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 SM ISO690:2012BUCHEL, Gabriel E., GAVRILUŢĂ, Anatolie, NOVAK (LEGINA), Maria, MEIER-MENCHES, Samuel M., JAKUPEC, Michael, CUZAN, Olesea, TURTA, Constantin, TOMMASINO, Jean Bernard, JEANNEAU, Erwann, NOVITSKY, Ghenadie, LUNEAU, Dominique, ARION, Vladimir. Striking difference in antiproliferative activity of ruthenium-and osmium-nitrosyl complexes with azole heterocycles. In: Inorganic Chemistry, 2013, vol. 52, pp. 6273-6285. ISSN 0020-1669. DOI: https://doi.org/10.1021/ic400555k |
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  Inorganic Chemistry |
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| Volumul 52 / 2013 / ISSN 0020-1669 | |
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| DOI:https://doi.org/10.1021/ic400555k | |
| Pag. 6273-6285 | |
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Ruthenium nitrosyl complexes of the general formulas (cation) +[cis-RuCl4(NO)(Hazole)]-, where (cation) + = (H2ind)+, Hazole = 1H-indazole (Hind) (1c), (cation)+ = (H2pz)+, Hazole = 1H-pyrazole (Hpz) (2c), (cation)+ = (H2bzim)+, Hazole = 1H-benzimidazole (Hbzim) (3c), (cation)+ = (H2im) +, Hazole = 1H-imidazole (Him) (4c) and (cation)+[trans- RuCl4(NO)(Hazole)]-, where (cation)+ = (H 2ind)+, Hazole = 1H-indazole (1t), (cation)+ = (H2pz)+, Hazole = 1H-pyrazole (2t), as well as osmium analogues of the general formulas (cation)+[cis-OsCl 4(NO)(Hazole)]-, where (cation)+ = (n-Bu 4N)+, Hazole =1H-indazole (5c), 1H-pyrazole (6c), 1H-benzimidazole (7c), 1H-imidazole (8c), (cation)+ = Na+; Hazole =1H-indazole (9c), 1H-benzimidazole (10c), (cation)+ = (H2ind)+, Hazole = 1H-indazole (11c), (cation)+ = H2pz+, Hazole = 1H-pyrazole (12c), (cation)+ = (H2im)+, Hazole = 1H-imidazole (13c), and (cation) +[trans-OsCl4(NO)(Hazole)]-, where (cation)+ = n-Bu4N+, Hazole = 1H-indazole (5t), 1H-pyrazole (6t), (cation)+ = Na+, Hazole = 1H-indazole (9t), (cation)+ = (H2ind)+, Hazole = 1H-indazole (11t), (cation)+ = (H2pz)+, Hazole = 1H-pyrazole (12t), have been synthesized. The compounds have been comprehensively characterized by elemental analysis, ESI mass spectrometry, spectroscopic techniques (IR, UV-vis, 1D and 2D NMR) and X-ray crystallography (1c·CHCl3, 1t·CHCl3, 2t, 3c, 6c, 6t, 8c). The antiproliferative activity of water-soluble compounds (1c, 1t, 3c, 4c and 9c, 9t, 10c, 11c, 11t, 12c, 12t, 13c) in the human cancer cell lines A549 (nonsmall cell lung carcinoma), CH1 (ovarian carcinoma), and SW480 (colon adenocarcinoma) has been assayed. The effects of metal (Ru vs Os), cis/trans isomerism, and azole heterocycle identity on cytotoxic potency and cell line selectivity have been elucidated. Ruthenium complexes (1c, 1t, 3c, and 4c) yielded IC50 values in the low micromolar concentration range. In contrast to most pairs of analogous ruthenium and osmium complexes known, they turned out to be considerably more cytotoxic than chemically related osmium complexes (9c, 9t, 10c, 11c, 11t, 12c, 12t, 13c). The IC50 values of Os/Ru homologs differ by factors (Os/Ru) of up to ∼110 and ∼410 in CH1 and SW480 cells, respectively. ESI-MS studies revealed that ascorbic acid may activate the ruthenium complexes leading to hydrolysis of one M-Cl bond, whereas the osmium analogues tend to be inert. The interaction with myoglobin suggests nonselective adduct formation; i.e., proteins may act as carriers for these compounds. |
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| Cuvinte-cheie MeSH Antineoplastic Agents, Azoles, Cell Line, tumor, cell proliferation, crystallography, X-ray, Dose-Response Relationship, drug, Drug Screening Assays, Antitumor, Heterocyclic Compounds, Humans, Models, Molecular, molecular structure, Nitroso Compounds, Organometallic Compounds, Osmium, Ruthenium, Structure-Activity Relationship EMTREE drug terms antineoplastic agent, heterocyclic compound, nitroso derivative, organometallic compound, Osmium, pyrrole derivative, ruthenium EMTREE medical terms article, cell proliferation, chemical structure, Chemistry, dose response, drug effect, Drug Screening, human, structure activity relation, synthesis, tumor cell line, X ray crystallography |
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