Synthesis and Biological Evaluation of (E)-19-Iodo-3,3-Dimethyl-18-Nonadecenoic Acid, a New Dimethyl-Branched Long-Chain Fatty Acid to Evaluate Regional Myocardial Fatty Acid Uptake

摘要

The synthetic method for the preparation of (E)-19-iodo-3,3-dimethyl-18-nonadecenoic acid (DMIVN) involved introduction of substituents into the 2- and 5-positions of a thiophene ring followed by sulfur extrusion of a 2,5-dialkyl thiophene derivative to provide a key 3,3-dimethyl-branched fatty acid intermediate, 17-iodo-3,3-dimethylheptadecanoic acid. Myocardial subcellular distribution studies of the sup 125 I-labeled DMIVN in fasted rats showed a higher association of radioactivity with the microsomes when compared to the results obtained with the 19-carbon straight chain analogue. With the nonfasted rats the distribution profiles of the two analogues showed differences that seemed to correlate with the differences in myocardial retention that fasting and feeding can induce. 5 refs., 3 figs., 2 tabs. (ERA citation 11:030661)