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Article

Ruthenium p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline-Based Ligands: Synthesis, Characterization, and Cytotoxic Properties

by
Afroditi Kokkosi
1,
Elpida Garofallidou
1,
Nikolaos Zacharopoulos
1,
Nikolaos Tsoureas
1,
Konstantina Diamanti
2,
Nikolaos S. Thomaidis
2,
Antigoni Cheilari
3,
Christina Machalia
4,
Evangelia Emmanouilidou
4 and
Athanassios I. Philippopoulos
1,*
1
Laboratory of Inorganic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece
2
Laboratory of Analytical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece
3
Department of Pharmacognosy and Natural Products Chemistry, Faculty of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece
4
Laboratory of Biochemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece
*
Author to whom correspondence should be addressed.
Molecules 2024, 29(13), 3215; https://doi.org/10.3390/molecules29133215
Submission received: 29 May 2024 / Revised: 30 June 2024 / Accepted: 3 July 2024 / Published: 6 July 2024
(This article belongs to the Special Issue Recent Advance in Transition Metal Complexes and Their Applications II)
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Abstract

Organometallic complexes of the formula [Ru(N^N)(p-cymene)Cl][X] (N^N = bidentate polypyridyl ligands, p-cymene = 1-methyl-4-(1-methylethyl)-benzene, X = counter anion), are currently studied as possible candidates for the potential treatment of cancer. Searching for new organometallic compounds with good to moderate cytotoxic activities, a series of mononuclear water-soluble ruthenium(II)–arene complexes incorporating substituted pyridine–quinoline ligands, with pending -CH2OH, -CO2H and -CO2Me groups in the 4-position of quinoline ring, were synthesized, for the first time, to study their possible effect to modulate the activity of the ruthenium p-cymene complexes. These include the [Ru(η6-p-cymene)(pqhyme)Cl][X] (X = Cl− (1-Cl), PF6− (1-PF6), pqhyme = 4-hydroxymethyl-2-(pyridin-2-yl)quinoline), [Ru(η6-p-cymene)(pqca)Cl][Cl] ((2-Cl), pqca = 4-carboxy-2-(pyridin-2-yl)quinoline), and [Ru(η6-p-cymene)(pqcame)Cl][X] (X = Cl− (3-Cl), PF6− (3-PF6), pqcame = 4-carboxymethyl-2-(pyridin-2-yl)quinoline) complexes, respectively. Identification of the complexes was based on multinuclear NMR and ATR-IR spectroscopic methods, elemental analysis, conductivity measurements, UV–Vis spectroscopic, and ESI-HRMS techniques. The solid-state structures of 1-PF6 and 3-PF6 have been elucidated by single-crystal X-ray diffraction revealing a three-legged piano stool geometry. This is the first time that the in vitro cytotoxic activities of these complexes are studied. These were conducted in HEK293T (human embryonic kidney cells) and HeLa cells (cervical cancer cells) via the MTT assay. The results show poor in vitro anticancer activities for the HeLa cancer cell lines and 3-Cl proved to be the most potent (IC50 > 80 μΜ). In both cell lines, the cytotoxicity of the ligand precursor pqhyme is significantly higher than that of cisplatin.
Keywords: 2,2′-pyridyl-quinoline ligands; p-cymene; ruthenium complexes; cytotoxicity; MTT 2,2′-pyridyl-quinoline ligands; p-cymene; ruthenium complexes; cytotoxicity; MTT
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MDPI and ACS Style

Kokkosi, A.; Garofallidou, E.; Zacharopoulos, N.; Tsoureas, N.; Diamanti, K.; Thomaidis, N.S.; Cheilari, A.; Machalia, C.; Emmanouilidou, E.; Philippopoulos, A.I. Ruthenium p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline-Based Ligands: Synthesis, Characterization, and Cytotoxic Properties. Molecules 2024, 29, 3215. https://doi.org/10.3390/molecules29133215

AMA Style

Kokkosi A, Garofallidou E, Zacharopoulos N, Tsoureas N, Diamanti K, Thomaidis NS, Cheilari A, Machalia C, Emmanouilidou E, Philippopoulos AI. Ruthenium p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline-Based Ligands: Synthesis, Characterization, and Cytotoxic Properties. Molecules. 2024; 29(13):3215. https://doi.org/10.3390/molecules29133215

Chicago/Turabian Style

Kokkosi, Afroditi, Elpida Garofallidou, Nikolaos Zacharopoulos, Nikolaos Tsoureas, Konstantina Diamanti, Nikolaos S. Thomaidis, Antigoni Cheilari, Christina Machalia, Evangelia Emmanouilidou, and Athanassios I. Philippopoulos. 2024. "Ruthenium p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline-Based Ligands: Synthesis, Characterization, and Cytotoxic Properties" Molecules 29, no. 13: 3215. https://doi.org/10.3390/molecules29133215

APA Style

Kokkosi, A., Garofallidou, E., Zacharopoulos, N., Tsoureas, N., Diamanti, K., Thomaidis, N. S., Cheilari, A., Machalia, C., Emmanouilidou, E., & Philippopoulos, A. I. (2024). Ruthenium p-Cymene Complexes Incorporating Substituted Pyridine–Quinoline-Based Ligands: Synthesis, Characterization, and Cytotoxic Properties. Molecules, 29(13), 3215. https://doi.org/10.3390/molecules29133215

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