Synthesis of a <sup>11</sup>C‐labelled taxane derivative by [1‐<sup>11</sup>C]acetylation

Mäding, P.; Zessin, J.; Pleiß, U.; Füchtner, F.; Wüst, F.

doi:10.1002/jlcr.1059

Cited by 10 publications

(6 citation statements)

References 9 publications

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“…[131,132] The complex biological molecule BAY 59-8862, a taxane derivative of interest as an oncology biomarker, has also been labeled in a similar way through reaction of its lithium precursor with [ 11 C]acetyl chloride; the latter species was prepared from the reaction of [ 11 C]CO 2 with methyl magnesium bromide and phthaloyl dichloride. [133] The synthesis of [carbonyl-11 C]amides has been achieved directly from [ 11 C]carboxymagnesium halides [134,135] and enhanced further by using microwave heating [136] (Scheme 28). Associ-ated challenges with the direct reaction of [ 11 C]CO 2 with organometallic reagents include contamination with atmospheric CO 2 , which adversely affects the specific activity of the produced tracer, and the sensitivity of the organometallic reagents to hydrolysis.…”

Section: Synthesis With [ 11 C]carbon Dioxidementioning

confidence: 99%

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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Positron emission tomography (PET) is a powerful and rapidly developing area of molecular imaging that is used to study and visualize human physiology by the detection of positron-emitting radiopharmaceuticals. Information about metabolism, receptor/enzyme function, and biochemical mechanisms in living tissue can be obtained directly from PET experiments. Unlike magnetic resonance imaging (MRI) or computerized tomography (CT), which mainly provide detailed anatomical images, PET can measure chemical changes that occur before macroscopic anatomical signs of a disease are observed. PET is emerging as a revolutionary method for measuring body function and tailoring disease treatment in living subjects. The development of synthetic strategies for the synthesis of new positron-emitting molecules is, however, not trivial. This Review highlights key aspects of the synthesis of PET radiotracers with the short-lived positron-emitting radionuclides (11)C, (18)F, (15)O, and (13)N, with emphasis on the most recent strategies.

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Section: Synthesis With [ 11 C]carbon Dioxidementioning

confidence: 99%

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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“…26 More indirectly, carboxylation can be followed by activation using reagents such as thionyl chloride or phthaloyl dichloride to prepare active acylation intermediates such as [ 11 C]acetyl and [ 11 C]propionyl chloride. [27][28][29][30] While Grignard reagents have proven useful in the synthesis of simple [ 11 C]carboxylic acids and a selection of their derivatives, their high reactivity inherently limits the potential scope of their applications and enforces requirements for careful handling procedures. Since Grignard reagents readily absorb CO from the atmosphere and are moisture-sensitive they are ideally prepared fresh and manipulated under an inert atmosphere This journal is c The Royal Society of Chemistry 2013 Chem.…”

Section: Grignard Reagentsmentioning

confidence: 99%

11CO2 fixation: a renaissance in PET radiochemistry

et al. 2013

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Carbon-11 labelled carbon dioxide is the cyclotron-generated feedstock reagent for most positron emission tomography (PET) tracers using this radionuclide. Most carbon-11 labels, however, are installed using derivative reagents generated from [11C]CO2. In recent years, [11C]CO2 has seen a revival in applications for the direct incorporation of carbon-11 into functional groups such as ureas, carbamates, oxazolidinones, carboxylic acids, esters, and amides. This review summarizes classical [11C]CO2 fixation strategies using organometallic reagents and then focuses on newly developed methods that employ strong organic bases to reversibly capture [11C]CO2 into solution, thereby enabling highly functionalized labelled compounds to be prepared. Reactions and radiopharmaceuticals that have been translated to the clinic are highlighted.

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“…To investigate the general pharmacokinetics of this drug in vivo with PET and to monitor the body's response after treatment with this drug, [ 11 C]BAY 59-8862 was synthesized [214] from [1-11 C]acetyl chloride [215], which was made by reaction of [ 11 C]CO 2 with MeMgBr followed by quenching the resulting [ 11 C]acetate solution with phthaloyl dichloride and 2,6-t-butylpyridine (Fig. (53)).…”

Section: Bay59-8862mentioning

confidence: 99%

C-11 Radiochemistry in Cancer Imaging Applications

Mach

2010

CTMC

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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.

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Synthesis of a ¹¹C‐labelled taxane derivative by [1‐¹¹C]acetylation

Abstract: SummaryThe 11 C-labelling of the taxane derivative BAY 59-8862 (1), a potent anticancer drug, was carried out as a module-assisted automated multi-step synthesis procedure.

Cited by 10 publications

References 9 publications

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

11CO2 fixation: a renaissance in PET radiochemistry

C-11 Radiochemistry in Cancer Imaging Applications

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Synthesis of a 11C‐labelled taxane derivative by [1‐11C]acetylation

Abstract: SummaryThe 11 C-labelling of the taxane derivative BAY 59-8862 (1), a potent anticancer drug, was carried out as a module-assisted automated multi-step synthesis procedure.

Cited by 10 publications

References 9 publications

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

11CO2 fixation: a renaissance in PET radiochemistry

C-11 Radiochemistry in Cancer Imaging Applications

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Synthesis of a ¹¹C‐labelled taxane derivative by [1‐¹¹C]acetylation

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography