Ligand Exchange/Scrambling Study of Gold(I)-Phosphine Complexes in the Solid Phase by DESI-MS Analysis
- 9 September 2019
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Society for Mass Spectrometry
- Vol. 30 (11), 2289-2296
- https://doi.org/10.1007/s13361-019-02319-y
Abstract
Only a few analytical techniques are available for the characterization of mechanochemical synthetic reaction products. We demonstrate here that DESI-MS is a powerful technique for this purpose, combining the selectivity of MS-based assays with the simplicity and in situ analysis capability of ambient ionization methods. In this work, we report that auranofin, a gold-based drug, and its precursor triethylphosphine gold(I) chloride undergo a complex array of ligand exchange/scrambling reactions with thiol-containing amino acids in the solid state. The products were readily characterized by DESI-MS analysis from the solid-phase reaction, clearly exhibiting ligand exchange and scrambling, with independent confirmation by solid state 13C-NMR. The thioglucose and triethylphosphine moieties exchanged with cysteine and its derivatives, whereas the glutathione replaced 2,3,4,6-tetra-o-acetyl-β-1-d-glucopyranose only. It was concluded that ligand exchange and scrambling reactions can be carried out in the solid state, and some of the unique products reported in this study can be conveniently prepared through mechanochemical synthesis in good yields (> 98%), as demonstrated by synthesis of (l-cysteinato-S)-triethylphosphine gold(I) from triethylphosphine gold(I) chloride and l-cysteine.Keywords
This publication has 31 references indexed in Scilit:
- Study of Electrochemical Reactions Using Nanospray Desorption Electrospray Ionization Mass SpectrometryAnalytical Chemistry, 2012
- An instrumentation perspective on reaction monitoring by ambient mass spectrometryTrAC Trends in Analytical Chemistry, 2012
- A high-throughput drug screen for Entamoeba histolytica identifies a new lead and targetNature Medicine, 2012
- Seleno-Auranofin (Et3PAuSe-tagl): Synthesis, Spectroscopic (EXAFS, 197Au Mössbauer, 31P, 1H, 13C, and 77Se NMR, ESI-MS) Characterization, Biological Activity, and Rapid Serum Albumin-Induced Triethylphosphine Oxide GenerationInorganic Chemistry, 2010
- Glutathionato-S-Gold(III) complexes formed as intermediates in the reduction of auricyanide by glutathioneJournal of Inorganic Biochemistry, 2008
- Solvent-free synthesis of metal complexesChemical Society Reviews, 2007
- A mass spectrometric investigation of the binding of gold antiarthritic agents and the metabolite [Au(CN)2]− to human serum albuminJBIC Journal of Biological Inorganic Chemistry, 2006
- Solvent-free mechanochemical synthesis of two Pt complexes: cis-(Ph3P)2PtCl2 and cis-(Ph3P)2PtCO3Electronic supplementary information (ESI) available: differential thermal analysis data, X-ray diffraction data. See http://www.rsc.org/suppdata/cc/b2/b203694k/Chemical Communications, 2002
- Solventless reaction dramatically accelerates supramolecular self-assemblyElectronic supplementary information (ESI) available: experimental details and CD spectra. See http://www.rsc.org/suppdata/cc/b2/b203651g/Chemical Communications, 2002
- Oral gold. Antiarthritic properties of alkylphosphinegold coordination complexesJournal of Medicinal Chemistry, 1972