Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid
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2019
Authors
Pantić, Darko N.Mihajlović-Lalić, Ljiljana

Aranđelović, Sandra

Radulović, Siniša

Grgurić-Šipka, Sanja

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Three new ruthenium(II)-arene halido complexes, [(η 6 -p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η 6 -p-cymene)RuX 2 ] 2 with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X – = Cl – (1), Br – (2), I – (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, 1 H and 13 C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC 50 values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffec...tive toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25 °C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20 min, confirming typical Ru-arene behavior in aqueous solutions.
Keywords:
arene ligand / benzimidazole derivatives / cytotoxicity / halido complex / Ruthenium(II)Source:
Journal of Coordination Chemistry, 2019, 72, 5-7, 908-919Funding / projects:
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
- Amorphous and nanostructural chalcogenides (RS-141026)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-256716)
Note:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3117
DOI: 10.1080/00958972.2019.1583332
ISSN: 0095-8972
WoS: 000468404900010
Scopus: 2-s2.0-85062477633
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Pantić, Darko N. AU - Mihajlović-Lalić, Ljiljana AU - Aranđelović, Sandra AU - Radulović, Siniša AU - Grgurić-Šipka, Sanja PY - 2019 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3116 AB - Three new ruthenium(II)-arene halido complexes, [(η 6 -p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η 6 -p-cymene)RuX 2 ] 2 with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X – = Cl – (1), Br – (2), I – (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, 1 H and 13 C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC 50 values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffective toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25 °C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20 min, confirming typical Ru-arene behavior in aqueous solutions. T2 - Journal of Coordination Chemistry T1 - Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid VL - 72 IS - 5-7 SP - 908 EP - 919 DO - 10.1080/00958972.2019.1583332 ER -
@article{ author = "Pantić, Darko N. and Mihajlović-Lalić, Ljiljana and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja", year = "2019", abstract = "Three new ruthenium(II)-arene halido complexes, [(η 6 -p-cymene) RuX(L)] (1–3), were synthesized in a reaction of [(η 6 -p-cymene)RuX 2 ] 2 with 5-chloro-1H-benzimidazole-2-carboxylic acid (HL) in ethanol (X – = Cl – (1), Br – (2), I – (3)). The complexes were characterized by elemental analysis, mass spectrometry, IR, 1 H and 13 C NMR spectroscopy. The cytotoxic activity of the ligand precursor and its ruthenium complexes was tested by MTT assay in human cancer cell lines: lung adenocarcinoma (A549), myelogenous leukemia (K562) as well as in one normal human fetal lung fibroblast cell line (MRC-5). The results show that ruthenium(II)-arene complexes possess enhanced cytotoxicity when compared to HL in the range of concentrations up to 300 µM. In terms of halido ligand substitution, cytotoxic activity toward A549 and K562 cell lines in 1–3 serie significantly increased (e.g., IC 50 values for K562: 1: 205.76 µM; 2: 174.77 µM; 3: 83.97 µM). All studied compounds were found to be ineffective toward MRC-5. Hydrolysis of 1–3 was followed by UV-vis spectroscopy at 25 °C, revealing ligand-substitution reactions at the Ru(II) center. Compounds 2 and 3 underwent rapid hydrolysis ranging from a few minutes for the aquation to ca. 20 min, confirming typical Ru-arene behavior in aqueous solutions.", journal = "Journal of Coordination Chemistry", title = "Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid", volume = "72", number = "5-7", pages = "908-919", doi = "10.1080/00958972.2019.1583332" }
Pantić, D. N., Mihajlović-Lalić, L., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid. in Journal of Coordination Chemistry, 72(5-7), 908-919. https://doi.org/10.1080/00958972.2019.1583332
Pantić DN, Mihajlović-Lalić L, Aranđelović S, Radulović S, Grgurić-Šipka S. Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid. in Journal of Coordination Chemistry. 2019;72(5-7):908-919. doi:10.1080/00958972.2019.1583332 .
Pantić, Darko N., Mihajlović-Lalić, Ljiljana, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Synthesis, characterization and cytotoxic activity of organoruthenium(II)-halido complexes with 5-chloro-1H-benzimidazole-2-carboxylic acid" in Journal of Coordination Chemistry, 72, no. 5-7 (2019):908-919, https://doi.org/10.1080/00958972.2019.1583332 . .