Baban

Barry

Bruno Therrien

Engel

Galanski

Gladkov

Govindaswamy

Levina

Maeda

Matsumura

Mattsson

Mendoza-Ferri

Nicolas P. E. Barry

Olivier Zava

Paul J. Dyson

Peacock

Rademaker-Lakhai

Ricchelli

Therrien

Timerbaev

Vieille-Petit

Warnecke

Zava

Zelonka

Self‐assembly of 5,10,15,20‐tetra(4‐pyridyl)porphyrin (tpp‐H2) and 5,10,15,20‐tetra(4‐pyridyl)porphyrin‐M(ii) (M = Ni (tpp‐Ni); Zn (tpp‐Zn)) tetradentate panels with the dinuclear p‐cymene ruthenium clips [Ru2(p-cymene)2(C2O4)Cl2] and [Ru2(p-cymene)2(C6H2O4)Cl2] (C2O4 = oxalato; C6H2O4 = 2,5‐dioxydo‐1,4‐benzoquinonato) affords the cationic organometallic cubes: [Ru8(p-cymene)8(tpp‐H2)2(C2O4)4]8+ (1); [Ru8(p-cymene)8(tpp‐Ni)2(C2O4)4]8+ (2); [Ru8(p-cymene)8(tpp‐Zn)2(C2O4)4]8+ (3); [Ru8(p-cymene)8(tpp‐H2)2(C6H2O4)4]8+ (4); [Ru8(p-cymene)8(tpp‐Ni)2(C6H2O4)4]8+ (5); and [Ru8(p-cymene)8(tpp‐Zn)2(C6H2O4)4]8+ (6). In addition, the new dinuclear arene ruthenium 2,5‐dioxydo‐1,4‐benzoquinonato clips [Ru2(indane)2(C6H2O4)Cl2] (7) and [Ru2(nonylbenzene)2(C6H2O4)Cl2] (8) react in methanol with tpp‐H2 in the presence of silver triflate to afford the corresponding cationic cubes [Ru8(indane)8(tpp‐H2)2(C6H2O4)4]8+ (9) and [Ru8(nonylbenzene)8(tpp‐H2)2(C6H2O4)4]8+ (10) respectively. All cationic metalla‐cubes were isolated as triflate salts and characterized by NMR, infrared, electro‐spray mass spectrometry and UV‐visible spectroscopy. Moreover, the formation of unsymmetrical metalla‐cubes built using a mixture of the different porphyrin panels during the self‐assembly of the 2,5‐dioxydo‐1,4‐benzoquinonato metalla‐cubes, [Ru8(p-cymene)8(tpp‐H2)(tpp‐Ni)(C6H2O4)4]8+ (11), [Ru8(p-cymene)8(tpp‐H2)(tpp‐Zn)(C6H2O4)4]8+ (12), and [Ru8(p-cymene)8(tpp‐Ni)(tpp‐Zn)(C6H2O4)4]8+ (13), was studied by electro‐spray mass spectrometry. The cytotoxicities of all metalla‐cubes as well as the mixtures containing the unsymmetrical metalla‐cubes were established on human ovarian A2780 and A2780cisR cancer cell lines. All symmetrical compounds are equally cytotoxic (IC50 = 7–15 μM) (IC50 being the drug concentration necessary for 50% inhibition of cell viability) against both A2780 and cisplatin‐resistant A2780cisR cancer cells, with stronger cytotoxicities (IC50 = 2–5 μM) observed for the mixtures containing the unsymmetrical 2,5‐dioxydo‐1,4‐benzoquinonato metalla‐cubes.</jats:p

Crossref

Australian Journal of Chemistry

Synthesis, Characterization and Anticancer Activity of Porphyrin-Containing Organometallic Cubes

http://doc.rero.ch/record/29028/files/Barry_Nicolas_P.E._-_Synthesis_Characterization_and_Anticancer_Activity_of_Porphyrin_20120426.pdf

Synthesis, Characterization and Anticancer Activity of Porphyrin-Containing Organometallic Cubes

Abstract

Similar works

Full text

Available Versions

Crossref