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Journal articles on the topic 'Organoruthenium compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 20 February 2023

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1

Trobec, Tomaž, Kristina Sepčić, Monika Cecilija Žužek, Jerneja Kladnik, Nina Podjed, Catarina Cardoso Páscoa, Iztok Turel, and Robert Frangež. "Fine Tuning of Cholinesterase and Glutathione-S-Transferase Activities by Organoruthenium(II) Complexes." Biomedicines 9, no. 9 (September 16, 2021): 1243. http://dx.doi.org/10.3390/biomedicines9091243.

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Cholinesterases (ChEs) show increased activities in patients with Alzheimer’s disease, and remain one of the main therapeutic targets for treatment of this neurodegenerative disorder. A library of organoruthenium(II) complexes was prepared to investigate the influence of their structural elements on inhibition of ChEs, and on another pharmacologically important group of enzymes, glutathione S-transferases (GSTs). Two groups of organoruthenium(II) compounds were considered: (i) organoruthenium(II) complexes with p-cymene as an arene ligand, and (ii) organoruthenium(II) carbonyl complexes as CO-releasing molecules. Eight organoruthenium complexes were screened for inhibitory activities against ChEs and GSTs of human and animal origins. Some compounds inhibited all of these enzymes at low micromolar concentrations, while others selectively inhibited either ChEs or GSTs. This study demonstrates the importance of the different structural elements of organoruthenium complexes for their inhibitory activities against ChEs and GSTs, and also proposes some interesting compounds for further preclinical testing as ChE or GST inhibitory drugs.

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2

Chow, Mun Juinn, Cynthia Licona, Giorgia Pastorin, Georg Mellitzer, Wee Han Ang, and Christian Gaiddon. "Structural tuning of organoruthenium compounds allows oxidative switch to control ER stress pathways and bypass multidrug resistance." Chemical Science 7, no. 7 (2016): 4117–24. http://dx.doi.org/10.1039/c6sc00268d.

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Varying the arene ligand on organoruthenium compounds induced the differential activation of ER stress pathways, leading to non-apoptotic programmed cell death and bypassing drug resistance mechanisms.

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3

Shakil, Md Salman, Shahida Parveen, Zohaib Rana, Fearghal Walsh, Sanam Movassaghi, Tilo Söhnel, Mayur Azam, et al. "High Antiproliferative Activity of Hydroxythiopyridones over Hydroxypyridones and Their Organoruthenium Complexes." Biomedicines 9, no. 2 (January 27, 2021): 123. http://dx.doi.org/10.3390/biomedicines9020123.

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Hydroxypyr(id)ones are a pharmaceutically important class of compounds that have shown potential in diverse areas of drug discovery. We investigated the 3-hydroxy-4-pyridones 1a–1c and 3-hydroxy-4-thiopyridones 1d–1f as well as their Ru(η6-p-cymene)Cl complexes 2a–2f, and report here the molecular structures of 1b and 1d as determined by X-ray diffraction analysis. Detailed cell biological investigations revealed potent cytotoxic activity, in particular of the 3-hydroxy-4-thiopyridones 1d–1f, while the Ru complexes of both compound types were less potent, despite still showing antiproliferative activity in the low μM range. The compounds did not modulate the cell cycle distribution of cancer cells but were cytostatic in A549 and cytotoxic in NCI-H522 non-small lung cancer cells, among other effects on cancer cells.

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4

Mondal, Ashaparna, and Priyankar Paira. "Synthesis and Biological Evaluations of Organoruthenium Scaffolds: A Comprehensive Update." Current Organic Synthesis 15, no. 2 (April 24, 2018): 179–207. http://dx.doi.org/10.2174/1570179414666170703143049.

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Background: Currently ruthenium complexes are immerging as effective anticancer agents due to their less toxicity, better antiproliferative and antimetastatic activity, better stability in cellular environment and most importantly variable oxidation and co-ordination states of ruthenium allows binding this molecule with a variety of ligands. So in past few years researchers have shifted their interest towards organoruthenium complexes having good fluorescent profile that may be applicable for cancer theranostics. Nowadays, photodynamic therapy has become more acceptable because of its easy and effective approach towards killing cancer cells. Objective: Objective of this review article is to shed light on synthesis, characterization, stability and fluorescence studies of various ruthenium [Ru(II) and Ru(III)] complexes and different bioactivity studies conducted with the synthesized compounds to test their candidacy as potent chemotherapeutic agents. Methods: Various heterocyclic ligands containing N,O and S as heteroatom mainly were prepared and subjected to complexation with ruthenium-p-cymene moiety. In most cases [Ru(η6-p-cymene)(µ-Cl)Cl]2 was used as ruthenium precursor and the reactions were conducted in various alcohol medium such as methanol, ethanol or propanol. The synthesized complexes were characterized by 1H NMR and 13C NMR spectroscopy, GC-MS, ESI-MS, elemental analysis and single crystal X-ray crystallography methods. Fluorescence study and stability study were conducted accordingly using water, PBS buffer or DMSO. Stable compounds were considered for cell viability studies. To study the efficacy of the compounds in ROS generation as photosensitizers, in few cases, singlet oxygen quantum yields in presence of light were calculated. Suitable compounds were selected for in vitro & in vivo antiproliferative, anti-invasive activity studies. Result: Many newly synthesized compounds were found to have less IC50 compared to a standard drug cysplatin. Those compounds were also stable preferably in physiological conditions. Good fluorescence profile and ROS generation ability were observed for few compounds. Conclusion: Numerous ruthenium complexes were developed which can be used as cancer theranostic agents. Few molecules were synthesized as photosensitizers which were supposed to generate reactive singlet oxygen species in targeted cellular environment in presence of a particular type of light and thereby ceasing cancer cell growth.

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5

Nogueira, Luciano J., Maria A. de Resende, Sheila R. Oliveira, Maria Helena de Araújo, Thais F. F. Magalhães, Milena B. de Oliveira, Cleide V. B. Martins, Miriam T. P. Lopes, Ana C. Araújo e Silva, and Claudio L. Donnici. "In vitro susceptibility of Aspergillus spp. to dithiocarbamate organoruthenium compounds." Mycoses 54, no. 5 (June 14, 2010): e323-e329. http://dx.doi.org/10.1111/j.1439-0507.2010.01914.x.

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6

Parveen, Shahida, Kelvin K. H. Tong, Muhammad Khawar Rauf, Mario Kubanik, Muhammad Ashraf Shaheen, Tilo Söhnel, Stephen M. F. Jamieson, Muhammad Hanif, and Christian G. Hartinger. "Coordination Chemistry of Organoruthenium Compounds with Benzoylthiourea Ligands and their Biological Properties." Chemistry – An Asian Journal 14, no. 8 (February 14, 2019): 1262–70. http://dx.doi.org/10.1002/asia.201801798.

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7

Nagy, Eszter Marta, and Dolores Fregona. "Critical comment on: ‘In vitro susceptibility of Aspergillus spp. to dithiocarbamate organoruthenium compounds’." Mycoses 55, no. 1 (August 8, 2011): 101. http://dx.doi.org/10.1111/j.1439-0507.2011.02085.x.

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8

Gomathi, Asaithambi, Paranthaman Vijayan, Periasamy Viswanathamurthi, Shanmugam Suresh, Raju Nandhakumar, and Takeshi Hashimoto. "Organoruthenium(II) compounds with pyridyl benzoxazole/benzthiazole moiety: studies on DNA/protein binding and enzyme mimetic activities." Journal of Coordination Chemistry 70, no. 10 (March 30, 2017): 1645–66. http://dx.doi.org/10.1080/00958972.2017.1309649.

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9

Cuccioloni, Massimiliano, Valentina Cecarini, Laura Bonfili, Riccardo Pettinari, Alessia Tombesi, Noemi Pagliaricci, Laura Petetta, Mauro Angeletti, and Anna Maria Eleuteri. "Enhancing the Amyloid-β Anti-Aggregation Properties of Curcumin via Arene-Ruthenium(II) Derivatization." International Journal of Molecular Sciences 23, no. 15 (August 5, 2022): 8710. http://dx.doi.org/10.3390/ijms23158710.

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Alzheimer’s disease (AD) is a fatal neurodegenerative disorder associated with severe dementia, progressive cognitive decline, and irreversible memory loss. Although its etiopathogenesis is still unclear, the aggregation of amyloid-β (Aβ) peptides into supramolecular structures and their accumulation in the central nervous system play a critical role in the onset and progression of the disease. On such a premise, the inhibition of the early stages of Aβ aggregation is a potential prevention strategy for the treatment of AD. Since several natural occurring compounds, as well as metal-based molecules, showed promising inhibitory activities toward Aβ aggregation, we herein characterized the interaction of an organoruthenium derivative of curcumin with Aβ(1–40) and Aβ(1–42) peptides, and we evaluated its ability to inhibit the oligomerization/fibrillogenesis processes by combining in silico and in vitro methods. In general, besides being less toxic to neuronal cells, the derivative preserved the amyloid binding ability of the parent compound in terms of equilibrium dissociation constants but (most notably) was more effective both in retarding the formation and limiting the size of amyloid aggregates by virtue of a higher hindering effect on the amyloid–amyloid elongation surface. Additionally, the complex protected neuronal cells from amyloid toxicity.

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10

Movassaghi, Sanam, Euphemia Leung, Muhammad Hanif, Betty Y. T. Lee, Hannah U. Holtkamp, Jason K. Y. Tu, Tilo Söhnel, Stephen M. F. Jamieson, and Christian G. Hartinger. "A Bioactive l-Phenylalanine-Derived Arene in Multitargeted Organoruthenium Compounds: Impact on the Antiproliferative Activity and Mode of Action." Inorganic Chemistry 57, no. 14 (June 27, 2018): 8521–29. http://dx.doi.org/10.1021/acs.inorgchem.8b01187.

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11

Hiraki, Katsuma, Naoyuki Ochi, Yoko Sasada, Hideki Hayashida, Yoshio Fuchita, and Shunichiro Yamanaka. "Organoruthenium(II) complexes formed by insertion reactions of some vinyl compounds and conjugated dienes into a hydrido–ruthenium bond." J. Chem. Soc., Dalton Trans., no. 5 (1985): 873–77. http://dx.doi.org/10.1039/dt9850000873.

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12

Wieteck, Marcel, Mie Højer Larsen née Vilhelmsen, Pascal Nösel, Jürgen Schulmeister, Frank Rominger, Matthias Rudolph, Markus Pernpointner, and A. Stephen K. Hashmi. "Conjugated Vinylgold(I)-Vinylideneruthenium(II) Complexes and Related Organoruthenium Compounds: Stable Analogues of Intermediates Proposed in Dual Gold Catalysis." Advanced Synthesis & Catalysis 358, no. 9 (April 27, 2016): 1449–62. http://dx.doi.org/10.1002/adsc.201600255.

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13

Bryndza, Henry E., Peter J. Domaille, Wilson Tam, Lawrence K. Fong, Rocco A. Paciello, and John E. Bercaw. "Comparison of metal-hydrogen, -oxygen, -nitrogen and -carbon bond strengths and evaluation of functional group additivity principles for organoruthenium and organoplatinum compounds." Polyhedron 7, no. 16-17 (January 1988): 1441–52. http://dx.doi.org/10.1016/s0277-5387(00)81773-8.

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14

Pavlović, Marijana, Stefan Nikolić, Nevenka Gligorijević, Biljana Dojčinović, Sandra Aranđelović, Sanja Grgurić-Šipka, and Siniša Radulović. "New organoruthenium compounds with pyrido[2′,3′:5,6]pyrazino[2,3-f][1, 10]phenanthroline: synthesis, characterization, cytotoxicity, and investigation of mechanism of action." JBIC Journal of Biological Inorganic Chemistry 24, no. 2 (February 14, 2019): 297–310. http://dx.doi.org/10.1007/s00775-019-01647-4.

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15

Bryndza, Henry E., Lawrence K. Fong, Rocco A. Paciello, Wilson Tam, and John E. Bercaw. "Relative metal-hydrogen, -oxygen, -nitrogen, and -carbon bond strengths for organoruthenium and organoplatinum compounds; equilibrium studies of Cp*(PMe3)2RuX and (DPPE)MePtX systems." Journal of the American Chemical Society 109, no. 5 (March 1987): 1444–56. http://dx.doi.org/10.1021/ja00239a026.

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16

Marques, F., L. Corte-Real, A. P. Alves de Matos, I. Alho, T. S. Morais, A. I. Tomaz, M. H. Garcia, and M. P. Bicho. "Intracellular distribution of antitumor Ru (II) compounds: The lysosome and the lysosomal enzymes as targets for anticancer metal-based drugs." Microscopy and Microanalysis 19, S4 (August 2013): 9–10. http://dx.doi.org/10.1017/s1431927613000664.

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The therapeutic usefulness of anticancer agents relies on their ability to kill cancer cells while sparing normal cells and tissues. Ruthenium complexes hold great potential as suitable alternative drugs to the current cisplatin in the treatment of cancer. Our approach in this field has been the study of organoruthenium complexes, [RuII(η5-Cp)] family, namely [RuII(η5-Cp)(bipy)(PPh3)]+ (PPh3 = triphenylphosphine; bipy = 2,2’-bipyridine), TM34. This compound was tested for antitumor activity against tumor cells representative of human cancer diseases. A large spectrum of activity was found, largely surpassing cisplatin in efficacy (Fig 1).How a drug distributes and localizes within cells is of fundamental importance as the drug must concentrate in the compartment that houses its target(s). The importance of cellular enzymes on the effects of anticancer drugs for which multiple biological pathways have been proposed led us to address the involvement of the lysosomes and lysosomal enzymes (AcPases) in the mechanism of cell death.The cytotoxicity of TM34 was tested using the MTT assay. TM34 cellular distribution was measured by ICP-MS. The effect of TM34 on the activity of acid phosphatase (AcPase) was evaluated by the hydrolysis of p-nitrophenyl phosphate to p-nitrophenol. AcPase localization was investigated by TEM using the Record and Griffing (1988) cerium-based method.Results showed that the sensitivity of AcPase assay is higher in comparison to cell proliferation assays based on the reduction of tetrazolium salts (MTT) (Fig 2). From TEM images AcPase reaction product appears as dark electron dense deposits in the lysosomes and dictiosomes. After 3h treatment TM34 provokes disruption and vesiculation of the Golgi apparatus, although some reaction product is present in the lysosomes (Fig 2).The lysosome could be considered a possible target for TM34. Morphological evidence was observed for the participation of the Golgi apparatus in the vesiculation induced by the compound.Supported by the Fundação para a Ciência e Tecnologia (FCT): PTDC/QUI-QUI/101187/2008.

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17

Kljun, Jakob, Renata Pavlič, Eva Hafner, Tanja Lipec, Sara Moreno-Da Silva, Primož Tič, Iztok Turel, Tomaž Büdefeld, Jure Stojan, and Tea Lanišnik Rižner. "Ruthenium complexes show potent inhibition of AKR1C1, AKR1C2, and AKR1C3 enzymes and anti-proliferative action against chemoresistant ovarian cancer cell line." Frontiers in Pharmacology 13 (August 11, 2022). http://dx.doi.org/10.3389/fphar.2022.920379.

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In this study, we present the synthesis, kinetic studies of inhibitory activity toward aldo-keto reductase 1C (AKR1C) enzymes, and anticancer potential toward chemoresistant ovarian cancer of 10 organoruthenium compounds bearing diketonate (1–6) and hydroxyquinolinate (7–10) chelating ligands with the general formula [(η6-p-cymene)Ru(chel)(X)]n+ where chel represents the chelating ligand and X the chlorido or pta ligand. Our studies show that these compounds are potent inhibitors of the AKR enzymes with an uncommon inhibitory mechanism, where two inhibitor molecules bind to the enzyme in a first fast and reversible step and a second slower and irreversible step. The binding potency of each step is dependent on the chemical structure of the monodentate ligands in the metalloinhibitors with the chlorido complexes generally acting as reversible inhibitors and pta complexes as irreversible inhibitors. Our study also shows that compounds 1–9 have a moderate yet better anti-proliferative and anti-migration action on the chemoresistant ovarian cancer cell line COV362 compared to carboplatin and similar effects to cisplatin.

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18

Riisom, Mie, Liam Eade, William D. J. Tremlett, and Christian G. Hartinger. "The aqueous stability and interactions of organoruthenium compounds with serum proteins, cell culture medium and human serum." Metallomics, June 25, 2022. http://dx.doi.org/10.1093/mtomcs/mfac043.

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Abstract Metal complexes bind to a wide variety of biomolecules and the control of the reactivity is essential when designing anticancer metallodrugs with a specific mode of action in mind. In this study, we used the highly cytotoxic compound [RuII(cym)(8-HQ)Cl] (cym = η6-p-cymene, 8-HQ = 8-hydroxyquinoline), the more inert derivative [RuII(cym)(8-HQ)(PTA)](SO3CF3) (PTA = 1,3,5-triaza-7-phosphaadamantane), and [RuII(cym)(PCA)Cl]Cl (PCA = pyridinecarbothioamide) as a derivative with a different coordination environment about the Ru center and investigated their stability, interactions with proteins and behavior in medium (αMEM) and human serum by capillary zone electrophoresis (CZE). The developed method was found to be robust and provides a quick and low-cost technique to monitor the interactions of such complexes with biomolecules. Each complex was found to behave very differently, emphasizing the importance of the choice of ligands and demonstrating the applicability of the developed method. Additionally, the human serum albumin binding site preference of [RuII(cym)(8-HQ)Cl] was investigated through displacement studies, revealing that the compound was able to bind to both sites I and site II, and the type of adducts formed with transferrin was determined by mass spectrometry.

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19

HIRAKI, K., N. OCHI, Y. SASADA, H. HAYASHIDA, Y. FUCHITA, and S. YAMANAKA. "ChemInform Abstract: ORGANORUTHENIUM(II) COMPLEXES FORMED BY INSERTION REACTIONS OF SOME VINYL COMPOUNDS AND CONJUGATED DIENES INTO A HYDRIDO-RUTHENIUM BOND." Chemischer Informationsdienst 16, no. 37 (September 17, 1985). http://dx.doi.org/10.1002/chin.198537275.

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20

BRYNDZA, H. E., P. J. DOMAILLE, W. TAM, L. K. FONG, R. A. PACIELLO, and J. E. BERCAW. "ChemInform Abstract: Comparison of Metal-Hydrogen, -Oxygen, -Nitrogen and -Carbon Bond Strengths and Evaluation of Functional Group Additivity Principles for Organoruthenium and Organoplatinum Compounds." ChemInform 20, no. 4 (January 24, 1989). http://dx.doi.org/10.1002/chin.198904098.

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21

BRYNDZA, H. E., L. K. FONG, R. A. PACIELLO, W. TAM, and J. E. BERCAW. "ChemInform Abstract: Relative Metal-Hydrogen, -Oxygen, -Nitrogen, and -Carbon Bond Strengths for Organoruthenium and Organoplatinum Compounds; Equilibrium Studies of Cp*(PMe3)2RuX and (DPPE)MePtX Systems." ChemInform 18, no. 28 (July 14, 1987). http://dx.doi.org/10.1002/chin.198728091.

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22

Meier-Menches, Samuel M., Benjamin Neuditschko, Lukas Janker, Marlene C. Gerner, Klaus G. Schmetterer, Albrecht Reichle, and Christopher Gerner. "A Proteomic Platform Enables to Test for AML Normalization In Vitro." Frontiers in Chemistry 10 (February 1, 2022). http://dx.doi.org/10.3389/fchem.2022.826346.

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Acute promyelocytic leukaemia (APL) can be cured by the co-administration of arsenic trioxide (ATO) and all-trans retinoic acid (ATRA). These small molecules relieve the differentiation blockade of the transformed promyelocytes and trigger their maturation into functional neutrophils, which are physiologically primed for apoptosis. This normalization therapy represents a compelling alternative to cytotoxic anticancer chemotherapy, but lacks an in vitro model system for testing the efficiency of novel combination treatments consisting of inducers of differentiation and metallopharmaceuticals. Here, using proteome profiling we present an experimental framework that enables characterising the differentiation– and metal-specific effects of the combination treatment in a panel of acute myeloid leukaemia (AML) cell lines (HL-60 and U937), including APL (NB4). Differentiation had a substantial impact on the proteome on the order of 10% of the identified proteins and featured classical markers and transcription factors of myeloid differentiation. Additionally, ATO provoked specific cytoprotective effects in the AML cell lines HL-60 and U937. In HL-60, these effects included an integrated stress response (ISR) in conjunction with redox defence, while proteasomal responses and a metabolic rewiring were observed in U937 cells. In contrast, the APL cell line NB4 did not display such adaptions indicating a lack of plasticity to cope with the metal-induced stress, which may explain the clinical success of this combination treatment. Based on the induction of these cytoprotective effects, we proposed a novel metal-based compound to be used for the combination treatment instead of ATO. The organoruthenium drug candidate plecstatin-1 was previously shown to induce reactive oxygen species and an ISR. Indeed, the plecstatin-1 combination was found to affect similar pathways compared to the ATO combination in HL-60 cells and did not lead to cytoprotective response signatures in NB4. Moreover, the monocytic cell line U937 showed a low plasticity to cope with the plecstatin-1 combination, which suggests that this combination might achieve therapeutic benefit beyond APL. We propose that the cytoprotective plasticity of cancer cells might serve as a general proxy to discover novel combination treatments in vitro.

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