Synthesis and characterization of thiocarbonato-linked platinum(iv) complexes. Issue 14 (21st March 2022)

• Record Type: Journal Article
• Authors: Barth, Marie-Christin; Lange, Stefanie; Häfner, Norman; Ueberschaar, Nico; Görls, Helmar; Runnebaum, Ingo B.; Weigand, Wolfgang
• Is Part Of: Dalton transactions. Volume 51:Issue 14(2022)
• Page Start: 5567
• Page End: 5576
• Publication Date: 2022-03-21
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/d2dt00318j
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : Novel platinum(iv ) complexes with thiocarbonate linkage were synthesized and their cytotoxic activity against ovarian carcinoma cell lines was investigated. Insights into the reaction with ascorbic acid were provided by UHPLC-HRMS. Abstract : Herein we show the formation of new oxaliplatin-based platinum(iv ) complexes by reaction with DSC-activated thiols via thiocarbonate linkage. Three model complexes based on aliphatic and aromatic thiols, as well as one complex with N -acetylcysteine as biologically active thiol were synthesized. This synthetic strategy affords the expansion of biologically active compounds other than those containing carboxylic, amine or hydroxy groups for coupling to the platinum(iv ) center. The complexes were characterized by high-resolution mass spectrometry, NMR spectroscopy ( 1 H, 13 C, 195 Pt) and elemental analysis. Their biological behavior was evaluated against two ovarian carcinoma cell lines and their cisplatin-resistant analogues. Remarkably, the platinum(iv ) samples show modest in vitro cytotoxicity against A2780 cells and comparable effects against A2780cis cells. Two complexes in particular demonstrate improved activity against SKOV3cis cells. The reduction experiment of complex 8, investigated by UHPLC-HRMS, provides evidence of interesting platinum-species formed during reaction with ascorbic acid.