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

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...

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Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2015-04, Vol.44 (16), p.7563-7569
Main Authors: Mohamed, Heba A, Lake, Benjamin R M, Laing, Thomas, Phillips, Roger M, Willans, Charlotte E
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - toxicity
Biological Products - chemistry
Caffeine - chemistry
Cell Line, Tumor
Cell Survival - drug effects
Coordination Complexes - chemical synthesis
Coordination Complexes - chemistry
Coordination Complexes - toxicity
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Heterocyclic Compounds - chemistry
Humans
Hydrophobic and Hydrophilic Interactions
Methane - analogs & derivatives
Methane - chemistry
Molecular Conformation
Silver - chemistry
Theobromine - chemistry
Theophylline - chemistry
Xanthine - chemistry
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Summary: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.
ISSN:1477-9226
1477-9234
DOI:10.1039/c4dt03679d