Synthesis, characterization, and biomedical evaluation of ethylene-bridged tetra-NHC Pd(II), Pt(II) and Au(III) complexes, with apoptosis-inducing properties in cisplatin-resistant neuroblastoma cells

Wolfgang R. E. Büchele; Tim P. Schlachta; Andreas L. Gebendorfer; Jenny Pamperin; Leon F. Richter; Michael J. Sauer; Aram Prokop; Fritz E. Kühn

doi:10.1039/D4RA01195C

Synthesis, characterization, and biomedical evaluation of ethylene-bridged tetra-NHC Pd(ii), Pt(ii) and Au(iii) complexes, with apoptosis-inducing properties in cisplatin-resistant neuroblastoma cells†

Wolfgang R. E. Büchele,

‡^a Tim P. Schlachta,

‡^a Andreas L. Gebendorfer,^a Jenny Pamperin,^cd Leon F. Richter,

^a Michael J. Sauer,^a Aram Prokop*^bcd and Fritz E. Kühn

*^a

Author affiliations

* Corresponding authors

^a Technical University of Munich, School of Natural Sciences, Department of Chemistry and Catalysis Research Center, Molecular Catalysis, Lichtenbergstraße 4, 85748 Garching, Germany
E-mail: fritz.kuehn@ch.tum.de
Tel: +49 89 289 13477

^b Department of Pediatric Hematology/Oncology, Children's Hospital Cologne, Amsterdamer Straße 59, 50735 Cologne, Germany

^c Department of Pediatric Oncology/Hematology, Helios Clinics Schwerin, Wismarsche Straße 393-397, 19055 Schwerin, Germany
E-mail: aram.prokop@helios-gesundheit.de

^d Department of Human Medicine, MSH Medical School Hamburg, Am Kaiserkai 1, 20457 Hamburg, Germany

Abstract

Synthesis and characterization of the first two cyclic ethylene-bridged tetradentate NHC ligands, with an unsaturated (imidazole) and saturated backbone (2-imidazoline), are described. Complexes of both ligands containing palladium(II) have been obtained. For platinum(II) and gold(III), only the unsaturated tetracarbene complexes could be isolated. The attempts to synthesize a methylene-bridged 2-imidazoline macrocycle are also described. Furthermore, a novel bisimidazolinium ligand precursor and its open-chain Pd^II and Pt^II tetracarbene complexes are obtained. Finally, it is shown that the unsaturated gold(III) tetracarbene is able to induce apoptosis in malignant SK-N-AS neuroblastoma cells via the mitochondrial and ROS pathway and overcomes resistance to cisplatin in vitro.

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DOI: https://doi.org/10.1039/D4RA01195C
Article type: Paper
Submitted: 16 Feb 2024
Accepted: 14 Mar 2024
First published: 27 Mar 2024
This article is Open Access

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RSC Adv., 2024,14, 10244-10254

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Synthesis, characterization, and biomedical evaluation of ethylene-bridged tetra-NHC Pd(II), Pt(II) and Au(III) complexes, with apoptosis-inducing properties in cisplatin-resistant neuroblastoma cells

W. R. E. Büchele, T. P. Schlachta, A. L. Gebendorfer, J. Pamperin, L. F. Richter, M. J. Sauer, A. Prokop and F. E. Kühn, RSC Adv., 2024, 14, 10244 DOI: 10.1039/D4RA01195C

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Synthesis, characterization, and biomedical evaluation of ethylene-bridged tetra-NHC Pd(ii), Pt(ii) and Au(iii) complexes, with apoptosis-inducing properties in cisplatin-resistant neuroblastoma cells†

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Synthesis, characterization, and biomedical evaluation of ethylene-bridged tetra-NHC Pd(II), Pt(II) and Au(III) complexes, with apoptosis-inducing properties in cisplatin-resistant neuroblastoma cells

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