Gold(I) and Palladium(II) Thiolato Complexes Containing Water‐Soluble Phosphane Ligands

Vergara, Elena; Miranda, Susana; Mohr, Fabian; Cerrada, Elena; Tiekink, Edward R. T.; Romero, Pilar; Mendía, Aránzazu; Laguna, Mariano

doi:10.1002/ejic.200700112

Cited by 66 publications

(69 citation statements)

References 39 publications

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“…[34,35] Nevertheless, one of the main limitations of these compounds is their poor water solubility, which can hinder bioavailability in vivo and lead to complicated formulation protocols. Based on a previous study describing compounds 1-5, [24,25] which contain hydrophilic phosphine ligands, we decided to further investigate the biological properties of these complexes, together with two novel related complexes 6 and 7 ( Figure 1). Complexes 6 and 7, containing the TPPTS ligand in place of PTA and DAPTA, were prepared analogously to the previously described compounds, as reported in the experimental section.…”

Section: Resultsmentioning

confidence: 99%

“…General methods and materials PTA, [50] DAPTA, [51] [AuCl(PTA)], [52] [AuCl(TPPTS)], [53] [AuCl(DAPTA)], [25] [Au(SPy)( (4) and [Au(SMePyrim)(DAPTA)] (5) were prepared according to literature procedures. [24,25] pUC19 plasmid DNA was purchased from Sigma.…”

Section: Methodsmentioning

confidence: 99%

“…[24,25] These compounds are not only water soluble, in contrast to related compounds with hydrophobic phosphines, but also exhibit excellent in vitro anticancer activity. Notably, several ruthenium complexes containing PTA ligands, [26][27][28][29][30] as well as osmium and rhodium derivatives, [31,32] have been shown to possess promising anticancer properties in recent years.…”

Section: Introductionmentioning

confidence: 99%

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Anticancer Therapeutics That Target Selenoenzymes: Synthesis, Characterization, in vitro Cytotoxicity, and Thioredoxin Reductase Inhibition of a Series of Gold(I) Complexes Containing Hydrophilic Phosphine Ligands

et al. 2009

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Gold(I) complexes bearing water-soluble phosphine ligands, including 1,3,5-triaza-7-phosphaadamantane (PTA), 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA), and sodium triphenylphosphine trisulfonate (TPPTS), in combination with thionate ligands, were screened for their antiproliferative activities against human ovarian cancer cell lines A2780 either sensitive or resistant to cisplatin. In addition, the compounds were screened for their inhibition of mammalian thioredoxin reductases (TrxR), enzymes that are overexpressed in many tumor cells and contribute to drug resistance. The gold(I)-phosphine complexes efficiently inhibited cytosolic and mitochondrial TrxRs at concentrations that did not affect the related oxidoreductase glutathione reductase (GR). Additional complementary information on the enzyme metallation process and potential gold binding sites was obtained through the application of a specific biochemical assay using a thiol-tagging reagent, BIAM (biotin-conjugated iodoacetamide).

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Anticancer Therapeutics That Target Selenoenzymes: Synthesis, Characterization, in vitro Cytotoxicity, and Thioredoxin Reductase Inhibition of a Series of Gold(I) Complexes Containing Hydrophilic Phosphine Ligands

et al. 2009

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“…Interestingly, in the presence of the surfactant SDS (sodium docecyl sulfate) these metal nanoparticles can be stabilized by the micelles thus allowing their effective recycling, a key factor for practical applications of this heterogeneous catalytic system. 40 44 which were prepared by following the methods reported in the literature. Flash chromatography was performed using Merck silica gel 60 (230-400 mesh).…”

Section: Discussionmentioning

confidence: 99%

Conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds in aqueous medium using Pd(ii) complexes with dihydroxy-2,2′-bipyridine ligands: homogeneous or heterogeneous nano-catalysis?

Tomás‐Mendivil

Dı́ez

Cadierno

2011

Catal. Sci. Technol.

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The conjugate addition of arylboronic acids to a,b-unsaturated carbonyl compounds in water under air has been studied using a series of palladium(II) derivatives containing symmetrically disubstituted-2,2 0 -bipyridine ligands. Among them, best results were obtained with complex [PdCl 2 {3,3 0 -(OH) 2 -2,2 0 -bipy}] (2a), which selectively provides the desired addition products in good to high yields under mild conditions. Catalytically active palladium nanoparticles are formed in the course of the reactions. In the presence of sodium dodecyl sulfate (SDS) these nanoparticles can be stabilized and recycled.Scheme 1 The catalytic 1,4-conjugate addition of arylboronic acids to a,b-unsaturated carbonyl compounds.

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“…While crystal structures were not obtained for 1, 2, or 4, despite best efforts, it is expected based on literature precedents of mononuclear phosphanegold(I) dithiocarbamates [39,41,47,[50][51][52][53][54][55][56], that each of 1, 2, and 4 feature a linear P-Au-S geometry arising from an essentially monodentate mode of coordination of the dithiocarbamate ligand. Finally, the stability of 1-4 in d6-DMSO solution was monitored by 1 H over a week.…”

Section: Chemistrymentioning

confidence: 99%

In vitro antibacterial and time kill evaluation of mononuclear phosphanegold(I) dithiocarbamates

Chen

Jamaludin

Khoo

et al. 2016

Journal of Inorganic Biochemistry

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Four compounds, R3PAu[S2CN(CH2CH2OH)2], R = Ph (1) and Cy (2), and Et3PAuS2CNRꞌ2, Rꞌ = Rꞌ = Et (3) and Rꞌ2 = (CH2)4 (4), have been evaluated for antibacterial activity against a panel of 24 Gram positive (8) and Gram negative (16) bacteria. Based on minimum inhibitory concentration (MIC) scores, compounds 1 and 2 were shown to be specifically potent against Gram positive bacteria whereas compounds 3 and, to a lesser extent, 4 exhibited broad range activity.All four compounds were active against methicillin resistant Staphylococcus aureus (MRSA).Time kill assays revealed the compounds to exhibit both time-and concentration-dependent pharmacokinetics against susceptible bacteria. Each compound was bactericidal against one or more bacteria with 3 being especially potent after 8 h exposure; compounds 1 and 3 were bactericidal against MRSA. Compound 3 was the most effective bactericide across the series especially toward B. subtilis, S. saprophyticus, A. hydrophilia, P. vulgaris, and V. parahaemolyticus. This study demonstrates the potential of this class of compounds as antibacterial agents, either broad range or against specific bacteria.

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Gold(I) and Palladium(II) Thiolato Complexes Containing Water‐Soluble Phosphane Ligands

Cited by 66 publications

References 39 publications

Anticancer Therapeutics That Target Selenoenzymes: Synthesis, Characterization, in vitro Cytotoxicity, and Thioredoxin Reductase Inhibition of a Series of Gold(I) Complexes Containing Hydrophilic Phosphine Ligands

Anticancer Therapeutics That Target Selenoenzymes: Synthesis, Characterization, in vitro Cytotoxicity, and Thioredoxin Reductase Inhibition of a Series of Gold(I) Complexes Containing Hydrophilic Phosphine Ligands

Conjugate addition of arylboronic acids to α,β-unsaturated carbonyl compounds in aqueous medium using Pd(ii) complexes with dihydroxy-2,2′-bipyridine ligands: homogeneous or heterogeneous nano-catalysis?

In vitro antibacterial and time kill evaluation of mononuclear phosphanegold(I) dithiocarbamates

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