Universität zu Köln

Ziatopolskiy, Boris D., Zischler, Johannes ORCID: 0000-0003-3996-7473, Schaefer, Dominique, Urusova, Elizaveta A., Guliyev, Mehrab, Bannykh, Olesia, Endepols, Heike ORCID: 0000-0002-6166-4818 and Neumaier, Bernd (2018). Discovery of 7-[F-18]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo. J. Med. Chem., 61 (1). S. 189 - 207. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-4804

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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 F-18 and their biological evaluation. 4-7-[F-18]Fluorotryptophans ([F-18]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[F-18]FTrps in different tumor cell lines. 4, 5-, and 6-[F-18]FTrps, although stable in vitro, suffered from rapid in vivo defluorination. In contrast, 7-[F-18]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-[F-18]FTrp accumulated in different tumor xenografts in a chick embryo CAM model. Thus, 7-[F-18]FTrp represents a highly promising PET probe for imaging of Trp metabolism.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Ziatopolskiy, Boris D. UNSPECIFIED UNSPECIFIED UNSPECIFIED Zischler, Johannes UNSPECIFIED orcid.org/0000-0003-3996-7473 UNSPECIFIED Schaefer, Dominique UNSPECIFIED UNSPECIFIED UNSPECIFIED Urusova, Elizaveta A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Guliyev, Mehrab UNSPECIFIED UNSPECIFIED UNSPECIFIED Bannykh, Olesia UNSPECIFIED UNSPECIFIED UNSPECIFIED Endepols, Heike UNSPECIFIED orcid.org/0000-0002-6166-4818 UNSPECIFIED Neumaier, Bernd UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-198927
DOI:	10.1021/acs.jmedchem.7b01245
Journal or Publication Title:	J. Med. Chem.
Volume:	61
Number:	1
Page Range:	S. 189 - 207
Date:	2018
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-4804
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ALPHA-AMINO-ACIDS; METHYL-L-TRYPTOPHAN; ASYMMETRIC-SYNTHESIS; NI(II) COMPLEXES; INDOLEAMINE 2,3-DIOXYGENASE; MEDIATED RADIOFLUORINATION; ADDITION-REACTIONS; CRYSTAL-STRUCTURE; HOMOLOGATION; RADIOSYNTHESIS Multiple languages Chemistry, Medicinal Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19892