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Süss-Fink, Georg

Nom
Süss-Fink, Georg
Affiliation principale
Fonction
Professeur ordinaire
Email
georg.suess-fink@unine.ch
Identifiants
https://libra.unine.ch/handle/123456789/385

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  • Publication
    Métadonnées seulement
    Arene ruthenium and pentamethylcyclopentadienyl rhodium and iridium complexes containing N,O-chelating ligands derived from piroxicam: Synthesis, molecular structure and cytotoxicity
    (2014)
    Raja, Mathiyazhagan Ulaganatha
    ;
    Tauchman, Jiri 
    ;
    Therrien, Bruno 
    ;
    Süss-Fink, Georg 
    ;
    Riedel, Tina
    ;
    Dyson, Paul J.
    The non-steroidal anti-inflammatory and anti-arthritic drug piroxicam (LH) reacts with arene ruthenium dichloride dimers in refluxing dichloromethane to give the complexes [(?6-arene)Ru(?2-N,O-L)Cl] (3: arene = C6H5Me, 4: arene = p-MeC6H4Pri, 5: arene = C6Me6). The reaction seems to proceed via the intermediates [(?6-arene)Ru(N-LH)Cl2], which can be obsd. for arene = C6H5Me (1) and isolated in the case of arene = p-MeC6H4Pri (2). The analogous reaction with pentamethylcyclopentadienyl rhodium and iridium gives the complexes [(?5-C5Me5)M(?2-N,O-L)Cl] (6: M = Rh, 7: M = Ir). The single-crystal x-ray structure analyses of the p-cymene ruthenium derivs. 4 and 2 show the metal atom in the archetypical piano stool geometry; in 4 the piroxicamato ligand is coordinated in a bidentate fashion through the pyridine nitrogen atom and the enolic oxygen atom, while in 2 the intact piroxicam ligand is coordinated in a monodentate fashion through the pyridine nitrogen atom. The piroxicamato complexes 3-5 are weakly cytotoxic towards human ovarian cancer cells. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Synthesis, characterisation and in vitro anticancer activity of hexanuclear thiolato-bridged arene ruthenium metalla-prisms
    (2013)
    Furrer, Mona A.
    ;
    Garci, Amine 
    ;
    Denoyelle-Di-Muro, Emmanuel
    ;
    Trouillas, Patrick
    ;
    Giannini, Federico
    ;
    Furrer, Julien
    ;
    Clavel, Catherine M.
    ;
    Dyson, Paul J.
    ;
    Süss-Fink, Georg 
    ;
    Therrien, Bruno 
    Hexanuclear hexacationic thiolato-bridged arene ruthenium metalla-prisms of the general formula [[(?6-p-cymene)Ru]6(?-SR)6(?3-tpt)2][OTf]6 (R = CH2Ph, CH2C6H4-p-tBu, CH2CH2Ph; tpt = 2,4,6-tri-4-pyridyl-1,3,5-triazine), obtained from the self-assembly of dinuclear precursors [(p-cymene)2Ru2(?-SR)2Cl2] with tpt and AgCF3SO3, have been isolated and fully characterized as triflate salts. The metalla-prisms are highly cytotoxic against human ovarian cancer cells, esp. towards the cisplatin-resistant cell line A2780cisR (IC50
  • Publication
    Métadonnées seulement
    Synthesis, molecular structure, computational study and in vitro anticancer activity of dinuclear thiolato-bridged pentamethylcyclopentadienyl Rh(III) and Ir(III) complexes
    (2013)
    Gupta, Gajendra
    ;
    Garci, Amine 
    ;
    Murray, Benjamin S.
    ;
    Dyson, Paul J.
    ;
    Fabre, Gabin
    ;
    Trouillas, Patrick
    ;
    Giannini, Federico
    ;
    Furrer, Julien
    ;
    Süss-Fink, Georg 
    ;
    Therrien, Bruno 
    Neutral dinuclear dithiolato-bridged pentamethylcyclopentadienyl Rh(III) complexes (C5Me5)2Rh2(?-SR)2Cl2 (R = CH2Ph, 1; R = CH2CH2Ph, 2) and cationic dinuclear trithiolato-bridged pentamethylcyclopentadienyl Rh(III) and Ir(III) complexes [(C5Me5)2M2(?-SR)3]+ (M = Rh, R = CH2Ph, 3; M = Rh, R = CH2CH2Ph, 5; M = Rh, R = CH2C6H4-p-tBu, 7: M = Ir, R = CH2Ph, 4; M = Ir, R = CH2CH2Ph, 6; M = Ir, R = CH2C6H4-p-tBu, 8) were synthesized from the chloro-bridged pentamethylcyclopentadienyl Rh(III) and Ir(III) dimers (C5Me5)2M2(?-Cl)2Cl2 by reaction with the corresponding thiol deriv. (RSH). Complexes 3-8 were isolated as chloride salts. All complexes were obtained in good yield and were fully characterized by spectroscopic methods. The mol. structures of the neutral complexes (1 and 2) show interesting features: the two Rh atoms are bridged by two thiolato ligands with no metal-metal bonds and the pentamethylcyclopentadienyl and chlorido ligands are oriented syn to each other, an uncommon conformation for such dinuclear complexes. These structural features were rationalized using DFT calcns. Addnl., the antiproliferative activity of the complexes was evaluated against the cancerous A2780 (cisplatin sensitive) and A2780cisR (cisplatin resistant) human ovarian cell lines and on the noncancerous HEK293 human embryonic kidney cells. All complexes are active and the cationic Ir complexes 4, 6 and 8 are particularly cytotoxic, with IC50 values in the nanomolar range (IC50 < 0.1 ?M). The catalytic activity of the complexes for the oxidn. of glutathione (GSH) to GSSG was evaluated by NMR spectroscopy. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity
    (2013)
    Khan, Farooq-Ahmad
    ;
    Therrien, Bruno 
    ;
    Süss-Fink, Georg 
    ;
    Zava, Olivier
    ;
    Dyson, Paul J.
    A series of p-cymene ruthenium dichloro complexes contg. isonicotinic ester ligands, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)n-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7: 4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepd. from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal x-ray anal. of 1 shows the mol. to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were obsd. only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C10 substituent contg. a terminal alc. function, NC5H4-4-COO-C6H4-p-O-(CH2)10-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)10-OH] (arene = C6H6: 9a, arene = p-MeC6H4Pri: 9b, arene = C6Me6: 9c) were prepd. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was obsd. for complex 9b, with IC50 values of 0.18 ?M for A2780 and 3.04 ?M for the cisplatin-resistant mutant A2780cisR. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Synthesis, Characterization and
    (2013)
    Giannini, Frederico
    ;
    Furrer, Julien
    ;
    Süss-Fink, Georg 
    ;
    Clavel, Catherine M.
    ;
    Dyson, Paul J.
  • 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
    ;
    Ibao, Anne-Flore
    ;
    Süss-Fink, Georg 
    ;
    Therrien, Bruno 
    ;
    Zava, Olivier
    ;
    Baquie, Mathurin
    ;
    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
    ;
    Therrien, Bruno 
    ;
    Süss-Fink, Georg 
    ;
    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
    Métadonnées seulement
  • Publication
    Métadonnées seulement
    Synthesis, Molecular Structure, and Anticancer Activity of Cationic Arene Ruthenium Metallarectangles
    (2009)
    Mattsson, Johan
    ;
    Govindaswamy, Padavattan
    ;
    Renfrew, Anna K.
    ;
    Dyson, Paul J.
    ;
    Stepnicka, Petr
    ;
    Süss-Fink, Georg 
    ;
    Therrien, Bruno 
    Cationic arene ruthenium-based tetranuclear complexes comprising rectangular structures have been obtained from the dinuclear arene ruthenium complexes [Ru2(arene)2(OO?OO)2Cl2] (arene = p-cymene, hexamethylbenzene; OO?OO = 2,5-dihydroxy-1,4-benzoquinonato, 2,5-dichloro-1,4-benzoquinonato) by reaction with pyrazine or bipyridine linkers (N?N = pyrazine, 4,4'-bipyridine, 1,2-bis(4-pyridyl)ethylene) in methanol in the presence of AgO3SCF3, forming tetranuclear cations of general formula [Ru4(arene)4(N?N)2(OO?OO)2]4+. All complexes were isolated in good yield as triflate salts and were characterized by NMR and IR spectroscopy and studied by cyclic voltammetry. The cytotoxicities of the water-sol. compds. of the 4,4'-bipyridine and 1,2-bis(4-pyridyl)ethylene series have been established using ovarian A2780 cancer cells. The large rectangles incorporating 1,2-bis(4-pyridyl)ethylene linkers are ca. 5 times more cytotoxic (IC50 ? 6 ?M) than the 4,4'-bipyridine-contg. cations (IC50 ? 30 ?M). Structural characterization by x-ray diffraction of two representative compds., i.e., the triflate salts of [Ru4(hexamethylbenzene)4(4,4'-bipyridine)2(2,5-dihydroxy-1,4-benzoquinonato)2]4+and [Ru4(hexamethylbenzene)4(1,2-bis(4-pyridyl)ethylene)2(2,5-dichloro-1,4-benzoquinonato)2]4+, reveals differently sized cavities, different flexibilities, and different packing arrangements, suggesting a correlation between these structural properties and the obsd. cytotoxicities. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Arene-ruthenium complexes with ferrocene-derived ligands: Synthesis and characterization of complexes of the type [Ru(?6-arene)(NC5H4CH2NHOC-C5H4FeC5H5)Cl2] and [Ru(?6-arene)(NC3H3N(CH2)2O2C-C5H4FeC5H5)Cl2]
    (2009)
    Auzias, Mathieu
    ;
    Gueniat, Joel
    ;
    Therrien, Bruno 
    ;
    Süss-Fink, Georg 
    ;
    Renfrew, Anna K.
    ;
    Dyson, Paul J.
    Pyridylferrocene and imidazolylferrocene arene-Ru complexes [Ru(?6-arene)(L)Cl2] where L = NC5H4CH2NHOCC5H4FeC5H5, arene = p-iPrC6H4Me (1) or C6Me6 (2); L = NC3H3N(CH2)2O2CC5H4FeC5H5, arene = p-iPrC6H4Me (3) or C6Me6 (4), and diruthenium-arene complexes [Ru(?6-arene)Cl2]2(L) where L = 1,1'-(NC5H4CH2NHOC)2C5H4FeC5H4, arene = p-iPrC6H4Me (5) or C6Me6 (6); L = 1,1'-(NC3H3N(CH2)2O2C)2C5H4FeC5H4, arene = p-iPrC6H4Me (7) or C6Me6 (8) were synthesized and characterized. The mol. structures of 1 and 3 were confirmed by single-crystal x-ray diffraction. The in vitro anticancer activities of complexes 1-8 were studied comparatively to the uncoordinated ligands. The complexes exhibit fairly low cytotoxicities in comparison to related ferrocene-derived arene-Ru complexes. [on SciFinder(R)]