Quinoline- and coumarin-based ligands and their rhenium(I) tricarbonyl complexes: synthesis, spectral characterization and antiproliferative activity on T-cell lymphoma.

Autor: Piškor M; Department of Organic Chemistry, University of Zagreb, Faculty of Chemical Engineering and Technology, Marulićev trg 19, 10000 Zagreb, Croatia., Ćorić I; Department of Medicinal Chemistry, Josip Juraj Strossmayer University of Osijek, Faculty of Medicine, Biochemistry and Clinical Chemistry, J. Huttlera 4, 31000 Osijek, Croatia., Perić B; Laboratory for Solid State and Complex Compounds Chemistry, Ruđer Bošković Institute, Division of Materials Chemistry, Bijenička cesta 54, 10 000 Zagreb, Croatia., Špoljarić KM; Department of Medicinal Chemistry, Josip Juraj Strossmayer University of Osijek, Faculty of Medicine, Biochemistry and Clinical Chemistry, J. Huttlera 4, 31000 Osijek, Croatia., Kirin SI; Laboratory for Solid State and Complex Compounds Chemistry, Ruđer Bošković Institute, Division of Materials Chemistry, Bijenička cesta 54, 10 000 Zagreb, Croatia., Glavaš-Obrovac L; Department of Medicinal Chemistry, Josip Juraj Strossmayer University of Osijek, Faculty of Medicine, Biochemistry and Clinical Chemistry, J. Huttlera 4, 31000 Osijek, Croatia. Electronic address: lgobrovac@mefos.hr., Raić-Malić S; Department of Organic Chemistry, University of Zagreb, Faculty of Chemical Engineering and Technology, Marulićev trg 19, 10000 Zagreb, Croatia. Electronic address: sraic@fkit.unizg.hr.
Jazyk: angličtina
Zdroj: Journal of inorganic biochemistry [J Inorg Biochem] 2024 Oct 29; Vol. 262, pp. 112770. Date of Electronic Publication: 2024 Oct 29.
DOI: 10.1016/j.jinorgbio.2024.112770
Abstrakt: Novel 6-substituted 2-(trifluoromethyl)quinoline 5a-5e and coumarin 6a-6d ligands with aldoxime ether linked pyridine moiety were synthesized by O-alkylation of quinoline and coumarin with (E)-picolinaldehyde oxime and subsequently with [Re(CO) 5 Cl] gave rhenium(I) tricarbonyl complexes 5a Re -5e Re and 6a Re -6d Re that were fully characterized by NMR, single-crystal X-ray diffraction, IR and UV-Vis spectroscopy. The results of antiproliferative evaluation of quinoline and coumarin ligands and their rhenium(I) tricarbonyl complexes on various human tumor cell lines, including acute lymphoblastic leukemia (CCRF-CEM), acute monocytic leukemia (THP1), cervical adenocarcinoma (HeLa), colon adenocarcinoma (CaCo-2), T-cell lymphoma (HuT78), and non-tumor human fibroblasts (BJ) showed that the quinoline complexes 5a Re -5e Re had higher inhibitory activity than coumarin complexes 6a Re -6d Re , particularly against T-cell lymphoma (HuT78) cells. 6-Methoxy-2-(trifluoromethyl)quinoline 5e and 6-methylcoumarin 6d, and their rhenium(I) tricarbonyl complexes 5e Re and 6d Re were found to arrest the cell cycle of HuT78 cells by causing a significant accumulation of cells in the G0/G1 phase and a marked decrease in the number of cells in the G2/M phase. These rhenium(I) tricarbonyl complexes also slightly increased ROS production and significantly decreased the mitochondrial membrane potential by 50 % (5e Re ) and 45 % (6d Re ) compared to untreated cells and cells treated with 5e and 6d. These results suggest that the cytotoxic effects of these compounds are mediated by their effects on mitochondrial membrane potential and the subsequent increase in ROS production.
Competing Interests: Declaration of competing interest The authors declare no conflict of interest.
(Copyright © 2024 Elsevier Inc. All rights reserved.)
Databáze: MEDLINE
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