The leading established metal-based drugs: a revisitation of their relevant physico-chemical data

Cirri, Damiano; Fabbrini, Maria Giulia; Pratesi, Alessandro; Ciofi, Lorenzo; Massai, Lara; Marzo, Tiziano; Messori, Luigi

doi:10.1007/s10534-019-00210-7

Cited by 20 publications

(17 citation statements)

References 11 publications

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“…Some of these complexes are now in different phases of clinical trials. 6,7 In addition, palladium(II), rhodium(III), and copper(II) complexes are shown to exhibit higher anticancer activity toward various human cancer cells than platinum-based drugs. [8][9][10] In this regard, palladium(II) complexes presented different anticancer properties against breast, lung, and prostate cancers than cisplatin.…”

Section: Introductionmentioning

confidence: 99%

Pd(II) and Rh(III) Complexes with Isoquinoline Derivatives Induced Mitochondria-Mediated Apoptotic and Autophagic Cell Death in HepG2 Cells

et al. 2021

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Nonplatinum metal complexes of [Pd(L 1 )Cl 2 ] (C1), [Rh (L 1 )Cl 3 (DMSO)] (C2), [Pd(L 2 )Cl 2 ] (C3), and [Rh(L 3 ) Cl 3 (DMSO)] (C4) with isoquinoline derivatives have been prepared and characterized. C1-C4 exhibited higher in vitro anticancer activity and lower toxicity than the corresponding ligands and cisplatin against HepG2 cells. The mechanistic studies revealed that C1 arrested the cell cycle at S-phase by regulation of cyclin and cyclin-dependent kinases. C1 was accumulated in mitochondria, which increased the generation of reactive oxygen species (ROS) and endoplasmic reticulum (ER)-stress response through mitochondrial dysfunction. Moreover, C1 stimulated Ca 2+ release, activated the caspase cascade, and triggered mitochondria-mediated apoptosis. The in vivo studies of C1 demonstrated higher safety than cisplatin and effective tumor growth inhibition. C1 is a potential anticancer drug candidate.

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Section: Introductionmentioning

confidence: 99%

Pd(II) and Rh(III) Complexes with Isoquinoline Derivatives Induced Mitochondria-Mediated Apoptotic and Autophagic Cell Death in HepG2 Cells

et al. 2021

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“…We next predicted the LogP values of 1a‐r using ADMETlab and listed in Table 1. We found that oxaliplatin (LogP value was −1.6) was more hydrophilic than 1,3‐dimethylbarbituric acid derivatives (LogP values ranged from 1.335 to 2.749) [17] . The LogP values of 1a‐r are within the standard range (0 to 3), suggesting they have proper lipid bilayer permeability and aqueous solubility, whereas, they exhibit less potent cytotoxicity.…”

Section: Discussionmentioning

confidence: 87%

“…As shown in Table 1, the LogP values of 1a‐r were within the standard range (0 to 3). The LogP values of oxaliplatin was −1.6, [17] demonstrating that oxaliplatin is more hydrophilic than 1,3‐dimethylbarbituric acid derivatives. Interestingly, compound 1c , with a 3‐CF 3 function on the benzyl ring, exhibited superior cytotoxicity against both A549 and HeLa cells compared to all other 1,3‐dimethylbarbituric acid derivatives.…”

Section: Resultsmentioning

confidence: 98%

“…In this work, barbituric acid derivatives ( 1a‐r ) were less potent than oxaliplatin against A549 and HeLa cells ( Table 1). The value of LogP, one of the medicinal chemical properties of drugs, play an important role on the lipid bilayer permeability and aqueous solubility [17] . We next predicted the LogP values of 1a‐r using ADMETlab and listed in Table 1.…”

Section: Discussionmentioning

confidence: 99%

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Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

Liu

et al. 2022

Chemistry & Biodiversity

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This work deals with the design and synthesis of 18 barbituric acid derivatives bearing 1,3‐dimethylbarbituric acid and cinnamic acid scaffolds to find potent anticancer agents. The target molecules were obtained through Knoevenagel condensation and acylation reaction. The cytotoxicity was assessed by the MTT assay. Flowcytometry was performed to determine the cell cycle arrest, apoptosis, ROS levels and the loss of MMP. The ratios of GSH/GSSG and the MDA levels were determined by using UV spectrophotometry. The results revealed that introducing substitutions (CF3, OCF3, F) on the meta‐ of the benzyl ring of barbituric acid derivatives led to a considerable increase in the antiproliferative activities compared with that of corresponding ortho‐ and para‐substituted barbituric acid derivatives. Mechanism investigation implied that the 1c could increase the ROS and MDA level, decrease the ratio of GSH/GSSG and MMP, and lead to cell cycle arrest. Further research is needed for structural optimization to enhance hydrophilicity, thereby improve the biological activity of these compounds.

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“…[12,29] Initially,ascratch wound-healing assay wasi ncluded here to evaluate the antimetastatic activity of Ru8 using the highly metastatic human HCC Huh-7 cell line (Figure4A). For comparison, NAMI-A, a potent antimetastatic agent undergoing clinical trials, [30] was selected as ar eference. Strikingly,e xposure of cells to Ru8 reduced cell migration, showingadose-dependent suppression activity.T he wound-healing ratio after incubation with 32 mm Ru8 was reduced to 2.9 %c ompared to untreated cells with 29.6 %m igrating cells ( Figure 4B).…”

Section: In Vitro Antimetastatic Activitymentioning

confidence: 99%

New Organometallic Ruthenium(II) Compounds Synergistically Show Cytotoxic, Antimetastatic and Antiangiogenic Activities for the Treatment of Metastatic Cancer

Wang

Jin

Shu

et al. 2020

Chemistry A European J

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In this study,w en ewly designed ands ynthesized as mall library of ten structurally relatedC ,N-cyclometalated ruthenium(II) complexes containing various pyridine-functionalized NHC ligand and chelating bipyridyl ligands(e.g., 2,2'-bipyridine, 5,5'-dimethyl-2,2'-bipyridine, and 1,10-phenanthroline(phen)). The complexes were well characterized by NMR, electrosprayi onization-mass spectrometry,a nd single-crystal X-ray structurea nalyses. Among the new ruthenium(II) derivatives, we identified that the complex Ru8 bearing bulky moieties(i.e.,phen and pentamethyl benzene) had the most potent cytotoxicity against all tested cancer cell lines, generating dose-and cell line-dependent IC 50 values at the range of 3.3-15.0 mm.M ore significantly, Ru8 not only efficiently inhibited the metastasis process against invasiona nd migration of tumor cells but also exhibited potent antivascular effects by suppressing HUVECc ellsm igration andt ube formationi nv itro and blockingv essel generation in vivo (chicken chorioallantoic membrane model). In am etastatic A2780 tumor xenograft-bearing mouse model, administration of Ru8 outperformed antimetastatic agent NAMI-Aa nd clinically approved cisplatin in terms of antitumor efficacy and inhibition of metastases to other organs. Overall,t hese data provided compellinge vidence that the new cyclometalated ruthenium complex Ru8 is an attractive agent because of synergistically suppressing bulky tumors and metastasized tumor nudes. Therefore, the complex Ru8 deserves furtherinvestigations.

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The leading established metal-based drugs: a revisitation of their relevant physico-chemical data

Cited by 20 publications

References 11 publications

Pd(II) and Rh(III) Complexes with Isoquinoline Derivatives Induced Mitochondria-Mediated Apoptotic and Autophagic Cell Death in HepG2 Cells

Pd(II) and Rh(III) Complexes with Isoquinoline Derivatives Induced Mitochondria-Mediated Apoptotic and Autophagic Cell Death in HepG2 Cells

Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives

New Organometallic Ruthenium(II) Compounds Synergistically Show Cytotoxic, Antimetastatic and Antiangiogenic Activities for the Treatment of Metastatic Cancer

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