo[d]imidazol-2-yl)methoxy)-2,2':6',2''-terpyridine () have been synthesized from commercially-available 4'-chloro-2,2':6',2''-terpyridine (), and their copper(ii) complexes have been obtained by reaction with copper(ii) nitrate. The DNA-interacting abilities of the corresponding compounds [Cu()(H2O)(NO3)2] (), [Cu()(NO3)(H2O)](NO3)(MeOH) () and [Cu()(NO3)(H2O)](NO3) () have been investigated using different techniques, and cytotoxicity assays with several cancer cell lines have revealed interesting features, viz. the more efficient complex is , which although it does not act as a DNA cleaver, displays the most effective DNA-interacting and cytotoxic properties, compared to and .

Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

“…[13] Some years ago, we have described three copperterpyridine nitrato complexes with interesting cytotoxic properties. [14] In this previous study, the effect of supramolecular interactions on the biological properties was investigated, and the complex [Cu(naphtpy)(NO3)(H2O)](NO3)(MeOH) (where naphtpy stands for 4'-((naphthalen-2-yl)methoxy)-2,2′:6′,2′′terpyridine; Figure 1) exhibited notable cell toxicity behavior against several cancer cell lines. [14] In the present study, the ligand naphtpy was used to prepare copper(II) complexes with CuCl2 and Cu(ClO4)2 as the metal sources (instead of Cu(NO3)2).…”

Controlling with light the interaction betweentrans-tetrapyridyl ruthenium complexes and an oligonucleotide

“…We found no indication here suggesting that the trans ruthenium complexes [1] + -[4] 2+ would form adducts with two or more oligonucleotides. Other interactions responsible for the binding of metallodrugs to DNA involve hydrogen bonding with especially the phoshphate backbone, 3,48,49 or pi-pi stacking interactions with the base pairs. [50][51][52] However, these interactions dramatically depend on the supramolecular assembly of nucleic acids (double-strands vs. single-strands, G-quadruplexes vs. 3-way junctions, etc.…”

Coumarin centered copper(ii) complex with appended-imidazole as cancer chemotherapeutic agents against lung cancer: molecular insight via DFT-based vibrational analysis

“…To a solution of 3-formyl-6methylchromone (0.188 g, 1 mmol) in methanol (10 ml) was added 8-aminoquinoline slowly (0.144 g, 1 mmol) dissolved in methanol (7 ml). The ligand appears immediately as a yellow colored precipitate; the mixture was stirred for 3 h at 60 C. (1). To a hot methanolic solution of ligand L (0.314 g, 1 mmol), was added Cu(NO 3 ) 2 -$3H 2 O (0.241 g, 1 mmol) drop-wise, a brown colored precipitate appeared.…”

“…Cisplatin obstructs DNA through binding to guanine bases is known, inducing kinks in the biomolecule, which leads to cell death. 1 Nevertheless, systemic side effects of cisplatin remain a challenge to overcome and result in new design strategies for developing efficacious antitumor drugs based on metals other than platinum. Next to ruthenium, copper complexes are regarded as the most promising alternatives for classical cisplatin-type drugs.…”