Molecular Pharmacology, Vol 7, 177-182, Copyright © 1971 by the American Society for Pharmacology and Experimental Therapeutics

An Infrared Study of the Interaction of Caffeine and Theophylline with 9-Ethyladenine in Chloroform Solution

¹ Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia

In deuterochloroform solution theophylline hydrogen bonds strongly with 9-ethyladenine, the strength of the association being comparable with that of the hydrogen bonding between 1-cyclohexyluracil and 9-ethyladenine reported previously, while caffeine associates relatively weakly with the latter. In a hydrophobic medium caffeine has greater solubility while theophylline self-associates extensively. The alleged role of caffeine in interfering with a DNA repair mechanism is discussed.

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ACKNOWLEDGMENTS The author wishes to thank Professor Richard C. Lord for suggesting this insvestigation, for valuable discussions, and for his generous support of this work, which was conducted in the Massachusetts Institute of Technology Spectroscopy Laboratory during the tenure of a Research Associateship in 1967-1968.