Design, synthesis and in vitro bioactivity of mixed ligand Ru(II) complexes bearing the fluoroquinolone antibacterial agents

Pulipaka, Ramadevi; Dash, Soumya Ranjan; Khanvilkar, Priyanka; Jana, Sarmita; Devkar, Ranjitsinh V.; Chakraborty, Debkumar

doi:10.1007/s11243-019-00341-3

Cited by 3 publications

(2 citation statements)

References 47 publications

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“…The presence of a p ‐cymene ligand was confirmed by the presence of 6‐proton doublet at δ = 1.93–1.02 ppm owing to two methyl protons of iso‐ propyl group [CH(CH 3 ) 2 ], 3‐proton singlet at δ = 2.49–1.91 ppm due to the Ar‐methyl group para to the iso‐ propyl group, 1‐proton quartet at δ = 3.95–2.24 ppm attributed to –CH of the iso‐ propyl group, and two 2‐proton doublets at δ = 7.01–5.44 ppm assigned to the 4 Ar‐protons of p ‐cymene. [ 44 ] The imine proton observed in the range δ = 8.36–10.17 ppm in free ligands is shifted upfield at δ = 8.22–8.69 ppm in the complexes indicating coordination via HC=N. All the aromatic protons present in pyrozole ring are observed in the excepted region.…”

Section: Resultsmentioning

confidence: 99%

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

Khanvilkar

Dash

Banerjee

et al. 2021

Applied Organom Chemis

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A series of pyrazol-derived thiosemicarbazone ligands (L1-L4) were synthesized and reacted with [Ru(p-cymene)(μ-Cl)Cl] 2 to yield a series of "piano-stool"-type binuclear ruthenium (II)-arene-thiosemicarbazone complexes (C1-C8) of the general type [(Ru(η 6 -p-cym)L) 2 (μ-im/azpy)] Cl 1-2 (L = diphenylpyrazole thiosemicarbazone; cym = p-cymene; im = imidazole; azpy = 4,4 0 -azopyridine). The thiosemicarbazone ligands act as N and S donors binding to the Ru(II) center via the imine nitrogen and the thione sulfur atoms. The complexes were characterized by NMR, FTIR, UV-Vis spectroscopy, and ESI + mass spectrometry. The binding of the complexes to calf thymus deoxyribonucleic acid (CT-DNA) and bovine serum albumin (BSA) was evaluated, and it has been established that the binuclear complexes have good binding efficacies with DNA (K b = 10 4 -10 5 M À1 ) and BSA (K a = 10 5 -10 6 M À1 ). This is attributed to the arene moieties present in the ligands of the complexes that can have hydrophobic interactions with DNA/BSA. Ethidium bromide (EB) displacement studies and DNA viscosity measurements revealed intercalative interaction of the complexes with DNA. Static interaction of the complexes with BSA was revealed by fluorescence quenching studies. Molecular docking studies confirmed base stacking, H-bonding, and hydrophobic interactions with the biomolecules. In vitro antiproliferative studies of the complexes affirmed that the complexes are cytotoxic towards the HeLa (human cervical cancer) cell line with IC 50 values in range of 17.3-41.3 μM. K E Y W O R D S binuclear ruthenium (II) complexes, DNA/BSA binding interactions, HeLa human cervical carcinoma, pyrazole-derived thiosemicarbazone

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Section: Resultsmentioning

confidence: 99%

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

Khanvilkar

Dash

Banerjee

et al. 2021

Applied Organom Chemis

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“…Furthermore, the compounds 102, 103, and 104 (p-cymene) type showed cytotoxic activities against MCF7 cancer cells with IC50, 209, 185, and 222 μM, respectively higher than references NAMI-A and RAPTA, IC50, ˃1600, 750 μM. The gene expression studies on BAX and BCL-2 genes and FACS analysis presented important evidence on the role of the complexes in triggering apoptosis in cancer cells and revealed the merits of the Ru(II) metal complexes containing fluoroquinolones as potent anticancer agents [130].…”

Section: Other Strategies Of Fluoroquinolones Modificationsmentioning

confidence: 92%

Recent Strategies in Design of Antitumor and Antibacterial Fluoroquinolones

Samir

Ramadan

Hamed

et al. 2021

Journal of advanced Biomedical and Pharmaceutical Sciences

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Fluoroquinolones are known widely used synthetic antibacterial agents. Generally, there were some obstacles associated with their therapeutic use. Moreover, many research studies all over the world proved the variable biological effects of fluoroquinolones such as antituberculosis, anticancer, or even antiviral activities. The current review is focused on modifications that occurred in the fluoroquinolone scaffold for their repositioning from antibacterial into anticancer agents especially modifications at C-7 or at the carboxylic C-3 groups. In addition, it includes the recent research studies carried out to improve the potency, spectrum of activity, or pharmacokinetics of antibacterial fluoroquinolones. Hence, this review may be useful for researchers in the design and synthesis of new fluoroquinolones with improved biological activities.

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A binuclear ruthenium polypyridyl complex: synthesis, characterization, pH luminescence sensor and electrochemical properties

et al. 2020

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Design, synthesis and in vitro bioactivity of mixed ligand Ru(II) complexes bearing the fluoroquinolone antibacterial agents

Cited by 3 publications

References 47 publications

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

Organoruthenium (II) complexes featuring pyrazole‐linked thiosemicarbazone ligands: Synthesis, DNA/BSA interactions, molecular docking, and cytotoxicity studies

Recent Strategies in Design of Antitumor and Antibacterial Fluoroquinolones

A binuclear ruthenium polypyridyl complex: synthesis, characterization, pH luminescence sensor and electrochemical properties

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