Myocardial imaging agents: Synthesis, characterization, and evaluation of (Z)- and (Z,E)-18-[82Br]bromo-5-tellura-17-octadecenoic acids

Article abstract of DOI:10.1021/jm00382a003

The effects of replacement of radioiodide with radiobromide on the biological properties of a model vinyl halide substituted tellurium fatty acid have been evaluated. The use of a facile radiobromination method involving the reaction of [⁸²Br]Br₂ with vinylmercuric bromide substrates has been investigated. Unexpectedly, both the cis- and trans-vinyl bromide products are formed as confirmed by chromatographic and spectral studies. With use of this technique, (E,Z)-1-[⁸²Br]bromo-13-iodo-1-tridecene was prepared and used as the substrate to prepare (E,Z)-18-[⁸²Br]bromo-5-tellura-17-octadecenoic acid (13-E,Z), which was evaluated in rats. Both [⁸²Br]-13-E,Z and [⁸²Br]-13-Z, prepared by an established procedure using N-chorosuccinimide-Br^- reaction with the trans-boronovinyl substrates, showed tissue distribution properties similar to those of (E)-18-[¹²⁵I]iodo-5-tellura-17-octadecenoic acid. These results demonstrate that replacement of I with Br and also the stereochemistry about the olefinic bond do not drastically affect heart uptake and retention.