Design of hydroxyl- and thioether-functionalized iron-platinum dimetallacyclopentenone complexes. Crystal and electronic structures, Hirshfeld and docking analyses and anticancer activity evaluated by in silico simulation

Mohamed, Ahmed Said; Jourdain, Isabelle; Knorr, Michael; Elmi, Abdirahman; Chtita, Samir; Scheel, Rebecca; Strohmann, Carsten; Hussien, Mostafa A.

doi:10.1016/j.molstruc.2021.131979

Cited by 7 publications

(6 citation statements)

References 79 publications

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“…The IR spectra of 2 – 4 (in CH 2 Cl 2 solution) share a common pattern with three absorptions, attributed to the terminal and bridging carbonyl ligands, and to the acyl group (e.g., for 2 , at 1972, 1800, and 1748 cm –1 , respectively) . The NMR spectra of 2 (acetone- d 6 solution; Figures S1–S2) consist of single sets of resonances, ascribable to the geometric isomer 2a (alkyne incorporation occurs by placing R = Fc on the β carbon of the dimetallacycle).…”

Section: Resultsmentioning

confidence: 91%

“…The IR spectra of 2−4 (in CH 2 Cl 2 solution) share a common pattern with three absorptions, attributed to the terminal and bridging carbonyl ligands, and to the acyl group (e.g., for 2, at 1972, 1800, and 1748 cm −1 , respectively). 39 The NMR spectra of 2 (acetone-d 6 solution; Figures S1−S2 45 In the 13 C NMR spectra, the carbonyl groups resonate at 236.6 ppm (bridging CO ligand), 220.9 ppm (acyl), and 201.6 ppm (terminal CO ligand).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Reactants and solvents were purchased from Alfa Aesar, Merck, Strem, or TCI Chemicals and were of the highest purity available. Diruthenacyclopentenone complex 1 and 3-ethynylphenyl 2-acetoxybenzoate , were prepared according to the literature. Reactions were conducted under a N 2 atmosphere using standard Schlenk techniques.…”

Section: Methodsmentioning

confidence: 99%

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Adding Diversity to a Diruthenium Biscyclopentadienyl Scaffold via Alkyne Incorporation: Synthesis and Biological Studies

et al. 2023

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We report the synthesis and the assessment of the anticancer potential of two series of diruthenium biscyclopentadienyl carbonyl complexes. Novel dimetallacyclopentenone compounds (2−4) were obtained (45−92% yields) from the thermal reaction (PhCCPh exchangeProtonation of 1−3 by HBF 4 afforded the corresponding μ-alkenyl derivatives 5−7, in 40−86% yields. All products were characterized by IR and NMR spectroscopy; moreover, cyclic voltammetry (1, 2, 5, 7) and single-crystal X-ray diffraction (5, 7) analyses were performed on representative compounds. Complexes 5−7 revealed a cytotoxic activity comparable to that of cisplatin in A549 (lung adenocarcinoma), SW480 (colon adenocarcinoma), and ovarian (A2780) cancer cell lines, and 2, 5, 6, and 7 overcame cisplatin resistance in A2780cis cells. Complexes 2, 5, and 7 (but not the aspirin derivative 6) induced an increase in intracellular ROS levels. Otherwise, 6 strongly stabilizes and elongates natural DNA (from calf thymus, CT-DNA), suggesting a possible intercalation binding mode, whereas 5 is less effective in binding CT-DNA, and 7 is ineffective. This trend is reversed concerning RNA, and in particular, 7 is able to bind poly(rA)poly(rU) showing selectivity for this nucleic acid. Complexes 5−7 can interact with the albumin protein with a thermodynamic signature dominated by hydrophobic interactions. Overall, we show that organometallic species based on the Ru 2 Cp 2 (CO) x scaffold (x = 2, 3) are active against cancer cells, with different incorporated fragments influencing the interactions with nucleic acids and the production of ROS.

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Section: Resultsmentioning

confidence: 91%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Adding Diversity to a Diruthenium Biscyclopentadienyl Scaffold via Alkyne Incorporation: Synthesis and Biological Studies

et al. 2023

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“…To the best of our knowledge, biological studies on dimetallacyclopentenone compounds have been limited to iron–platinum complexes, investigated for their interactions with cancer-relevant proteins. 80 We conducted an in vitro cytotoxicity screening of selected complexes on a panel of nine human cancer cell lines, while the selectivity was evaluated on the normal cell line MRC-5. Cisplatin and RAPTA-C 13 were employed as standards for comparative purposes.…”

Section: Resultsmentioning

confidence: 99%

Anticancer Potential of Diruthenium Complexes with Bridging Hydrocarbyl Ligands from Bioactive Alkynols

Bresciani,

Vančo,

Funaioli

et al. 2023

Inorg. Chem.

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Diruthenacyclopentenone complexes of the general composition [Ru2Cp2(CO)2{μ–η1:η3-CHC(C(OH)(R))C(O)}] (2a–c; Cp = η5-C5H5) were synthesized in 94–96% yields from the reactions of [Ru2Cp2(CO)2{μ–η1:η3-C(Ph)C(Ph)C(O)}] (1) with 1-ethynylcyclopentanol, 17α-ethynylestradiol, and 17-ethynyltestosterone, respectively, in toluene at reflux. Protonation of 2a–c by HBF4 afforded the corresponding allenyl derivatives [Ru2Cp2(CO)3{μ–η1:η2-CHCR}]BF4 (3a–c) in 85–93% yields. All products were thoroughly characterized by elemental analysis, mass spectrometry, and IR, UV–vis, and nuclear magnetic resonance spectroscopy. Additionally, 2a and 3a were investigated by cyclic voltammetry, and the single-crystal diffraction method was employed to establish the X-ray structures of 2b and 3a. The cytotoxicity in vitro of 2b and 3a–c was evaluated against nine human cancer cell lines (A2780, A2780R, MCF-7, HOS, A549, PANC-1, Caco-2, PC-3, and HeLa), while the selectivity was assessed on normal human lung fibroblast (MRC-5). Overall, complexes exert stronger cytotoxicity than cisplatin, and 3b (comprising 17α-estradiol derived ligand) emerged as the best-performing complex. Inductively coupled plasma mass spectrometry cellular uptake studies in A2780 cells revealed a higher level of internalization for 3b and 3c compared to 2b, 3a, and the reference compound RAPTA-C. Experiments conducted on A2780 cells demonstrated a noteworthy impact of 3a and 3b on the cell cycle, leading to the majority of the cells being arrested in the G0/G1 phase. Moreover, 3a moderately induced apoptosis and oxidative stress, while 3b triggered autophagy and mitochondrial membrane potential depletion.

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“…66 The geometry of the studied compounds (ligands) was optimised with the density functional theory (DFT) theory at the B3LYP/6-31G(d,p) (basis set) using the Gaussian 09 and GaussView software, then recorded in PDB format for the simulation of molecular docking. 67 The molecular docking was performed with the reference molecule to validate the protocol, and the RMSD value between the experimental reference and the docked reference was calculated. 68 Studies have suggested that the RMSD value should be less than 2.0 Å for the procedure to be reliable.…”

Section: Molecular Dockingmentioning

confidence: 99%

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

Zrinej,

Elmchichi,

Alaqarbeh

et al. 2023

New J. Chem.

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Design of hydroxyl- and thioether-functionalized iron-platinum dimetallacyclopentenone complexes. Crystal and electronic structures, Hirshfeld and docking analyses and anticancer activity evaluated by in silico simulation

Cited by 7 publications

References 79 publications

Adding Diversity to a Diruthenium Biscyclopentadienyl Scaffold via Alkyne Incorporation: Synthesis and Biological Studies

Adding Diversity to a Diruthenium Biscyclopentadienyl Scaffold via Alkyne Incorporation: Synthesis and Biological Studies

Anticancer Potential of Diruthenium Complexes with Bridging Hydrocarbyl Ligands from Bioactive Alkynols

Computational approach: 3D-QSAR, molecular docking, ADMET, molecular dynamics simulation investigations, and retrosynthesis of some curcumin analogues as PARP-1 inhibitors targeting colon cancer

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