New myocardial imaging agents: stabilization of radioiodine as a terminal vinyl iodide moiety on tellurium fatty acids
To determine the myocardial uptake and retention properties of radioiodinated tellurium fatty acids, we prepared two new tellurium fatty acids in which iodine-/sup 125/ has been chemically stabilized by attachment as a trans-vinyl iodide (I-CH . CH-R-Te-R'-COOH) and evaluated them in rats. Fabrication of 18-iodo-13-tellura-17-octadecenoic acid was accomplished by coupling 1,5-diiodo-1-pentene with sodium 12-(methoxycarbonyl)-n-dodecan-1-yl telluride. The (5-/sup 125/I)-1,5-diiodo-1-pentene was prepared by an organoborane technique involving /sup 125/I+ treatment of 5-iodo-1-penten-1-ylboronic acid (I(CH/sub 2/)/sub 3/CH . CHB(OH)/sub 2/). The absolute heart uptake of this agent was moderate (1.47-2.52% dose/g after 60 min), but the heart/blood ratios were low (approximately 2.6:1). Only marginal in vivo deiodination occurred, since the thyroid uptake was low (15-18% dose/g after 60 min). The effect of tellurium in position 13 was unexpected. To determine if the low heart specificity and low heart/blood ratios were dependent upon the position of the tellurium, we prepared an analogue with the same chain length, 18-(/sup 125/I)iodo-7-tellura-17-octadecenoic acid, in the same manner by reaction of (11-/sup 125/I)-1,11-diiodo-1-undecene with sodium 6-(methoxycarbonyl)-n-hexan-1-yl telluride. This agent showed pronounced heart uptake (2.47-3.94% dose/g after 60 min) and prolonged retention (1.76-3.14% dose/g after 4 h) in rats. Furthermore, the heart/blood ratios remained high for several hours (13:1 after 60 min; 9:1 after 4 h). Iodine-123 labeled 18-iodo-7-tellura-17-octadecenoic acid is an attractive new compound for evaluation as a myocardial imaging agent.
- Research Organization:
- Nuclear Medicine Group, Health and Safety Research Division, Oak Ridge National Laboratory, Tennessee
- OSTI ID:
- 5656158
- Journal Information:
- J. Med. Chem.; (United States), Journal Name: J. Med. Chem.; (United States) Vol. 26:9; ISSN JMCMA
- Country of Publication:
- United States
- Language:
- English
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62 RADIOLOGY AND NUCLEAR MEDICINE
ANIMALS
BETA DECAY RADIOISOTOPES
BODY
CARBOXYLIC ACIDS
CARDIOVASCULAR SYSTEM
CHEMICAL PREPARATION
CHEMISTRY
DAYS LIVING RADIOISOTOPES
ELECTRON CAPTURE RADIOISOTOPES
HEART
HOURS LIVING RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINE 123
IODINE 125
IODINE ISOTOPES
ISOTOPES
LABELLED COMPOUNDS
LABELLING
MAMMALS
MUSCLES
MYOCARDIUM
NUCLEI
ODD-EVEN NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANS
RADIOCHEMISTRY
RADIOISOTOPES
RATS
RODENTS
SYNTHESIS
TELLURIUM COMPOUNDS
UPTAKE
VERTEBRATES