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Pharmaceutics
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Metallodrugs in Cancer Therapy: The Newest Candidates in the Field
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Metallodrugs in Cancer Therapy: The Newest Candidates in the Field

A special issue of Pharmaceutics (ISSN 1999-4923). This special issue belongs to the section "Drug Targeting and Design".

Deadline for manuscript submissions: closed (20 March 2023) | Viewed by 14729

Special Issue Editors

Dr. Andreia Marques Valente

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Guest Editor
Centro de Química Estrutural, Institute of Molecular Sciences and Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal
Interests: anticancer drugs; cancer multidrug resistance; polymer–metal conjugates; drug delivery
Special Issues, Collections and Topics in MDPI journals
Dr. Ana Isabel Tomaz

E-Mail Website
Guest Editor
Centro de Ciências Moleculares e Materiais, Departamento de Química e Bioquímica Faculdade de Ciências da Universidade de Lisboa, Campo Grande, 1749-016 Lisboa, Portugal
Interests: metallodrugs; anti-cancer coordination compounds; biospeciation; therapeutic ruthenium/iron/copper compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Metal ions play key roles in myriad biological processes known to be essential to life. Living organisms have developed mechanisms to maintain cellular levels of metal ions, which are tightly regulated; excess or deficiency in these ions result in disease, including cancer disorders. The use of metals and of their compounds as medicines has been known since ancient times, even though insight into their modes of action was merely empiric, and the distinction between therapeutic or toxic dose was a major challenge. Metal compounds were long regarded with suspicion and undefined as humans’ ‘friends’ or ‘foes’; this was true until Rosenberg’s breakthrough on the properties of cisplatin more than sixty years ago, which consolidated the interest in metal compounds as useful potential therapeutics. Since then, three platinum complexes (cisplatin, oxaliplatin and carboplatin) have been approved for clinical use worldwide, and still stand out as the most often prescribed chemotherapeutics (applied in essentially every second therapeutic routine), being listed as ‘essential medicines’ by the World Health Organization despite the toxicity inherent to their use and multidrug resistance.

These benefits (remarkable high efficiency) and drawbacks (toxicity and resistance) ignited the interest in metallodrugs for chemotherapy. Today, this is a highly dynamic field of research that has spread to other metal-containing complexes as novel potential anticancer drugs. 

This Special Issue is intended to collect recent research/discoveries in the field of cancer prospective metallopharmaceuticals. This is an area in constant evolution, and we welcome submissions (research papers/focused reviews) on subjects including, but not limited to:

  • Synthetic methods/characterization and biological activity of novel metal-based compounds;
  • Structure–activity studies;
  • Drug delivery for metal-based compounds;
  • Metal complexes overcoming MDR (metallodrug resistance to treatment);
  • Mode of action, uptake, cell targets and (cyto)toxicity;
  • Metal complexes as theranostics;
  • Biospeciation of metal ions and anti-cancer metal-based compounds.

Dr. Andreia Marques Valente
Dr. Ana Isabel Tomaz
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Pharmaceutics is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2900 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • metal-based compounds
  • cancer therapy
  • metallodrugs
  • drug delivery
  • multidrug resistance
  • anti-cancer activity

Published Papers (8 papers)

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Research

14 pages, 2314 KiB  
Article
Cytotoxic Effects of New Palladium(II) Complexes with Thiazine or Thiazoline Derivative Ligands in Tumor Cell Lines
by Elena Fernández-Delgado, Samuel Estirado, Ana B. Rodríguez, Francisco Luna-Giles, Emilio Viñuelas-Zahínos, Javier Espino and José Antonio Pariente
Pharmaceutics 2023, 15(2), 696; https://doi.org/10.3390/pharmaceutics15020696 - 18 Feb 2023
Cited by 2 | Viewed by 1490
Abstract
The synthesis of analogs of cisplatin, which is a widely used chemotherapeutic agent, using other metal centers could be an alternative for cancer treatment. Pd(II) could be a substitute for Pt(II) due to its coordination chemistry similarity. For that reason, six squared-planar Pd(II) [...] Read more.
The synthesis of analogs of cisplatin, which is a widely used chemotherapeutic agent, using other metal centers could be an alternative for cancer treatment. Pd(II) could be a substitute for Pt(II) due to its coordination chemistry similarity. For that reason, six squared-planar Pd(II) complexes with thiazine and thiazoline ligands and formula [PdCl2(L)] were synthesized and characterized in this work. The potential anticarcinogenic ability of the compounds was studied via cytotoxicity assay in three different human tumor cell lines, i.e., epithelial cervix carcinoma (HeLa), promyelocytic leukemia (HL-60), and histiocytic lymphoma (U-937). Data obtained showed that complexes with methyl substitutions did not modify cell viability, while no-methyl substituted compounds had a moderate cytotoxic effect on all three cell lines. The complexes with phenyl substitutions displayed the lowest IC50 values, which ranged between 46.39 ± 3.99 μM and 62.74 ± 6.45 μM. Moreover, Pd accumulation inside the cell was observed after incubation with any of the four complexes mentioned, and the two complexes with phenyl rings were found to induce an increase in the percentage of apoptotic cells. These results suggested that the presence of bulky substitutions on the ligands such as phenyl groups may influence the cytotoxicity of the chemotherapeutic agents synthesized. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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21 pages, 5343 KiB  
Article
Influence of the Fatty Acid Metabolism on the Mode of Action of a Cisplatin(IV) Complex with Phenylbutyrate as Axial Ligands
by Theresa Mendrina, Isabella Poetsch, Hemma Schueffl, Dina Baier, Christine Pirker, Alexander Ries, Bernhard K. Keppler, Christian R. Kowol, Dan Gibson, Michael Grusch, Walter Berger and Petra Heffeter
Pharmaceutics 2023, 15(2), 677; https://doi.org/10.3390/pharmaceutics15020677 - 16 Feb 2023
Cited by 2 | Viewed by 1374
Abstract
For a variety of cancer types, platinum compounds are still among the best treatment options. However, their application is limited by side effects and drug resistance. Consequently, multi-targeted platinum(IV) prodrugs that target specific traits of the malignant tissue are interesting new candidates. Recently, [...] Read more.
For a variety of cancer types, platinum compounds are still among the best treatment options. However, their application is limited by side effects and drug resistance. Consequently, multi-targeted platinum(IV) prodrugs that target specific traits of the malignant tissue are interesting new candidates. Recently, cisPt(PhB)2 was synthesized which, upon reduction in the malignant tissue, releases phenylbutyrate (PhB), a metabolically active fatty acid analog, in addition to cisplatin. In this study, we in-depth investigated the anticancer properties of this new complex in cell culture and in mouse allograft experiments. CisPt(PhB)2 showed a distinctly improved anticancer activity compared to cisplatin as well as to PhB alone and was able to overcome various frequently occurring drug resistance mechanisms. Furthermore, we observed that differences in the cellular fatty acid metabolism and mitochondrial activity distinctly impacted the drug’s mode of action. Subsequent analyses revealed that “Warburg-like” cells, which are characterized by deficient mitochondrial function and fatty acid catabolism, are less capable of coping with cisPt(PhB)2 leading to rapid induction of a non-apoptotic form of cell death. Summarizing, cisPt(PhB)2 is a new orally applicable platinum(IV) prodrug with promising activity especially against cisplatin-resistant cancer cells with “Warburg-like” properties. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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24 pages, 5186 KiB  
Article
Half-Sandwich Rhodium Complexes with Releasable N-Donor Monodentate Ligands: Solution Chemical Properties and the Possibility for Acidosis Activation
by János P. Mészáros, Wolfgang Kandioller, Gabriella Spengler, Alexander Prado-Roller, Bernhard K. Keppler and Éva A. Enyedy
Pharmaceutics 2023, 15(2), 356; https://doi.org/10.3390/pharmaceutics15020356 - 20 Jan 2023
Cited by 1 | Viewed by 1883
Abstract
Cancer chemotherapeutics usually have serious side effects. Targeting the special properties of cancer and activation of the anticancer drug in the tumor microenvironment in situ may decrease the intensity of the side effects and improve the efficacy of therapy. In this study, half-sandwich [...] Read more.
Cancer chemotherapeutics usually have serious side effects. Targeting the special properties of cancer and activation of the anticancer drug in the tumor microenvironment in situ may decrease the intensity of the side effects and improve the efficacy of therapy. In this study, half-sandwich Rh complexes are introduced, which may be activated at the acidic, extracellular pH of the tumor tissue. The synthesis and aqueous stability of mixed-ligand complexes with a general formula of [Rh(η5-Cp*)(N,N/O)(N)]2+/+ are reported, where (N,N/O) indicates bidentate 8-quinolate, ethylenediamine and 1,10-phenanthroline and (N) represents the releasable monodentate ligand with a nitrogen donor atom. UV-visible spectrophotometry, 1H NMR, and pH-potentiometry were used to determine the protonation constants of the monodentate ligands, the proton dissociation constants of the coordinated water molecules in the aqua complexes, and the formation constants of the mixed-ligand complexes. The obtained data were compared to those of the analogous Ru(η6-p-cymene) complexes. The developed mixed-ligand complexes were tested in drug-sensitive and resistant colon cancer cell lines (Colo205 and Colo320, respectively) and in four bacterial strains (Gram-positive and Gram-negative, drug-sensitive, and resistant) at different pH values (5–8). The mixed-ligand complexes with 1-methylimidazole displayed sufficient stability at pH 7.4, and their activation was found in cancer cells with decreasing pH; moreover, the mixed-ligand complexes demonstrated antimicrobial activity in Gram-positive and Gram-negative bacteria, including the resistant MRSA strain. This study proved the viability of incorporating releasable monodentate ligands into mixed-ligand half-sandwich complexes, which is supported by the biological assays. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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14 pages, 2523 KiB  
Article
Dinuclear Iron Complexes of Iminopyridine-Based Ligands as Selective Cytotoxins for Tumor Cells and Inhibitors of Cancer Cell Migration
by Jessica Castro, Marlon Bravo, Meritxell Albertí, Anaís Marsal, María José Alonso-De Gennaro, Oriol Martínez-Ferraté, Carmen Claver, Piet W. N. M. van Leeuwen, Isabel Romero, Antoni Benito and Maria Vilanova
Pharmaceutics 2022, 14(12), 2801; https://doi.org/10.3390/pharmaceutics14122801 - 14 Dec 2022
Cited by 1 | Viewed by 1217
Abstract
A family of dinuclear iron (II) compounds with iminopyridine-based ligands displays selective cytotoxic activity against cancer cell lines. All compounds have IC50 values 2–6 fold lower than that of cisplatin, and 30–90 fold lower than that of carboplatin for the tumor cell [...] Read more.
A family of dinuclear iron (II) compounds with iminopyridine-based ligands displays selective cytotoxic activity against cancer cell lines. All compounds have IC50 values 2–6 fold lower than that of cisplatin, and 30–90 fold lower than that of carboplatin for the tumor cell lines assayed. Comparing the IC50 values between tumor and non-tumor cell lines, the selectivity indexes range from 3.2 to 34, compound 10, [Fe2(4)2(CH3CN)4](BF4)4, showing the highest selectivity. Those compounds carrying substituents on the iminopyridine ring show the same cytotoxicity as those without substituents. However, the electronic effects of the substituents on position 6 may be important for the cytotoxicity of the complexes, and consequently for their selectivity. All compounds act over DNA, promoting cuts on both strands in the presence of reactive oxygen species. Since compound 10 presented the highest selectivity, its cytotoxic effect was further characterized. It induces apoptosis, affects cell cycle phase distribution in a cell-dependent manner, and its cytotoxic effect is linked to reactive oxygen species generation. In addition, it decreases tumor cell migration, showing potential antimetastatic effects. These properties make compound 10 a good lead antitumor agent among all compounds studied here. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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22 pages, 4821 KiB  
Article
Potent Platinum(IV) Prodrugs That Incorporate a Biotin Moiety to Selectively Target Cancer Cells
by Aleen Khoury, Jennette A. Sakoff, Jayne Gilbert, Shawan Karan, Christopher P. Gordon and Janice R. Aldrich-Wright
Pharmaceutics 2022, 14(12), 2780; https://doi.org/10.3390/pharmaceutics14122780 - 12 Dec 2022
Cited by 7 | Viewed by 1444
Abstract
Four platinum(IV) prodrugs incorporating a biotin moiety to selectively target cancer cells were synthesised, characterised, and their biological activity assessed. All complexes exhibited exceptional in vitro cytotoxicity against a panel of cancer cell lines, with [Pt(5,6-dimethyl-1,10-phenanthroline)(1S,2S-diaminocyclohexane)(biotin)(hydroxido)](NO3)2 [...] Read more.
Four platinum(IV) prodrugs incorporating a biotin moiety to selectively target cancer cells were synthesised, characterised, and their biological activity assessed. All complexes exhibited exceptional in vitro cytotoxicity against a panel of cancer cell lines, with [Pt(5,6-dimethyl-1,10-phenanthroline)(1S,2S-diaminocyclohexane)(biotin)(hydroxido)](NO3)2, (2) exhibiting the lowest GI50 of 4 nM in the prostate Du145 cancer cell line. Each complex displayed significantly enhanced activity compared to cisplatin, with 2 being 1000-fold more active in the HT29 colon cancer cell line. Against the MCF-7 breast cancer cell line, in which high levels of biotin receptors are expressed, 2, [Pt(4,7-dimethoxy-1,10-phenanthroline)(1S,2S-diaminocyclohexane)(biotin)(hydroxido)](NO3)2, (3), and [Pt(5-methyl-1,10-phenanthroline)(1S,2S-diaminocyclohexane)(biotin)(hydroxido)](NO3)2, (4) exhibited enhanced activity compared to their platinum(II) cores, with 4 being 6-fold more active than its platinum(II) precursor. Furthermore, 3 exhibited 3-fold greater selectivity towards MCF-7 breast cancer cells compared to MCF10A breast healthy cells, and this was further confirmed by platinum uptake studies, which showed 3 to have almost 3-fold greater uptake in MCF-7 cells, compared to MCF10A cells. The results show that lipophilicity and selectivity both contributed to the cellular uptake of 1–4; however, this was not always translated to the observed cytotoxicity. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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29 pages, 5233 KiB  
Article
Metal Coordination and Biological Screening of a Schiff Base Derived from 8-Hydroxyquinoline and Benzothiazole
by Nádia Ribeiro, Pedro F. Farinha, Jacinta O. Pinho, Hugo Luiz, János P. Mészáros, Adelino M. Galvão, João Costa Pessoa, Éva A. Enyedy, Catarina Pinto Reis, Isabel Correia and Maria Manuela Gaspar
Pharmaceutics 2022, 14(12), 2583; https://doi.org/10.3390/pharmaceutics14122583 - 24 Nov 2022
Cited by 6 | Viewed by 2294
Abstract
Designing new metallodrugs for anticancer therapy is a driving force in the scientific community. Aiming to contribute to this field, we hereby report the development of a Schiff base (H2L) derived from the condensation of 2-carbaldehyde-8-hydroxyquinoline with 2-hydrazinobenzothiazole and its complexation [...] Read more.
Designing new metallodrugs for anticancer therapy is a driving force in the scientific community. Aiming to contribute to this field, we hereby report the development of a Schiff base (H2L) derived from the condensation of 2-carbaldehyde-8-hydroxyquinoline with 2-hydrazinobenzothiazole and its complexation with transition metal ions. All compounds were characterised by analytical and spectroscopic techniques, which disclosed their structure: [Cu(HL)Cl], [Cu(HL)2], [Ni(HL)(acetate)], [Ni(HL)2], [Ru(HL)Cl(DMSO)], [VO(HL)2] and [Fe(HL)2Cl(H2O)]. Different binding modes were proposed, showing the ligand’s coordination versatility. The ligand proton dissociation constants were determined, and the tested compounds showed high lipophilicity and light sensitivity. The stability of all complexes in aqueous media and their ability to bind to albumin were screened. Based on an antiproliferative in vitro screening, [Ni(HL)(acetate)] and [Ru(HL)Cl(DMSO)] were selected for further studies aiming to investigate their mechanisms of action and therapeutic potential towards colon cancer. The complexes displayed IC50 < 21 μM towards murine (CT-26) and human (HCT-116) colon cancer cell lines. Importantly, both complexes exhibited superior antiproliferative properties compared to the clinically approved 5-fluorouracil. [Ni(HL)(acetate)] induced cell cycle arrest in S phase in CT-26 cells. For [Ru(HL)Cl(DMSO)] this effect was observed in both colon cancer cell lines. Additionally, both compounds significantly inhibited cell migration particularly in the human colon cancer cell line, HCT-116. Overall, the therapeutic potential of both metal complexes was demonstrated. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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25 pages, 2014 KiB  
Article
Platinum(IV) Complexes of the 1,3,5-Triamino Analogue of the Biomolecule Cis-Inositol Designed as Innovative Antineoplastic Drug Candidates
by Vyara Velcheva, Kaspar Hegetschweiler, Georgi Momekov, Stefka Ivanova, Angel Ugrinov, Bernd Morgenstern and Galina Gencheva
Pharmaceutics 2022, 14(10), 2057; https://doi.org/10.3390/pharmaceutics14102057 - 27 Sep 2022
Cited by 3 | Viewed by 1795
Abstract
Metal complexes occupy a special place in the field of treatment and diagnostics. Their main advantages stem from the possibility of fine-tuning their thermodynamic properties and kinetic behavior in the biological milieu by applying different approaches such as properly constructed inner coordination sphere, [...] Read more.
Metal complexes occupy a special place in the field of treatment and diagnostics. Their main advantages stem from the possibility of fine-tuning their thermodynamic properties and kinetic behavior in the biological milieu by applying different approaches such as properly constructed inner coordination sphere, appropriate choice of ligands, metal oxidation state, redox potential, etc., which are specific to these compounds. Here we discuss the design and synthesis of two octahedral cationic Pt(IV) complexes of the tridentate ligand all-cis-2,4,6-triaminocyclohexane-1,3,5-triol (taci) with composition, fac-[Pt(taci)I3]+, 1 and bis-[Pt(taci)2]4+, 2 as well as the potential for their application as antineoplastic agents. The complexes have been isolated in a solid state as: fac-[Pt(taci)I3]I·3H2O (1A), fac-[Pt(taci)I3]I (1B), fac-[Pt(taci)I3]I·2DMF (1C), bis-[Pt(taci)2](CO3)2·6H2O (2A) by changing the acidity of the reaction systems, the molar ratios of the reagents and the counterions, and by re-crystallization. The ligand taci is coordinated through the NH2-groups, each molecule occupying three coordination places in the inner coordination sphere of Pt(IV). Monitoring of the hydrolysis processes of 1A and 2A at different acidity showed that while 2A remained stable over the study period, the I−-ions in 1A were successively substituted, with the main product under physiologically mimetic conditions being fac,cis-[Pt(taci)I(OH)2]+ (h2). The antiproliferative tests involved eight cancer cell models, among which chemosensitive (derived from leukemias and solid tumors) and chemoresistant human Acute myeloid leukemia lines (HL-60/Dox, HL-60/CDDP), as well as the non-malignant kidney’ cells HEK-293T showed that the complexes 1A and 2A are characterized by a fundamentally different profile of chemosensitivity and spectrum of cytotoxic activity compared to cisplatin. The new Pt(IV) complexes were shown to be more effective in selectively inhibiting the proliferation of human malignant cells compared to cisplatin. Remarkable activity was recorded for 1A, which showed an effect (IC50 = 8.9 ± 2.4) at more than 16-fold lower concentration than cisplatin (IC50 = 144.4 ± 9.8) against the resistant cell line HL-60/CDDP. In parallel, 1A exhibited virtually the same cytotoxic effect against the parental HL-60 cells (IC50 = 9.0 ± 1.2), where cisplatin displays comparable chemosensitivity (IC50 = 8.3 ± 0.8). The determined resistance indices (RI~1) show unequivocally that the resistant lines are sensitive to both compounds tested; therefore, they are capable of overcoming the mechanisms of cisplatin resistance. The structural features of these compounds and their promising pharmacological properties justify their inclusion in the group of “non-classical metal-based antitumor compounds” and are a prerequisite for the admission of alternative mechanisms of action. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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20 pages, 2428 KiB  
Article
Ruthenium(II)–Cyclopentadienyl-Derived Complexes as New Emerging Anti-Colorectal Cancer Drugs
by Catarina Teixeira-Guedes, Ana Rita Brás, Ricardo G. Teixeira, Andreia Valente and Ana Preto
Pharmaceutics 2022, 14(6), 1293; https://doi.org/10.3390/pharmaceutics14061293 - 17 Jun 2022
Cited by 10 | Viewed by 2177
Abstract
Colorectal cancer (CRC) is one of the most common malignancies and one of the leading causes of cancer-related death worldwide, urging the need for new and more efficient therapeutic approaches. Ruthenium complexes have emerged as attractive alternatives to traditional platinum-based compounds in the [...] Read more.
Colorectal cancer (CRC) is one of the most common malignancies and one of the leading causes of cancer-related death worldwide, urging the need for new and more efficient therapeutic approaches. Ruthenium complexes have emerged as attractive alternatives to traditional platinum-based compounds in the treatment of CRC. This work aims to evaluate anti-CRC properties, as well as to identify the mechanisms of action of ruthenium complexes with the general formula [Ru(η5-C5H4R)(PPh3)(4,4′-R′-2,2′-bipyridine)][CF3SO3], where R = CH3, CHO or CH2OH and R′ = H, CH3, CH2OH, or dibiotin ester. The complexes (Ru 1–7) displayed high bioactivity, as shown by low IC50 concentrations against CRC cells, namely, RKO and SW480. Four of the most promising ruthenium complexes (Ru 2, 5–7) were phenotypically characterized and were shown to inhibit cell viability by decreasing cell proliferation, inducing cell cycle arrest, and increasing apoptosis. These findings were in accordance with the inhibition of MEK/ERK and PI3K/AKT signaling pathways. Ruthenium complexes also led to a decrease in cellular clonogenic ability and cell migration, which was associated with the disruption of F-actin cytoskeleton integrity. Here, we demonstrated that ruthenium complexes, especially Ru7, have a high anticancer effect against CRC cells and are promising drugs to be used as a new therapeutical strategy for CRC treatment. Full article
(This article belongs to the Special Issue Metallodrugs in Cancer Therapy: The Newest Candidates in the Field)
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