Synthesis, crystal structure, DFT calculation and DNA binding studies of new water-soluble derivatives of dppz

Aminzadeh, Mohammad; Eslami, Abbas; Kia, Reza; Aleeshah, Roghayeh

doi:10.1016/j.molstruc.2017.05.038

Cited by 6 publications

(3 citation statements)

References 61 publications

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“…Fluorescence titrations were done to ensure the interaction of compounds 1b , 1c with and without Ct–DNA, presented in Figure . From the results, it was found that fluorescent intensity increases regularly on addition of Ct–DNA which suggested that compounds get into hydrophobic environment inside the DNA helix prevented quenching effect of solvent molecule which is due to transfer of photoelectron from the guanine to the excited states of the compounds ,. Thus, it has been concluded that compounds bind with DNA through classical intercalative binding mode and results are well corroborated with other methods.…”

Section: Chemistrysupporting

confidence: 52%

Synthesis, In Vitro Biological Evaluation and In Silico Studies of Some New Heterocyclic Schiff Bases

et al. 2018

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2‐Hydroxy‐naphthaldehyde based heterocyclic Schiff base derivatives (1 a‐1 h) were prepared and characterized by multi‐spectroscopic techniques and elemental analysis. Antibacterial activity of all the compounds was tested against Streptococcus pneumoniae, Enterococcus faecalis, Pseudomonas aeruginosa, Salmonella enterica, Klebsiella pneumoniae and Escherichia coli bacterial strains. The antifungal potential of the synthesized compounds was also tested against three Candida strains (Candida albicans, Candida glabrata and Candida tropicalis). In the antibacterial activity, the compounds showed high MIC values and thus found less potent against all the tested bacterial strains. Interestingly, compounds 1 b and 1 c exhibited significant activity with MIC 125 μg/ml against all the tested fungal strains. Hemolytic assay against human RBCs revealed that compounds 1 b and 1 c showed less toxicity than the standard drug fluconazole at each tested concentration (25‐1000 μg/ml). In growth kinetics studies, compounds 1 b and 1 c significantly inhibited the growth of Candida cells at 2MIC and MIC concentrations. The interaction ability of lead compounds (1 b and 1 c) with Ct–DNA was carried out by absorption, fluorescence, hydrodynamic, cyclic voltammetery measurements and circular dichroism. Results suggested that compound 1 b and 1 c bind to Ct–DNA via an intercalative mode supported by molecular docking studies. The antioxidant potential of heterocyclic derivatives 1 b and 1 c was estimated by DPPH free radical and hydrogen peroxide assay which confirm that compounds exhibited significant antioxidant activity.

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Section: Chemistrysupporting

confidence: 52%

Synthesis, In Vitro Biological Evaluation and In Silico Studies of Some New Heterocyclic Schiff Bases

et al. 2018

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“…13−16 However, the biological properties of water-soluble, metal-free derivatives of these DNA intercalating ligands are considerably less studied. 17 We have reported that cationic derivatives of these compounds, such as 1 2+ and 2 2+ , bind to DNA with affinities comparable to many metal complexes and are capable of photo-oxidizing DNA in cell-free studies. 18−20 Elmes et al reported that a related system based on an electron deficient ligand is cell permeant, localizes in the cytoplasm, and�although not intrinsically cytotoxic�displays significant phototoxicity through the generation of ROS.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Luminescent ruthenium(II) polypyridyl complexes containing coordinated dppz and dppn ligands are well documented as cellular imaging agents and anticancer therapeutics. − And in this context, we have reported on a number of dinuclear complexes incorporating such ligands as potential phototherapeutics and theranostics. − However, the biological properties of water-soluble, metal-free derivatives of these DNA intercalating ligands are considerably less studied . We have reported that cationic derivatives of these compounds, such as 1 2+ and 2 2+ , bind to DNA with affinities comparable to many metal complexes and are capable of photo-oxidizing DNA in cell-free studies. − Elmes et al reported that a related system based on an electron deficient ligand is cell permeant, localizes in the cytoplasm, andalthough not intrinsically cytotoxicdisplays significant phototoxicity through the generation of ROS …”

Section: Introductionmentioning

confidence: 99%

Phenazine Cations as Anticancer Theranostics

Noakes,

Smitten,

Maple

et al. 2024

J. Am. Chem. Soc.

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The biological properties of two water-soluble organic cations based on polypyridyl structures commonly used as ligands for photoactive transition metal complexes designed to interact with biomolecules are investigated. A cytotoxicity screen employing a small panel of cell lines reveals that both cations show cytotoxicity toward cancer cells but show reduced cytotoxicity to noncancerous HEK293 cells with the more extended system being notably more active. Although it is not a singlet oxygen sensitizer, the more active cation also displayed enhanced potency on irradiation with visible light, making it active at nanomolar concentrations. Using the intrinsic luminescence of the cations, their cellular uptake was investigated in more detail, revealing that the active compound is more readily internalized than its less lipophilic analogue. Colocalization studies with established cell probes reveal that the active cation predominantly localizes within lysosomes and that irradiation leads to the disruption of mitochondrial structure and function. Stimulated emission depletion (STED) nanoscopy and transmission electron microscopy (TEM) imaging reveal that treatment results in distinct lysosomal swelling and extensive cellular vacuolization. Further imaging-based studies confirm that treatment with the active cation induces lysosomal membrane permeabilization, which triggers lysosome-dependent cell-death due to both necrosis and caspase-dependent apoptosis. A preliminary toxicity screen in the Galleria melonella animal model was carried out on both cations and revealed no detectable toxicity up to concentrations of 80 mg/kg. Taken together, these studies indicate that this class of synthetically easy-to-access photoactive compounds offers potential as novel therapeutic leads.

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A new palladium-based antiproliferative agent: synthesis, characterization, computational calculations, cytotoxicity, and DNA binding properties

et al. 2021

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Synthesis, crystal structure, DFT calculation and DNA binding studies of new water-soluble derivatives of dppz

Cited by 6 publications

References 61 publications

Synthesis, In Vitro Biological Evaluation and In Silico Studies of Some New Heterocyclic Schiff Bases

Synthesis, In Vitro Biological Evaluation and In Silico Studies of Some New Heterocyclic Schiff Bases

Phenazine Cations as Anticancer Theranostics

A new palladium-based antiproliferative agent: synthesis, characterization, computational calculations, cytotoxicity, and DNA binding properties

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