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

Paul Joseph Dyson, Olivier Pierre Zava
2010
Journal paper
Abstract

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 addn., 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) resp. All cationic metalla-cubes were isolated as triflate salts and characterized by NMR, IR, electro-spray mass spectrometry and UV-visible spectroscopy. Moreover, the formation of unsym. metalla-cubes built using a mixt. 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 mixts. contg. the unsym. metalla-cubes were established on human ovarian A2780 and A2780cisR cancer cell lines. All sym. compds. are equally cytotoxic (IC50=7-15μM) (IC50 being the drug concn. necessary for 50% inhibition of cell viability) against both A2780 and cisplatin-resistant A2780cisR cancer cells, with stronger cytotoxicities (IC50=2-5μM) obsd. for the mixts. contg. the unsym. 2,5-dioxydo-1,4-benzoquinonato metalla-cubes.

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Related concepts (23)
Metalloid
A metalloid is a type of chemical element which has a preponderance of properties in between, or that are a mixture of, those of metals and nonmetals. There is no standard definition of a metalloid and no complete agreement on which elements are metalloids. Despite the lack of specificity, the term remains in use in the literature of chemistry. The six commonly recognised metalloids are boron, silicon, germanium, arsenic, antimony and tellurium. Five elements are less frequently so classified: carbon, aluminium, selenium, polonium and astatine.
Tetraphenylporphyrin
Tetraphenylporphyrin, abbreviated TPP or H2TPP, is a synthetic heterocyclic compound that resembles naturally occurring porphyrins. Porphyrins are dyes and cofactors found in hemoglobin and cytochromes and are related to chlorophyll and vitamin B12. The study of naturally occurring porphyrins is complicated by their low symmetry and the presence of polar substituents. Tetraphenylporphyrin is hydrophobic, symmetrically substituted, and easily synthesized.
Ultraviolet–visible spectroscopy
UV spectroscopy or UV–visible spectrophotometry (UV–Vis or UV/Vis) refers to absorption spectroscopy or reflectance spectroscopy in part of the ultraviolet and the full, adjacent visible regions of the electromagnetic spectrum. Being relatively inexpensive and easily implemented, this methodology is widely used in diverse applied and fundamental applications. The only requirement is that the sample absorb in the UV-Vis region, i.e. be a chromophore. Absorption spectroscopy is complementary to fluorescence spectroscopy.
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