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Organometallic Compounds: Synthesis and Biological Activity

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organometallic Chemistry".

Deadline for manuscript submissions: closed (28 February 2021) | Viewed by 14070

Special Issue Editors


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Guest Editor
Institute of Inorganic Chemistry, Leipzig University, Johannisallee 29, D-04103 Leipzig, Germany
Interests: inorganic chemistry; (chiral, functionalised) phosphorus compounds; carboranes; homogeneous catalysis with mono- and multinuclear transition metal complexes; biological and medicinal chemistry with inorganic compounds
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COMET-NANO Group, Department of Biology and Geology, Physics and Inorganic Chemistry, ESCET, Universidad Rey Juan Carlos, Calle Tulipán s/n, E-28933 Móstoles, Madrid, Spain
Interests: bioinorganic chemistry; medicinal chemistry; coordination chemistry; nanomaterials; drug discovery; pharmacological investigations; catalysis; photocatalysis
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Department of Engineering and Natural Sciences, University of Applied Sciences Merseburg,Eberhard-Leibnitz-Strasse 2, 06217 Merseburg, Germany
Interests: antitumor drugs; molecular oncology; drug targeting; medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Organometallic compounds are important as homogeneous catalysts for the production of pharmaceuticals, among many other products. However, since the reports of the first organometallic chemotherapeutic agent, salvarsan, by Paul Ehrlich (1854–1915, Nobel Prize in Physiology or Medicine in 1908), it has been realized that they can also play an important role as biologically active compounds in the design of novel pharmaceuticals. While only a few organometallic complexes that contain at least one direct metal-carbon bond occur in nature, such as vitamin B12 and some iron and nickel hydrogenases, many organometallic complexes have been studied for biological and medicinal applications. This Special Issue will collect the most recent contributions on the synthesis and biological activities of organometallic complexes in the treatment of viral, fungal, bacterial, and parasitic infections, as well as in the diagnosis and treatment of cancer (also as theranostics), as NO- or CO-releasing molecules, radiopharmaceuticals or for bioanalytical applications.

Prof. Dr. Evamarie Hey-Hawkins
Prof. Dr. Santiago Gómez-Ruiz
Prof. Dr. Goran Kaluđerović
Guest Editor

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.

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Keywords

  • Antitumour agents
  • Antimicrobial agents 
  • CO-releasing molecules
  • NO-releasing molecules
  • Radiopharmaceuticals
  • Bioanalytics
  • Theranostics

Published Papers (5 papers)

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Research

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10 pages, 5495 KiB  
Article
Ruthenacarborane and Quinoline: A Promising Combination for the Treatment of Brain Tumors
by Dijana Drača, Milan Marković, Marta Gozzi, Sanja Mijatović, Danijela Maksimović-Ivanić and Evamarie Hey-Hawkins
Molecules 2021, 26(13), 3801; https://doi.org/10.3390/molecules26133801 - 22 Jun 2021
Cited by 5 | Viewed by 1784
Abstract
Gliomas and glioblastomas are very aggressive forms of brain tumors, prone to the development of a multitude of resistance mechanisms to therapeutic treatments, including cytoprotective autophagy. In this work, we investigated the role and mechanism of action of the combination of a ruthenacarborane [...] Read more.
Gliomas and glioblastomas are very aggressive forms of brain tumors, prone to the development of a multitude of resistance mechanisms to therapeutic treatments, including cytoprotective autophagy. In this work, we investigated the role and mechanism of action of the combination of a ruthenacarborane derivative with 8-hydroxyquinoline (8-HQ), linked via an ester bond (complex 2), in rat astrocytoma C6 and human glioma U251 cells, in comparison with the two compounds alone, i.e., the free carboxylic acid (complex 1) and 8-HQ, and their non-covalent combination ([1 + 8-HQ], in 1:1 molar ratio). We found that only complex 2 was able to significantly affect cellular viability in glioma U251 cells (IC50 11.4 μM) via inhibition of the autophagic machinery, most likely acting at the early stages of the autophagic cascade. Contrary to 8-HQ alone, complex 2 was also able to impair cellular viability under conditions of glucose deprivation. We thus suggest different mechanisms of action of ruthenacarborane complex 2 than purely organic quinoline-based drugs, making complex 2 a very attractive candidate for evading the known resistances of brain tumors to chloroquine-based therapies. Full article
(This article belongs to the Special Issue Organometallic Compounds: Synthesis and Biological Activity)
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15 pages, 1710 KiB  
Article
In Vitro Evaluation of Antiproliferative Properties of Novel Organotin(IV) Carboxylate Compounds with Propanoic Acid Derivatives on a Panel of Human Cancer Cell Lines
by Nebojša Đ. Pantelić, Bojan Božić, Bojana B. Zmejkovski, Nebojša R. Banjac, Biljana Dojčinović, Ludger A. Wessjohann and Goran N. Kaluđerović
Molecules 2021, 26(11), 3199; https://doi.org/10.3390/molecules26113199 - 27 May 2021
Cited by 17 | Viewed by 2687
Abstract
The synthesis of novel triphenyltin(IV) compounds, Ph3SnLn (n = 1–3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3, has been performed. The ligands represent commercial drugs [...] Read more.
The synthesis of novel triphenyltin(IV) compounds, Ph3SnLn (n = 1–3), with oxaprozin (3-(4,5-diphenyloxazol-2-yl)propanoic acid), HL1, and the new propanoic acid derivatives 3-(4,5-bis(4-methoxylphenyl)oxazol-2-yl)propanoic acid, HL2, and 3-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)propanoic acid, HL3, has been performed. The ligands represent commercial drugs or their derivatives and the tin complexes have been characterized by standard analytical methods. The in vitro antiproliferative activity of both ligands and organotin(IV) compounds has been evaluated on the following tumour cell lines: human prostate cancer (PC-3), human colorectal adenocarcinoma (HT-29), breast cancer (MCF-7), and hepatocellular cancer (HepG2), as well as on normal mouse embryonic fibroblast cells (NIH3T3) with the aid of MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-12 diphenyltetrazolium bromide) and CV (crystal violet) assays. Contrary to the inactive ligand precursors, all organotin(IV) carboxylates showed very good activity with IC50 values ranging from 0.100 to 0.758 µM. According to the CV assay (IC50 = 0.218 ± 0.025 µM), complex Ph3SnL1 demonstrated the highest cytotoxicity against the caspase 3 deficient MCF-7 cell line. Inductively coupled plasma mass spectrometry (ICP-MS) analysis indicated a two-fold lower concentration of tin in MCF-7 cells in comparison to platinum. To investigate the mechanism of action of the compound Ph3SnL1 on MCF-7 cells, morphological, autophagy and cell cycle analysis, as well as the activation of caspase and ROS/RNS and NO production, has been performed. Results suggest that Ph3SnL1 induces caspase-independent apoptosis in MCF-7 cells. Full article
(This article belongs to the Special Issue Organometallic Compounds: Synthesis and Biological Activity)
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15 pages, 2191 KiB  
Article
Arene Ruthenium(II) Complexes Bearing the κ-P or κ-P,κ-S Ph2P(CH2)3SPh Ligand
by Sören Arlt, Vladana Petković, Gerd Ludwig, Thomas Eichhorn, Heinrich Lang, Tobias Rüffer, Sanja Mijatović, Danijela Maksimović-Ivanić and Goran N. Kaluđerović
Molecules 2021, 26(7), 1860; https://doi.org/10.3390/molecules26071860 - 25 Mar 2021
Cited by 3 | Viewed by 2729
Abstract
Neutral [Ru(η6-arene)Cl2{Ph2P(CH2)3SPh-κP}] (arene = benzene, indane, 1,2,3,4-tetrahydronaphthalene: 2a, 2c and 2d) and cationic [Ru(η6-arene)Cl(Ph2P(CH2)3SPh-κPS)]X complexes (arene = [...] Read more.
Neutral [Ru(η6-arene)Cl2{Ph2P(CH2)3SPh-κP}] (arene = benzene, indane, 1,2,3,4-tetrahydronaphthalene: 2a, 2c and 2d) and cationic [Ru(η6-arene)Cl(Ph2P(CH2)3SPh-κPS)]X complexes (arene = mesitylene, 1,4-dihydronaphthalene; X = Cl: 3b, 3e; arene = benzene, mesitylene, indane, 1,2,3,4-tetrahydronaphthalene, and 1,4-dihydronaphthalene; X = PF6: 4a4e) complexes were prepared and characterized by elemental analysis, IR, 1H, 13C and 31P NMR spectroscopy and also by single-crystal X-ray diffraction analyses. The stability of the complexes has been investigated in DMSO. Complexes have been assessed for their cytotoxic activity against 518A2, 8505C, A253, MCF-7 and SW480 cell lines. Generally, complexes exhibited activity in the lower micromolar range; moreover, they are found to be more active than cisplatin. For the most active ruthenium(II) complex, 4b, bearing mesitylene as ligand, the mechanism of action against 8505C cisplatin resistant cell line was determined. Complex 4b induced apoptosis accompanied by caspase activation. Full article
(This article belongs to the Special Issue Organometallic Compounds: Synthesis and Biological Activity)
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18 pages, 1253 KiB  
Article
Coumarin-Annulated Ferrocenyl 1,3-Oxazine Derivatives Possessing In Vitro Antimalarial and Antitrypanosomal Potency
by Mziyanda Mbaba, Laura M. K. Dingle, Ayanda I. Zulu, Dustin Laming, Tarryn Swart, Jo-Anne de la Mare, Heinrich C. Hoppe, Adrienne L. Edkins and Setshaba D. Khanye
Molecules 2021, 26(5), 1333; https://doi.org/10.3390/molecules26051333 - 2 Mar 2021
Cited by 14 | Viewed by 2574
Abstract
A tailored series of coumarin-based ferrocenyl 1,3-oxazine hybrid compounds was synthesized and investigated for potential antiparasitic activity, drawing inspiration from the established biological efficacy of the constituent chemical motifs. The structural identity of the synthesized compounds was confirmed by common spectroscopic techniques: NMR, [...] Read more.
A tailored series of coumarin-based ferrocenyl 1,3-oxazine hybrid compounds was synthesized and investigated for potential antiparasitic activity, drawing inspiration from the established biological efficacy of the constituent chemical motifs. The structural identity of the synthesized compounds was confirmed by common spectroscopic techniques: NMR, HRMS and IR. Biological evaluation studies reveal that the compounds exhibit higher in vitro antiparasitic potency against the chemosensitive malarial strain (3D7 P. falciparum) over the investigated trypanosomiasis causal agent (T. b. brucei 427) with mostly single digit micromolar IC50 values. When read in tandem with the biological performance of previously reported structurally similar non-coumarin, phenyl derivatives (i.e., ferrocenyl 1,3-benzoxazines and α-aminocresols), structure-activity relationship analyses suggest that the presence of the coumarin nucleus is tolerated for biological activity though this may lead to reduced efficacy. Preliminary mechanistic studies with the most promising compound (11b) support hemozoin inhibition and DNA interaction as likely mechanistic modalities by which this class of compounds may act to produce plasmocidal and antitrypanosomal effects. Full article
(This article belongs to the Special Issue Organometallic Compounds: Synthesis and Biological Activity)
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Review

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24 pages, 5704 KiB  
Review
Recent Advances in the Reactions of Cyclic Carbynes
by Qian Su, Jipeng Ding, Zhihui Du, Yunrong Lai, Hongzuo Li, Ming-An Ouyang, Liyan Song and Ran Lin
Molecules 2020, 25(21), 5050; https://doi.org/10.3390/molecules25215050 - 30 Oct 2020
Cited by 1 | Viewed by 3026
Abstract
The acyclic organic alkynes and carbyne bonds exhibit linear shapes. Metallabenzynes and metallapentalynes are six- or five-membered metallacycles containing carbynes, whose carbine-carbon bond angles are less than 180°. Such distortion results in considerable ring strain, resulting in the unprecedented reactivity compared with acyclic [...] Read more.
The acyclic organic alkynes and carbyne bonds exhibit linear shapes. Metallabenzynes and metallapentalynes are six- or five-membered metallacycles containing carbynes, whose carbine-carbon bond angles are less than 180°. Such distortion results in considerable ring strain, resulting in the unprecedented reactivity compared with acyclic carbynes. Meanwhile, the aromaticity of these metallacycles would stabilize the ring system. The fascinating combination of ring strain and aromaticity would lead to interesting reactivities. This mini review summarized recent findings on the reactivity of the metal–carbon triple bonds and the aromatic ring system. In the case of metallabenzynes, aromaticity would prevail over ring strain. The reactions are similar to those of organic aromatics, especially in electrophilic reactions. Meanwhile, fragmentation of metallacarbynes might be observed via migratory insertion if the aromaticity of metallacarbynes is strongly affected. In the case of metallapentalynes, the extremely small bond angle would result in high reactivity of the carbyne moiety, which would undergo typical reactions for organic alkynes, including interaction with coinage metal complexes, electrophilic reactions, nucleophilic reactions and cycloaddition reactions, whereas the strong aromaticity ensured the integrity of the bicyclic framework of metallapentalynes throughout all reported reaction conditions. Full article
(This article belongs to the Special Issue Organometallic Compounds: Synthesis and Biological Activity)
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