Arene ruthenium(II) complexes formed by dehydrogenation of cyclohexadienes with ruthenium(III) trichloride

Bennett, Martin A.; Smith, Anthony K.

doi:10.1039/dt9740000233

Cited by 1,128 publications

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“…The previously reported [20][21][22] complexes 5 and 6 and the simple monopyridyl arene ruthenium derivatives 9 and 10, depicted in Fig. 1, were also included in this study.…”

Section: Synthesesmentioning

confidence: 99%

“…Wavelengths and extinction coefficients of absorption bands of 1-8 in dichloromethane are presented in Table 1, [20][21][22] together with fluorescence and singlet oxygen quantum yields measured after 414-nm excitation. Like the parent porphyrins, complexes 1-8 exhibit the four Q bands between 510 and 650 nm and the intense Soret-type band around 420 nm.…”

Section: Synthesesmentioning

confidence: 99%

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Combined arene ruthenium porphyrins as chemotherapeutics and photosensitizers for cancer therapy

et al. 2008

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Mononuclear 5-(4-pyridyl)-10,15,20-triphenylporphyrin and 5-(3-pyridyl)-10,15,20-triphenylporphyrin as well as tetranuclear 5,10,15,20-tetra(4-pyridyl)porphyrin (tetra-4-pp) and 5,10,15,20-tetra(3-pyridyl)porphyrin) (tetra-3-pp) arene ruthenium(II) derivatives (arene is C 6 H 5 Me or p-Pr i C 6 H 4 Me) were prepared and evaluated as potential dual photosensitizers and chemotherapeutics in human Me300 melanoma cells. In the absence of light, all tetranuclear complexes were cytotoxic (IC 50 B 20 lM), while the mononuclear derivatives were not (IC 50 C 100 lM). Kinetic studies of tritiated thymidine and tritiated leucine incorporations in cells exposed to a low concentration (5 lM) of tetranuclear p-cymene derivatives demonstrated a rapid inhibition of DNA synthesis, while protein synthesis was inhibited only later, suggesting arene ruthenium-DNA interactions as the initial cytotoxic process. All complexes exhibited phototoxicities toward melanoma cells when exposed to laser light of 652 nm. At low concentration (5 lM), LD 50 of the mononuclear derivatives was between 5 and 10 J/cm 2 , while for the tetranuclear derivatives LD 50 was approximately 2.5 J/cm 2 for the [Ru 4 (g 6 -arene) 4 (tetra-4-pp)Cl 8 ] complexes and less than 0.5 J/cm 2 for the [Ru 4 (g 6 -arene) 4 (tetra-3-pp)Cl 8 ] complexes. Examination of cells under a fluorescence microscope revealed the [Ru 4 (g 6 -arene) 4 (tetra-4-pp)Cl 8 ] complexes as cytoplasmic aggregates, whereas the [Ru 4 (g 6 -arene) 4 (tetra-3-pp)Cl 8 ] complexes were homogenously dispersed in the cytoplasm. Thus, these complexes present a dual synergistic effect with good properties of both the arene ruthenium chemotherapeutics and the porphyrin photosensitizer.

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“…The previously reported [20][21][22] complexes 5 and 6 and the simple monopyridyl arene ruthenium derivatives 9 and 10, depicted in Fig. 1, were also included in this study.…”

Section: Synthesesmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

Combined arene ruthenium porphyrins as chemotherapeutics and photosensitizers for cancer therapy

et al. 2008

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“…6 Other investigations have reported that [(η 6 -arene)Ru(P(n-Bu) 3 )Cl 2 ] dissolved in aromatic solvents undergoes exchange of coordinated and solvent arenes when irradiated with UVA. 7 A few dinuclear complexes based on the typical half-sandwich motif have been also studied. Amongst them, the complex [{(η 6 -ind)Ru(Cl)} 2 (μ-2,3-dpp) 2 ] 2+ where dpp is 2,3-bis(2-pyridyl)pyrazine 8 releases the arene upon irradiation generating vacant coordination sites that make it more reactive towards DNA binding.…”

Section: Introductionmentioning

confidence: 99%

“…cym)Ru(bpm)(4-MePy)] 2+ (2), [(η 6 -p-cym)Ru(bpm)(4-BzPy)] 2+ (6), [(η 6 -p-cym)Ru(bpm)(trz)] 2+ (7), [(η 6 -p-cym)Ru(phen)(Py)] 2+ (10), and [(η 6 -ind)Ru(bpy)(Py)] 2+ (13). These complexes can selectively photodissociate the monodentate ligand (L) when excited with UVA or white light allowing strict control of the formation of the reactive aqua species [(η 6 -arene)Ru(N,N')(OH 2 )] 2+ that otherwise would not form in the dark.…”

mentioning

confidence: 99%

Photoactivatable Organometallic Pyridyl Ruthenium(II) Arene Complexes

et al. 2012

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The synthesis and characterization of a family of piano-stool Ru II arene complexes of the type [(η 6 -arene)Ru(N,N')(L)] [PF 6 ] 2 where arene is para-cymene (p-cym), hexamethylbenzene (hmb) or indane (ind); N,N' is 2,2'-bipyrimidine (bpm), 1,10-phenanthroline (phen), 1,10-phenanthroline-5,6-dione (phendio), 4,7-diphenyl-1,10-phenanthroline (bathophen), and L is pyridine (Py), 4-methylpyridine (4-MePy), 4-methoxypyridine (4-MeOPy), 4,4'-bipyridine (4,4'-biPy), 4-phenylpyridine (4-PhPy), 4-benzylpyridine (4-BzPy), 1,2,4-triazole (trz), 3-acetylpyridine (3-AcPy), nicotinamide (NA), or 3-acetatepyridine (3-AcOPy) are reported; including the X-ray crystal structures of [(η 6 -p-[(η 6 -p-cym)Ru(phen)(Py)] 2+ (10), and [(η 6 -ind)Ru(bpy)(Py)] 2+ (13). These complexes can selectively photodissociate the monodentate ligand (L) when excited with UVA or white light allowing strict control of the formation of the reactive aqua species [(η 6 -arene)Ru(N,N')(OH 2 )] 2+ that otherwise would not form in the dark. The photoproducts were characterized by UV-vis absorption and 1 H NMR spectroscopy. DFT and TD-DFT calculations were employed to characterize the excited states and to obtain information on the photochemistry of the complexes. All the Ru II pyridine complexes follow a relatively similar photochemical L-ligand dissociation mechanism, likely to occur from a series of 3 MC triplet states with dissociative character. The photochemical process proved to be much more efficient when UVA-range irradiation was used. More strikingly, light activation was used to photo-trigger binding of these potential anticancer agents with discriminating preference towards 9-ethylguanine (9-EtG) over 9-ethyladenine (9-EtA). Calf-thymus (CT)-DNA binding studies showed that the irradiated complexes bind to CT-DNA whereas the non-irradiated forms, bind negligibly.

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“…Deuterated NMR solvents were purchased from Cambridge Isotope Laboratories, Inc. The starting dinuclear complexes [Ru(C 6 Me 6 )Cl 2 ] 2 [16] and [Ru(C 6 H 6 )-Cl 2 ] 2 [13] were prepared according to published methods.…”

Section: Synthesesmentioning

confidence: 99%

The water-soluble cluster cation [H3Ru3(C6H6)(C6Me6)2(O)]+: Improved synthesis, aerobic oxidation, electrochemical properties and ligand exchange studies

et al. 2005

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Arene ruthenium(II) complexes formed by dehydrogenation of cyclohexadienes with ruthenium(III) trichloride

Cited by 1,128 publications

References 0 publications

Combined arene ruthenium porphyrins as chemotherapeutics and photosensitizers for cancer therapy

Combined arene ruthenium porphyrins as chemotherapeutics and photosensitizers for cancer therapy

Photoactivatable Organometallic Pyridyl Ruthenium(II) Arene Complexes

The water-soluble cluster cation [H3Ru3(C6H6)(C6Me6)2(O)]+: Improved synthesis, aerobic oxidation, electrochemical properties and ligand exchange studies

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