ArticleJournal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry2016
Novel antitumor adamantane-azole gold(I) complexes as potential inhibitors of thioredoxin reductase.
Article in Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 63 citations in OpenAlex.
- Amebicidal Effect of Adamantane-Azole Gold(I) Complexes: Cell Death Mechanisms and Synergistic Action with Chlorhexidine againstACS omega · 2026Article
- Combining Gold and Selenium as Emerging Bioactive Compounds: From Synthesis to Therapeutic Potential.ACS omega · 2026Review
- Anticancer Activity of Metallodrugs and Metallizing Host Defense Peptides-Current Developments in Structure-Activity Relationship.International journal of molecular sciences · 2024Review
- Auranofin-Loaded Chitosan Nanoparticles Demonstrate Potency against Triple-Negative Breast Cancer.ACS applied bio materials · 2024Article
- Synthesis and biological evaluation of novel bi-gold mitocans in lung cancer cells.Frontiers in chemistry · 2023Article
- Organometallic gold(I) and gold(III) complexes for lung cancer treatment.Frontiers in pharmacology · 2022Review
- Computational Studies of Au(I) and Au(III) Anticancer MetalLodrugs: A Survey.Molecules (Basel, Switzerland) · 2021Review
- Thiourea-Derived Chelating Ligands and Their Organometallic Compounds: Investigations into Their Anticancer Activity.Molecules (Basel, Switzerland) · 2020Article
- Evaluating Ligand Modifications of the Titanocene and Auranofin Moieties for the Development of More Potent Anticancer Drugs.Inorganics · 2020Article
- Mono and dinuclear platinum and palladium complexes containing adamantane-azole ligands: DNA and BSA interaction and cytotoxicity.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2019Article
- Gold as a Possible Alternative to Platinum-Based Chemotherapy for Colon Cancer Treatment.Cancers · 2019Review
- Crystal structures and Hirshfeld surface analysis of 2-(adamantan-1-yl)-5-(4-fluoro-phen-yl)-1,3,4-oxa-diazole and 2-(adamantan-1-yl)-5-(4-chloro-phen-yl)-1,3,4-oxa-diazole.Acta crystallographica. Section E, Crystallographic communications · 2019Article
- Article
- Reactivity of the [Au(C^N^C)Cl] complex in the presence of HJournal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2018Article
- Planarians as models to investigate the bioactivity of gold(I) complexes in vivo.Scientific reports · 2018Article
- Gold-Based Medicine: A Paradigm Shift in Anti-Cancer Therapy?Molecules (Basel, Switzerland) · 2018Review
- Colorectal Carcinoma: A General Overview and Future Perspectives in Colorectal Cancer.International journal of molecular sciences · 2017Review
- In Vitro Antitumor Active Gold(I) Triphenylphosphane Complexes Containing 7-Azaindoles.International journal of molecular sciences · 2016Article
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Authors and funding
8 authors at 2 institutions in 1 country.
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No grant is acknowledged in the PubMed record.
Abstract
Gold complexes that could act as antitumor agents have attracted great attention. Heterocyclic compounds and their metal complexes display a broad spectrum of pharmacological properties. The present study reports the preparation and characterization of four novel gold(I) complexes containing tertiary phosphine and new ligands 5-adamantyl-1,3-thiazolidine-2-thione, 3-methyladamantane-1,3,4-oxadiazole-2-thione. Spectroscopic data suggest that gold is coordinated to the exocyclic sulfur atom in all cases, as confirmed by X-ray crystallographic data obtained for complex (1) and supported by quantum-mechanical calculations. The cytotoxicity of the compounds has been evaluated in comparison to cisplatin and auranofin in three different tumor cell lines, colon cancer (CT26WT), metastatic skin melanoma (B16F10), mammary adenocarcinoma (4T1) and kidney normal cell (BHK-21). The gold complexes were more active than their respective free ligands and able to inhibit the thioredoxin reductase (TrxR) enzyme, even in the presence of albumin. Molecular modeling studies were carried out to understand the interaction between the compounds and the TrxR enzyme, considered as a potential target for new compounds in cancer treatment. The docking results show that the adamantane ring is essential to stabilize the ligand-enzyme complex prior the formation of covalent bond with gold center. The structure of the new gold compounds was established on the basis of spectroscopic data, DFT calculations and X-ray diffraction. TrxR inhibition was evaluated and the results correlated with the assays in tumor cells, suggesting the TrxR as possible target for these compounds.
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