Properties and biological activity of [Rh(COD)(N–N)]BF4 and [IrCl2(COD)(N–N)]BF4 polypyridyl complexes

Śliwińska-Hill, Urszula; Pruchnik, Florian P.; Latocha, Małgorzata; Nawrocka-Musiał, Dominika; Ułaszewski, Stanisław

doi:10.1016/j.ica.2013.02.002

Cited by 8 publications

(6 citation statements)

References 33 publications

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“…In order to confirm the apparent similarities between [η 4 -Cp*H] and [1,5-cyclooctadiene] complexes of rhodium with α-diimine ligands, we prepared the literature complex [(cod)Rh(bpy)]BF 4 ( 6 ; cod = 1,5-cyclooctadiene) for structural, spectroscopic, and electrochemical comparison with our isolated (Cp*H)Rh(bpy)Br ( 2 ). Complex 6 can be isolated in good yield by treatment of the dimeric Rh(I) compound [(cod)RhCl] 2 with a solution of HBF 4 in ethanol . Single-crystals of 6 suitable for X-ray diffraction studies were obtained by vapor diffusion of Et 2 O into a solution of 6 in MeCN.…”

Section: Results and Discussionmentioning

confidence: 99%

Structural and Electrochemical Consequences of [Cp*] Ligand Protonation

et al. 2017

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There are few examples of the isolation of analogous metal complexes bearing [η-Cp*] and [η-Cp*H] (Cp* = pentamethylcyclopentadienyl) complexes within the same metal/ligand framework, despite the relevance of such structures to catalytic applications. Recently, protonation of Cp*Rh(bpy) (bpy = 2,2'-bipyridyl) has been shown to yield a complex bearing the uncommon [η-Cp*H] ligand, rather than generating a [Rh-H] complex. We now report the purification and isolation of this protonated species, as well as characterization of analogous complexes of 1,10-phenanthroline (phen). Specifically, reaction of Cp*Rh(bpy) or Cp*Rh(phen) with 1 equiv of EtNHBr affords rhodium compounds bearing endo-η-pentamethylcyclopentadiene (η-Cp*H) as a ligand. NMR spectroscopy and single-crystal X-ray diffraction studies confirm protonation of the Cp* ligand, rather than formation of metal hydride complexes. Analysis of new structural data and electronic spectra suggests that phen is significantly reduced in Cp*Rh(phen), similar to the case of Cp*Rh(bpy). Backbonding interactions with olefinic motifs are activated by formation of [η-Cp*H]; protonation of [Cp*] stabilizes the low-valent metal center and results in loss of reduced character on the diimine ligands. In accord with these changes in electronic structure, electrochemical studies reveal a distinct manifold of redox processes that are accessible in the [Cp*H] complexes in comparison with their [Cp*] analogues; these processes suggest new applications in catalysis for the complexes bearing endo-η-Cp*H.

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Section: Results and Discussionmentioning

confidence: 99%

Structural and Electrochemical Consequences of [Cp*] Ligand Protonation

et al. 2017

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“…Alongside these new classes of complexes, work by Maftei et al highlighted asymmetric (12) and symmetric (13) neutral iridium(I)-NHC trifluoromethylpyridine derivatives which surprisingly have no cellular activity, and IC 50 values against all 12 cell lines were >100¯M. 90 More recently, triazole and thiazolederived iridium(I) NHC complexes have emerged, (1416) 91 and exhibit significant interactions with model proteins and hex-americ oligonucleotide ODN1. This highlights the necessity of fine-tuning of the ligand environment and a need to investigate structure-activity relationships.…”

Section: Iridium(i) Compoundsmentioning

confidence: 99%

Organometallic Iridium Arene Compounds: The Effects ofC-Donor Ligands on Anticancer Activity

Lord

McGowan

2019

Chem. Lett.

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Rianne M. Lord obtained her Ph.D. degree in chemistry in 2014 under the supervision of Professor Patrick C. McGowan at the University of Leeds (U.K.). Following this, she joined the research team of Professor Polly L. Arnold at the University of Edinburgh (U.K.) as a postdoctoral research associate. In 2016, Rianne began her independent career as a lecturer of bioinorganic chemistry at the University of Bradford (U.K.) and currently holds an August-Wilhelm Scheer visiting professorship at the Technische Universität München (Germany). Her research interests focus on the development of new transition metal cancer therapeutics and designing effective drug delivery systems.

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“…[32][33][34][35][36][37][38][39][40] Biological studies on rhodium(I) complexes as anticancer agents are less frequent. [31,[41][42][43][44] One recent report by McAlpine and co-workers described the alteration of cell migration, DNA replication, and DNA condensation by a Rh I -NHC derivative. [31] The choice of Rh I as metal center appears promising because it is isoelectronic with platinum(II) and exhibits a square-planar geometry like cisplatin-type tumor therapeutics.…”

Section: Introductionmentioning

confidence: 99%

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

Oehninger

Küster

Schmidt

et al. 2013

Chemistry A European J

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Rhodium(I) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these organometallics. A series of Rh(I)-NHC derivatives with 1,5-cyclooctadiene and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with moderate inhibitory activity of thioredoxin reductase (TrxR) and efficient binding to biomolecules (DNA, albumin). Biodistribution studies showed that the presence of albumin lowered the cellular uptake and confirmed the transport of rhodium into the nuclei. Changes in the mitochondrial membrane potential (MMP) were observed as well as DNA fragmentation in wild-type and daunorubicin- or vincristine-resistant Nalm-6 leukemia cells. Overall, these studies indicated that Rh(I)-NHC fragments could be used as partial structures of new antitumor agents, in particular in those drugs designed to address resistant malignant tissues.

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Properties and biological activity of [Rh(COD)(N–N)]BF4 and [IrCl2(COD)(N–N)]BF4 polypyridyl complexes

Cited by 8 publications

References 33 publications

Structural and Electrochemical Consequences of [Cp*] Ligand Protonation

Structural and Electrochemical Consequences of [Cp*] Ligand Protonation

Organometallic Iridium Arene Compounds: The Effects ofC-Donor Ligands on Anticancer Activity

A Chemical–Biological Evaluation of Rhodium(I) N‐Heterocyclic Carbene Complexes as Prospective Anticancer Drugs

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