Synthesis and Evaluation of Radioiodinated (E)-18-Iodo-17-octadecenoic Acid as a Model Iodoalkenyl Fatty Acid for Myocardial Imaging

F. F. Knapp, M. M. Goodman, George Kabalka, K. A.R. Sastry

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

125I-labeled CE)-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 iodivinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by Nal-chloramine-T treatment of (17-carbomethoxyheptadec-l-en-l-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 125I-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 123I-labeled agent.

Original languageEnglish (US)
Pages (from-to)94-97
Number of pages4
JournalJournal of Medicinal Chemistry
Volume27
Issue number1
DOIs
StatePublished - Jan 1 1984
Externally publishedYes

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Fatty Acids
Tellurium
Boronic Acids
Acids
Hydrolysis
Dogs
Injections
Therapeutics
18-iodo-17-octadecenoic acid
chloramine-T
17-octadecynoic acid

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Synthesis and Evaluation of Radioiodinated (E)-18-Iodo-17-octadecenoic Acid as a Model Iodoalkenyl Fatty Acid for Myocardial Imaging. / Knapp, F. F.; Goodman, M. M.; Kabalka, George; Sastry, K. A.R.

In: Journal of Medicinal Chemistry, Vol. 27, No. 1, 01.01.1984, p. 94-97.

Research output: Contribution to journalArticle

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abstract = "125I-labeled CE)-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 iodivinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by Nal-chloramine-T treatment of (17-carbomethoxyheptadec-l-en-l-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 125I-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 123I-labeled agent.",
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