Synthesis of PEG-modified derivatives of perillyl alcohol

ORGN 505

Donald W. Zehnder II1, Andrew J. Wiemer2, Raymond J. Hohl2, and David F. Wiemer1. (1) Department of Chemistry, University of Iowa, 305 Chemistry Building, Iowa City, IA 52242, (2) Department of Internal Medicine, University of Iowa, Iowa City, IA 52242

Perillyl alcohol has been reported to display cancer preventive and therapeutic activity through possible mechanisms including regulation of protein expression, inhibition of protein prenylation, and disruption of protein phosphorylation.  In an effort to identify specific cellular targets for perillyl alcohol binding, a series of potential probes was created by extension of a PEG chain from the heteroatom, C-2, C-7, and C-10.  The PEG tail has been modified to allow linkage with fluorescent probes or with agents such as biotin that might be used in affinity chromatography.  Synthesis of these compounds, as well as Western analyses of their impact on expression of prenylated proteins, will be presented.