Issue 48, 2022

Hydrazone- and imine-containing [PdPtL4]4+ cages: a comparative study of the stability and host–guest chemistry

Abstract

A new [PdPtL4]4+ heterobimetallic cage containing hydrazone linkages has been synthesised using the sub-component self-assembly approach. 1H and DOSY nuclear magnetic resonance (NMR) spectroscopy and electrospray ionisation mass spectrometry (ESIMS) data were consistent with the formation of the [PdPtL4]4+ architecture. The cage was stimulus-responsive and could be partially disassembled and reassembled by the addition of dimethylaminopyridine (DMAP) and p-tolenesulfonic acid (TsOH), respectively. Additionally, the stability of the hydrazone cage against hydrolysis in the presence of water and nucleophilic decomposition in the presence of guest molecules was compared to a previously synthesised imine-containing [PdPtL4]4+ cage. It was established that the hydrazone linkage was more resistant to hydrolysis. Furthermore, the host–guest (HG) chemistry with a series of drug and drug-like molecules was examined. The hydrazone cage was shown to interact with cisplatin while the smaller imine cage was shown to interact with 5-fluorouracil and oxaliplatin in CD3CN. No HG interactions were observed in the more polar d6-DMSO. In vitro antiproliferative activity studies demonstrated both cages were active against the cancer cell lines tested and displayed half-maximal inhibitory (IC50) values in the range of 25–35 μM. Most [PdPtL4]4+-drug mixtures tested had higher IC50 values than the hosts. However, the [PdPtL4]4+ cages, and [PdPtL4]4+:drug mixtures were less cytotoxic than the well established anticancer drugs cisplatin, oxaliplatin and 5-fluorouracil.

Graphical abstract: Hydrazone- and imine-containing [PdPtL4]4+ cages: a comparative study of the stability and host–guest chemistry

Supplementary files

Article information

Article type
Paper
Submitted
19 Aga 2022
Accepted
15 Nov 2022
First published
15 Nov 2022

Dalton Trans., 2022,51, 18438-18445

Hydrazone- and imine-containing [PdPtL4]4+ cages: a comparative study of the stability and host–guest chemistry

L. S. Lisboa, M. Riisom, H. J. Dunne, D. Preston, S. M. F. Jamieson, L. J. Wright, C. G. Hartinger and J. D. Crowley, Dalton Trans., 2022, 51, 18438 DOI: 10.1039/D2DT02720H

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