Radioiodinated 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid: a useful new agent to evaluate myocardial fatty acid uptake
Radioiodinated 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP) has been prepared as a new terminal iodophenyl-substituted fatty acid containing dimethyl-branching at the beta position. For the synthesis of this new agent, chain homologation was accomplished by fabrication of a 2,5-disubstituted thiophene by successive Friedel-Crafts acylation and Wolff-Kishner reduction reactions, followed by thiophene ring opening. The dimethyl-branching was introduced using the monomethyl ester of dimethylglutaryl chloride. Radioiodination of the 15-phenyl-3,3-dimethylpentadecanoic acid substrate in the para position then gave DMIPP. Iodine-125-labeled DMIPP showed rapid, high myocardial uptake (min, mean % injected dose/g) in fasted rats (5, 4.67; 30, 5.06; 60, 4.79; 120, 4.37), and also exhibited good heart:blood ratios (min, heart:blood: 5, 3:1; 30, 12:1; 60, 12:1; 120, 13:1). To further evaluate the effects of dimethyl-branching, the biodistribution properties of DMIPP were compared with the 3-monomethyl-branched (15-(p-iodophenyl)-3-R,S-methylpentadecanoic acid; BMIPP) and the unbranched (15-(p-iodophenyl)pentadecanoic acid; IPP) analogs. A triple-labeled (/sup 123/I)DMIPP/(/sup 131/I)BMIPP/(/sup 125/I)IPP mixture was administered to groups of fasted rats. These results confirmed the greater myocardial retention and higher heart:blood ratios observed with DMIPP in comparison with both the 3-monomethyl-(BMIPP) and unbranched (IPP) analogs. These data suggest that (/sup 123/3I)DMIPP is an excellent candidate for clinical evaluation of regional energy substrates (fatty acid) uptake.
- Research Organization:
- Oak Ridge National Lab., TN
- OSTI ID:
- 5206076
- Journal Information:
- J. Nucl. Med.; (United States), Vol. 4
- Country of Publication:
- United States
- Language:
- English
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Nuclear medicine: Progress report for quarter ending September 30, 1986
Radioiodinated 15-(p-iodophenyl)-3,3-dimethylpentadecanoic acid (DMIPP): A new agent to evaluate regional myocardial fatty acid uptake
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IODINATION
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IODINE 125
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RADIOPHARMACEUTICALS
RATS
TISSUE DISTRIBUTION
UPTAKE
ANIMALS
BETA DECAY RADIOISOTOPES
BETA-MINUS DECAY RADIOISOTOPES
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DIGESTIVE SYSTEM
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DRUGS
ELECTRON CAPTURE RADIOISOTOPES
GLANDS
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HEART
HOURS LIVING RADIOISOTOPES
INTERMEDIATE MASS NUCLEI
IODINE ISOTOPES
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LABELLED COMPOUNDS
MAMMALS
MONOCARBOXYLIC ACIDS
MUSCLES
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