Synthesis, radiosynthesis and first in vitro evaluation of novel PET-tracers for the dopamine transporter: [11C]IPCIT and [18F]FE@IPCIT

Rami-Mark, Christina; Bornatowicz, Birgit; Fink, Cornel; Otter, Paul; Ungersboeck, Johanna; Vraka, Chrysoula; Haeusler, Daniela; Nics, Lukas; Spreitzer, Helmut; Hacker, Marcus; Mitterhauser, Markus; Wadsak, Wolfgang

doi:10.1016/j.bmc.2013.10.046

Cited by 8 publications

(4 citation statements)

References 33 publications

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“…Cocaine (480)w as heated at reflux with HCl for 6h,f ollowed by treatment with POCl 3 and MeOH,a ffording intermediate 481.AMichael addition reaction of 481 with PhMgBr gave adduct 482,w hich was subjected to an iodinationr eactiont og ive 483.T reatmento f483 with 1-chloroethyl-chloroformate under reflux in DCE for 24 h, followed by reflux in CH 3 OH for 4h,g ave the secondary amine 484. [187] An alkylation reactionb etween amine 484 and 1bromo-3-fluoropropane in the presence of Et 3 Nand KI afforded fluoroalkylated amine 485.AP d-catalyzedc oupling reaction between 485 and 1,1,1,2,2,2-hexamethyldistannane provided intermediate 486,w hich was substituted with 123 Ia nions to afford 479. [188] 9.…”

Section: Sar164653mentioning

confidence: 99%

“…A Michael addition reaction of 481 with PhMgBr gave adduct 482 , which was subjected to an iodination reaction to give 483 . Treatment of 483 with 1‐chloroethyl‐chloroformate under reflux in DCE for 24 h, followed by reflux in CH 3 OH for 4 h, gave the secondary amine 484 . An alkylation reaction between amine 484 and 1‐bromo‐3‐fluoropropane in the presence of Et 3 N and KI afforded fluoroalkylated amine 485 .…”

Section: β‐Aasmentioning

confidence: 99%

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Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Mei

Han

White

et al. 2020

Chemistry A European J

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Structural analysis of modern pharmaceutical practices allows for the identification of two rapidly growing trends: the introduction of tailor‐made amino acids and the exploitation of fluorinated motifs. Curiously, the former represents one of the most ubiquitous classes of naturally occurring compounds, whereas the latter is the most xenobiotic and comprised virtually entirely of man‐made derivatives. Herein, 39 selected compounds, featuring both of these traits in the same molecule, are profiled. The total synthesis, source of the corresponding amino acids and fluorinated residues, and medicinal chemistry aspects and biological properties of the molecules are discussed.

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Section: Sar164653mentioning

confidence: 99%

Section: β‐Aasmentioning

confidence: 99%

Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Mei

Han

White

et al. 2020

Chemistry A European J

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“…Similarly, when ranking candidate radiotracers for BBB penetration, it is important to include in the analysis known successful radiotracers. A recently proposed methodology uses high performance liquid chromatography for rapid screening and ranking of candidate radiotracers in terms of permeability, plasma protein binding and compound-membrane interaction ( Tavares et al, 2012b ) ( Figure 4 ) and has been adopted by different research groups working on novel radiotracer development ( Blair et al, 2013 ; Gilfillan et al, 2013 ; Mark et al, 2013 ; Philippe et al, 2013a , b ; Rami-Mark et al, 2013 ). This chromatography method uses compound retention time information to derive permeability, plasma protein binding and compound-membrane interaction and vs. a calibration curve.…”

Section: The Process Of Radiotracer Discovery and Developmentmentioning

confidence: 99%

Rapidly (and Successfully) Translating Novel Brain Radiotracers From Animal Research Into Clinical Use

Shaw

Tamagnan²,

Tavares

2020

Front. Neurosci.

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The advent of preclinical research scanners for in vivo imaging of small animals has added confidence into the multi-step decision-making process of radiotracer discovery and development. Furthermore, it has expanded the utility of imaging techniques available to dissect clinical questions, fostering a cyclic interaction between the clinical and the preclinical worlds. Significant efforts from medicinal chemistry have also made available several high-affinity and selective compounds amenable for radiolabeling, that target different receptors, transporters and enzymes in vivo . This substantially increased the range of applications of molecular imaging using positron emission tomography (PET) or single photon emission computed tomography (SPECT). However, the process of developing novel radiotracers for in vivo imaging of the human brain is a multi-step process that has several inherent pitfalls and technical difficulties, which often hampers the successful translation of novel imaging agents from preclinical research into clinical use. In this paper, the process of radiotracer development and its relevance in brain research is discussed; as well as, its pitfalls, technical challenges and future promises. Examples of successful and unsuccessful translation of brain radiotracers will be presented.

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“…In contrast to phenolic O-alkylation, no increase in yield was observed in the presence of sodium iodide. 75 Another coupling reaction with an acid precursor was conducted by Philippe et al, in order to obtain a derivative of the melanin concentrating hormone receptor 1 antagonist SNAP-7941 52. Despite screening different solvents, temperatures and reaction times, no reaction of the radiolabelled building block was observed.…”

Section: [ 18 F]fluoroethyl Halides and Sulfonatesmentioning

confidence: 99%

Fluorine-18 labelled building blocks for PET tracer synthesis

et al. 2017

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Positron emission tomography (PET) is an important driver for present day healthcare. Fluorine-18 is the most widely used radioisotope for PET imaging and a thorough overview of the available radiochemistry methodology is a prerequisite for selection of a synthetic approach for new fluorine-18 labelled PET tracers. These PET tracers can be synthesised either by late-stage radiofluorination, introducing fluorine-18 in the last step of the synthesis, or by a building block approach (also called modular build-up approach), introducing fluorine-18 in a fast and efficient manner in a building block, which is reacted further in one or multiple reaction steps to form the PET tracer. This review presents a comprehensive overview of the synthesis and application of fluorine-18 labelled building blocks since 2010.

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Synthesis, radiosynthesis and first in vitro evaluation of novel PET-tracers for the dopamine transporter: [11C]IPCIT and [18F]FE@IPCIT

Cited by 8 publications

References 33 publications

Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Tailor‐Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals

Rapidly (and Successfully) Translating Novel Brain Radiotracers From Animal Research Into Clinical Use

Fluorine-18 labelled building blocks for PET tracer synthesis

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