DNA Interaction Studies of a Copper (II) Complex Containing an Antiviral Drug, Valacyclovir: The Effect of Metal Center on the Mode of Binding

Shahabadi, Nahid; Fatahi, Parvin

doi:10.1089/dna.2011.1592

Cited by 18 publications

(8 citation statements)

References 49 publications

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“…The binding of compounds 1−5 to DNA was then investigated by UV-Vis spectroscopy. [27] Absorption spectra were recorded for 25 μM solutions of each complex to which were added increasing amounts of ct-DNA (from 1 to 25 μM). The corresponding spectra (range 190-400 nm) for 1, which are representative for all the other compounds (viz.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

et al. 2020

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Five copper complexes supported by terpyridine ligands were prepared and characterized, viz. 4) and [Cu(Cltpy)2](ClO4)2 ( 5); (where Naphtpy stands for 4'-((naphthalen-2-yl)methoxy)-2,2′:6′,2′′-terpyridine and Cltpy for 4′-chloro-2,2′:6′,2′′-terpyridine). Their DNA-interaction abilities were investigated, and their cytotoxic behaviors were examined with three cells lines, namely with human ovarian carcinoma cells (A2780) and its derived cisplatin-resistant line (A2780cis), and human cervix adenocarcinoma cells (HeLa). All compounds show good cytotoxic properties (especially after 72 h incubation). Remarkably, two compounds, i.e. 4 and 5, are almost inactive after 24 h (particularly 4), but are highly active after 72 h, with IC50 values in the low micromolar to submicromolar range. Compounds 1 and 2 induce necrosis, whereas late apoptosis is observed with 3−5, 4 exhibiting a behaviour close to that of cisplatin. Results and Discussion Preparation of the copper complexesReaction of Naphtpy with 1.5 equiv. of CuCl2•2H2O in methanol at 40 ºC produces the mixed-valence Cu I Cu II compound [a]

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Section: Accepted Manuscriptmentioning

confidence: 99%

Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

et al. 2020

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“…Molecular absorption spectroscopy in the UV-vis region is an efficient tool for investigating the binding of compounds to DNA [50,51]. The UV-vis absorption spectra of compounds 1-10 are significantly perturbed by the addition of increasing amounts of DNA.…”

Section: Uv-vis Absorption Spectroscopymentioning

confidence: 99%

Zinc(II) Terpyridine Complexes: Substituent Effect on Photoluminescence, Antiproliferative Activity, and DNA Interaction

Liu

Jiang

et al. 2019

Molecules

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A series of ZnCl2 complexes (compounds 1–10) with 4′-(substituted-phenyl)-2,2′:6′,2′′-terpyridine that bears hydrogen (L1), p-methyl (L2), p-methoxy (L3), p-phenyl (L4), p-tolyl (L5), p-hydroxyl (L6), m-hydroxyl (L7), o-hydroxyl (L8), p-carboxyl (L9), or p-methylsulfonyl (L10) were prepared and then characterized by 1H NMR, electrospray mass-spectra (ESI-MS), IR, elemental analysis, and single crystal X-ray diffraction. In vitro cytotoxicity assay was used to monitor the antiproliferative activities against tumor cells. Absorption spectroscopy, fluorescence titration, circular dichroism spectroscopy, and molecular modeling studied the DNA interactions. All of the compounds display interesting photoluminescent properties and different maximal emission peaks due to the difference of the substituent groups. The cell viability studies indicate that the compounds have excellent antiproliferative activity against four human carcinoma cell lines, A549, Bel-7402, MCF-7, and Eca-109, with the lowest IC50 values of 0.33 (10), 0.66 (6), 0.37 (7), and 1.05 (7) μM, respectively. The spectrophotometric results reveal that the compounds have strong affinity binding with DNA as intercalator and induce DNA conformational transition. Molecular docking studies indicate that the binding is contributed by the π…π stacking and hydrogen bonds, providing an order of nucleotide sequence binding selectivity as ATGC > ATAT > GCGC. These compounds intercalate into the base pairs of the DNA of the tumor cells to affect their replication and transcription, and the process is supposed to play an important role in the anticancer mechanism.

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“…51,52 Therefore, absorption spectra have been recorded at a constant complex concentration of 25 µM and increasing amounts of calf-thymus DNA (ct-DNA), from 0 to 100 µM. The corresponding spectra for 1 are shown in Fig.…”

Section: Figmentioning

confidence: 99%

“…Molecular absorption spectroscopy in the ultraviolet (UV) and visible (vis) region is an efficient tool to investigate the binding of (coordination) compounds to DNA. 51,52 Therefore, absorption spectra have been recorded at a constant complex concentration of 25 μM and with increasing amounts of calf-thymus DNA (ct-DNA), from 0 to 100 μM. The corresponding spectra for 1 are shown in Fig.…”

Section: Uv-vis Spectroscopymentioning

confidence: 99%

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

et al. 2015

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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 .

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DNA Interaction Studies of a Copper (II) Complex Containing an Antiviral Drug, Valacyclovir: The Effect of Metal Center on the Mode of Binding

Cited by 18 publications

References 49 publications

Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Time‐Dependent Cytotoxic Properties of Terpyridine‐Based Copper Complexes

Zinc(II) Terpyridine Complexes: Substituent Effect on Photoluminescence, Antiproliferative Activity, and DNA Interaction

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

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