1021-65-4Relevant articles and documents
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.
, p. 7563 - 7569 (2015)
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.
A Symmetrical Model for the Self-association of Xanthines in Aqueous Solution
Yanuka, Yehuda,Zahalka, Jamal,Donbrow, Max
, p. 911 - 916 (2007/10/02)
The self-association of caffeine, 7-ethyl-, 7-propyl-, and 7-butyl-theophylline, theophylline, 1,3-diethylxanthine, and 3-isobutyl-1-methylxanthine in aqueous solution was explored in this study.Detailed analyses of all the proton shifts in CDCl3 and D2O solutions were undertaken, measuring both concentration- and temperature-dependence.Operative factors determining the chemical shift values include solvent-structuring effects, polarizability capacities, and hydrogen bonding involving water bridges.Evidence is given to support a symmetric mode of association induced by hydrophobic interaction and hydrophilic hydration between contiguous groups.The chemical shifts of theophylline and two of its analogues were measured in D2O, CD3OD, and CDCl3 solutions.Only in CD3OD did the shifts show different trends which were interpreted on the basis of the solvation capacity of CD3OD and steric hindrance to the specific solvation.