Article
Biochemistry & Molecular Biology
Prinessa Chellan, Vicky M. Avery, Sandra Duffy, Kirkwood M. Land, Christina C. Tam, Jong H. Kim, Luisa W. Cheng, Isolda Romero-Canelon, Peter J. Sadler
Summary: The reaction of dihydroartemisinin (DHA) with 4-methyl-4'-carboxy-2,2'-bipyridine yielded a novel ester derivative L1. Subsequent synthesis of organometallic half-sandwich complexes with pentamethylcyclopentadienyl, tetramethylphenylcyclopentadienyl, or tetramethylbiphenylcyclopentadienyl ligands exhibited potent antiplasmodial and anticancer activities, with iridium complex 3 emerging as a promising candidate for further studies.
JOURNAL OF INORGANIC BIOCHEMISTRY
(2021)
Review
Biochemistry & Molecular Biology
Artur V. da Silva, Simoni M. P. Meneghetti, Mario R. Meneghetti
Summary: Studies have shown that the combination of organometallic compounds with psychoactive benzodiazepine drugs has potential pharmacological activity, which warrants further research for their applications in new drug design and cancer treatment alternatives.
Review
Chemistry, Inorganic & Nuclear
Tasha R. Steel, Fearghal Walsh, Anna Wieczorek-Blauz, Muhammad Hanif, Christian G. Hartinger
Summary: Metallodrugs play a central role in the treatment and diagnosis of diseases, and the choice of ligands coordinated to the metal center is crucial for the biological activity of metal-based anticancer agents. Introducing bioactive ligands may lead to synergistic activity between the metal center and the ligand system, and Ru half-sandwich compounds are a promising class of anticancer agents that have been extensively studied.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Inorganic & Nuclear
Ashaparna Mondal, Utsav Sen, Nilmadhab Roy, Venkatesan Muthukumar, Suban Kumar Sahoo, Bipasha Bose, Priyankar Paira
Summary: A library of half sandwich Ru(ii)-p-cymene-N<^>N complexes was synthesized using a convenient one pot protocol, showing significant potency and selectivity against cancer cell lines. The Ru(ii)-arene complexes exhibited excellent DNA binding efficacy and fluorescence properties, making them potential candidates for cancer theranostic treatment.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Sonia Infante-Tadeo, Vanessa Rodriguez-Fanjul, Abraha Habtemariam, Ana M. Pizarro
Summary: This study introduces a new family of osmium arene complexes and investigates their mechanism of action inside cells. The complexes are shown to catalyze the conversion of organic substrates, demonstrating potential anti-cancer drug activity.
Article
Chemistry, Inorganic & Nuclear
Wen-Rui Lv, Rong-Jian Li, Zhen-Jiang Liu, Yan Jin, Zi-Jian Yao
Summary: A series of N,O-coordinate iridium(III) complexes with Schiff base ligands were synthesized for catalytic hydrogenation of nitro and carbonyl substrates, showing efficient catalytic activity and high yields. The molecular structures of the complexes were well characterized and the highest TON values were achieved for the hydrogenation reactions of carbonyl and nitro substrates.
INORGANIC CHEMISTRY
(2021)
Review
Chemistry, Inorganic & Nuclear
William D. J. Tremlett, David M. Goodman, Tasha R. Steel, Saawan Kumar, Anna Wieczorek-Blauz, Fearghal P. Walsh, Matthew P. Sullivan, Muhammad Hanif, Christian G. Hartinger
Summary: The article discusses strategies to enhance the activity and reduce the side effects of metal-based drugs, as well as how these strategies can be applied to half-sandwich organoruthenium anticancer compounds.
COORDINATION CHEMISTRY REVIEWS
(2021)
Article
Chemistry, Medicinal
Khaled Habas, Joan J. Soldevila-Barreda, Maria Azmanova, Laia Rafols, Anais Pitto-Barry, Diana Anderson, Nicolas P. E. Barry
Summary: The study found that the two 16-electron organoruthenium complexes have no significant effect on the cell viability of human lymphocytes from healthy individuals, but induce an increase in DNA damage, presumably through oxidative stress production.
Article
Chemistry, Multidisciplinary
Daniel P. Harrison, Varshini J. Kumar, Johanna N. Noppers, Josef B. G. Gluyas, Alexandre N. Sobolev, Stephen A. Moggach, Paul J. Low
Summary: This article describes a convenient modification to established synthetic routes for the preparation of complexes, as well as the differences in oxidation processes between iron and ruthenium analogues. The study also reveals limited differences in the gross electronic structures of Cp vs. Cp* derivatives in both iron and ruthenium series through redox properties and spectroelectrochemical investigations.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Wei-Guo Jia, Xue-Ting Zhi, Xiao-Dong Li, Jun-Peng Zhou, Rui Zhong, Haibo Yu, Richmond Lee
Summary: A mild and environmentally friendly method was reported for synthesizing half-sandwich ruthenium complexes through the Wittig reaction using phosphorus ylide mechanochemically. The synthesized complexes exhibited high catalytic activity in the transfer hydrogenation of ketones without the need for harsh reaction conditions and organic solvents. Density functional theory was used to propose a mechanism for the transfer hydrogenation process, highlighting the importance of the labile p-cymene ligand in modulating catalyst reactivity.
INORGANIC CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Roman I. Nekrasov, Tat'yana A. Peganova, Ivan V. Fedyanin, Evgenii I. Gutsul, Oleg A. Filippov, Natalia V. Belkova, Alexander M. Kalsin
Summary: A series of pentamethylcyclopentadienyl rhodium complexes were synthesized and characterized, and some complexes were found to have low stability and high nucleophilicity and reactivity.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Carsten Mueller, Justin Schu, Bernd Morgenstern, Michael Zimmer, Marc Schmidtmann, Andre Schaefer
Summary: Phosphanyl-substituted tin(ii) half sandwich complexes, which form head-to-tail dimers due to the Lewis acidic tin center and Lewis basic phosphorous atom, were reported. Their properties and reactivities were investigated both experimentally and theoretically. Furthermore, related transition metal complexes of these species are presented.
Article
Pharmacology & Pharmacy
Janos P. Meszaros, Wolfgang Kandioller, Gabriella Spengler, Alexander Prado-Roller, Bernhard K. Keppler, Eva A. Enyedy
Summary: This study introduces half-sandwich Rh complexes that can be activated in the acidic, extracellular pH of tumor tissue, reducing the side effects and improving the efficacy of chemotherapy.
Article
Chemistry, Physical
Lisa Wirtz, Kinza Yasmin Ghulam, Bernd Morgenstern, Andre Schaefer
Summary: The synthesis, characterization, and catalytic application of a series of constrained geometry ansa-half-sandwich complexes of magnesium are reported in this study. These versatile s-block catalysts were applied in various dehydrocoupling and hydroelementation reactions, demonstrating a broad applicability, with particularly remarkable performance in dehydrocoupling reactions.
Review
Biochemistry & Molecular Biology
Agata Gurba, Przemyslaw Taciak, Mariusz Sacharczuk, Izabela Mlynarczuk-Bialy, Magdalena Bujalska-Zadrozny, Jakub Fichna
Summary: Cancer is a major cause of illness and death worldwide. Colorectal cancer is the third most common cancer in men and the second most common in women. Standard antitumor therapies, such as cisplatin, have limitations due to their lack of specificity for tumor cells, drug resistance development, and severe side effects. Therefore, new methods and strategies for treating colorectal cancer are urgently needed. Current research focuses on novel platinum and other metal-based drugs, such as gold, silver, iridium, or ruthenium. Au(III) compounds are considered promising candidates for colorectal cancer treatment due to their structural similarity to Pt(II). However, their stability under physiological conditions needs improvement by combining with various ligands. This review summarizes the progress in developing stable Au(III) complexes with potential cytotoxic activity against cancer cells. Additionally, it highlights that the anticancer effects of Au derivatives are mediated by protein structures, such as thioredoxin reductase, rather than nucleic acids. The current state of in vivo studies is also discussed.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Valentin Fuchs, Klaudia Cseh, Michaela Hejl, Petra Vician, Benjamin Neuditschko, Samuel M. Meier-Menches, Lukas Janker, Andrea Bileck, Natalie Gajic, Julia Kronberger, Martin Schaier, Sophie Neumayer, Gunda Koellensperger, Christopher Gerner, Walter Berger, Michael A. Jakupec, Michael S. Malarek, Bernhard K. Keppler
Summary: A series of highly lipophilic Cp-substituted molybdenocenes with different bioactive chelating ligands were synthesized and characterized. They showed significantly increased cytotoxic potency compared to non-Cp-substituted counterparts. In vivo experiments demonstrated tumor growth inhibition for the most active complex containing the thioflavone ligand, along with significant regulation of tubulin-associated and mitochondrial inner membrane proteins.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Analytical
Olga V. Kuznetsova, Bernhard K. Keppler, Andrei R. Timerbaev
Summary: This study developed a unified protocol for the preparation of seawater samples for ICP-MS analysis of nanoparticles, which involved acidification and ultrafiltration to stabilize the particles and facilitate metal analysis. High-resolution ICP-MS method was used to achieve very low limits of detection.
Article
Pharmacology & Pharmacy
Janos P. Meszaros, Wolfgang Kandioller, Gabriella Spengler, Alexander Prado-Roller, Bernhard K. Keppler, Eva A. Enyedy
Summary: This study introduces half-sandwich Rh complexes that can be activated in the acidic, extracellular pH of tumor tissue, reducing the side effects and improving the efficacy of chemotherapy.
Article
Chemistry, Inorganic & Nuclear
Christopher Wittmann, Tim Gruene, Alexander Prado-Roller, Sandra Arandelovic, Johannes Reynisson, Vladimir B. B. Arion
Summary: A series of latonduine derivatives were synthesized and characterized using spectroscopic and mass spectrometry techniques. The molecular structures of some compounds were confirmed by X-ray diffraction or electron diffraction. The antiproliferative activity of these compounds in different cancer cells and normal cells was evaluated by MTT assays.
Article
Chemistry, Multidisciplinary
Philipp Spiess, Ana Sirvent, Irmgard Tiefenbrunner, Jules Sargueil, Anthony J. Fernandes, Ana Arroyo-Bondia, Ricardo Meyrelles, David Just, Alexander Prado-Roller, Saad Shaaban, Daniel Kaiser, Nuno Maulide
Summary: p-Toluenesulfonyl (Tosyl) and nitrobenzenesulfonyl (Nosyl) are widely used sulfonyl protecting groups for amines in organic synthesis. However, p-toluenesulfonamides are difficult to remove in multistep synthesis, while nitrobenzenesulfonamides are not stable under various reaction conditions. In this study, we introduce a new sulfonamide protecting group called Nms, which overcomes these limitations and shows superiority in terms of stability and cleavability.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Pharmacology & Pharmacy
Yvonne Lerchbammer-Kreith, Michaela Hejl, Petra Vician, Michael A. Jakupec, Walter Berger, Mathea S. Galanski, Bernhard K. Keppler
Summary: Based on their drug delivery properties and activity against tumors, PAMAM dendrimers were combined with platinum(IV) complexes to improve anticancer treatment. The conjugates showed faster reduction behavior compared to the platinum(IV) complexes and exhibited significantly increased cytotoxic activity in human cell lines. In vivo experiments demonstrated tumor growth inhibition and prolonged animal survival.
Article
Pharmacology & Pharmacy
Theresa Mendrina, Isabella Poetsch, Hemma Schueffl, Dina Baier, Christine Pirker, Alexander Ries, Bernhard K. K. Keppler, Christian R. R. Kowol, Dan Gibson, Michael Grusch, Walter Berger, Petra Heffeter
Summary: Platinum compounds are effective treatment options for various cancer types, but their use is limited by side effects and drug resistance. A new multi-targeted platinum(IV) prodrug, cisPt(PhB)(2), has shown promising anticancer activity and the ability to overcome drug resistance mechanisms. The drug's mode of action is influenced by cellular fatty acid metabolism and mitochondrial activity. Specifically, it is more effective against cisplatin-resistant cancer cells with Warburg-like properties. This orally applicable prodrug has the potential to improve cancer treatment outcomes.
Article
Chemistry, Multidisciplinary
Alexander Kastner, Hemma Schueffl, Patrick A. Yassemipour, Bernhard K. Keppler, Petra Heffeter, Christian R. Kowol
Summary: Platinum(IV) prodrugs are promising alternatives to platinum(II) anticancer therapeutics. This study investigated the reactivity and synthetic usability of a platinum(IV) complex with hydrolyzable equatorial ligands, and successfully synthesized stable platinum(IV) complexes suitable for long-circulating tumor-targeting strategies. Additionally, platinum(IV) complexes with equatorial maleimides were synthesized, showing prolonged plasma half-life and improved anticancer activity compared to oxaliplatin.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Correction
Oncology
Mathea Sophia Galanski, Bernhard K. K. Keppler
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY
(2023)
Article
Materials Science, Paper & Wood
Yuko Yoneda, Toshinari Kawada, Markus Bacher, Alexander Prado-Roller, Hubert Hettegger, Antje Potthast, Alfred D. French, Thomas Rosenau
Summary: Cellulose model compounds are widely used in cellulose research to study the polymer's properties. By synthesizing methyl 4-O-methyl beta-D-glucopyranoside derivatives with different substitution patterns, the solid-state structures of these compounds were determined using X-ray diffraction. Solid-state C-13 NMR measurements confirmed the influence of packing arrangement on the chemical shifts of the substituted carbons.
Article
Pharmacology & Pharmacy
Klaudia Cseh, Iker Berasaluce, Valentin Fuchs, Alexandra Banc, Andreas Schweikert, Alexander Prado-Roller, Michaela Hejl, Debora Wernitznig, Gunda Koellensperger, Michael A. Jakupec, Wolfgang Kandioller, Michael S. Malarek, Bernhard K. Keppler
Summary: This paper describes the synthesis, characterization and biological activity of tungstenocenes with different biologically active chelates, such as (O,O-), (S,O-) and (N,O-). The complexes were analyzed using various techniques, including NMR, mass spectrometry, spectroscopy and X-ray diffraction. Their stability, electrochemical behavior, cytotoxicity and mode of action were investigated. The results showed that complexes containing (S,O-) chelates exhibited higher activity than those with (O,O-) and (N,O-) chelates. Notably, two complexes with a W-S or W-O bond showed different distribution patterns and strong inhibitory effects in tumor spheroid models.
Article
Biochemistry & Molecular Biology
Predrag Kalaba, Katharina Pacher, Philip John Neill, Vladimir Dragacevic, Martin Zehl, Judith Wackerlig, Michael Kirchhofer, Simone B. Sartori, Hubert Gstach, Shima Kouhnavardi, Anna Fabisikova, Matthias Pillwein, Francisco Monje-Quiroga, Karl Ebner, Alexander Prado-Roller, Nicolas Singewald, Ernst Urban, Thierry Langer, Christian Pifl, Jana Lubec, Johann Jakob Leban, Gert Lubec
Summary: The high structural similarity among dopamine, norepinephrine, and serotonin transporters, especially in transmembrane regions, presents a challenge for specifically targeting individual transporters. Ligand design is limited by chemists' tendency to modify lead compounds in a way that reduces the number of chiral centers, thus limiting the chemical space of synthetic ligands. However, increasing molecular complexity by introducing additional chiral centers has been shown to lead to more selective and potent dopamine reuptake inhibitors. The establishment of a compound library with defined absolute configurations lays the foundation for computational chemists to optimize and design specific monoamine transporter reuptake inhibitors.
Article
Chemistry, Medicinal
Yvonne Lerchbammer-Kreith, Michaela Hejl, Nadine S. Sommerfeld, Xian Weng-Jiang, Uchechukwu Odunze, Ryan D. Mellor, David G. Workman, Michael A. Jakupec, Andreas G. Schaetzlein, Ijeoma F. Uchegbu, Mathea S. Galanski, Bernhard K. Keppler
Summary: In this study, cytotoxic platinum(IV) conjugates of cisplatin, carboplatin and oxaliplatin were synthesized and coupled to quaternary ammonium palmitoyl glycol chitosan (GCPQ) polymers. The conjugates showed significantly increased cytotoxic activity compared to their respective platinum(IV) complexes and outperformed the platinum(II) counterparts. Biodistribution experiment revealed an increased accumulation of an oxaliplatin-based GCPQ conjugate in lung tissue. These findings suggest promising opportunities for further studies on tumor activity, particularly in lung tissue.
Article
Biochemistry & Molecular Biology
Martin Schaier, Enrico Falcone, Tomas Prstek, Bertrand Vileno, Sonja Hager, Bernhard K. Keppler, Petra Heffeter, Gunda Koellensperger, Peter Faller, Christian R. Kowol
Summary: Thiosemicarbazones (TSCs) are biologically active compounds that have potential anticancer activity by chelating iron and targeting ribonucleotide reductase. Recent findings suggest that the stability and reduction properties of copper complexes are essential for the action of specific TSC derivatives. This study investigated the interaction between TSCs and human serum albumin (HSA) as a potential source of copper, and found that TSCs specifically chelate copper from HSA and form ternary HSA conjugates.