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162 results on '"Hejl, Michaela"'

1. New Iron(III)-Containing Composite of Salinomycinic Acid with Antitumor Activity—Synthesis and Characterization.

Author

Ivanova, Juliana, Kukeva, Rositsa, Stoyanova, Radostina, Zhivkova, Tanya, Abudalleh, Abedulkadir, Dyakova, Lora, Alexandrova, Radostina, Pashkunova-Martic, Irena, Theiner, Johannes, Dorkov, Peter, Hejl, Michaela, Jakupec, Michael A., Keppler, Bernhard, and Grabchev, Ivo

Subjects
ELECTRON paramagnetic resonance spectroscopy, ELECTROSPRAY ionization mass spectrometry, ANTINEOPLASTIC agents, DIFFERENTIAL thermal analysis, X-ray powder diffraction, NON-small-cell lung carcinoma, ELEMENTAL analysis, IRON chlorides
Abstract

In this study we demonstrated for the first time synthetic procedures for composites of salinomycin (SalH) and two-line ferrihydrite. The products were characterized by various methods such as elemental analysis, attenuated total reflectance–Fourier-transform spectroscopy (ATR-FTIR), electron paramagnetic resonance spectroscopy (EPR), powder X-ray diffraction analysis (XRD), electrospray-ionization mass spectrometry (ESI-MS), thermogravimetric analysis with differential thermal analysis (DTA) and mass spectrometry (TG-DTA/MS). The EPR spectra of the isolated compounds consisted of signals associated with both isolated Fe3+ ions and magnetically coupled Fe3+ ions. Powder XRD analyses of the isolated products showed two intense and broad peaks at 9° and 15° 2Θ, corresponding to salinomycinic acid. Broad peaks with very low intensity around 35°, assigned to two-line ferrihydrite, were also registered. Based on the experimental results, we concluded that salinomycin sodium reacted with Fe(III) chloride to form composites consisting of two-line ferrihydrite and salinomycinic acid. One of the composites exerted pronounced antitumor activity in the sub-micromolar concentration range against human cervical cancer (HeLa), non-small-cell lung cancer (A549), colon cancer (SW480), and ovarian teratocarcinoma (CH1/PA1) cells. [ABSTRACT FROM AUTHOR]

Published
2024
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3. Investigating the anticancer potential of 4-phenylthiazole derived Ru(ii) and Os(ii) metalacycles

Author

Getreuer, Paul, primary, Marretta, Laura, additional, Toyoglu, Emine, additional, Dömötör, Orsolya, additional, Hejl, Michaela, additional, Prado-Roller, Alexander, additional, Cseh, Klaudia, additional, Legin, Anton A., additional, Jakupec, Michael A., additional, Barone, Giampaolo, additional, Terenzi, Alessio, additional, Keppler, Bernhard K., additional, and Kandioller, Wolfgang, additional

Published
2024
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6. Quaternary Ammonium Palmitoyl Glycol Chitosan (GCPQ) Loaded with Platinum-Based Anticancer Agents—A Novel Polymer Formulation for Anticancer Therapy

Author

Lerchbammer-Kreith, Yvonne, primary, Hejl, Michaela, additional, Sommerfeld, Nadine S., additional, Weng-Jiang, Xian, additional, Odunze, Uchechukwu, additional, Mellor, Ryan D., additional, Workman, David G., additional, Jakupec, Michael A., additional, Schätzlein, Andreas G., additional, Uchegbu, Ijeoma F., additional, Galanski, Mathea S., additional, and Keppler, Bernhard K., additional

Published
2023
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7. Anticancer Tungstenocenes with a Diverse Set of (O,O–), (O,S–) and (O,N–) Chelates—A Detailed Biological Study Using an Improved Evaluation via 3D Spheroid Models

Author

Cseh, Klaudia, primary, Berasaluce, Iker, additional, Fuchs, Valentin, additional, Banc, Alexandra, additional, Schweikert, Andreas, additional, Prado-Roller, Alexander, additional, Hejl, Michaela, additional, Wernitznig, Debora, additional, Koellensperger, Gunda, additional, Jakupec, Michael A., additional, Kandioller, Wolfgang, additional, Malarek, Michael S., additional, and Keppler, Bernhard K., additional

Published
2023
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11. Not the usual suspect – an unexpected organometallic product during the synthesis of cytotoxic platinum(II) complexes.

Author

Maier, Thomas, Wutschitz, Judith, Gajic, Natalie, Hejl, Michaela, Cseh, Klaudia, Mai, Sebastian, Jakupec, Michael A., Galanski, Mathea S., and Keppler, Bernhard K.

Subjects
CANCER cell growth, PLATINUM, MALEIC acid, DNA structure, CYTOTOXINS, DIAMINES, NUCLEAR magnetic resonance spectroscopy
Abstract

The reaction of (1R,2R)-(cyclohexane-1,2-diamine)dichloridoplatinum(II) with maleic acid unexpectedly resulted in the formation of an organometallic platinum(II) complex featuring a C,O-coordinating ligand. Additionally, a small series of close derivatives with increasing lipophilicity was synthesized. All complexes were fully characterized by multinuclear one- and two-dimensional (1H, 13C, 15N, and 195Pt) NMR spectroscopy, high resolution mass spectrometry, and in one case by X-ray diffraction. The lipophilicity and the impact on the DNA secondary structure as well as the cytotoxic properties in three human cancer cell lines (A549, SW480, and CH1/PA-1) were investigated. Unexpectedly, no clear-cut trend in cytotoxicity was observed with increasing lipophilicity. Also unexpectedly, the complexes showed only a low potential to inhibit cancer cell growth and no sign of interaction with DNA, in sharp contrast to the parent drug oxaliplatin, which seems to be caused by the low reactivity of the investigated compounds. [ABSTRACT FROM AUTHOR]

Published
2023
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12. Anticancer Tungstenocenes with a Diverse Set of (O,O –), (O , S –) and (O , N –) Chelates—A Detailed Biological Study Using an Improved Evaluation via 3D Spheroid Models.

Author

Cseh, Klaudia, Berasaluce, Iker, Fuchs, Valentin, Banc, Alexandra, Schweikert, Andreas, Prado-Roller, Alexander, Hejl, Michaela, Wernitznig, Debora, Koellensperger, Gunda, Jakupec, Michael A., Kandioller, Wolfgang, Malarek, Michael S., and Keppler, Bernhard K.

Subjects
CHELATES, CANCER cells, X-ray spectroscopy, CYCLIC voltammetry, CELL lines
Abstract

The synthesis, characterization and biological activity of tungstenocenes with varying biologically active (O,O–), (S,O–) and (N,O–) chelates are described. Complexes were characterized by 1H and 13C NMR, elemental analysis, ESI-mass spectrometry, FT-IR spectroscopy and X-ray diffraction analysis. The aqueous stability was studied by UV/Vis spectroscopy and the WIV to WV process by cyclic voltammetry. The cytotoxicity was determined by the MTT assay in A549, CH1/PA-1 and SW480 cancer cells as well as in IMR-90 human fibroblasts. Extensive biological evaluation was performed in three other human cancer cell lines (HCT116, HT29 and MCF-7) in monolayer and multicellular tumor spheroid cultures to better understand the mode of action. Lead compounds showed promising in vitro anticancer activity in all cancer cell lines. Further studies yielded important insights into apoptosis induction, ROS generation, different patterns in metal distribution (detected by LA-ICP-TOF-MS), changes in KI67 (proliferation marker) expression and DNA interactions. The results based on qualitative and quantitative research designs show that complexes containing (S,O–) chelates are more active than their (O,O–) and (N,O–) counterparts. The most striking results in spheroid models are the high antiproliferative capacity and the different distribution pattern of two complexes differing only in a W–S or W–O bond. [ABSTRACT FROM AUTHOR]

Published
2023
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13. Highly Cytotoxic Molybdenocenes with Strong Metabolic Effects Inhibit Tumour Growth in Mice

Author

Fuchs, Valentin, primary, Cseh, Klaudia, additional, Hejl, Michaela, additional, Vician, Petra, additional, Neuditschko, Benjamin, additional, Meier‐Menches, Samuel M., additional, Janker, Lukas, additional, Bileck, Andrea, additional, Gajic, Natalie, additional, Kronberger, Julia, additional, Schaier, Martin, additional, Neumayer, Sophie, additional, Köllensperger, Gunda, additional, Gerner, Christopher, additional, Berger, Walter, additional, Jakupec, Michael A., additional, Malarek, Michael S., additional, and Keppler, Bernhard K., additional

Published
2022
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14. Arene Variation of Highly Cytotoxic Tridentate Naphthoquinone-Based Ruthenium(II) Complexes and In-Depth In Vitro Studies

Author

Cseh, Klaudia, primary, Geisler, Heiko, additional, Stanojkovska, Kristina, additional, Westermayr, Julia, additional, Brunmayr, Philipp, additional, Wenisch, Dominik, additional, Gajic, Natalie, additional, Hejl, Michaela, additional, Schaier, Martin, additional, Koellensperger, Gunda, additional, Jakupec, Michael A., additional, Marquetand, Philipp, additional, and Kandioller, Wolfgang, additional

Published
2022
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15. Novel Salinomycin-Based Paramagnetic Complexes—First Evaluation of Their Potential Theranostic Properties

Author

Pashkunova-Martic, Irena, primary, Kukeva, Rositsa, additional, Stoyanova, Radostina, additional, Pantcheva, Ivayla, additional, Dorkov, Peter, additional, Friske, Joachim, additional, Hejl, Michaela, additional, Jakupec, Michael, additional, Hohagen, Mariam, additional, Legin, Anton, additional, Lubitz, Werner, additional, Keppler, Bernhard K., additional, Helbich, Thomas H., additional, and Ivanova, Juliana, additional

Published
2022
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16. Highly Cytotoxic Molybdenocenes with Strong Metabolic Effects Inhibit Tumour Growth in Mice.

Author

Fuchs, Valentin, Cseh, Klaudia, Hejl, Michaela, Vician, Petra, Neuditschko, Benjamin, Meier‐Menches, Samuel M., Janker, Lukas, Bileck, Andrea, Gajic, Natalie, Kronberger, Julia, Schaier, Martin, Neumayer, Sophie, Köllensperger, Gunda, Gerner, Christopher, Berger, Walter, Jakupec, Michael A., Malarek, Michael S., and Keppler, Bernhard K.

Subjects
MITOCHONDRIAL membranes, MASS spectrometry, MEMBRANE proteins, TUMORS, MICE, PROTEOMICS
Abstract

A series of six highly lipophilic Cp‐substituted molybdenocenes bearing different bioactive chelating ligands was synthesized and characterized by NMR spectroscopy, mass spectrometry and X‐ray crystallography. In vitro experiments showed a greatly increased cytotoxic potency when compared to the non‐Cp‐substituted counterparts. In vivo experiments performed with the dichlorido precursor, (Ph2C−Cp)2MoCl2 and the in vitro most active complex, containing the thioflavone ligand, showed an inhibition of tumour growth. Proteomic studies on the same two compounds demonstrated a significant regulation of tubulin‐associated and mitochondrial inner membrane proteins for both compounds and a strong metabolic effect of the thioflavone containing complex. [ABSTRACT FROM AUTHOR]

Published
2023
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18. The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects

Author

Berasaluce, Iker, Cseh, Klaudia, Roller, Alexander, Hejl, Michaela, Heffeter, Petra, Berger, Walter, Jakupec, Michael A., Kandioller, Wolfgang, Malarek, Michael S., and Keppler, Bernhard K.

Subjects
Cell Survival, Nitrogen, tris(pyrazolyl)borate, Molecular Conformation, Antineoplastic Agents, anticancer, Crystallography, X-Ray, Ligands, Mice, Drug Stability, Coordination Complexes, biological tests, Cell Line, Tumor, Neoplasms, Borates, Animals, Humans, Chelating Agents, Molybdenum, Mice, Inbred BALB C, Full Paper, Full Papers, in vivo experiments, Oxygen, Pyrazoles, Drug Screening Assays, Antitumor, Sulfur
Abstract

The synthesis, characterization and biological activity of molybdenum(IV) complexes containing Trofimenko's scorpionato ligand, hydrotris(3‐isopropylpyrazolyl)borate (TpiPr), in addition to varying biologically active as well as other conventional ligands is described. Ligands employed include (O,O‐) (S,O‐) (N,N‐) donors that have been successfully coordinated to the molybdenum center by means of oxygen‐atom transfer (OAT) reactions from the known MoVI starting material, TpiPrMoO2Cl. The synthesized complexes were characterized by standard analytical methods and where possible by X‐ray diffraction analysis. The aqueous stability of the compounds was studied by means of UV/Vis spectroscopy and the impact of the attached ligand scaffolds on the oxidation potentials (MoIV to MoV) was studied by cyclic voltammetry. Utilizing polyvinylpyrrolidone (PVP) as a solubilizing agent, adequate aqueous solubility for biological tests was obtained. Anticancer activity tests and preliminary mode of action studies have been performed in vitro and in vivo., Giving a sting to cancer: The synthesis, characterization and biological activity of molybdenum(IV) complexes containing Trofimenko's scorpionato ligand, hydrotris(3‐isopropylpyrazolyl)borate, in addition to varying biologically active as well as other conventional ligands is described. The anticancer activity and preliminary mode of action studies have been performed in vitro and in vivo.

Published
2019

20. Tridentate 3-Substituted Naphthoquinone Ruthenium Arene Complexes: Synthesis, Characterization, Aqueous Behavior, and Theoretical and Biological Studies

Author

Geisler, Heiko, primary, Westermayr, Julia, additional, Cseh, Klaudia, additional, Wenisch, Dominik, additional, Fuchs, Valentin, additional, Harringer, Sophia, additional, Plutzar, Sarah, additional, Gajic, Natalie, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Marquetand, Philipp, additional, and Kandioller, Wolfgang, additional

Published
2021
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23. Synthesis, Modification, and Biological Evaluation of a Library of Novel Water‐Soluble Thiopyridone‐Based Organometallic Complexes and Their Unexpected (Biological) Behavior

Author

Harringer, Sophia, primary, Happl, Barbara, additional, Ozenil, Marius, additional, Kast, Caroline, additional, Hejl, Michaela, additional, Wernitznig, Debora, additional, Legin, Anton A., additional, Schweikert, Andreas, additional, Gajic, Natalie, additional, Roller, Alexander, additional, Koellensperger, Gunda, additional, Jakupec, Michael A., additional, Kandioller, Wolfgang, additional, and Keppler, Bernhard K., additional

Published
2020
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25. IntroducingN-,P-, andS-donor leaving groups: an investigation of the chemical and biological properties of ruthenium, rhodium and iridium thiopyridone piano stool complexes

Author

Harringer, Sophia, primary, Wernitznig, Debora, additional, Gajic, Natalie, additional, Diridl, Andreas, additional, Wenisch, Dominik, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Theiner, Sarah, additional, Koellensperger, Gunda, additional, Kandioller, Wolfgang, additional, and Keppler, Bernhard K., additional

Published
2020
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26. The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O ‐, S,O ‐, and N , N‐ Chelate Effects

Author

Berasaluce, Iker, primary, Cseh, Klaudia, additional, Roller, Alexander, additional, Hejl, Michaela, additional, Heffeter, Petra, additional, Berger, Walter, additional, Jakupec, Michael A., additional, Kandioller, Wolfgang, additional, Malarek, Michael S., additional, and Keppler, Bernhard K., additional

Published
2019
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32. Introducing N-, P-, and S-donor leaving groups: an investigation of the chemical and biological properties of ruthenium, rhodium and iridium thiopyridone piano stool complexes.

Author

Harringer, Sophia, Wernitznig, Debora, Gajic, Natalie, Diridl, Andreas, Wenisch, Dominik, Hejl, Michaela, Jakupec, Michael A., Theiner, Sarah, Koellensperger, Gunda, Kandioller, Wolfgang, and Keppler, Bernhard K.

Subjects
LASER ablation inductively coupled plasma mass spectrometry, CHEMICAL properties, CANCER cell culture, REACTIVE oxygen species, RHODIUM, IRIDIUM, DNA
Abstract

A series of 15 piano-stool complexes featuring either a RuII, RhIII or IrIII metal center, a bidentate thiopyridone ligand, and different leaving groups was synthesized. The leaving groups were selected in order to cover a broad range of different donor atoms. Thus, 1-methylimidazole served as a N-donor, 1,3,5-triaza-7-phosphaadamantane (pta) as a P-donor, and thiourea as a S-donor. Additionally, three complexes featuring different halido leaving groups (Cl, Br, I) were added. Leaving group alterations were carried out with respect to a possible influence on pharmacokinetic and pharmacodynamic parameters, as well as the cytotoxicity of the respective compounds. The complexes were characterized via NMR spectroscopy, X-ray diffraction (where possible), mass spectrometry, and elemental analysis. Cytotoxicity was assessed in 2D cultures of human cancer cell lines by microculture and clonogenic assays as well as in multicellular tumor spheroids. Furthermore, cellular accumulation studies, flow-cytometric apoptosis and ROS assays, DNA plasmid assays, and laser ablation ICP-MS studies for analyzing the distribution in sections of multicellular tumor spheroids were conducted. This work demonstrates the importance of investigating each piano-stool complexes' properties, as the most promising candidates showed advantages over each other in certain tests/assays. Thus, it was not possible to single out one lead compound, but rather a group of complexes with enhanced cytotoxicity and activity. [ABSTRACT FROM AUTHOR]

Published
2020
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33. The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of O,O‐, S,O‐, and N,N‐Chelate Effects.

Author

Berasaluce, Iker, Cseh, Klaudia, Roller, Alexander, Hejl, Michaela, Heffeter, Petra, Berger, Walter, Jakupec, Michael A., Kandioller, Wolfgang, Malarek, Michael S., and Keppler, Bernhard K.

Subjects
MOLYBDENUM, BORATES, X-ray diffraction, LIGANDS (Chemistry), SOLUBILITY
Abstract

The synthesis, characterization and biological activity of molybdenum(IV) complexes containing Trofimenko's scorpionato ligand, hydrotris(3‐isopropylpyrazolyl)borate (TpiPr), in addition to varying biologically active as well as other conventional ligands is described. Ligands employed include (O,O‐) (S,O‐) (N,N‐) donors that have been successfully coordinated to the molybdenum center by means of oxygen‐atom transfer (OAT) reactions from the known MoVI starting material, TpiPrMoO2Cl. The synthesized complexes were characterized by standard analytical methods and where possible by X‐ray diffraction analysis. The aqueous stability of the compounds was studied by means of UV/Vis spectroscopy and the impact of the attached ligand scaffolds on the oxidation potentials (MoIV to MoV) was studied by cyclic voltammetry. Utilizing polyvinylpyrrolidone (PVP) as a solubilizing agent, adequate aqueous solubility for biological tests was obtained. Anticancer activity tests and preliminary mode of action studies have been performed in vitro and in vivo. [ABSTRACT FROM AUTHOR]

Published
2020
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34. Novel phthiocol-based organometallics with tridentate coordination motif and their unexpected cytotoxic behaviour.

Author

Geisler, Heiko, Wernitznig, Debora, Hejl, Michaela, Gajic, Natalie, Jakupec, Michael A., Kandioller, Wolfgang, and Keppler, Bernhard K.

Subjects
CELL culture, AQUEOUS solutions, BEHAVIOR, MICROWAVES
Abstract

Novel phthiocol-based organometallics with in situ formed tridentate N,O,O-coordination motif were established via three-component microwave assisted one-pot reaction. These complexes exhibited enhanced stability in aqueous solution compared to the parental compound KP2048 and showed unexpected cytotoxic behaviour and selectivity in 2D and 3D cell cultures. [ABSTRACT FROM AUTHOR]

Published
2020
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35. Rollover Cyclometalated Bipyridine Platinum Complexes as Potent Anticancer Agents: Impact of the Ancillary Ligands on the Mode of Action

Author

Babak, Maria V., primary, Pfaffeneder-Kmen, Martin, additional, Meier-Menches, Samuel M., additional, Legina, Maria S., additional, Theiner, Sarah, additional, Licona, Cynthia, additional, Orvain, Christophe, additional, Hejl, Michaela, additional, Hanif, Muhammad, additional, Jakupec, Michael A., additional, Keppler, Bernhard K., additional, Gaiddon, Christian, additional, and Hartinger, Christian G., additional

Published
2018
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37. [[Os.sup.IV][Cl.sub.5](hazole)]- complexes: synthesis, structure, spectroscopic properties, and antiproliferative activity

Author

Bochel, Gabriel E., Stepanenko, Iryna N., Hejl, Michaela, Jakupec, Michael A., Arion, Vladimir B., and Keppler, Bernhard K.

Subjects
Carcinoma -- Research, Cancer -- Research, Hydrolysis -- Analysis, Infrared spectroscopy -- Usage, Osmium -- Chemical properties, Osmium -- Structure, Pyrazoles -- Chemical properties, Pyrazoles -- Structure, X-ray crystallography -- Usage, Chemistry
Published
2009

38. Inside Back Cover: An Organoruthenium Anticancer Agent Shows Unexpected Target Selectivity For Plectin (Angew. Chem. Int. Ed. 28/2017)

Author

Meier, Samuel M., primary, Kreutz, Dominique, additional, Winter, Lilli, additional, Klose, Matthias H. M., additional, Cseh, Klaudia, additional, Weiss, Tamara, additional, Bileck, Andrea, additional, Alte, Beatrix, additional, Mader, Johanna C., additional, Jana, Samir, additional, Chatterjee, Annesha, additional, Bhattacharyya, Arindam, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Heffeter, Petra, additional, Berger, Walter, additional, Hartinger, Christian G., additional, Keppler, Bernhard K., additional, Wiche, Gerhard, additional, and Gerner, Christopher, additional

Published
2017
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39. Innenrücktitelbild: Ein Organoruthenium-Tumortherapeutikum mit unerwartet hoher Selektivität für Plectin (Angew. Chem. 28/2017)

Author

Meier, Samuel M., primary, Kreutz, Dominique, additional, Winter, Lilli, additional, Klose, Matthias H. M., additional, Cseh, Klaudia, additional, Weiss, Tamara, additional, Bileck, Andrea, additional, Alte, Beatrix, additional, Mader, Johanna C., additional, Jana, Samir, additional, Chatterjee, Annesha, additional, Bhattacharyya, Arindam, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Heffeter, Petra, additional, Berger, Walter, additional, Hartinger, Christian G., additional, Keppler, Bernhard K., additional, Wiche, Gerhard, additional, and Gerner, Christopher, additional

Published
2017
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40. An Organoruthenium Anticancer Agent Shows Unexpected Target Selectivity For Plectin

Author

Meier, Samuel M., primary, Kreutz, Dominique, additional, Winter, Lilli, additional, Klose, Matthias H. M., additional, Cseh, Klaudia, additional, Weiss, Tamara, additional, Bileck, Andrea, additional, Alte, Beatrix, additional, Mader, Johanna C., additional, Jana, Samir, additional, Chatterjee, Annesha, additional, Bhattacharyya, Arindam, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Heffeter, Petra, additional, Berger, Walter, additional, Hartinger, Christian G., additional, Keppler, Bernhard K., additional, Wiche, Gerhard, additional, and Gerner, Christopher, additional

Published
2017
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41. Ein Organoruthenium-Tumortherapeutikum mit unerwartet hoher Selektivität für Plectin

Author

Meier, Samuel M., primary, Kreutz, Dominique, additional, Winter, Lilli, additional, Klose, Matthias H. M., additional, Cseh, Klaudia, additional, Weiss, Tamara, additional, Bileck, Andrea, additional, Alte, Beatrix, additional, Mader, Johanna C., additional, Jana, Samir, additional, Chatterjee, Annesha, additional, Bhattacharyya, Arindam, additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Heffeter, Petra, additional, Berger, Walter, additional, Hartinger, Christian G., additional, Keppler, Bernhard K., additional, Wiche, Gerhard, additional, and Gerner, Christopher, additional

Published
2017
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42. Back Cover: Functionalization of Ruthenium(II)(η6 -p -cymene)(3-hydroxy-2-pyridone) Complexes with (Thio)Morpholine: Synthesis and Bioanalytical Studies (ChemPlusChem 6/2017)

Author

Hanif, Muhammad, primary, Meier, Samuel M., additional, Adhireksan, Zenita, additional, Henke, Helena, additional, Martic, Sanela, additional, Movassaghi, Sanam, additional, Labib, Mahmoud, additional, Kandioller, Wolfgang, additional, Jamieson, Stephen M. F., additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Kraatz, Heinz-Bernhard, additional, Davey, Curt A., additional, Keppler, Bernhard K., additional, and Hartinger, Christian G., additional

Published
2017
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43. Functionalization of Ruthenium(II)(η6 -p -cymene)(3-hydroxy-2-pyridone) Complexes with (Thio)Morpholine: Synthesis and Bioanalytical Studies

Author

Hanif, Muhammad, primary, Meier, Samuel M., additional, Adhireksan, Zenita, additional, Henke, Helena, additional, Martic, Sanela, additional, Movassaghi, Sanam, additional, Labib, Mahmoud, additional, Kandioller, Wolfgang, additional, Jamieson, Stephen M. F., additional, Hejl, Michaela, additional, Jakupec, Michael A., additional, Kraatz, Heinz-Bernhard, additional, Davey, Curt A., additional, Keppler, Bernhard K., additional, and Hartinger, Christian G., additional

Published
2017
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47. Synthesis, Characterization, Cytotoxicity, and Time‐Dependent NMR Spectroscopic Studies of (SP‐4‐3)‐Oxalato[(1R,2R,4R/1S,2S,4S)‐(4‐trifluoromethyl‐cyclohexane‐1,2‐diamine)]platinum(II).

Author

Hizal, Selin, Hejl, Michaela, Jungmann, Christoph, Jakupec, Michael A., Galanski, Markus, and Keppler, Bernhard K.

Subjects
*CELL-mediated cytotoxicity, *NUCLEAR magnetic resonance spectroscopy, *PLATINUM isotopes, *CYCLOHEXANE, *RACEMIC mixtures
Abstract

The oxaliplatin derivative (SP‐4‐3)‐oxalato[(1R,2R,4R/1S,2S,4S)‐(4‐trifluoromethyl‐cyclohexane‐1,2‐diamine)]platinum(II) hosting a trifluoromethyl group at position 4 of the cyclohexane ring is presented. The ligand was synthesized as an 1R,2R,4R/1S,2S,4S racemic mixture starting from 4‐trifluoromethyl‐cyclohexanol over five steps and coordinated to platinum to yield first the dichlorido and subsequently the oxalato complex. This novel compound and its analogue featuring a (13C2)oxalate ligand were characterized by multinuclear (1H, 13C, 15N, 19F, 195Pt) one‐ and two‐dimensional NMR spectroscopy. Ligand exchange and adduct formation reactions with DMSO, NaCl, CaCl2, l‐methionine, and 5′‐GMP were investigated via time‐dependent measurements by 19F and 13C NMR spectroscopy. The cytotoxicity of the title complex was investigated in three human cancer cell lines; the IC50 values were found in the low micromolar range, attesting moderate to high antiproliferative activity, depending on the cell line. A racemic mixture of an analogue of the clinically established anticancer drug oxaliplatin featuring a CF3 group at position 4 of the cyclohexane ring was synthesized and fully characterized. Its binding to DMSO, chloride, 5′‐GMP, and l‐methionine was investigated by 19F and 13C NMR spectroscopy. [ABSTRACT FROM AUTHOR]

Published
2019
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