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

Heba A. Mohamed, Benjamin R M Lake, Thomas Laing, Roger M. Phillips, Charlotte E. Willans

Research output: Contribution to journalArticle

37 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)7563-7569
Number of pages7
JournalDalton Transactions
Volume44
Issue number16
DOIs
Publication statusPublished - 28 Apr 2015

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Theobromine
Xanthine
Theophylline
Hydrophobicity
Caffeine
Hydrophobic and Hydrophilic Interactions
Silver
Cisplatin
Hydrophilicity
Cytotoxicity
Biological Products
X ray diffraction analysis
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Cells
Ligands
X-Ray Diffraction
Mass Spectrometry
Magnetic Resonance Spectroscopy
Chemical analysis

Cite this

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Synthesis and anticancer activity of silver(I)-N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine. / Mohamed, Heba A.; Lake, Benjamin R M; Laing, Thomas; Phillips, Roger M.; Willans, Charlotte E.

In: Dalton Transactions, Vol. 44, No. 16, 28.04.2015, p. 7563-7569.

Research output: Contribution to journalArticle

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AU - Phillips, Roger M.

AU - Willans, Charlotte E.

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