Synthesis of 4-([<sup>18</sup>F]fluoromethyl)-2-chlorophenylisothiocyanate: A novel bifunctional <sup>18</sup>F-labelling agent

Wüst, F.; Müller, M.; Bergmann, Ralf

doi:10.1524/ract.92.4.349.35590

Cited by 12 publications

(9 citation statements)

References 20 publications

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“…The introduction of [ 18 F]fluoride into the benzylic position of precursors occurs as previously described for aliphatic compounds, under milder reaction conditions in most of the cases due to the comparatively higher reactivity of the benzylic position. In this regard, the metabolic stability of benzyl [ 18 F]fluorides is also decreased [20]. Additionally, similar observations were made for allyl fluorides [21].…”

Section: Introductionmentioning

confidence: 70%

Methods to Increase the Metabolic Stability of 18F-Radiotracers

2015

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Abstract:The majority of pharmaceuticals and other organic compounds incorporating radiotracers that are considered foreign to the body undergo metabolic changes in vivo. Metabolic degradation of these drugs is commonly caused by a system of enzymes of low substrate specificity requirement, which is present mainly in the liver, but drug metabolism may also take place in the kidneys or other organs. Thus, radiotracers and all other pharmaceuticals are faced with enormous challenges to maintain their stability in vivo highlighting the importance of their structure. Often in practice, such biologically active molecules exhibit these properties in vitro, but fail during in vivo studies due to obtaining an increased metabolism within minutes. Many pharmacologically and biologically interesting compounds never see application due to their lack of stability. One of the most important issues of radiotracers development based on fluorine-18 is the stability in vitro and in vivo. Sometimes, the metabolism of

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Section: Introductionmentioning

confidence: 70%

Methods to Increase the Metabolic Stability of 18F-Radiotracers

2015

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“…To avoid using harsh reaction conditions for a nucleophilic introduction of [ 18 F]fluoride into aromatic compounds, the 4‐fluoromethylbenzoate moiety was chosen instead allowing an introduction of [ 18 F]fluoride under milder conditions . Furthermore, the cross‐coupling strategy was chosen to overcome problems with the oxidation of the phosphorous during the introduction of fluorine‐18.…”

Section: Direct Approachmentioning

confidence: 99%

Recent progress using the Staudinger ligation for radiolabeling applications

Mamat

Gott

Steinbach

2018

Labelled Comp Radiopharmac

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The increasing application of positron emission tomography and single-photon emission computer tomography in radiopharmacy and nuclear medicine has stimulated the development of a multitude of novel and versatile bioorthogonal conjugation techniques. Currently, there is particular interest in radiolabeling biologically active, high molecular weight compounds like peptides, proteins, or antibodies, but also for the labeling of small organic compounds. An enormous challenge in radiolabeling these biologically active molecules is that the introduction of radiohalogens like fluorine-18 as well as various radiometals proceeds under harsh conditions, which could destroy the biomolecule. The Staudinger ligation is one of the most powerful bioorthogonal conjugation techniques. The reaction proceeds over wide temperature and pH ranges; an amide (peptide) bond is formed as the ligation unit, which minimizes distortion of the structure; no isomers are obtained; and the reaction proceeds without any metal catalyst. Due to this adaptability, this robust ligation type is a perfect candidate with a high potential for various applications in the field of radiopharmacy for the labeling of biomolecules under mild conditions. This review summarizes recent research concerning the implementation of the Staudinger ligation for radiolabeling applications.

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“…There are anecdotal reports of potential anti-tumour activity of D-glucosamine; apoptosis is induced in cells at high concentration in a non-tumour selective manner. 1 In the early 1990s, N-[ 18 F]uoroacetyl-D-glucosamine (1) was the rst D-glucosamine analogue to be radiolabelled with 18 F, using [ 18 F]uoroethylbromoacetate as the prosthetic group (Fig. 1).…”

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confidence: 99%

“…[2][3][4] This radiotracer has been used specically to distinguish between bacterial and non-bacterial inammation, one of the only PET tracers able to do this. The only other 18 F-labelled glucosamine radiotracer of note, is N-(2-[ 18 F]uoro-4-nitrobenzoyl)glucosamine (2), which was shown to have a relatively low tumour uptake of 0.44 AE 0.12% ID per g at 60 minutes. 5 Both 68 Ga and 99m Tc radiometal-labelled glucosamine analogues, have also been reported, showing the potential of novel appropriately labelled glucosamine compounds for tumour imaging.…”

mentioning

confidence: 99%

“…6,7 Our aim was to increase the available library of 18 F-labelled glucosamine analogues, in an attempt to nd a positron emitting radiotracer for tumour imaging applications. Regarding compound design, we explored three separate prosthetic group approaches that are readily accessible to 18 F radiochemistryimine formation by aldehyde condensation, alkylation, and copper-catalysed click chemistry (Fig. 2).…”

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confidence: 99%

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