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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
    Efficient photodynamic therapy of cancer using chemotherapeutic porphyrin-ruthenium metalla-cubes
    (2012)
    Schmitt, Frederic
    ;
    Barry, Nicolas P. E.
    ;
    Juillerat-Jeanneret, Lucienne
    ;
    Therrien, Bruno 
    Two cationic octanuclear metalla-cubes [Ru8(?6-C6H5Me)8(tpp-H2)2(dhbq)4]8+ and [Ru8(?6-p-iPrC6H4Me)8(tpp-H2)2(dhbq)4]8+ were prepd. and evaluated as dual photosensitizers and chemotherapeutics in cancer cells. In the dark, the complexes presented high cytotoxicity towards only melanoma and ovarian cancer cells. However, the complexes exhibited good phototoxicities toward all cancer cells (1 ?M concn., LD50 = 2-7 J/cm2), thus suggesting a dual synergistic effect with good properties of both the arene ruthenium chemotherapeutics and the porphyrin photosensitizers. [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)]
  • Publication
    Métadonnées seulement
    Systems biology approach for in vivo photodynamic therapy optimization of ruthenium-porphyrin compounds
    (2012)
    Pernot, Marlene
    ;
    Bastogne, Thierry
    ;
    Barry, Nicolas P. E.
    ;
    Therrien, Bruno 
    ;
    Koellensperger, Gunda
    ;
    Hann, Stephan
    ;
    Reshetov, Vadzim
    ;
    Barberi-Heyob, Muriel
    Two arene ruthenium porphyrin compds. showing interesting photodynamic activity in vitro, [Ru(?6-p-PriC6H4Me)(PMP)Cl2] (PMP = 5-(3-pyridyl)-10,15,20-triphenylporphyrin) and [Ru4(?6-p-PriC6H4Me)4(PTP)Cl8] (PTP = 5,10,15,20-tetra(3-pyridyl)porphyrin) coined Rut1 and Rut4 resp., have been evaluated in vivo. Porphyrins alone and the arene ruthenium porphyrin derivs. (Rut1 and Rut4) showed comparable spectroscopic and photophys. properties. The in vivo study consisted in selecting the optimal arene ruthenium porphyrin photosensitizer by using an original exptl. design approach on mice bearing an ectopic human oral carcinoma xenograft. The model of exptl. design demonstrated to be well suited to the empirical model-building of photodynamic therapy (PDT) response. Arene ruthenium porphyrins concn. and fluence level demonstrated no statistically significant influence on the tumor growth. On the contrary, the presence of ruthenium groups improved the in vivo photodynamic efficiency. By optical fiber fluorimetry, we demonstrated that both compds. exhibited enhanced accumulation in KB tumors from 24 h to 96 h post-i.v. injection. These expts. were completed by inductively coupled plasma mass spectrometry quantification of ruthenium in different organs including tumor tissue. Despite a statistically significant in vivo photodynamic efficiency for Rut4, cellular localization in human oral carcinoma KB cells using fluorescence microscopy demonstrated that both conjugates Rut1 and Rut4 accumulated only in cytoplasm of KB cells but not in the nucleus. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Encapsulation of hydrophobic pyrenyl-cycloplatinate complexes within a water-soluble arene ruthenium metalla-cage
    (2012)
    Barry, Nicolas P. E.
    ;
    Zava, Olivier
    ;
    Wu, Wenting
    ;
    Zhao, Jianzhang
    ;
    Therrien, Bruno 
    Two hydrophobic pyrenyl-contg. cycloplatinate complexes {2-(1-pyrenyl)pyridine}Pt(acac) (Pt-1) and {2-(4-(1-pyrenyl)phenyl)pyridine}Pt(acac) (Pt-2) (acac = acetylacetonato) were encapsulated in the hexacationic water-sol. metalla-cage [(p-cymene)6Ru6(donq)3(tpt)2]6 + (donq = 5,8-dioxido-1,4-naphthoquinonato, tpt = 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine). The host-guest systems [(Pt-1)?cage]6 + and [(Pt-2)?cage]6 + were characterized by NMR and UV-visible spectroscopy, thus confirming the encapsulation of the Pt complexes in the hexa-Ru metalla-cage. The cytotoxicities of the complex-in-a-complex systems were established using human ovarian A2780 and A2780cisR cancer cell lines. This study shows IC50 values in the lower micromolar range for both compds. and on both cancer cell lines (IC50 ? 1 ?M), these values being higher than the empty metalla-cage which possesses an IC50 > 3 ?M. This amplified overall cytotoxicity for the complex-in-a-complex systems suggests an efficient delivery of the hydrophobic complexes by the water-sol. arene Ru metalla-cage. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Ru2(CO)4(OOCR)2L2 sawhorse-type complexes containing axial 5-(4-pyridyl)-10,15,20-triphenylporphyrin ligands
    (2011)
    Gras, Michael
    ;
    Barry, Nicolas P. E.
    ;
    Therrien, Bruno 
    ;
    Süss-Fink, Georg 
    The thermal reaction of Ru3(CO)12 with various carboxylic acids (benzoic, 4-hydroxyphenylacetic, ferrocenic, stearic, oleic, 4-(octadecyloxy)benzoic) in refluxing THF, followed by addn. of 5-(4-pyridyl)-10,15,20-triphenylporphyrin (L), gives the dinuclear complexes Ru2(CO)4(OOCR)2L2 (1: R = -C6H5, 2: R = -CH2-p-C6H4OH, 3: R = -C5H4FeC5H5, 4: R = -(CH2)16CH3, 5: R = -(CH2)7CH=CH(CH2)7CH3, 6: R = -p-C6H4O(CH2)17CH3). Complexes 1-6 were characterized by IR, NMR, and ESI-MS as well as by elemental anal. The UV-visible spectra show the Soret band centered at 417 nm and the Q bands at 515, 550, 590 and 645 nm, resp. [on SciFinder(R)]
  • Publication
    Accès libre
    Encapsulation of Pyrene-Functionalized Poly(benzyl ether) Dendrons into a Water-Soluble Organometallic Cage
    (2011)
    Pitto-Barry, Anaïs
    ;
    Barry, Nicolas P. E.
    ;
    Zava, Olivier
    ;
    Deschenaux, Robert 
    ;
    Therrien, Bruno 
    Two generations of lipophilic pyrenyl functionalized poly(benzyl ether) dendrimers (P1 and P2) have been synthesized. The thermal properties of the two functionalized dendrimers have been investigated, and the pyrenyl group of the dendritic molecules encapsulated in the arene–ruthenium metalla-cage, [Ru6(p-cymene)6(tpt)2(donq)3]6+ ([1]6+) (tpt=2,4,6-tri(pyridin-4-yl)-1,3,5-triazine; donq=5,8-dioxydo-1,4-naphthoquinonato). The host–guest properties of [P1⊂1]6+ and [P2⊂1]6+ were studied in solution by NMR and UV/Vis spectroscopic methods, thus allowing the determination of the affinity constants. Moreover, the cytotoxicity of these water-soluble host–guest systems was evaluated on human ovarian cancer cells.
  • Publication
    Accès libre
    Double Targeting of Tumours with Pyrenyl-Modified Dendrimers Encapsulated in an Arene–Ruthenium Metallaprism
    (2011)
    Pitto-Barry, Anaïs
    ;
    Barry, Nicolas P. E.
    ;
    Zava, Olivier
    ;
    Deschenaux, Robert 
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene–ruthenium building blocks and 5,8-dioxido-1,4-naphthoquinonato (donq) bridges, in the presence of pyrenyl-containing dendrimers of different generations (P0, P1 and P2), affords the triangular prismatic host–guest compounds [Pn⊂Ru6(p-cymene)6(tpt)2(donq)3]6+ ([Pn⊂1]6+). The host–guest nature of these systems, with the pyrenyl moiety being encapsulated in the hydrophobic cavity of the cage and the dendritic functional group pointing outwards, was confirmed by NMR spectroscopy (1H, 2D and DOSY). The host–guest properties of these systems were studied in solution by NMR and UV/Vis spectroscopic methods, allowing the determination of their affinity constants (Ka). Moreover, the ability of these water-soluble host–guest systems to carry the pyrenyl-containing dendrimers into cancer cells was evaluated on human ovarian cancer cells. The host–guest systems are all more cytotoxic than the empty cage [1][CF3SO3]6 (IC50≈4 μM), with the most active compound, [P0⊂1][CF3SO3]6, being an order of magnitude more cytotoxic.
  • Publication
    Accès libre
    Double Targeting of Tumors with Pyrenyl-Modified Dendrimers Encapsulated in an Arene-Ruthenium Metallaprism
    (2011)
    Pitto-Barry, Anais
    ;
    Barry, Nicolas P. E.
    ;
    Zava, Olivier
    ;
    Deschenaux, Robert 
    ;
    Dyson, Paul J.
    ;
    Therrien, Bruno 
    The self-assembly of 2,4,6-tris(pyridin-4-yl)-1,3,5-triazine (tpt) triangular panels with p-cymene-ruthenium building blocks and 5,8-dioxido-1,4-naphthoquinonato (donq) bridges, in the presence of pyrenyl-contg. dendrimers of different generations (P0, P1 and P2), affords the triangular prismatic host-guest compds. [Pn?Ru6(p-cymene)6(tpt)2(donq)3]6+ ([Pn?1]6+). The host-guest nature of these systems, with the pyrenyl moiety being encapsulated in the hydrophobic cavity of the cage and the dendritic functional group pointing outwards, was confirmed by NMR spectroscopy (1H, 2D and DOSY). The host-guest properties of these systems were studied in soln. by NMR and UV/Vis spectroscopic methods, allowing the detn. of their affinity consts. (Ka). Moreover, the ability of these water-sol. host-guest systems to carry the pyrenyl-contg. dendrimers into cancer cells was evaluated on human ovarian cancer cells. The host-guest systems are all more cytotoxic than the empty cage [1][CF3SO3]6 (IC50?4 ?M), with the most active compd., [P0?1][CF3SO3]6, being an order of magnitude more cytotoxic. [on SciFinder(R)]
  • Publication
    Métadonnées seulement
    Permanent Encapsulation or Host-Guest Behavior of Aromatic Molecules in Hexanuclear Arene Ruthenium Prisms
    (2010)
    Freudenreich, Julien 
    ;
    Barry, Nicolas P. E.
    ;
    Süss-Fink, Georg 
    ;
    Therrien, Bruno 
    Cationic arene Ru metallaprisms [Ru6(p-cymene)6(tpt)2(OO?OO)3]6+ {tpt = 2,4,6-tris(4-pyridyl)-1,3,5-triazine; OO?OO = 9,10-dioxo-9,10-dihydroanthracene-1,4-diolato [1]6+, 6,11-dioxo-6,11-dihydronaphthacene-5,12-diolato [2]6+} were obtained from the corresponding dinuclear arene Ru complexes [Ru2(p-cymene)2(OO?OO)Cl2] by reaction with tpt and Ag trifluoromethanesulfonate. Arom. mols. (phenanthrene, pyrene, triphenylene, coronene) present during the synthesis of these metallaprisms are permanently encapsulated to give carceplex systems. All empty cages ([1]6+ and [2]6+) and carceplex systems ([guest?1]6+ and [guest?2]6+) were isolated in good yield as trifluoromethanesulfonate salts and characterized by NMR, UV, and IR spectroscopy. The host-guest properties of [1]6+ and [2]6+ were studied in soln. in the presence of small arom. mols. (phenanthrene and pyrene). The stability const. of assocn. (Ka) was estd. by NMR spectroscopy for the following host-guest systems: [phenanthrene?1]6+, [pyrene?1]6+ and [phenanthrene?2]6+, [pyrene?2]6+. All Ka values are larger than 2.0 × 104 M-1 for these host-guest systems ([D3]acetonitrile, 21°). [on SciFinder(R)]