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Synthesis and evaluation of radioiodinated terminal-substituted 5-iodo-(2-thienyl) fatty acids as new myocardial imaging agents

Journal Article · · J. Heterocycl. Chem.; (United States)

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 (/sup 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-thienyl)heptadecanoic acid and 13-(2-thienyl)tridecanoic acid by K-/sup 125/I treatment of their corresponding 5-(bis-(trifluoroacetoxyl))thallium derivatives. Tissue distribution studies in rats with 17-(5-(/sup 125/I)iodo(2-thienyl)heptadecanoic acid shows significant heart uptake and prolonged retention accompanied by in vivo deiodination and moderate blood levels. A comparison of the heart uptake of the 17 carbon fatty acid with a 13 carbon analogue, 13-(5-(/sup 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. 17 references, 2 tables.

Research Organization:
Oak Ridge National Lab., TN
DOE Contract Number:
AC05-84OR21400
OSTI ID:
5965242
Journal Information:
J. Heterocycl. Chem.; (United States), Journal Name: J. Heterocycl. Chem.; (United States) Vol. 21; ISSN JHTCA
Country of Publication:
United States
Language:
English