Felix Bacher1, Christopher Wittmann1, Márta Nové2, Gabriella Spengler2, Małgorzata A Marć3, Eva A Enyedy3, Denisa Darvasiová4, Peter Rapta4, Thomas Reiner5, Vladimir B Arion1. 1. Institute of Inorganic Chemistry of the University of Vienna, Währinger Strasse 42, A-1090 Vienna, Austria. felix.bacher@univie.ac.at vladimir.arion@univie.ac.at. 2. Department of Medical Microbiology and Immunobiology, University of Szeged, Dóm tér 10, H-6720 Szeged, Hungary. 3. Department of Inorganic and Analytical Chemistry, Interdisciplinary Excellence Centre, University of Szeged, Dóm tér 7, H-6720 Szeged, Hungary. 4. Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, 81237 Bratislava, Slovak Republic. 5. Department of Radiology, Weill Cornell Medical College, New York City, NY 10065, USA and Department of Radiology, Memorial Sloan Kettering Cancer Center, New York City, NY 10065, USA and Chemical Biology Program, Memorial Sloan Kettering Cancer Center, New York City, NY 10065, USA.
Abstract
Four Schiff bases derived from 7-hydrazin-yl-5,8-dihydroindolo[2,3-d][2]benzazepin-(6H)-one and its bromo-substituted analogue (HL1-HL4) and four copper(ii) complexes 1-4 have been synthesised and fully characterised by standard spectroscopic methods (1H and 13C NMR, UV-vis), ESI mass spectrometry, single crystal X-ray diffraction and spectroelectrochemistry. In addition, two previously reported complexes with paullone ligands 5 and 6 were prepared and studied for comparison reasons. The CuII ion in 1-4 is five-coordinate and adopts a square-pyramidal or slightly distorted square-pyramidal coordination geometry. The ligands HL1-4 act as tridentate, the other two coordination places are occupied by two chlorido co-ligands. The organic ligands in 2 and 3 are bound tighter to copper(ii) when compared to related paullone ligands in 5 and 6. The new compounds show very strong cytotoxic activity against human colon adenocarcinoma doxorubicin-sensitive Colo 205 and multidrug resistant Colo 320 cancer cell lines with IC50 values in the low micromolar to nanomolar concentration range.
Four Schiff bases derived from n class="Chemical">7-hydrazin-yl-5,8-dihydroindolo[2,3-d][2]benzazepin-(6H)-one and its bromo-substituted analogue (HL1-HL4) and four copper(ii) complexes 1-4 have been synthesised and fully characterised by standard spectroscopic methods (1H and 13CNMR, UV-vis), ESI mass spectrometry, single crystal X-ray diffraction and spectroelectrochemistry. In addition, two previously reported complexes with paullone ligands 5 and 6 were prepared and studied for comparison reasons. The CuII ion in 1-4 is five-coordinate and adopts a square-pyramidal or slightly distorted square-pyramidal coordination geometry. The ligands HL1-4 act as tridentate, the other two coordination places are occupied by two chlorido co-ligands. The organic ligands in 2 and 3 are bound tighter to copper(ii)when compared to related paullone ligands in 5 and 6. The new compounds show very strong cytotoxic activity against humancolon adenocarcinomadoxorubicin-sensitive Colo 205 and multidrug resistant Colo 320 cancer cell lines with IC50 values in the low micromolar to nanomolar concentration range.
Authors: Christopher Wittmann; Anastasiia S Sivchenko; Felix Bacher; Kelvin K H Tong; Navjot Guru; Thomas Wilson; Junior Gonzales; Hartmut Rauch; Susanne Kossatz; Thomas Reiner; Maria V Babak; Vladimir B Arion Journal: Inorg Chem Date: 2022-01-07 Impact factor: 5.165
Authors: Ana Vesković; Đura Nakarada; Olga Vasiljević; Anatolie Dobrov; Gabriella Spengler; Éva A Enyedy; Vladimir B Arion; Ana Popović Bijelić Journal: Pharmaceutics Date: 2022-05-30 Impact factor: 6.525
Authors: Irina Kuznetcova; Felix Bacher; Samah Mutasim Alfadul; Max Jing Rui Tham; Wee Han Ang; Maria V Babak; Peter Rapta; Vladimir B Arion Journal: Inorg Chem Date: 2022-06-17 Impact factor: 5.436
Authors: Christopher Wittmann; Felix Bacher; Eva A Enyedy; Orsolya Dömötör; Gabriella Spengler; Christian Madejski; Jóhannes Reynisson; Vladimir B Arion Journal: J Med Chem Date: 2022-02-01 Impact factor: 7.446