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Synthesis and evaluation of radioiodinated terminal‐substituted 5‐iodo‐(2‐thienyl) fatty acids as new myocardial imaging agents
Author(s) -
Goodman Mark M.,
Kirsch Gilbert,
Knapp Furn F.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210602
Subject(s) - chemistry , moiety , fatty acid , myocardial imaging , in vivo , thallium , distribution (mathematics) , carbon fibers , carbon 14 , stereochemistry , biochemistry , organic chemistry , medicine , mathematical analysis , materials science , microbiology and biotechnology , mathematics , composite number , composite material , biology , physics , quantum mechanics
In order to evaluate the stability of radioiodide attached to the 5 position of thiophenes substituted at the 2‐position with tissue‐specific groups as new radiopharmaceuticals, two [ 125 I]iodothienyl‐substituted long‐chain fatty acids have been prepared and evaluated in rats. Radioiodide was introduced into the 5 position of 17‐(2‐thienyi)heptadecanoic acid and 13‐(2‐thienyl)tridecanoic acid by K‐ 125 I treatment of their corresponding 5‐[ bis ‐(trifluoroacetoxy)]thallium derivatives. Tissue distribution studies in rats with 17‐[5‐[ 125 I]iodo(2‐thienyl)]heptadecanoic acid shows significant heart uptake and prolonged retention accompanied by in vivo deiod‐ination and moderate blood levels. A comparison of the heart uptake of the 17 carbon fatty acid with a 13 carbon analogue, 13‐[5‐[ 135 I]iodo(2‐thienyl)]tridecanoic acid, demonstrated a significantly greater myocardial uptake for the 17 carbon fatty acid than the 13 carbon analogue. These results suggest that the 5‐iodothienyl moiety substituted at the terminal position of long chain fatty acids does not interfere with myocardial uptake and that such compounds may be of value as a new class of myocardial imaging agents.