Synthesis and Evaluation of Radioiodinated (E)-18-Iodo-17-octadecenoic Acid as a Model Iodoalkenyl Fatty Acid for Myocardial Imaging

Article abstract of DOI:10.1021/jm00367a021

125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism.This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13).The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes .The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28percent dose/g) with 45percent washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom.Deiodination was low for the first 2 h after injection (2 h, 61percent dose/g).Excellent myocardial images were obtained in a dog with the 123I-labeled agent.