Synthesis and preliminary evaluation of [1-11C]hexanoate as a PET tracer of fatty acid metabolism

Ishiwata, Kiichi; Ogawa, Koji; Sasaki, Toru; Toyama, Hinako; Ishii, Shin‐ichi; Nozaki, Tadashi; Senda, Michio

doi:10.1007/bf03165010

Cited by 11 publications

(13 citation statements)

References 36 publications

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“…Regarding the usefulness of "C-fatty acids other than [1-"C]octanoate, [1-' 1 C] acetate has been used as a tracer of the TCA cycle flux and thus overall oxidative metabolism in the myocardium." In addition, Ishiwata K et al 15 suggested the potential use of [1-"Clhexanoate for imaging the oxidation process in the myocardium and brain. Referring to these 1 'C-fatty acids, [1-"C]octanoate also seems to be available for measuring the oxidative metabolism in the brain.…”

Section: Discussionmentioning

confidence: 98%

“…13 Nagatsugi F et al 14 synthesized 8- [ 18 F]fluorooctanoic acid and its related compounds and showed their biodistribution and brain uptake in rats. Recently, Ishiwata K et al 15 evaluated the potential of [1-"C]hexanoate ("C-HA) as a radiopharmaceutical for assessing fatty acid metabolism in the myocardium and brain by means of biodistribution studies in mice. They confirmed that "C-HA is taken up into the brain rather more efficiently than [1-' 4C]acetate or [1-14C]palmitate.…”

Section: Introductionmentioning

confidence: 99%

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Brain uptake and metabolism of [1-11C]octanoate in rats: Pharmacokinetic basis for its application as a radiopharmaceutical for studying brain fatty acid metabolism

et al. 1995

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The uptake of octanoate in rat brain and its metabolism were investigated by means of intravenously injecting [1-11C] or [1-14C]octanoate as a tracer. The radioactivity in the cerebrum was increased by an injection of [1-11C]octanoate, and reached its peak level (0.33% ID/g) in about 2 to 5 min, and then decreased slowly. The cerebrum-to-blood ratio of the radioactivity increased with time over a period of 30 min. At 30 sec, [1-11C]octanoate that remained unchanged in the cerebrum accounted for only 8% of the total radioactivity, in spite of there being about 90% in the blood. By means of an injection of [1-14C]octanoate, more than 70% of the total radioactivity in the cerebrum was found to be attributable to radiolabeled glutamate and glutamine at each time point measured between 30 sec and 30 min. The results show that [1-11C]octanoate enters rat brain easily and is trapped in the cerebrum, probably in the form of glutamate and glutamine, and the usefulness of [1-11C]octanoate as a radiopharmaceutical for studying brain fatty acid metabolism by positron emission tomography is therefore suggested.

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Section: Discussionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Brain uptake and metabolism of [1-11C]octanoate in rats: Pharmacokinetic basis for its application as a radiopharmaceutical for studying brain fatty acid metabolism

et al. 1995

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“…24,25 We have developed a fullyautomated apparatus for the preparation of the [1-11 C]carboxylic acids and used it for routinely supplying [1-11 C]octanoic acid to PET studies. 26 In the manipulation of radioactivity, it is most important to minimize the operator's exposure to radiation.…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, we have found that [1- 11 C]octanoic acid, which is obtainable from [ 11 C]CO 2 and the Grignard reagent heptylmagnesium bromide, has potential as a radiotracer in PET imaging of brain functions. , We have developed a fully-automated apparatus for the preparation of the [1- 11 C]carboxylic acids and used it for routinely supplying [1- 11 C]octanoic acid to PET studies . In the manipulation of radioactivity, it is most important to minimize the operator's exposure to radiation.…”

Section: Introductionmentioning

confidence: 99%

Kinetic Study on the Reaction of Heptylmagnesium Bromide with Carbon Dioxide Using Non-Carrier-Added C-11 Labeled Carbon Dioxide

et al. 1996

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We studied the chemical kinetics of the Grignard reaction between heptylmagnesium bromide and carbon dioxide with a new experimental method utilizing positron emitter C-11 labeled CO 2 . A series of experiments was carried out in the presence of a large excess of heptylmagnesium bromide (C 7 H 15 MgBr ) ca. 1.0 × 10 -4 mol) relative to carbon dioxide (CO 2 ) ca. 1.2 × 10 -8 mol). An empirical scheme was assumed based on the results obtained in experiments at the reaction temperature of 20°C. Differential equations were determined by the scheme. It was possible to calculate rate constant values at each temperature of the reaction (at 10, 20, and 30°C) by fitting the equations to experimental measurements. We obtained the value 1.76 × 10 4 J/mol as the activation energy of the main reaction between C 7 H 15 MgBr and CO 2 from the Arrhenius plot (r 2 ) 0.9986) of the rate constants. The reaction simulated with the equations and the activation energy value were in good agreement with the ones obtained experimentally. The obtained value for the activation energy of the main reaction would be applicable to the more common type of Grignard carboxylation with a large excess of CO 2 .

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“…512 In PET imaging, it has been evaluated to assess FA metabolism in myocardial and brain tissue. 513,514 • Linoleic acid is an essential FA crucial for the biosynthesis of arachidonic acid. Due to its biological role, it could be used for visualizing FAs metabolism in physio-/pathological conditions.…”

Section: Fatty Acidsmentioning

confidence: 99%

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

et al. 2022

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The presence of positron emission tomography (PET) centers at most major hospitals worldwide, along with the improvement of PET scanner sensitivity and the introduction of total body PET systems, has increased the interest in the PET tracer development using the short-lived radionuclides carbon-11. In the last few decades, methodological improvements and fully automated modules have allowed the development of carbon-11 tracers for clinical use. Radiolabeling natural compounds with carbon-11 by substituting one of the backbone carbons with the radionuclide has provided important information on the biochemistry of the authentic compounds and increased the understanding of their in vivo behavior in healthy and diseased states. The number of endogenous and natural compounds essential for human life is staggering, ranging from simple alcohols to vitamins and peptides. This review collates all the carbon-11 radiolabeled endogenous and natural exogenous compounds synthesised to date, including essential information on their radiochemistry methodologies and preclinical and clinical studies in healthy subjects.

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Synthesis and preliminary evaluation of [1-11C]hexanoate as a PET tracer of fatty acid metabolism

Cited by 11 publications

References 36 publications

Brain uptake and metabolism of [1-11C]octanoate in rats: Pharmacokinetic basis for its application as a radiopharmaceutical for studying brain fatty acid metabolism

Brain uptake and metabolism of [1-11C]octanoate in rats: Pharmacokinetic basis for its application as a radiopharmaceutical for studying brain fatty acid metabolism

Kinetic Study on the Reaction of Heptylmagnesium Bromide with Carbon Dioxide Using Non-Carrier-Added C-11 Labeled Carbon Dioxide

Radiosynthesis, Preclinical, and Clinical Positron Emission Tomography Studies of Carbon-11 Labeled Endogenous and Natural Exogenous Compounds

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