Radiolabeled 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine-I. Synthesis and purification

Kenneth W. Reed; Clarence T. Ueda; Wallace J. Murray; Samuel C. Augustine

doi:10.1016/0883-2889(89)90168-8

Radiolabeled 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine-I. Synthesis and purification

Kenneth W. Reed, Clarence T. Ueda, Wallace J. Murray, Samuel C. Augustine

Research output: Contribution to journal › Article

1 Scopus citations

Abstract

The purpose of this investigation was to synthesize and purify radiolabeled 9- or 10-monoiodostearyl carnitine for potential use as a perfusion and metabolic imaging agent for the heart. Oleic acid was iodinated via a free radical addition reaction of HI across the double bond to give 9- or 10-monoiodostearic acid which in turn was esterified with carnitine. The identify of 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine was determined using nuclear magnetic resonance (NMR), infrared (i.r.), ultraviolet (u.v.), and mass spectroscopy. The purity of the fatty acid and carnitine ester was established by thin layer chromatography. 9- or 10-Monoiodo[¹²⁵I]stearic acid and 9- or 10-monoiodo[¹²⁵I]stearyl carnitine were synthesized via the isotopic exchange of ¹²⁵I for cold iodine bonded to 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine.

Original language	English (US)
Pages (from-to)	27-31
Number of pages	5
Journal	International Journal of Radiation Applications and Instrumentation. Part
Volume	40
Issue number	1
DOIs	https://doi.org/10.1016/0883-2889(89)90168-8
State	Published - 1989
Externally published	Yes

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All Science Journal Classification (ASJC) codes

Radiation
Engineering(all)

Cite this

Reed, K. W., Ueda, C. T., Murray, W. J., & Augustine, S. C. (1989). Radiolabeled 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine-I. Synthesis and purification. International Journal of Radiation Applications and Instrumentation. Part, 40(1), 27-31. https://doi.org/10.1016/0883-2889(89)90168-8

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abstract = "The purpose of this investigation was to synthesize and purify radiolabeled 9- or 10-monoiodostearyl carnitine for potential use as a perfusion and metabolic imaging agent for the heart. Oleic acid was iodinated via a free radical addition reaction of HI across the double bond to give 9- or 10-monoiodostearic acid which in turn was esterified with carnitine. The identify of 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine was determined using nuclear magnetic resonance (NMR), infrared (i.r.), ultraviolet (u.v.), and mass spectroscopy. The purity of the fatty acid and carnitine ester was established by thin layer chromatography. 9- or 10-Monoiodo[125I]stearic acid and 9- or 10-monoiodo[125I]stearyl carnitine were synthesized via the isotopic exchange of 125I for cold iodine bonded to 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine.",

author = "Reed, {Kenneth W.} and Ueda, {Clarence T.} and Murray, {Wallace J.} and Augustine, {Samuel C.}",

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AU - Ueda, Clarence T.

AU - Murray, Wallace J.

AU - Augustine, Samuel C.

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N2 - The purpose of this investigation was to synthesize and purify radiolabeled 9- or 10-monoiodostearyl carnitine for potential use as a perfusion and metabolic imaging agent for the heart. Oleic acid was iodinated via a free radical addition reaction of HI across the double bond to give 9- or 10-monoiodostearic acid which in turn was esterified with carnitine. The identify of 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine was determined using nuclear magnetic resonance (NMR), infrared (i.r.), ultraviolet (u.v.), and mass spectroscopy. The purity of the fatty acid and carnitine ester was established by thin layer chromatography. 9- or 10-Monoiodo[125I]stearic acid and 9- or 10-monoiodo[125I]stearyl carnitine were synthesized via the isotopic exchange of 125I for cold iodine bonded to 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine.

AB - The purpose of this investigation was to synthesize and purify radiolabeled 9- or 10-monoiodostearyl carnitine for potential use as a perfusion and metabolic imaging agent for the heart. Oleic acid was iodinated via a free radical addition reaction of HI across the double bond to give 9- or 10-monoiodostearic acid which in turn was esterified with carnitine. The identify of 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine was determined using nuclear magnetic resonance (NMR), infrared (i.r.), ultraviolet (u.v.), and mass spectroscopy. The purity of the fatty acid and carnitine ester was established by thin layer chromatography. 9- or 10-Monoiodo[125I]stearic acid and 9- or 10-monoiodo[125I]stearyl carnitine were synthesized via the isotopic exchange of 125I for cold iodine bonded to 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine.

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10.1016/0883-2889(89)90168-8