Synthesis, spectroscopic characterization, antineoplastic,<i>in vitro</i>-cytotoxic, and antibacterial activities of mononuclear ruthenium(II) complexes

Thota, Sreekanth; Imran, Mohammad; Udugula, Manasa; Karki, Subhas S.; Narasimha, K. Rama; Yerra, Rajeshwar; Balzarini, Jan; Clercq, Erik De

doi:10.1080/00958972.2012.663082

Cited by 13 publications

(3 citation statements)

References 24 publications

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“…[6e] The complexes reported show equivalent activity at 0.2 mg to the ruthenium complexes with quinazoline and thiosemicarbazone ligands reported by Thota et al. In addition, the complexes showed better activity when compared to the ruthenium(III) complexes reported by Sathya and co‐workers, the ruthenium(III) complexes containing ONO donor ligands and ruthenium(II) carbonyl complexes with thiosemicarbazone ligands . In addition, the complexes' activity was comparable to the ruthenium(II) complexes with mono‐nucleating tetradentate ligands reported by Arunachalam and co‐workers …”

Section: Resultsmentioning

confidence: 87%

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺

Gichumbi

Omondi

Lazarus

et al. 2017

Z. Anorg. Allg. Chem.

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New complexes [(η 6 -p-cymene)Ru(C 5 H 4 N-2-CH=N-Ar)X]PF 6 [X = Br (1), I (2); Ar = 4-fluorophenyl (a), 4-chlorophenyl (b), 4bromophenyl (c), 4-iodophenyl (d), 2,5-dichlorophenyl (e)] were prepared, as well as 3a-3e (X = Cl) and the new complexes [(η 6 -arene) RuCl(N-N)]PF 6 (arene = C 6 H 5 OCH 2 CH 2 OH, N-N = 2,2Ј-bipyridine (4), 2,6-(dimethylphenyl)-pyridin-2-yl-methylene amine (5), 2,6-(diisopropylphenyl)-pyridin-2-yl-methylene amine (6); arene = p-cymene, N-N = 4-(aminophenyl)-pyridin-2-yl-methylene amine (7)]. X-ray diffraction studies were performed for 1a, 1b, 1c, 1d, 2b, 5, and 7. Cytotoxicities of 1a-1d and 2 were established versus human cancer cells epithelial colorectal adenocarcinoma (Caco-2) (IC 50 : 35.8-631.0 μM), breast adenocarcinoma (MCF7) (IC 50 : 36.3-128.8.0 μM), and hepato-* Prof. H. B. Friedrich Fax: +27-312603091 E-Mail: friedric@ukzn.ac.za [a]699 cellular carcinoma (HepG2) (IC 50 : 60.6-439.8 μM), 3a-3e were tested against HepG2 and Caco-2, and 4-7 were tested against Caco-2. 1-7 were tested against non-cancerous human epithelial kidney cells. 1 and 2 were more selective towards tumor cells than the anticancer drug 5fluorouracil (5-FU), but 3a-3e (X = Cl) were not selective. 1 and 2 had good activity against MCF7, some with lower IC 50 than 5-FU. Complexes with X = Br or I had moderate activity against Caco-2 and HepG2, but those with Cl were inactive. Antibacterial activities of 1a, 2b, 3a, and 7 were tested against antibacterial susceptible and resistant Gram-negative and -positive bacteria. 1a, 2b, and 3a showed activity against methicillin-resistant S. aureus (MIC = 31-2000 μg·mL -1 ). 700Scheme 1. Schematic representation of the synthetic procedure for complexes 1a-1e and 2a-2e. Scheme 2. Preparation of the monomeric arene Ru II complexes 4-7.

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Section: Resultsmentioning

confidence: 87%

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺

Gichumbi

Omondi

Lazarus

et al. 2017

Z. Anorg. Allg. Chem.

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“…The research aims to contribute to understanding the interactions between these complexes and biomolecules, which form the basis of their anti-cancer activity. [12][13][14] The study involves the synthesis and characterization of the ruthenium complexes, evaluation of their anti-proliferative properties, determination of density functional theory (DFT) optimized molecular structures, and conducting molecular docking studies to elucidate potential molecular interactions. Through these comprehensive analyses, the goal was to provide insights into the potential therapeutic applications of these ruthenium complexes in breast cancer treatment.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, the objective of this study was to investigate the anti‐proliferative activities of newly synthesized ruthenium (II/III) polypyridyl complexes on breast cancer cell line. The research aims to contribute to understanding the interactions between these complexes and biomolecules, which form the basis of their anti‐cancer activity 12–14 . The study involves the synthesis and characterization of the ruthenium complexes, evaluation of their anti‐proliferative properties, determination of density functional theory (DFT) optimized molecular structures, and conducting molecular docking studies to elucidate potential molecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, molecular docking, and cytotoxicity study of ruthenium (II/III) polypyridyl complexes

Julius,

Mapolelo,

Demissie

et al. 2023

Applied Organom Chemis

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A new polypyridyl ligand 4‐(4‐nitrophenoxy)‐N,N‐bis (pyridin‐2‐ylmethyl)aniline (L1) and its three ruthenium (II/III) complexes, [Ru (Cl)3L1] (C1), [Ru(L1)2]Cl (C2), and [RuCl (dpa)L1] (C3) where dpa = 2,2‐dipyridylamine, have been successfully synthesized and characterized using Fourier‐transform infrared spectroscopy (FTIR), elemental analysis, proton nuclear magnetic resonance (1H NMR), high‐resolution electrospray ionization mass spectrometry (HR‐ESI‐MS), thermal analysis (thermogravimetric analysis [TGA] and differential scanning calorimetry [DSC]), UV/Vis absorption, and magnetic susceptibility. The structures of the ligand and the complexes were optimized, and the structural characteristics were determined by density functional theory (DFT) using the B3LYP‐GD3/6‐311G++(d,p) method. Optimized FTIR vibrational frequencies and 1H NMR chemical shifts agreed well with the corresponding experimental FTIR and 1H NMR data. In vitro cytotoxicity of the ligand and the complexes were evaluated against the MCF‐7 breast cancer cell line. Ligand L1 was the most potent with an IC50 of 38.45 μM, followed by C2 with an IC50 of 45.23 μM. However, the ligand and the complexes showed low antiproliferative activity compared to cisplatin, which had an IC50 of 9.67 μM. To predict the reactivity trend of L1 and the complexes, frontier molecular orbital (FMO) analysis was performed. The FMO energy gap (Eg = ELUMO − EHOMO) for C2 was found to be 1.675 eV, which was the lowest among all the complexes or L1. In addition, molecular docking studies were carried out so as to predict the binding capacity of L1 and the complexes to estrogen receptor alpha (ER‐α). The results showed that C2 has the most negative binding energy score (−9.63 kcal/mol), which indicates more stable adducts with the key amino acid residues at the active sites of ER‐α. Furthermore, C2 displayed the lowest inhibition constant (Ki) of 0.09 μM compared to all the complexes or L1. These results are very promising and show that the novel complex C2 may help in the development of anticancer drugs.

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Synthesis of Bis(hydroxylmethylfurfuryl)amine Monomers from 5‐Hydroxymethylfurfural

Yan

Liu

et al. 2016

ChemSusChem

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We report the synthesis of bis(hydroxylmethylfurfuryl)amine (BHMFA) from 5-hydroxymethylfurfural (5-HMF) by reacting 5-HMF with primary amines in the presence of homogeneous Ru(II) catalysts having sterically strained ligands. BHMFA is a group of furan-based monomers that offer great potential to form functional biopolymers with tunable properties. A range of primary amines, such as aliphatic and benzyl amines, are readily converted with 5-HMF to form the corresponding BHMFA in good yields. The reaction proceeds through reductive amination of 5-HMF with primary amine to form secondary amine, followed by reductive amination of 5-HMF with in situ generated secondary amine to produce BHMFA.

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Synthesis, spectroscopic characterization, antineoplastic,in vitro-cytotoxic, and antibacterial activities of mononuclear ruthenium(II) complexes

Cited by 13 publications

References 24 publications

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺

Synthesis, characterization, molecular docking, and cytotoxicity study of ruthenium (II/III) polypyridyl complexes

Synthesis of Bis(hydroxylmethylfurfuryl)amine Monomers from 5‐Hydroxymethylfurfural

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Synthesis, spectroscopic characterization, antineoplastic,in vitro-cytotoxic, and antibacterial activities of mononuclear ruthenium(II) complexes

Cited by 13 publications

References 24 publications

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η6 -arene)(C5 H4 N-2-CH=N-Ar)]+

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η6 -arene)(C5 H4 N-2-CH=N-Ar)]+

Synthesis, characterization, molecular docking, and cytotoxicity study of ruthenium (II/III) polypyridyl complexes

Synthesis of Bis(hydroxylmethylfurfuryl)amine Monomers from 5‐Hydroxymethylfurfural

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Product

Resources

About

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺

Influence of Halogen Substitution in the Ligand Sphere on the Antitumor and Antibacterial Activity of Half-sandwich Ruthenium(II) Complexes [RuX(η⁶ -arene)(C₅ H₄ N-2-CH=N-Ar)]⁺