Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging
/sup 125/I-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 /sup 125/I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% 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, 61% dose/g). Excellent myocardial images were obtained in a dog with the /sup 123/I-labeled agent.
- Research Organization:
- Oak Ridge National Lab., TN
- OSTI ID:
- 6801360
- Journal Information:
- J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 27:1; ISSN JMCMA
- Country of Publication:
- United States
- Language:
- English
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62 RADIOLOGY AND NUCLEAR MEDICINE
BETA DECAY RADIOISOTOPES
BODY
CARBOXYLIC ACIDS
CARDIOVASCULAR SYSTEM
CHEMICAL PREPARATION
DAYS LIVING RADIOISOTOPES
DRUGS
ELECTRON CAPTURE RADIOISOTOPES
HEART
HOURS LIVING RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINE 123
IODINE 125
IODINE ISOTOPES
ISOTOPE APPLICATIONS
ISOTOPES
LABELLED COMPOUNDS
LABELLING
MUSCLES
MYOCARDIUM
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RADIOISOTOPES
RADIOPHARMACEUTICALS
SYNTHESIS
TRACER TECHNIQUES
UPTAKE