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Therrien, Bruno

Nom
Therrien, Bruno
Affiliation principale
Fonction
Professeur titulaire
Email
bruno.therrien@unine.ch
Identifiants
https://libra.unine.ch/handle/123456789/382
_
0000-0002-0388-2745

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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
    Neutral and cationic osmium(II)-arene metallodendrimers: Synthesis, characterisation and anticancer activity
    (2014)
    Govender, Preshendren
    ;
    Edafe, Fabio
    ;
    Makhubela, Banothile C. E.
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    ;
    Smith, Gregory S.
    Two neutral and two cationic half-sandwich Os(II)-arene metallodendrimers, [DAB-PPI-{(?6-p-cym)Os((C7H5NO)-?2-N,O)Cl}n] and [DAB-PPI-{(?6-p-cym)Os((C6H5N2)-?2-N,N)Cl}n][PF6]n (n = 4 (G1) or 8 (G2)) were synthesized. Two cationic half-sandwich Os(II)-arene metallodendrimers, contg. PTA (1,3,5-triaza-7-phosphatricyclo[3.3.1.1.] decane), [DAB-PPI-{(?6-p-cym)Os((C7H5NO)-?2-N,O)PTA}n][PF6]n are also reported. All complexes were characterized using anal. (i.e. HR-ESI or EI mass spectrometry and elemental anal.) and spectroscopic (i.e.1H, 13C{1H} NMR and IR) methods. Model mononuclear analogs were prepd. and their mol. structures detd. by single-crystal x-ray crystallog. The cytotoxicity of the complexes were evaluated against the A2780 and A2780cisR human ovarian carcinoma cell lines and some display moderate activity. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    The influence of RAPTA moieties on the antiproliferative activity of peripheral-functionalised poly(salicylaldiminato) metallodendrimers
    (2013)
    Govender, Preshendren
    ;
    Sudding, Lara C.
    ;
    Clavel, Catherine M.
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    ;
    Smith, Gregory S.
    Cationic N,O-chelating dendrimers functionalised on the periphery with RAPTA-like (ruthenium(II)-arene-1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane) moieties have been synthesized and characterized using NMR and IR spectroscopy, elemental anal. and MALDI-TOF/HR-ESI mass spectrometry. Metallodendrimers from the first to the fourth-generation contg. up to 32 peripheral ruthenium-arene-PTA moieties were obtained. Model mononuclear analogs, [{Ru(?6-p-cymene)((C7H5NO)-?2-N,O)(PTA)}((CH2)3)][PF6] and [{Ru(?6hexamethylbenzene)((C7H5NO)-?2-N,O)(PTA)}((CH2)3)][PF6], have been prepd. and their structures were detd. by single crystal X-ray diffraction anal. The cytotoxicities of the metallodendrimers and their mononuclear analogs were established on A2780 and A2780cisR human ovarian carcinoma cancer cells and model human embryonic kidney (HEK) 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
    Neutral and cationic multinuclear half-sandwich rhodium and iridium complexes coordinated to poly(propyleneimine) dendritic scaffolds: Synthesis and cytotoxicity
    (2013)
    Payne, Richard
    ;
    Govender, Preshendren
    ;
    Therrien, Bruno 
    ;
    Clavel, Catherine M.
    ;
    Dyson, Paul J.
    ;
    Smith, Gregory S.
    The development of multinuclear pentamethylcyclopentadienyl (Cp*) rhodium and iridium complexes from first- and second-generation 2-iminopyridyl and salicylaldimine based poly(propyleneimine) dendrimer scaffolds of the type, DAB-(NH2)n (n = 4 or 8, DAB = diaminobutane) has been accomplished. Eight compds. were synthesized, viz. (Cp*MCl)4Gn (1-8), by first reacting DAB-(NH2)n with either 2-pyridinecarboxaldehyde or salicylaldehyde and subsequently metalating the Schiff-base dendrimers with [Cp*MCl2]2 (where M = Rh, Ir). Related mononuclear complexes [Cp*MCl(L)] (L = iminopyridyl or salicylaldimine) (9-12) were obtained in a similar manner. The mol. structures of 9-12 have been detd. by single-crystal x-ray diffraction anal. and the in vitro anticancer activities of 1-12 were evaluated against the A2780 and A2780cisR human ovarian carcinoma cell lines. [on SciFinder(R)]
  • 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
    Encapsulation of inorganic and organic guest molecules into an organometallic hexacationic arene osmium metalla-prism: Synthesis, characterization and anticancer activity
    (2012)
    Barry, Nicolas P. E.
    ;
    Zava, Olivier
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    The arene Os metalla-prism [(p-cymene)6Os6(donq)3(tpt)2]6+ ([2]6+) (donq = 5,8-dioxydo-1,4-naphthoquinonato, tpt = 2,4,6-tri(pyridin-4-yl)-1,3,5-triazine) was prepd. from the dinuclear arene Os precursor [(p-cymene)2Os2(donq)Cl2] (1) in the presence of the tridentate panel tpt and Ag triflate. The assembly of the arene Os metalla-prism also was achieved in the presence of one equiv. of planar guest mols., Pt(acac)2 (acac = acetylacetonato) and 1-(4,6-dichloro-1,3,5-triazin-2-yl)pyrene (pyrene-R), to give the corresponding guest-encapsulated systems, [Pt(acac)2?2]6+ and [pyrene-R?2]6+. All complexes were isolated as triflate salts and characterized by IR, UV-visible, NMR and by elemental anal. The empty metalla-prism also was characterized by mass spectrometry. The cytotoxicities of the dinuclear and hexanuclear Os complexes were established using ovarian A2780 and A2780cisR cancer cell lines and compared with the cytotoxicities of their Ru analogs. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Delivery of Floxuridine derivatives to cancer cells by water-soluble organometallic cages
    (2012)
    Yi, Jeong Wu
    ;
    Barry, Nicolas P. E.
    ;
    Furrer, Mona A.
    ;
    Zava, Olivier
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    ;
    Kim, Byeang Hyean
    Ruthenium water-sol. organometallic cage compds., assembled by 1,2,4,5-benzenetetrolato (dobq), 1,4,5,8-naphthalenetetrolato (donq) and 2,4,6-tri-4-pyridyl-1,3,5-triazine (tpt) ligands gave carceplex inclusion compds. I and II (L = ?6-cymene), resp., with amino acids and nucleoside antitumor agent, Floxuridine (2'-deoxy-5-fluorouridine) pyrene conjugates [R = (CH2)3CONHCHYCO2-5'-O-Floxuridine; Y = H, CH2Ph; R = (CH2)3CO2-5'-O-Floxuridine]. The self-assembly of tpt triangular panels with areneruthenium building blocks [(?6-p-cymene)RuCl]2Q (Q = dobq, donq) in the presence of a pyrenyl-nucleoside derivs. (1-R-pyrene), affords the triangular prismatic host-guest compds. I and II [(pyrene-R)?1]6+ and [(pyrene-R)?2]6+, resp. The inclusion of six monosubstituted pyrenyl-nucleosides [1-R-pyrene; R = R1-R6, where R1 = (CH2)3CO2-5'-O-2'-deoxyuridine, R2 = (CH2)3CO2-5-fluoro-5'-O-2'-deoxyuridine, R3 = (CH2)3CONHCH2CO2-5'-O-2'-deoxyuridine, R4 = (CH2)3CONHCH2CO2-5-fluoro-5'-O-2'-deoxyuridine, R5 = (CH2)3CONHCH(CH2Ph)2CO2-5'-O-2'-deoxyuridine, R6 = (CH2)3CONHCH(CH2Ph)CO2-5-fluoro-5'-O-2'-deoxyuridine] has been accomplished. The carceplex nature of [(pyrene-R)?1]6+ with the pyrenyl moiety firmly encapsulated in the hydrophobic cavity of the cage with the nucleoside groups pointing outward was confirmed by NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS), while the host-guest nature of [(pyrene-R)?2]6+ was studied in soln. by NMR techniques. In contrast to the floxuridine compds. used in the clinic, the host-guest complexes are highly water-sol. Consequently, the cytotoxicities of these water-sol. compds. have been established using human ovarian A2780 and A2780cisR cancer cells. All the host-guest systems are more cytotoxic than the empty cages alone ([1][CF3SO3]6, IC50 = 23 ?M; [2][CF3SO3]6, IC50 = 10 ?M), the most active compd. [1-R4-pyrene?1][CF3SO3]6 being 2 orders of magnitude more cytotoxic (IC50 = 0.3 ?M) on these human ovarian cancer cell lines (A2780 and A2780cisR). [on SciFinder(R)]