Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo.

doi:10.1021/acs.jmedchem.7b01245

Paper

Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo.

Published Jan 11, 2018 · B. Zlatopolskiy, J. Zischler, D. Schäfer

Journal of medicinal chemistry

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58

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Abstract

Tryptophan and its metabolites are involved in different physiological and pathophysiological processes. Consequently, positron emission tomography (PET) tracers addressing tryptophan metabolic pathways should allow the detection of different pathologies like neurological disorders and cancer. Herein we report an efficient method for the preparation of fluorotryptophans labeled in different positions with 18F and their biological evaluation. 4-7-[18F]Fluorotryptophans ([18F]FTrps) were prepared according to a modified protocol of alcohol-enhanced Cu-mediated radiofluorination in 30-53% radiochemical yields. In vitro experiments demonstrated high cellular uptake of 4-7-[18F]FTrps in different tumor cell lines. 4, 5-, and 6-[18F]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[18F]FTrp demonstrated a high in vivo stability and enabled a clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains. Moreover 7-[18F]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[18F]FTrp represents a highly promising PET probe for imaging of Trp metabolism.

In Vitro Study

Study Snapshot

7-[18F]Fluorotryptophan is a promising PET probe for imaging tryptophan metabolism in vivo, enabling clear delineation of serotonergic areas and melatonin-producing pineal gland in rat brains and tumor xenografts

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo.

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References

Citations

Tryptophan Kynurenine Pathway-Based Imaging Agents for Brain Disorders and Oncology—From Bench to Bedside

Tryptophan-based radiotracers show potential for imaging brain disorders and oncology, but barriers remain in clinical translation.

The Chicken Embryo: An Old but Promising Model for In Vivo Preclinical Research

The chicken embryo is a valuable model for preclinical research due to its accessibility, affordability, and relevance to human biology, enabling real-time studies of tissue development, tumor growth, angiogenesis, and drug delivery.

Automation of Copper-Mediated 18F-Fluorination of Aryl Pinacol Boronates Using 4-Dimethylaminopyridinium Triflate

The automated synthesis of 6-L-[18F]FDOPA using the Cu(OTf)2(Py)4 catalyst and DMAPOTf elution on the TRACERlab automation platform achieved a comparable activity yield to previous work using Bu4NOTf as the PTC.

Evaluation of chicken chorioallantoic membrane model for tumor imaging and drug development: Promising findings.

The chicken chorioallantoic membrane model is a promising tool for quickly determining the in vivo properties of radiolabeled peptides targeting biomarkers, potentially benefiting early monitoring of new drug effects through PET imaging.

Escherichia coli adapts metabolically to 6- and 7-fluoroindole, enabling proteome-wide fluorotryptophan substitution

E. coli successfully adapts to 6- and 7-fluoroindole, enabling proteome-wide fluorotryptophan substitution, enabling fluorine-based life and a potential new food source.

Preparation of NIn-Methyl-6-[18F]fluoro- and 5-Hydroxy-7-[18F]fluorotryptophans as Candidate PET-Tracers for Pathway-Specific Visualization of Tryptophan Metabolism

NIn-methyl-6-[18F]fluorotryptophan and 5-hydroxy-7-[18F]fluorotryptophan show promise as promising candidate probes for pathway-specific visualization of tryptophan metabolism in preclinical evaluation.

Escherichia coli adapts metabolically to 6- and 7-fluoroindole, enabling proteome-wide fluorotryptophan substitution

Escherichia coli successfully adapts to 6- and 7-fluoroindole, enabling proteome-wide fluorotryptophan substitution, enabling fluorine-based life and a potential new food source.