New Myocardial Imaging Agents: Stabilization of Radioiodine as a Terminal Vinyl Iodide Moiety on Tellurium Fatty Acids

F. F. Knapp, M. M. Goodman, A. P. Callahan, L. A. Ferren, George Kabalka, K. A.R. Sastry

Research output: Contribution to journalArticle

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Abstract

To determine the myocardial uptake and retention properties of radioiodinated tellurium fatty acids, we prepared two new tellurium fatty acids in which iodine-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-l-pentene with sodium 12-(methoxycarbonyl)-n-dodecan-l-yl telluride. The [5-125I]-l,5-diiodo-l-pentene was prepared by an organoborane technique involving 125I+ treatment of 5-iodo-1-penten-l-ylboronic acid [I(CH2)3CH=CHB(OH)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 (~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-[126I]iodo-7-tellura-17-octadecenoic acid, in the same manner by reaction of [11-I25I]-l,ll-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.

Original languageEnglish (US)
Pages (from-to)1293-1300
Number of pages8
JournalJournal of Medicinal Chemistry
Volume26
Issue number9
DOIs
StatePublished - Jan 1 1983

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Tellurium
Fatty Acids
Alkenes
Iodine
Sodium
vinyl iodide
Thyroid Gland
Acids

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

New Myocardial Imaging Agents : Stabilization of Radioiodine as a Terminal Vinyl Iodide Moiety on Tellurium Fatty Acids. / Knapp, F. F.; Goodman, M. M.; Callahan, A. P.; Ferren, L. A.; Kabalka, George; Sastry, K. A.R.

In: Journal of Medicinal Chemistry, Vol. 26, No. 9, 01.01.1983, p. 1293-1300.

Research output: Contribution to journalArticle

Knapp, F. F. ; Goodman, M. M. ; Callahan, A. P. ; Ferren, L. A. ; Kabalka, George ; Sastry, K. A.R. / New Myocardial Imaging Agents : Stabilization of Radioiodine as a Terminal Vinyl Iodide Moiety on Tellurium Fatty Acids. In: Journal of Medicinal Chemistry. 1983 ; Vol. 26, No. 9. pp. 1293-1300.
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N2 - To determine the myocardial uptake and retention properties of radioiodinated tellurium fatty acids, we prepared two new tellurium fatty acids in which iodine-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-l-pentene with sodium 12-(methoxycarbonyl)-n-dodecan-l-yl telluride. The [5-125I]-l,5-diiodo-l-pentene was prepared by an organoborane technique involving 125I+ treatment of 5-iodo-1-penten-l-ylboronic acid [I(CH2)3CH=CHB(OH)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 (~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-[126I]iodo-7-tellura-17-octadecenoic acid, in the same manner by reaction of [11-I25I]-l,ll-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.

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