New heteronuclear gold(I)–platinum(II) complexes with cytotoxic properties: Are two metals better than one?

Wenzel, Margot N.; Bigaeva, Emilia; Richard, Philippe; Gendre, Pierre Le; Picquet, Michel; Casini, Angela; Bodio, Ewen

doi:10.1016/j.jinorgbio.2014.07.011

Cited by 61 publications

(68 citation statements)

References 36 publications

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“…The formation of compound B was confirmed, among all, by [58] P{ 1 H} NMR analysis, where the phosphorous atom gave rise to a broad singlet shifted 4 ppm downfield from the corresponding signal in A. This is in agreement with the substitution of the chlorido ligand by a thiolato one [47]. Moreover, in the far-infrared (FIR) spectrum, the v Au-Cl vibration band was replaced by a broader and less intense v Au-S band at 372 cm −1 [58].…”

Section: Synthesis and Characterizationsupporting

confidence: 58%

“…In general, all the new compounds reported were much more effective in the A2780 cell line than in other ovarian cancer cells (SKOV3) or A549 lung cancer cells. Previous studies reported the increasing toxicity and increased uptake of gold-based compounds due to the presence of the thio-β-d-glucose tetraacetate moiety [47,55,56]. However, in the case of the dinuclear Au(I) complexes 3-4, this strategy did not improve the antiproliferative properties of the homobimetallic scaffold compared to the precursor 2 (Table 1) on any cell lines.…”

Section: Antiproliferative Activity In Vitromentioning

confidence: 85%

“…Replacing the chlorido ligand that is coordinated on the gold centre by an acetylated thioglucose moiety, as in auranofin, often increases the cytotoxicity of the resulting metal complex [47,55,56]. Thus, we first attempted to coordinate the thiosugar derivative on the gold centre of compound 1.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…1) [44][45][46][47][48]. Indeed, multinuclearity often increases cytotoxicity and/or selectivity and the phenomenon of resistance is overcome because of the combined properties, and sometimes the mechanism of action of the two metal moieties.…”

Section: Introductionmentioning

confidence: 99%

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Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

et al. 2015

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While N-heterocyclic carbenes (NHC) are ubiquitous ligands in catalysis for organic or industrial syntheses, their potential to form transition metal complexes for medicinal applications has still to be exploited. Within this frame, we synthesized new homo- and heterobimetallic complexes based on the Au(I)-NHC scaffold. The compounds were synthesized via a microwave-assisted method developed in our laboratories using Au(I)-NHC complexes carrying a pentafluorophenol ester moiety and another Au(I) phosphane complex or a bipyridine ligand bearing a pendant amine function. Thus, we developed two different methods to prepare homo- and heterobimetallic complexes (Au(I)/Au(I) or Au(I)/Cu(II), Au(I)/Ru(II), respectively). All the compounds were fully characterized by several spectroscopic techniques including far infrared, and were tested for their antiproliferative effects in a series of human cancer cells. They showed moderate anticancer properties. Their toxic effects were also studied ex vivo using the precision-cut tissue slices (PCTS) technique and initial results concerning their reactivity with the seleno-enzyme thioredoxin reductase were obtained.

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Section: Synthesis and Characterizationsupporting

confidence: 58%

Section: Antiproliferative Activity In Vitromentioning

confidence: 85%

Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

et al. 2015

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“…In this context, the gold(I)-thioglucose and {PtCl 2 } moieties were linked through a P,N,N'-spacer affording compound Au-6 [117]. The latter proved more cytotoxic in vitro than the individual auranofin and cisplatin, in particular when tested on cisplatin-resistant cell lines, although lack of tumor selectivity was a major drawback.…”

Section: Auranofin and Its Analoguesmentioning

confidence: 99%

Metal-based glycoconjugates and their potential in targeted anticancer chemotherapy

Pettenuzzo¹,

Pigot²,

Ronconi³

2016

Metallodrugs

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Glucose is a key source of energy and an essential nutrient for cell growth. Rapidly dividing cancer cells are well-known to require more nutrients and energy than normal ones to sustain their higher proliferation rates, and glucose is no exception. Therefore, the biomolecules involved in the promotion/regulation of the glycolytic flux may be regarded as potential targets for tackling tumor progression. Among all, glucose transporters (GLUTs), devoted to the recognition and cellular internalization of glucose, are largely overexpressed in tumors, thus indicating glycolysis as the major anaerobic glucose metabolism. Accordingly, such increased demand of glucose by fast-proliferating cancer cells makes it very attractive to selectively target tumor sites. In particular, tailored glucose-like substrates can be conjugated to chemotherapeutics (including metal-containing anticancer agents) so as to attain the site-specific delivery of drugs into the affected tissues. Progress in the development of metal-based glycoconjugates are here summarized and discussed.

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Heterometallic bridged Pt(II)‐Zn(II) complexes: Influence of the substituent in 4′‐position in inert terpy ligand on antigenotoxicity, potential antitumor activity and mechanism of interactions of the complexes with biomolecules

Serezlić,

Hasić,

Ašanin

et al. 2024

Applied Organom Chemis

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The synthesis and characterization of novel hetrometallic complexes [{cis‐PtCl(NH3)2(μ‐4,4′‐bipyridyl)ZnCl(terpy‐Cl)}](ClO4)2 (C1a), [{trans‐PtCl(NH3)2(μ‐4,4′‐bipyridyl)ZnCl(terpy)}](ClO4)2 (C2a), [{cis‐PtCl(NH3)2(μ‐pyrazine)ZnCl(terpy‐Cl)}](ClO4)2 (C3a) and [{trans‐PtCl(NH3)2(μ‐pyrazine)ZnCl(terpy‐Cl)}](ClO4)2 (C4a) (where terpy‐Cl = 4′‐chloro‐2,2′:6′,2′′‐terpyridine) was done. Acid–base titrations were performed by UV–Vis spectrophotometric method to evaluate the pKa values of corresponding aqua complexes. Interactions between complexes and important biomolecules, guanosine‐5′‐monophosphate (5′‐GMP) and glutathione (GSH) were examined by 1H NMR spectroscopy. The chloride substituent at the 4′ position on the middle pyridine ring of terpyridine ligand significantly affects the coordination of biomolecules, as well as overall stability of complexes. The complexes were evaluated in vitro for the antioxidant prevention of DNA damages. All tested novel complexes demonstrated a significant reduction in DNA damage against oxidative modifications of DNA caused by the hydroxyl and peroxyl radicals. Also, cytotoxicity evaluation showed that significant cytotoxicity occurs only after long‐term effect of C1a, C2a and C3a, complexes in HCT‐116 cells. Molecular docking studies predict results in agreement with experimental research.

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New heteronuclear gold(I)–platinum(II) complexes with cytotoxic properties: Are two metals better than one?

Cited by 61 publications

References 36 publications

Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

Metal-based glycoconjugates and their potential in targeted anticancer chemotherapy

Heterometallic bridged Pt(II)‐Zn(II) complexes: Influence of the substituent in 4′‐position in inert terpy ligand on antigenotoxicity, potential antitumor activity and mechanism of interactions of the complexes with biomolecules

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