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    Coordination-driven self-assembly of arene ruthenium metalla-rectangles
    (Elsevier Science Sa, 2017) Orhan, Ersin; Garci, Amine; Therrien, Bruno
    Series of tetranuclear arene ruthenium complexes of the general formula [Ru-4(p-cymene)(4)(mu(2)-N boolean AND N)(2) (mu(4)-OO boolean AND OO2][CF3SO3](4) (N boolean AND N = 2,5- dipyridyl-thiophene (dptp), 3,6-dipyridyl-1,2,4,5-tetrazine (dptz), 3,6-dipyridyl-1,4-dihydro-1,2,4,5-tetrazine (dpdt)) were prepared by reacting the dinuclear arene ruthenium complexes Ru-2(p-cymene)(2)(mu(4)-OO boolean AND OO)Cl-2 (OO boolean AND OO = oxalato (oxa), 2,5-dioxido-1,4-benzoquinonato (dobq), 2,5-dichloro-1,4-benzoquinonato (dClbq), 2,5-dioxido-3-undecyl-1,4-benzoquinonato (dubq), 5,8-dioxido-1,4-naphtoquinonato (donq)) with silver trifluoromethanesulfonate, followed by the addition of the corresponding N boolean AND N linkers. All metalla-rectangles were characterized by standard techniques, including infrared, UV-visible, H-1, C-13 NMR spectroscopy and ESI mass spectrometry: Thus confirming the rectangular structure of the complexes, and showing the facility of forming tetranuclear arene ruthenium metalla-rectangles. (C) 2017 Elsevier B. V. All rights reserved.
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    Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance
    (Elsevier Science Sa, 2016) Orhan, Ersin; Garci, Amine; Riedel, Tina; Soudani, Mylene; Dyson, Paul J.; Therrien, Bruno
    Tetranuclear arene ruthenium complexes of the general formula [{Ru-2(p-cymene)(2)(mu(4)-L)}(2)(mu(4)-tpom)](4+) (tpom = tetrakis(4-pyridyloxymethylene)methane) were obtained from the corresponding dinuclear arene ruthenium complexes [Ru-2(p-cymene)(2)(m(4)-L)Cl-2] (L = diethyl-1,2-diazenedicarboxylato (dadc), oxalato (oxa), bis(2-hydroxyethyl)oxamidato (bho), bis{2-(2-hydroxyethoxy)ethyl}ethanediamidato (bhe), 2,5-dioxido-1,4-benzoquinonato (dobq), 2,5-dihydroxy-3-phenyl-1,4-benzoquinonato (dhpb), 2,5-dibromo-1,4-benzoquinonato (dBrbq), 2,5-dioxido-3-undecyl-1,4-benzoquinonato (dubq), 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinonato (dhdb), 2,5-dihydroxy-3,6-(3,5-dimethylphenyl)-1,4-benzoquinonato (dhdm), 5,8-dioxido-1,4-naphtoquinonato (donq)) by reaction with the tetradentate tpom ligand and silver trifluoromethanesulfonate. The antiproliferative activity of the tetranuclear complexes was evaluated on cancerous (A2780 and A2780cisR) and non-cancerous (HEK293) cell lines, showing in most cases cancer cell selectivity and, in some cases, low micromolar cytotoxicities (similar to 1 mu M) against a cancer cell line that has acquired resistance to cisplatin. (C) 2015 Elsevier B.V. All rights reserved.
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    Cytotoxicity of arene ruthenium metalla-rectangles incorporating bis-pyridyl diimide linkers
    (Elsevier Science Sa, 2016) Orhan, Ersin; Garci, Amine; Riedel, Tina; Dyson, Paul J.; Therrien, Bruno
    A series of tetranuclear arene ruthenium complexes of the general formula [Ru-4(p-cymene)(4)(mu(2)-L)(2)(mu(4)-OO boolean AND OO)(2)][CF3SO3](4) (L-1 = N,N'-bis(4-pyridylmethyl)-pyromellitic diimide, L-2 = N,N'-bis(4-pyridylmethyl)-naphthalene diimide) were obtained from the corresponding dinuclear arene ruthenium complexes Ru-2(p-cymene)(2)(mu 4-OO boolean AND OO)Cl-2 (OO boolean AND OO = oxalato (oxa), 2,5-dioxido-1,4-benzoquinonato (dobq), 2,5-dihydroxy-3-phenyl-1,4-benzoquinonato (dhpb), 2,5-dichloro-1,4-benzoquinonato (dClbq), 2,5-dioxido-3-undecyl-1,4-benzoquinonato (dubq), 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinonato (dhdb), 5,8-dioxido-1,4-naphtoquinonato (donq)) by reaction with the bidentate ligands (L-1 and L-2) and silver trifluoromethanesulfonate. The antiproliferative activity of the tetranuclear arene ruthenium metalla-rectangles was evaluated on cancerous (A2780 and A2780cisR) and non-cancerous (HEK293) cell lines, showing in all cases cancer cell selectivity. In general, the metalla-rectangles obtained with L-2 are more potent than those incorporating L-1, and with the exception of [Ru-4(p-cymene)(4)(mu(2)-L-1)(2)(m(4)-dClbq)(2)][CF3SO3](4), they are all more active than cisplatin on the cisplatin resistant A2780cisR cell line. (C) 2016 Elsevier B.V. All rights reserved.
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    Flexible arene ruthenium metalla-prisms
    (Elsevier Science Sa, 2015) Orhan, Ersin; Garci, Amine; Therrien, Bruno
    Cationic arene ruthenium metalla-prisms of the general formula [Ru-6(p-cymene)(6)(tpmtt)(2)(OO boolean AND OO)(3)](6+) (tpmtt = 1,3,5-tris(pyridin-4-ylmethyl)-1,3,5-triazinane-2,4,6-trione) have been obtained from the corresponding dinuclear arene ruthenium complexes [Ru-2(p-cymene)(2)(OO boolean AND OO)Cl-2] (OO boolean AND OO = oxalato (ox), 2,5-dioxido-1,4-benzoquinonato (dobq), 2,5-dichloro-1,4-benzoquinonato (dClbq), 2,5-dioxido-3-undecyl-1,4-benzoquinonato (dubq), 5,8-dioxido-1,4-naphtoquinonato (donq)) by reaction with the tridentate tpmtt ligand and silver trifluoromethanesulfonate. These cationic arene ruthenium metalla-prisms have been isolated and characterized as their triflate salts. Upon formation of the metalla-prisms, the two tpmtt panels are in close proximity and do not allow encapsulation of guest molecules. (C) 2015 Elsevier B.V. All rights reserved.
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    Tunable Arene Ruthenium Metallaprisms to Transport, Shield, and Release Porphin in Cancer Cells
    (Amer Chemical Soc, 2015) Garcı, Amine; Mbakidi, Jean-Pierre; Chaleix, Vincent; Sol, Vincent; Orhan, Ersin; Therrien, Bruno
    Three neutral dinuclear p-cymene ruthenium complexes (1a-1c) of the general formula (p-cymene)(2)Ru-2(mu(4)-L)Cl-2, bridged by substituted hydroxybenzoquinonato spacers (L-a = 2,5-dihydroxy-3-pheny1-1,4-benzoquinonato; L-b = 2,5-dihydroxy-3,6-diphenyl-1,4-benzoquinonato; L-c = 2,5-dihydroxy-3,6-(3,5-dimethylphenyl)-1,4-benzoquinonato) have been synthesized and characterized. The corresponding p-cymene ruthenium metallaprisms, [{(p-cymene)(2)Ru-2(mu(4)-L)}(3)(tpt)(2)][CF3SO3](6) (2a-2c), were obtained by mixing in methanol the neutral dinuclear complexes 1a-1c, AgCF3SO3, and 2,4,6-tri(pyridin-4-yl)-1,3,5-triazine (tpt). In a similar fashion, addition of porphin during the formation of the metallaprisms afforded the host guest systems [porphin subset of{(p-cymene)(2)Ru-2(mu(4)-L)}(3)(tpt)(2)][CF3SO3](6) ([porphin subset of 2][CF3SO3](6)). The biological activity of all complexes was estimated on the colon cancer cell line HT-29, showing low cytotoxicity in the dark (IC50 > 5 mu M). On the other hand, the phototoxicity of the porphin-in-the-cage systems under standard irradiation conditions (20 J/cm(2)) is quite spectacular, being in the lower nanomolar range for [porphin subset of 2c] [CF3SO3](6).