A cytotoxic bis(carbene)gold(<scp>i</scp>) complex of ferrocenyl complexes: synthesis and structural characterisation

Horvath, Ulrike E. I.; Bentivoglio, Gino; Hummel, Michael; Schottenberger, Herwig; Wurst, Klaus; Nell, Margo; Rensburg, C. E. J. Van; Cronje, Stephanie; Raubenheimer, Helgard G.

doi:10.1039/b713917a

Cited by 70 publications

(48 citation statements)

References 46 publications

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“…Thanks to their favorable and peculiar chemical and biological properties, gold(I) Nheterocyclic carbene compounds have been tested extensively in recent years as antiarthritic 15 , antibacterial 16 and anticancer agents 2,[11][12][13][14][18][19][20][21][22][23][24][25][26] .…”

Section: Reaction Between the Gold N-heterocyclic Carbene Compound Aumentioning

confidence: 99%

First Crystal Structure for a Gold Carbene–Protein Adduct

2016

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The X-ray structure of the adduct formed in the reaction between the gold N-heterocyclic carbene compound Au(NHC)Cl (with NHC = 1-butyl-3-methyl-imidazole-2-ylidene) and the model protein thaumatin is reported here. The structure reveals binding of Au(NHC)(+) fragments to distinct protein sites. Notably, binding of the gold compound occurs at lysine side chains and at the N-terminal tail; the metal binds the protein after releasing Cl(-) ligand, but retaining NHC fragment.

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Section: Reaction Between the Gold N-heterocyclic Carbene Compound Aumentioning

confidence: 99%

First Crystal Structure for a Gold Carbene–Protein Adduct

2016

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“…Single crystals suitable for X-ray analysis were obtained by slow crystallisation from MeOH at room temperature by slow evaporation (1) or from CH 2 Cl 2 layered with ether at -20 °C (18,26). A Bruker SMART Apex CCD diffractometer [56] with graphite-monochromated Mo-K α radiation (λ = 0.71073 Å) was used for data collection.…”

Section: Crystal Structure Determinationsmentioning

confidence: 99%

“…An azole -platinum compound displaying in vitro anticancer activity comparable to that of cisplatin is only slightly more active against cisplatin-resistant cancer cells [17]. In another approach, and by using Lin"s method, Raubenheimer and co-workers [18] have reported a heterobimetallic N-heterocyclic carbene (NHC) complex of gold conjugatively attached to a ferrocenyl moiety. This phosphine-free "complex of a complex" is tumour specific against the HeLa and Jurkat cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Horvath

Dobrzańska

Strasser

et al. 2012

Journal of Inorganic Biochemistry

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Synopsis __________________________________________________________________________Among a new series of gold(I) complexes that contain diphosphine and deprotonated N-heterocyclic ring systems as ligands, the compounds containing diphenyl(phosphino)pentane and pyrazolate (lypophilic) or 1,2,4,-triazolate (hydrophilic) have high anti-tumour specificities. They induce an apoptic cell death pathway and have the maximum tolerated dose of 1.5 μmol/kg when administered to Balb/C mice. ___________________________________________________________________ *Synopsis for the Graphical abstract  In 25 new complexes diphosphines and azolate-type ligands coordinate to gold  Solvent molecules and counterions appear within channels of a crystalline complex  Cytotoxicity is dependent upon aliphatic C chain length in the ligands  An apoptosis cell death with certain mitochondrial involvement is indicated  Tolerated doses compared to [Au(dppe) 2 ]Cl, tumour specificity is much better *Highlights A B S T R A C T ------------------------------------------------------------------------A series of new neutral mononuclear or dinuclear gold(I) complexes and a cyclic cationic tetranuclear amidogold(I) complex comprising of the phosphines 1,2-bis(dimethylphosphino)ethane (dmpe), μ-1,2-bis(diphenylphosphino)ethane (dppe), μ-1,3-bis(diphenylphosphino)propane (dppp), μ-1,5-bis(diphenylphosphino)pentane (dpppe), μ-1,6-bis(diphenylphosphino)hexane (dpph) or trimethylphosphine, and several N-heterocyclic ring systems (imidazolate, pyrazolate, 1,2,3-triazolate, 1,2,4-triazolate, pyrrolate, 9H-purine-9-ate or 9H-purine-6-amine-9-ate) as ligands, reveal intermolecular aurophilic interactions and 2D channels available for solvent molecules in some of their crystal structures. The antitumou r 2 activity of the acyclic gold(I) compounds is highly dependent on the substituents on the phosphorus atoms being highest for phenyl groups and lower for methyl groups. The activity of these compounds against selected cell lines is linked to the length of the carbon bridge between the two phosphorus atoms being highest with a bridge consisting of 5 or 6 carbons. Two compounds with the highest tumour specifities that contain dpppe and pyrazolate (a lipophilic compound) or 1,2,4-triazolate (a hydrophilic compound) induce the apoptic cell death pathway and tolerate a maximum dose of 1.5 μmol/kg when administered to Balb/C mice.

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“…1B, C). 14 The cytotoxicity 15 and antimicrobial activity 16 Although the literature shows an increasing biomedical interest in NHC-metal complexes, only a few reports regarding their toxicity are currently available and these limit themselves to analyzing their potential to kill tumoral cells or pathogens 6,14,17 ; according to our knowledge, no animal models have been used for this purpose. As far as ruthenium compounds are concerned, it has been shown 18 that exposure to a chiral organoruthenium half-sandwich compound gives rise to differential zebrafish (Danio rerio) embryo phenotypes according to which enantiomer is used.…”

Section: Introductionmentioning

confidence: 98%

Biomedical Properties of a Series of Ruthenium-N-Heterocyclic Carbene Complexes Based on Oxidant Activity In Vitro and Assessment In Vivo of Biosafety in Zebrafish Embryos

et al. 2010

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N-Heterocyclic carbene (NHC) ligands have attracted great interest over the last decade for their use in the design of homogenous catalysts. NHC-based metal complexes have interesting potential biomedical applications, such as in antimicrobial and cancer therapy, which are beginning to be explored more fully. We have studied here the oxidant activities of a series of Ru(II) complexes in vitro and zebrafish (Danio rerio) have been used as a model in vivo to investigate and characterize the toxicity of some of these compounds. Dual behavior was observed for the NHC-based complexes as they behaved as antioxidants at low concentrations but showed pro-oxidant capacity at higher concentrations. Zebrafish embryos were exposed to Ru(II) complexes under several different conditions (0 or 24 h postfertilization, with or without the chorion) and various parameters, such as viability, edema, heart rate, blood coagulation, pigmentation, scoliosis, malformation, and hatching, were tested. In general, zebrafish embryos were not harmed by exposure to Ru(II) complexes whatever the experimental conditions. Several toxicity profiles were observed depending upon the chemical structure of the compound in question. Their characteristics as pro-oxidant and/or antioxidant agents together with their biosafety may point to their having biomedical applications as antitumoral or neuroprotective drugs.

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A cytotoxic bis(carbene)gold(i) complex of ferrocenyl complexes: synthesis and structural characterisation

Cited by 70 publications

References 46 publications

First Crystal Structure for a Gold Carbene–Protein Adduct

First Crystal Structure for a Gold Carbene–Protein Adduct

Amides of gold(I) diphosphines prepared from N-heterocyclic sources and their in vitro and in vivo screening for anticancer activity

Biomedical Properties of a Series of Ruthenium-N-Heterocyclic Carbene Complexes Based on Oxidant Activity In Vitro and Assessment In Vivo of Biosafety in Zebrafish Embryos

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