Synthesis of [11C-carbonyl]hydroxyureas by a rhodium-mediated carbonylation reaction using [11C]carbon monoxide

Barletta, Julien; Karimi, Farhad; Långström, Bengt

doi:10.1002/jlcr.1062

Cited by 25 publications

(36 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Although it has been reported that heated zinc can reduce 11 C]CO 2 to 11 C]CO, this reaction did not work in our lab [36]. A possible explanation could be the use of 0.5% oxygen in the target gas, which is a factor 10 higher than used previously [24,36]. To circumvent potential deactivation of zinc by rapid oxidation, a column containing silica gel (100/120 mesh) was implemented to chromatographically purify 11 C]CO 2 .…”

Section: Resultsmentioning

confidence: 81%

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

et al. 2012

View full text Add to dashboard Cite

BackgroundAt present, several positron emission tomography (PET) tracers are in use for imaging P-glycoprotein (P-gp) function in man. At baseline, substrate tracers such as R-[11C]verapamil display low brain concentrations with a distribution volume of around 1. [11C]phenytoin is supposed to be a weaker P-gp substrate, which may lead to higher brain concentrations at baseline. This could facilitate assessment of P-gp function when P-gp is upregulated. The purpose of this study was to synthesize [11C]phenytoin and to characterize its properties as a P-gp tracer.Methods[11C]CO was used to synthesize [11C]phenytoin by rhodium-mediated carbonylation. Metabolism and, using PET, brain pharmacokinetics of [11C]phenytoin were studied in rats. Effects of P-gp function on [11C]phenytoin uptake were assessed using predosing with tariquidar.Results[11C]phenytoin was synthesized via [11C]CO in an overall decay-corrected yield of 22 ± 4%. At 45 min after administration, 19% and 83% of radioactivity represented intact [11C]phenytoin in the plasma and brain, respectively. Compared with baseline, tariquidar predosing resulted in a 45% increase in the cerebral distribution volume of [11C]phenytoin.ConclusionsUsing [11C]CO, the radiosynthesis of [11C]phenytoin could be improved. [11C]phenytoin appeared to be a rather weak P-gp substrate.

show abstract

Section: Resultsmentioning

confidence: 81%

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

et al. 2012

View full text Add to dashboard Cite

show abstract

“…[ (Fig. (47)), its structural analogue 1-hydroxy-3-phenyl[ 11 C]urea was synthesized using similar methods with 35±4% radiochemical yield decay-corrected (EOB) and a specific activity of 686 GBq/μmol [201]. This method provides a new way of synthesizing [ 11 C]hydroxyurea with more accurate chemical yield and greater radiochemical purity compared to earlier methods [202].…”

Section: Rhodium-mediated Carbonylationmentioning

confidence: 99%

C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

View full text Add to dashboard Cite

Carbon-11 (C-11) radiotracers are widely used for the early diagnosis of cancer, monitoring therapeutic response to cancer treatment, and pharmacokinetic investigations of anticancer drugs. PET imaging permits non-invasive monitoring of metabolic processes and molecular targets, while carbon-11 radiotracers allow a "hot-for cold" substitution of biologically active molecules. Advances in organic synthetic chemistry and radiochemistry as well as improved automated techniques for radiosynthesis have encouraged investigators in developing carbon-11 tracers for use in oncology imaging studies. The short half-life of carbon-11 (20.38 minutes) creates special challenges for the synthesis of C-11 labeled tracers; these include the challenges of synthesizing C-11 target compounds with high radiochemical yield, high radiochemical purity and high specific activity in a short time and on a very small scale. The optimization of conditions for making a carbon-11 tracer include the late introduction of the C-11 isotope, the rapid formation and purification of the target compound, and the use of automated systems to afford a high yield of the target compound in a short time. In this review paper, we first briefly introduce some basic principles of PET imaging of cancer; we then discuss principles of carbon-11 radiochemistry, focus on specific advances in radiochemistry, and describe the synthesis of C-11 radiopharmaceuticals developed for cancer imaging. The carbon-11 radiochemistry approaches described include the N,O, and S-alkylations of [(11)C]methyl iodide/[(11)C]methyl triflate and analogues of [(11)C]methyl iodide and their applications for making carbon-11 tracers; we then address recent advances in exploring a transmetallic complex mediated [(11)C]carbonyl reaction for oncologic targets.

show abstract

“…[110] Abgelöst wurde dieses Verfahren durch die Einführung von Hochdruckreaktionssystemen (HPLC-Mikroautoklaven) [36,37] [117] oder 1,2,2,6,6-Pentamethylpiperidin [118] Rhodiumvermittelte Carbonylierungen [122][123][124] sind eine weitere Möglichkeit zur Einführung von [ 11 C]CO in organische Moleküle.…”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

“…11 C-markierte Malonate, [123] Hydroxyharnstoffe, [122] Carbamate [124] und Diphenylharnstoffe [124] …”

Section: Bei Den Stille-kreuzkupplungen Mit [unclassified

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

et al. 2008

View full text Add to dashboard Cite

Die Positronenemissionstomographie (PET) ist eine leistungsfähige Bildgebungsmethode, die zur Untersuchung und Visualisierung der menschlichen Physiologie eingesetzt wird. Das Funktionsprinzip der PET beruht auf der Detektion positronenemittierender Radiopharmazeutika. Aus PET‐Experimenten können direkte Informationen über Stoffwechselvorgänge, Rezeptor‐Enzym‐Funktionen und biochemische Mechanismen im lebenden Gewebe erhalten werden. Anders als die Magnetresonanztomographie (MRT) und die Computertomographie (CT), die in erster Linie anatomische Bilder liefern, kann die PET chemische Veränderungen messen, die bereits vor dem Auftreten anatomischer Krankheitszeichen auftreten. Die PET ist dabei, sich als eine revolutionäre Methode für die Diagnostik von Körperfunktionen zu etablieren, die die Anwendung individueller, auf den Patienten zugeschnittener Behandlungsmethoden ermöglicht. Allerdings ist die Entwicklung von Synthesestrategien für neuartige positronenemittierende Moleküle nicht trivial. In diesem Aufsatz diskutieren wir die entscheidenden Aspekte bei der Synthese von PET‐Radiotracern mit den kurzlebigen Positronenemittern 11C, 18F, 15O und 13N. Der Schwerpunkt liegt auf den jüngsten Fortschritten bei der Entwicklung von Radiomarkierungsstrategien. Wir hoffen, dass dieser Aufsatz das Interesse von Synthesechemikern auch außerhalb der Radiochemie finden wird und die Bedeutung der PET in der molekularen Bildgebung sowie den Bedarf an neuen, innovativen chemischen Strategien für verbesserte Radiomarkierungstechniken aufzeigt.

show abstract

Synthesis of [11C-carbonyl]hydroxyureas by a rhodium-mediated carbonylation reaction using [11C]carbon monoxide

Abstract: Summary

Cited by 25 publications

References 19 publications

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

C-11 Radiochemistry in Cancer Imaging Applications

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie

Contact Info

Product

Resources

About

Synthesis of [11C-carbonyl]hydroxyureas by a rhodium-mediated carbonylation reaction using [11C]carbon monoxide

Abstract: Summary

Cited by 25 publications

References 19 publications

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

[11C]phenytoin revisited: synthesis by [11C]CO carbonylation and first evaluation as a P-gp tracer in rats

C-11 Radiochemistry in Cancer Imaging Applications

Synthese von 11C‐, 18F‐, 15O‐ und 13N‐Radiotracern für die Positronenemissionstomographie

Contact Info

Product

Resources

About

Synthese von ¹¹C‐, ¹⁸F‐, ¹⁵O‐ und ¹³N‐Radiotracern für die Positronenemissionstomographie