Piškor, Martina; Ćorić, Ivan; Perić, Berislav; Špoljarić, Katarina Mišković; Kirin, Srećko I.; Glavaš-Obrovac, Ljubica; Raić-Malić, Silvana (2024) Quinoline- and coumarin-based ligands and their rhenium(I) tricarbonyl complexes: synthesis, spectral characterization and antiproliferative activity on T-cell lymphoma. Journal of Inorganic Biochemistry, 262 . ISSN 01620134
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Abstract
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)5Cl] gave rhenium(I) tricarbonyl complexes 5aRe-5eRe and 6aRe-6dRe 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 nontumor human fibroblasts (BJ) showed that the quinoline complexes 5aRe-5eRe had higher inhibitory activity than coumarin complexes 6aRe-6dRe, particularly against T-cell lymphoma (HuT78) cells. 6-Methoxy-2-(trifluoromethyl)quinoline 5e and 6-methylcoumarin 6d, and their rhenium(I) tricarbonyl complexes 5eRe and 6dRe 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 % (5eRe) and 45 % (6dRe) 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.
| Item Type: | Article | ||||||||
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| Uncontrolled Keywords: | Quinolines; Coumarins; Rhenium(I) complexes; Antiproliferative activity; ROS; Mitochondrial membrane potential | ||||||||
| Subjects: | BIOMEDICINE AND HEALTHCARE > Clinical Medical Sciences > Clinical Biochemistry BIOMEDICINE AND HEALTHCARE > Pharmacy > Medical Biochemistry |
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| Divisions: | Division of Materials Chemistry | ||||||||
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| Depositing User: | Ema Buhin Šaler | ||||||||
| Date Deposited: | 08 Apr 2026 08:41 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/11609 | ||||||||
| DOI: | 10.1016/j.jinorgbio.2024.112770 |
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