ArticleDalton transactions (Cambridge, England : 2003)2019
Anti-cancer organoruthenium(ii) complexes and their interactions with cysteine and its analogues. A mass-spectrometric study.
Article in Dalton transactions (Cambridge, England : 2003), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 24 citations in OpenAlex.
- Antiparasitic and Antifungal Activities of Cetyl-Maritima, a NewAntibiotics (Basel, Switzerland) · 2025Article
- Host-Guest Interactions of Ruthenium(II) Arene Complexes with Cucurbit[7/8]uril.Inorganic chemistry · 2024Article
- Potent Ruthenium-Ferrocene Bimetallic Antitumor Antiangiogenic Agent That Circumvents Platinum Resistance: From Synthesis and Mechanistic Studies toJournal of medicinal chemistry · 2022Article
- Enantioselective Cytotoxicity of Chiral Diphosphine Ruthenium(II) Complexes Against Cancer Cells.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Ruthenium complexes show potent inhibition of AKR1C1, AKR1C2, and AKR1C3 enzymes and anti-proliferative action against chemoresistant ovarian cancer cell line.Frontiers in pharmacology · 2022Article
- Determination of Relative Stabilities of Metal-Peptide Bonds in the Gas Phase.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Comparison of Solution Chemical Properties and Biological Activity of Ruthenium Complexes of SelectedPharmaceuticals (Basel, Switzerland) · 2021Article
- Organoruthenium Complexes with Benzo-Fused Pyrithiones Overcome Platinum Resistance in Ovarian Cancer Cells.Cancers · 2021Article
- Structural Isomerism and Enhanced Lipophilicity of Pyrithione Ligands of Organoruthenium(II) Complexes Increase Inhibition on AChE and BuChE.International journal of molecular sciences · 2020Article
- Binding Kinetics of Ruthenium Pyrithione Chemotherapeutic Candidates to Human Serum Proteins Studied by HPLC-ICP-MS.Molecules (Basel, Switzerland) · 2020Article
- Binding mechanisms of half-sandwich Rh(III) and Ru(II) arene complexes on human serum albumin: a comparative study.Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry · 2019Article
Corrections and comments
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Authors and funding
4 authors at 3 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The ruthenium complexes [Ru(CYM)(p-Cl-dkt)(Cl)] (1), [Ru(CYM)(pta)(p-Cl-dkt)]PF6 (2), and [Ru(CYM)(pta)Cl2] (3, RAPTA-C) (CYM = para-cymene, p-Cl-dkt = 1-(4-chlorophenyl)-4,4,4-trifluorobutane-1,3-dione, pta = 1,3,5-triaza-7-phosphaadamantane) are biologically active and show anti-cancer activities, albeit with different mechanisms. To further understand these mechanisms, we compared their speciation in aqueous solutions with an amino acid (cysteine), with an amino acid derivative (N-acetylcysteine) and with a tripeptide (glutathione) by Mass Spectrometry (MS). Here, we show that all ruthenium complexes have high selectivity for cysteine and cysteine-derived molecules. On one hand, [Ru(CYM)(p-Cl-dkt)(Cl)] undergoes solvolysis in water and forms [Ru2(CYM)2(OH)3]+. Subsequently, all hydroxyl anions are exchanged by deprotonated cysteine. Infrared Photodissociation Spectroscopy (IRPD) showed that cysteine binds to the ruthenium atoms via the deprotonated thiol group and that sulfur bridges the ruthenium centers. On the other hand, the pta-bearing complexes remain monometallic and undergo only slow Cl or p-Cl-dkt exchange by deprotonated cysteine. Therefore, the pta ligand protects the ruthenium complexes from ligand exchange with water and from the formation of biruthenium clusters, possibly explaining why the mechanism of pta-bearing ruthenium complexes is not based on ROS production but on their reactivity as monometallic complexes.
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Registered trials
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