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  • Publication
    Métadonnées seulement
    Highly cytotoxic trithiophenolatodiruthenium complexes of the type [(?6-p-MeC6H4Pri)2Ru2(SC6H4-p-X)3]+: synthesis, molecular structure, electrochemistry, cytotoxicity, and glutathione oxidation potential
    (2012)
    Giannini, Federico
    ;
    Furrer, Julien
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    Ibao, Anne-Flore
    ;
    ; ;
    Zava, Olivier
    ;
    Baquie, Mathurin
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    Dyson, Paul J.
    ;
    Stepnicka, Petr
    A series of cationic binuclear areneruthenium tris(arenethiolato)-bridged complexes [(?6-p-cymene)2Ru2(?-SC6H4-p-X)3]+ (1-11; X = H, Me, Ph, Br, OH, NO2, OMe, CF3, F, iPr, tBu) were prepd. by complexation of the chloride-bridged dimer [(?6-p-cymene)2Ru2(?-Cl)2Cl2] with the corresponding thiols, isolated as the chloride salts, and further studied for their electrochem. properties, cytotoxicity towards human ovarian cancer cells, and catalytic activity for glutathione (GSH) oxidn. Complex 1 was also compared with the benzene and hexamethylbenzene analogs [(?6-C6H6)2Ru2(?-SC6H5)3]+ (12) and [(?6-C6Me6)2Ru2(?-SC6H5)3]+ (13). The most active compd. [11]Cl was structurally studied by single-crystal x-ray diffraction anal. The concns. corresponding to 50% inhibition of cancer cell growth (IC50 values) in the A2780 and A2780cisR cell lines of these complexes except for 6 were in the submicromolar range, complex 11 showing an IC50 value of 0.03 ?M in both cell lines. The high in vitro anticancer activity of these complexes may be at least partially due to their catalytic potential for the oxidn. of GSH, although there is no clear correlation between the IC50 values and the turnover frequencies at about 50% conversion. However, the cytotoxicity is tentatively correlated to the physicochem. properties of the compds. detd. by the electronic influence of the substituents X (Hammett consts. ?p) and the lipophilicity of the thiols p-XC6H4SH (calcd. log P parameters). [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Thiolato-Bridged Arene-Ruthenium Complexes: Synthesis, Molecular Structure, Reactivity, and Anticancer Activity of the Dinuclear Complexes [(arene)2Ru2(SR)2Cl2]
    (2012)
    Ibao, Anne-Flore
    ;
    Gras, Michael
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    ; ;
    Zava, Olivier
    ;
    Dyson, Paul J.
    Treatment of an arene-Ru dichloride dimer with thiols RSH to lead to cationic trithiolato complexes [(arene)2Ru2(SR)3]+ proceeds through the neutral thiolato complexes [(arene)2Ru2(SR)2Cl2], which were isolated and characterized for arene = p-MeC6H4CHMe2 and R = CH2Ph (1), CH2CH2Ph (2), CH2C6H4CMe3 (3), and C6H11 (4). The single-crystal x-ray structure anal. of the p-tert-butylbenzyl deriv. 3 reveals that the two Ru atoms are bridged by the two thiolato ligands without a metal-metal bond. The neutral dithiolato complexes[(arene)2Ru2(SR)2Cl2] (1-3) are intermediates in the formation of the cationic trithiolato complexes [(arene)2Ru2(SR)3]+ (5-7). Of the new [(arene)2Ru2(SR)2Cl2] complexes, deriv. 2 is highly cytotoxic against human ovarian cancer cells, with IC50 values of 0.20 ? for the A2780 cell line and 0.31 for the cisplatin-resistant cell line A2780cisR. [on SciFinder(R)]
  • Publication
    Accès libre
    Thiolato-Bridged Arene–Ruthenium Complexes: Synthesis, Molecular Structure, Reactivity, and Anticancer Activity of the Dinuclear Complexes [(arene)2Ru2 (SR)2Cl2]
    (2012)
    Ibao, Anne-Flore
    ;
    Gras, Michaël
    ;
    ; ;
    Zava, Olivier
    ;
    Dyson, Paul J.
    Treatment of an arene–ruthenium dichloride dimer with thiols RSH to lead to cationic trithiolato complexes of the type [(arene) 2Ru2(SR)3]+ was shown to proceed through the neutral thiolato complexes [(arene)2Ru2(SR)2Cl2], which have been isolated and characterized for arene = p-MeC6H4iPr and R = CH2Ph (1), CH2CH2Ph (2), CH2C6H4-p-tBu (3), and C6H11 (4). The single-crystal X-ray structure analysis of the p-tert-butylbenzyl derivative 3 reveals that the two ruthenium atoms are bridged by the two thiolato ligands without a metal–metal bond. The neutral dithiolato complexes[(arene)2Ru2(SR)2Cl2] (1–3) are intermediates in the formation of the cationic trithiolato complexes [(arene)2Ru2(SR)3]+ (5–7). Of the new [(arene)2Ru2(SR)2Cl2] complexes, derivative 2 is highly cytotoxic against human ovarian cancer cells, with IC50 values of 0.20 μM for the A2780 cell line and 0.31 for the cisplatin-resistant cell line A2780cisR.