Radiolabeled 9- or 10-monoiodostearic acid and 9- or 10-monoiodostearyl carnitine--I. Synthesis and purification.
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 identity 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.
Reed
K W
KW
Department of Pharmaceutical Sciences, College of Pharmacy, University of Nebraska Medical Center, Omaha 68105-1065.
Ueda
C T
CT
Murray
W J
WJ
Augustine
S C
SC
D002331:Carnitine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D007457:Iodine Radioisotopes; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013229:Stearic Acids / Q000138:chemical synthesis / Q000302:isolation & purification*
D007457:Iodine Radioisotopes; D013229:Stearic Acids; C059308:9-iodooctadecanoic acid; C059309:10-iodooctadecanoic acid; C059310:9-iodostearyl carnitine; C059311:10-iodostearyl carnitine; D002331:Carnitine