Organometallic ruthenium-based antitumor compounds with novel modes of action

Ang, Wee Han; Casini, Angela; Sava, Gianni; Dyson, Paul J.

doi:10.1016/j.jorganchem.2010.11.009

Cited by 339 publications

(284 citation statements)

References 88 publications

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“…This is a result of the reductive atmosphere in tumours due to fast anabolic processes [9,19]. DNA and cellular proteins like kinases or other enzymes were suggested as intracellular targets [20,21].…”

Section: [Tetrachlorido(1h-imidazole)(dimethylsulfoxide-κs)ruthenate(mentioning

confidence: 99%

“…More recently, organometallic pseudo octahedral "piano-stool" Ru(II)(η 6 -arene) complexes with the metal ion stabilized in +2 oxidation state by different arene-type ligands have shown potential for the development of anticancer agents with a wide variety of modes of action [21][22][23]. They exhibit a well-balanced lipophilic/hydrophilic character to the complex allowing potential intravenous administration [22].…”

Section: [Tetrachlorido(1h-imidazole)(dimethylsulfoxide-κs)ruthenate(mentioning

confidence: 99%

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Solution equilibrium studies of anticancer ruthenium(II)-η6-p-cymene complexes of pyridinecarboxylic acids

et al. 2014

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Stoichiometry and stability of antitumor ruthenium(II)-η 6 -p-cymene complexes of picolinic acid and its 6-methyl and 6-carboxylic acid derivatives were determined by pHpotentiometry, 1 H NMR spectroscopy and UV/Vis spectrophotometry in aqueous solution in the presence or absence of coordinating chloride ions. The picolinates form exclusively monoligand complexes in which they can coordinate via the bidentate (O,N) mode and a chloride or a water molecule is found at the third binding site of the ruthenium(II)-η 6 -p-cymene moiety depending on the conditions. [Ru(η 6 -p-cymene)(L)(H 2 O/Cl)] species are predominant at physiological pH in all studied cases. Hydrolysis of the aqua complex or the chlorido/hydroxido co-ligand exchange results in the formation of the mixed-hydroxido species [Ru(η 6 -p-cymene)(L)(OH)] in the basic pH range. There is no indication for the decomposition of the mono-ligand complexes during 24 h in the ruthenium(II)-η 6 -pcymene−picolinic acid system between pH 3 and 11; however, a slight dissociation with a low reaction rate was found in the other two systems leading to the appearance of the dinuclear trihydroxido-bridged species [Ru 2 (η 6 -p-cymene) 2 (OH) 3 ] + and free ligands at pH > 10. The replacement of the chlorido by an aqua ligand in [Ru(η 6 -p-cymene)(L)Cl] was also monitored and equilibrium constants for the exchange process were determined.

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Section: [Tetrachlorido(1h-imidazole)(dimethylsulfoxide-κs)ruthenate(mentioning

confidence: 99%

Section: [Tetrachlorido(1h-imidazole)(dimethylsulfoxide-κs)ruthenate(mentioning

confidence: 99%

Solution equilibrium studies of anticancer ruthenium(II)-η6-p-cymene complexes of pyridinecarboxylic acids

et al. 2014

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“…In the last decade, numerous organometallic ruthenium(II)- 6 -arene complexes mainly with piano-stool structure were synthesized and tested in in vitro assays regarding their bioactivity. In these Ru II [5][6][7][8][9][10][11][12]. The chloride ligand acts a leaving group and its replacement by a water molecule facilitates the reaction with biological targets.…”

Section: The Two Ru(iii) Complexes Imidazolium Trans-[tetrachlorido(dmentioning

confidence: 99%

“…The chloride ligand acts a leaving group and its replacement by a water molecule facilitates the reaction with biological targets. Although, the ultimate biotarget of these [Ru II ( 6 -pcymene)(XY)Cl] complexes is still unclear [13,14], DNA is considered to be a potential intracellular target [9,15].…”

Section: The Two Ru(iii) Complexes Imidazolium Trans-[tetrachlorido(dmentioning

confidence: 99%

Solution equilibria of anticancer ruthenium(II)-(η6-p-cymene)-hydroxy(thio)pyr(id)one complexes: Impact of sulfur vs. oxygen donor systems on the speciation and bioactivity

Enyedy

Sija

Jakusch

et al. 2013

Journal of Inorganic Biochemistry

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“…This similarity is not unexpected, because the targets and resistance mechanisms for arene-ruthenium compounds are believed to be distinct from those of cisplatin. [37] Despite the high stability of the host-guest systems in biological media, it is not clear if the guest is released or not after cellular internalization of the host-guest systems. Nevertheless, it is worth noting that per metal [1] 6 + and [P n &1] 6 + are less cytotoxic than cisplatin, but caution should be applied when making this type of comparison as ruthenium compounds tend to be better tolerated by the body.…”

Section: Cytotoxicity Studiesmentioning

confidence: 99%

Encapsulation of Pyrene‐Functionalized Poly(benzyl ether) Dendrons into a Water‐Soluble Organometallic Cage

Barry

Zava

Deschenaux

et al. 2011

Chemistry An Asian Journal

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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.

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Organometallic ruthenium-based antitumor compounds with novel modes of action

Cited by 339 publications

References 88 publications

Solution equilibrium studies of anticancer ruthenium(II)-η6-p-cymene complexes of pyridinecarboxylic acids

Solution equilibrium studies of anticancer ruthenium(II)-η6-p-cymene complexes of pyridinecarboxylic acids

Solution equilibria of anticancer ruthenium(II)-(η6-p-cymene)-hydroxy(thio)pyr(id)one complexes: Impact of sulfur vs. oxygen donor systems on the speciation and bioactivity

Encapsulation of Pyrene‐Functionalized Poly(benzyl ether) Dendrons into a Water‐Soluble Organometallic Cage

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