Issue 16, 2015

Synthesis and anticancer activity of silver(i)–N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine

Abstract

A new library of silver(I)–N-heterocyclic carbene complexes prepared from the natural products caffeine, theophylline and theobromine is reported. The complexes have been fully characterised using a combination of NMR spectroscopy, mass spectrometry, elemental analysis and X-ray diffraction analysis. Furthermore, the hydrophobicity of the complexes has been measured. The silver(I)–N-heterocyclic carbenes have been evaluated for their antiproliferative properties against a range of cancer cell lines of different histological types, and compared to cisplatin. The data shows different profiles of response when compared to cisplatin in the same panel of cells, indicating a different mechanism of action. Furthermore, it appears that the steric effect of the ligand and the hydrophobicity of the complex both play a role in the chemosensitivity of these compounds, with greater steric bulk and greater hydrophilicity delivering higher cytotoxicity.

Graphical abstract: Synthesis and anticancer activity of silver(i)–N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine

Supplementary files

Article information

Article type
Paper
Submitted
01 Dec 2014
Accepted
15 Mar 2015
First published
26 Mar 2015

Dalton Trans., 2015,44, 7563-7569

Author version available

Synthesis and anticancer activity of silver(I)–N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine

H. A. Mohamed, B. R. M. Lake, T. Laing, R. M. Phillips and C. E. Willans, Dalton Trans., 2015, 44, 7563 DOI: 10.1039/C4DT03679D

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