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Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity

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2019
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Authors
Nikolić, Stefan
Mihajlović-Lalić, Ljiljana
Vidosavljević, Marija
Aranđelović, Sandra
Radulović, Siniša
Grgurić-Šipka, Sanja
Article (Accepted Version)
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Abstract
Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viab...ility of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.

Keywords:
Antitumor activity / Arene ligand / Picolinic acid / Ruthenium
Source:
Journal of Organometallic Chemistry, 2019, 902
Funding / projects:
  • Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
  • Pharmacodynamic and pharmacogenomic research of new drugs in the treatment of solid tumors (RS-41026)
Note:
  • This is peer-reviewed version of the following article: Nikolić, S.; Mihajlović-Lalić, L. E.; Vidosavljević, M.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S. Mono- and Binuclear Ru(II) Arene Complexes with (Fluoro Substituted) Picolinic Acid: Synthesis, Characterization and Cytotoxicity. Journal of Organometallic Chemistry 2019, 902. https://doi.org/10.1016/j.jorganchem.2019.120966
  • Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3642

DOI: 10.1016/j.jorganchem.2019.120966

ISSN: 0022-328X

WoS: 000493061500009

Scopus: 2-s2.0-85072830741
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URI
https://cherry.chem.bg.ac.rs/handle/123456789/3641
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  • Publikacije
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Nikolić, Stefan
AU  - Mihajlović-Lalić, Ljiljana
AU  - Vidosavljević, Marija
AU  - Aranđelović, Sandra
AU  - Radulović, Siniša
AU  - Grgurić-Šipka, Sanja
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3641
AB  - Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.
T2  - Journal of Organometallic Chemistry
T1  - Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity
VL  - 902
DO  - 10.1016/j.jorganchem.2019.120966
ER  - 
@article{
author = "Nikolić, Stefan and Mihajlović-Lalić, Ljiljana and Vidosavljević, Marija and Aranđelović, Sandra and Radulović, Siniša and Grgurić-Šipka, Sanja",
year = "2019",
abstract = "Four mono- (1–4) and four binuclear Ru(II) arene (5–8) complexes have been isolated from the reaction of [Ru(η6-benzene)Cl(μ-Cl)]2 or [Ru(η6-toluene)Cl(μ-Cl)]2 with 2-pyridinecarboxylic acid and 6-fluoro-2-pyridinecarboxylic acid. Their structural characterization included IR and NMR spectroscopy and MS spectrometry. The cytotoxic potential of the compounds has been tested by MTT assay in seven human cancer cell lines: alveolar basal adenocarcinoma (A549), large cell lung carcinoma (HTB177), colorectal carcinoma (HCT116), malignant melanoma (A375), prostate adenocarcinoma (PC3), breast carcinoma (MDA-MB-453), cervix adenocarcinoma (HeLa), and one human non-malignant lung fibroblast cell line (MRC-5). Mononuclear complexes 1 and 3 carrying 2-pyridinecarboxylic acid have displayed moderate antiproliferative effect toward HCT116 and HeLa, slightly better in comparison to their binuclear analogues, 5 and 7. The highest activity and cytoselectivity has been observed 1 as it has reduced viability of HCT116 cells 1.5 times more efficiently (IC50 = 27.5 μM), than of the MRC-5 cells (IC50 = 41.3 μM). In contrast to 1 and 3, compounds 2, 4–8 have been found to exhibit lack of cytotoxicity or mild cytotoxicity with IC50 values ranging from 100 to 300 μM.",
journal = "Journal of Organometallic Chemistry",
title = "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity",
volume = "902",
doi = "10.1016/j.jorganchem.2019.120966"
}
Nikolić, S., Mihajlović-Lalić, L., Vidosavljević, M., Aranđelović, S., Radulović, S.,& Grgurić-Šipka, S.. (2019). Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry, 902.
https://doi.org/10.1016/j.jorganchem.2019.120966
Nikolić S, Mihajlović-Lalić L, Vidosavljević M, Aranđelović S, Radulović S, Grgurić-Šipka S. Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity. in Journal of Organometallic Chemistry. 2019;902.
doi:10.1016/j.jorganchem.2019.120966 .
Nikolić, Stefan, Mihajlović-Lalić, Ljiljana, Vidosavljević, Marija, Aranđelović, Sandra, Radulović, Siniša, Grgurić-Šipka, Sanja, "Mono- and binuclear Ru(II) arene complexes with (fluoro substituted) picolinic acid: Synthesis, characterization and cytotoxicity" in Journal of Organometallic Chemistry, 902 (2019),
https://doi.org/10.1016/j.jorganchem.2019.120966 . .

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