Synthesis, structure, properties, and cytotoxicity of a (quinoline)RuCp<sup>+</sup> complex

Hou, Zhilin; Vanecek, Allison; Tepe, Jetze J.; Odom, Aaron L.

doi:10.1039/d2dt03484k

Cited by 5 publications

(1 citation statement)

References 70 publications

(164 reference statements)

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“…The cytotoxic activity against two multiple myeloma cell lines of novel full-sandwich quinoline complexes, η 5 -Cp-Ru- η 6 -quinoline, and their stability in vitro and in cell culture was investigated. Despite that, the complexes showed poor cellular proteasome inhibition and demonstrated good cytotoxicity with IC 50 of a few μM [ 16 ]. Neutral ruthenocenyl complexes, including substituted Cp ligands, show weaker cytotoxic activity in comparison to similar cationic counterparts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Sifnaiou,

Tsolis,

Ypsilantis

et al. 2023

Molecules

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Novel full-sandwich (η5-Cp)-Ru-paraphenylene complexes with the general formula [(η5-Cp)nRu(η6-L)](PF6)n where n = 1–3 and L = biphenyl, p-terphenyl and p-quaterphenyl, were synthesized and characterized by means of spectroscopic and analytical techniques. The structures of the complexes [(η5-Cp)Ru(η6-biphenyl)](PF6) (1), [(η5-Cp)Ru(η6-terphenyl)](PF6) (3) and [(η5-Cp)2Ru(η6-terphenyl)](PF6)2 (4) was determined by X-ray single crystal methods. The interaction of the complexes [(η5-Cp)Ru(η6-quaterphenyl)]Cl, (6)Cl, and [(η5-Cp)2Ru(η6-quaterphenyl)]Cl2, (7)Cl2, with the DNA duplex d(5′-CGCGAATTCGCG-3′)2 was studied using NMR techniques. The results showed that both complexes interacted non-specifically with both the minor and major grooves of the helix. Specifically, (6)Cl exhibited partial binding through intercalation between the T7 and T8 bases of the sequence without disrupting the C–G and A–T hydrogen bonds. Fluorometric determination of the complexes’ binding constants revealed a significant influence of the number of connected phenyl rings in the paraphenylene ligand (L) on the binding affinity of their complexes with the d(5′-CGCGAATTCGCG-3′)2. The complexes (6)Cl and (7)Cl2 were found to be highly cytotoxic against the A549 lung cancer cell line, with complex (6) being more effective than (7) (IC50 for (6)Cl: 17.45 ± 2.1 μΜ, IC50 for (7)Cl2: 65.83 ± 1.8 μΜ) and with a selectivity index (SI) (SI for (6)Cl: 1.1 and SI for (7)Cl2: 4.8).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Sifnaiou,

Tsolis,

Ypsilantis

et al. 2023

Molecules

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Evaluating Quinolines: Molecular Dynamics Approach to Assess Their Potential as Acetylcholinesterase Inhibitors for Alzheimer's Disease.

Prejanò,

Romeo,

Felipe Hernández‐Ayala

et al. 2024

ChemPhysChem

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Quinoline represents a promising scaffold for developing potential drugs because of the wide range of biological and pharmacological activities it exhibits. In the present study, quinoline derivatives obtained from CADMA‐Chem docking protocol were investigated in the mean of molecular dynamics simulations as potential inhibitors of acetylcholinesterase enzyme. The examined species can be partitioned between neutral, dq815 (2,3 dihydroxyl‐quinoline‐4‐carbaldehyde), dq829 (2,3 dihydroxyl‐quinoline‐8‐carboxylic acid methane ester), dq1356 (3,4 dihydroxyl‐quinoline‐6‐carbaldehyde), dq1368 (3,4 dihydroxyl‐quinoline‐8‐carboxylic acid methane ester) and dq2357 (5,6 dihydroxyl‐quinoline‐8‐carboxylic acid methane ester), and deprotonated, dq815_dep, dq829_dep, dq1356_dep and dq2357_dep. Twelve molecular dynamics simulations were performed including those of natural acetylcholine, of the well‐known donepezil inhibitor and of the founder quinoline chosen as reference. Key intermolecular interactions were detected and discussed to describe the different dynamic behavior of all the considered species. Binding energies calculation from MMPBSA well accounts for the dynamic behavior observed in the simulation time proposing dq1368 as promising candidate for the inhibition of acetylcholinesterase. Retrosynthetic route for the production of the investigated compounds is also proposed.

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Quinoline-based metal complexes: Synthesis and applications

Kumar,

Thakur,

Sachin

et al. 2024

Coordination Chemistry Reviews

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Synthesis, structure, properties, and cytotoxicity of a (quinoline)RuCp⁺ complex

Abstract: Metal quinoline complexes were prepared using a quinoline-based proteasome inhibitor (Quin1) and an inactive quinoline ligand (Quin2), and their cytotoxicities are reported towards multiple myeloma-related cell lines.

Cited by 5 publications

References 70 publications

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Evaluating Quinolines: Molecular Dynamics Approach to Assess Their Potential as Acetylcholinesterase Inhibitors for Alzheimer's Disease.

Quinoline-based metal complexes: Synthesis and applications

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Synthesis, structure, properties, and cytotoxicity of a (quinoline)RuCp+ complex

Abstract: Metal quinoline complexes were prepared using a quinoline-based proteasome inhibitor (Quin1) and an inactive quinoline ligand (Quin2), and their cytotoxicities are reported towards multiple myeloma-related cell lines.

Cited by 5 publications

References 70 publications

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Synthesis and Characterization of Ruthenium-Paraphenylene-Cyclopentadienyl Full-Sandwich Complexes: Cytotoxic Activity against A549 Lung Cancer Cell Line and DNA Binding Properties

Evaluating Quinolines: Molecular Dynamics Approach to Assess Their Potential as Acetylcholinesterase Inhibitors for Alzheimer's Disease.

Quinoline-based metal complexes: Synthesis and applications

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Synthesis, structure, properties, and cytotoxicity of a (quinoline)RuCp⁺ complex