Home / Articles / 11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders

11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders

Boris D Zlatopolskiy 1, 2, 3, 4, 5
Boris D Zlatopolskiy
, 
Heike Endepols 1, 2, 3, 5, 6
Heike Endepols
, 
Raisa Nikolaevna Krasikova 7
Raisa Nikolaevna Krasikova
, 
Olga Stallitovna Fedorova 7
Olga Stallitovna Fedorova
, 
Johannes Ermert 2
Johannes Ermert
, 
Bernd Neumaier 1, 2, 3, 4, 5
Bernd Neumaier
1 University of Cologne, Institute of Radiochemistry and Experimental Molecular Imaging, Germany
2 Forschungszentrum Jülich GmbH, Institute of Neuroscience and Medicine, Nuclear Chemistry (INM-5), Germany
3 University of Cologne, Faculty of Medicine, Germany
4 Max Planck Institute for Metabolism Research, Germany
5 University of Cologne, University Hospital Cologne, Germany
6 University of Cologne, Nuclear Medicine Department, Germany
7 N.P. Bechtereva Institute of the Human Brain, St. Petersburg
10.1070/RCR4954
Published 30 November 2019
Review , RCR4954, Volume 89, Issue 9, 879-896
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Zlatopolskiy B. D. et al. 11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders // Russian Chemical Reviews. 2019. Vol. 89. No. 9. pp. 879-896.
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Zlatopolskiy B. D., Endepols H., Krasikova R. N., Fedorova O. S., Ermert J., Neumaier B. 11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders // Russian Chemical Reviews. 2019. Vol. 89. No. 9. pp. 879-896.
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TY - JOUR
DO - 10.1070/RCR4954
UR - https://rcr.colab.ws/publications/10.1070/RCR4954
TI - 11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders
T2 - Russian Chemical Reviews
AU - Zlatopolskiy, Boris D
AU - Endepols, Heike
AU - Krasikova, Raisa Nikolaevna
AU - Fedorova, Olga Stallitovna
AU - Ermert, Johannes
AU - Neumaier, Bernd
PY - 2019
DA - 2019/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 879-896
IS - 9
VL - 89
ER -
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@article{2019_Zlatopolskiy,
author = {Boris D Zlatopolskiy and Heike Endepols and Raisa Nikolaevna Krasikova and Olga Stallitovna Fedorova and Johannes Ermert and Bernd Neumaier},
title = {11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders},
journal = {Russian Chemical Reviews},
year = {2019},
volume = {89},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4954},
number = {9},
pages = {879--896},
doi = {10.1070/RCR4954}
}
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Zlatopolskiy, Boris D., et al. “11C- and 18F-labelled tryptophans as PET-tracers for imaging of altered tryptophan metabolism in age-associated disorders.” Russian Chemical Reviews, vol. 89, no. 9, Nov. 2019, pp. 879-896. https://rcr.colab.ws/publications/10.1070/RCR4954.
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Keywords

carbon-11
fluorine-18
neurodegenerative diseases
oncology
positron emission tomography
radiolabeling
tryptophan metabolism

Abstract

The ageing of the world's population is the result of increased life expectancy observed in almost all countries throughout the world. Consequently, a rising tide of ageing-associated disorders, like cancer and neurodegenerative diseases, represents one of the main global challenges of the 21st century. The ability of mankind to overcome these challenges is directly dependent on the capability to develop novel methods for therapy and diagnosis of age-associated diseases. One hallmark of age-related pathologies is an altered tryptophan metabolism. Numerous pathological processes including neurodegenerative and neurological diseases like epilepsy, Parkinson's and Alzheimer's diseases, cancer and diabetes exhibit marked changes in tryptophan metabolism. Visualization of key processes of tryptophan metabolic pathways, especially using positron emission tomography (PET) and related hybrid methods like PET/CT and PET/MRI, can be exploited to early detect the aforementioned disorders with considerable accuracy, allowing appropriate and timely treatment of patients. Here we review the published 11C- and 18F-labelled tryptophans with respect to the production and also preclinical and clinical evaluation as PET-tracers for visualization of different branches of tryptophan metabolism.

The bibliography includes 159 references.

Funders

Russian Science Foundation
20-53-12030\20
Deutsche Forschungsgemeinschaft
ZL 65/4-1

References

1.
rcr_89_9_879bib1
Orr
1957
2.
The changing landscape in translocator protein (TSPO) function
Selvaraj V., Stocco D.M.
Trends in Endocrinology and Metabolism , 2015
3.
L-Tryptophan: Basic Metabolic Functions, Behavioral Research and Therapeutic Indications
Richard D.M., Dawes M.A., Mathias C.W., Acheson A., Hill-Kapturczak N., Dougherty D.M.
International Journal of Tryptophan Research , 2009
6.
Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase
Rafice S., Chauhan N., Efimov I., Basran J., Raven E.
Biochemical Society Transactions , 2009
7.
Role of indoleamine 2,3-dioxygenase in health and disease
Yeung A.S., Terentis A., King N.C., Thomas S.
Clinical Science , 2015
8.
Tryptophan 2,3-dioxygenase is a key modulator of physiological neurogenesis and anxiety-related behavior in mice
Kanai M., Funakoshi H., Takahashi H., Hayakawa T., Mizuno S., Matsumoto K., Nakamura T.
Molecular Brain , 2009
9.
Kynurenine Pathway of Tryptophan Metabolism: Regulatory and Functional Aspects
Badawy A.A.
International Journal of Tryptophan Research , 2017
11.
IDO expression in the brain: a double-edged sword
Kwidzinski E., Bechmann I.
Journal of Molecular Medicine , 2007
12.
Kynurenines in the mammalian brain: when physiology meets pathology
Schwarcz R., Bruno J.P., Muchowski P.J., Wu H.
Nature Reviews Neuroscience , 2012
13.
Studies on Purified 3-Hydroxyanthranilic Acid Oxidase
Vescia A., di Prisco G.
Journal of Biological Chemistry , 1962
14.
Characterization of the Kynurenine Pathway in Human Neurons
Guillemin G.J., Cullen K.M., Lim C.K., Smythe G.A., Garner B., Kapoor V., Takikawa O., Brew B.J.
Journal of Neuroscience , 2007
15.
Serotonin: A never-ending story
Olivier B.
European Journal of Pharmacology , 2015
16.
Serotonin in the gut: Blessing or a curse
Banskota S., Ghia J., Khan W.I.
Biochimie , 2019
17.
rcr_89_9_879bib17
Maximino
2012
19.
Melatonin: Pharmacology, Functions and Therapeutic Benefits
Tordjman S., Chokron S., Delorme R., Charrier A., Bellissant E., Jaafari N., Fougerou C.
Current Neuropharmacology , 2017
20.
Melatonin—A pleiotropic, orchestrating regulator molecule
Hardeland R., Cardinali D.P., Srinivasan V., Spence D.W., Brown G.M., Pandi-Perumal S.R.
Progress in Neurobiology , 2011
21.
rcr_89_9_879bib21
Hardeland
Aging Dis. , 2012
22.
The kynurenine pathway and neurodegenerative disease
Maddison D.C., Giorgini F.
Seminars in Cell and Developmental Biology , 2015
23.
Serotonin in Parkinson's disease
Politis M., Niccolini F.
Behavioural Brain Research , 2015
24.
The serotonergic system in ageing and Alzheimer's disease
Rodríguez J.J., Noristani H.N., Verkhratsky A.
Progress in Neurobiology , 2012
25.
rcr_89_9_879bib25
Rubin de Celis Ferrari
Clinics , 2018
26.
Tumor immune escape mediated by indoleamine 2,3-dioxygenase
Zamanakou M., Germenis A.E., Karanikas V.
Immunology Letters , 2007
27.
Geisler S., Mayersbach P., Becker K., Schennach H., Fuchs D., Gostner J.M.
Pteridines , 2015
28.
The Plasma [Kynurenine]/[Tryptophan] Ratio and Indoleamine 2,3-Dioxygenase: Time for Appraisal
Badawy A.A., Guillemin G.
International Journal of Tryptophan Research , 2019
29.
Whole-Body 11C-5-Hydroxytryptophan Positron Emission Tomography as a Universal Imaging Technique for Neuroendocrine Tumors: Comparison with Somatostatin Receptor Scintigraphy and Computed Tomography
Orlefors H., Sundin A., Garske U., Juhlin C., Oberg K., Skogseid B., Langstrom B., Bergstrom M., Eriksson B.
Journal of Clinical Endocrinology and Metabolism , 2005
31.
5-HT radioligands for human brain imaging with PET and SPECT
Paterson L.M., Kornum B.R., Nutt D.J., Pike V.W., Knudsen G.M.
Medicinal Research Reviews , 2011
33.
rcr_89_9_879bib33
Bucherer
J. Prakt. Chem. , 1934
34.
rcr_89_9_879bib34
Washburn
J. Nucl. Med. , 1979
35.
Synthesis and purification of 11C-carboxyl-labeled amino acids
Hayes R.L., Washburn L.C., Wieland B.W., Sun T.T., Anon J.B., Butler T.A., Callahan A.P.
The International Journal of Applied Radiation and Isotopes , 1978
36.
rcr_89_9_879bib36
Hayes
J. Nucl. Med. , 1976
37.
Synthesis of 11C-dl-tryptophan and its purification using high-pressure liquid chromatography
Zalutsky M.R., Wu J., Harper P.V., Wickland T.
The International Journal of Applied Radiation and Isotopes , 1981
38.
Methods for (11) C- and (18) F-labelling of amino acids and derivatives for positron emission tomography imaging.
Ermert J., Coenen H.H.
Journal of Labelled Compounds and Radiopharmaceuticals , 2013
39.
Asymmetric Synthesis of Carbon-11 Labelled α-Amino Acids for PET
Popkov A., Elsinga P.
Current Organic Chemistry , 2013
41.
Efficient Enzymatic Preparation of13N-Labelled Amino Acids: Towards Multipurpose Synthetic Systems
da Silva E.S., Gómez-Vallejo V., Baz Z., Llop J., López-Gallego F.
Chemistry - A European Journal , 2016
42.
rcr_89_9_879bib42
Bjurling
1989
43.
5-Fluoro-[β-11C]-L-tryptophan is a functional analogue of 5-hydroxy-[β-11C]-L-tryptophan in vitro but not in vivo
Eriksson O., Selvaraju R., Borg B., Asplund V., Estrada S., Antoni G.
Nuclear Medicine and Biology , 2013
44.
The synthesis of [3-11C]pyruvic acid, a useful synthon, via an enzymatic route
Bjurling P., Watanabe Y., Långström B.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1988
45.
Synthesis of L-[β-11C]amino acids using immobilized enzymes
Ikemoto M., Sasaki M., Haradahira T., Yada T., Omura H., Furuya Y., Watanabe Y., Suzuki K.
Applied Radiation and Isotopes , 1999
46.
Automatic synthesis of l-[β-11C]amino acids using an immobilized enzyme column
Sasaki M., Ikemoto M., Mutoh M., Haradahira T., Tanaka A., Watanabe Y., Suzuki K.
Applied Radiation and Isotopes , 2000
47.
Development of a reliable remote-controlled synthesis ofβ-[11C]-5-hydroxy-L-tryptophan on a Zymark robotic system
Neels O.C., Jager P.L., Koopmans K.P., Eriks E., de Vries E.G., Kema I.P., Elsinga P.H.
Journal of Labelled Compounds and Radiopharmaceuticals , 2006
48.
Development of an automated synthesis apparatus for l-[3-11C] labeled aromatic amino acids
Harada N., Nishiyama S., Sato K., Tsukada H.
Applied Radiation and Isotopes , 2000
49.
Measuring serotonin synthesis: from conventional methods to PET tracers and their (pre)clinical implications
Visser A.K., van Waarde A., Willemsen A.T., Bosker F.J., Luiten P.G., den Boer J.A., Kema I.P., Dierckx R.A.
European Journal of Nuclear Medicine and Molecular Imaging , 2010
50.
Brain kinetics of 11 C-labelled L-tryptophan and 5-hydroxy-L-tryptophan in the Rhesus monkey
Hartvig P., Lindner K.J., Tedroff J., Andersson Y., Bjurling P., L�ngstr�m B.
Journal of Neural Transmission , 1992
51.
5-Hydroxy-l-[β-11C]tryptophan versus α-[11C]Methyl-l-tryptophan for Positron Emission Tomography Imaging of Serotonin Synthesis Capacity in the Rhesus Monkey Brain
Lundquist P., Hartvig P., Blomquist G., Hammarlund-Udenaes M., Långström B.
Journal of Cerebral Blood Flow and Metabolism , 2006
53.
Serotonin synthesis rate and the tryptophan hydroxylase-2: G-703T polymorphism in social anxiety disorder
Furmark T., Marteinsdottir I., Frick A., Heurling K., Tillfors M., Appel L., Antoni G., Hartvig P., Fischer H., Långström B., Eriksson E., Fredrikson M.
Journal of Psychopharmacology , 2016
54.
Mood changes correlate to changes in brain serotonin precursor trapping in women with premenstrual dysphoria
Eriksson O., Wall A., Marteinsdottir I., Ågren H., Hartvig P., Blomqvist G., Långström B., Naessén T.
Psychiatry Research - Neuroimaging , 2006
55.
Low brain uptake of L-[11C]5-hydroxytryptophan in major depression: a positron emission tomography study on patients and healthy volunteers
Agren H., Reibring L., Hartvig P., Tedroff J., Bjurling P., Hörnfeldt K., Andersson Y., Lundqvist H., Langström B.
Acta Psychiatrica Scandinavica , 1991
56.
Positron Emission Tomography Ligand [11C]5-Hydroxy-Tryptophan Can Be Used as a Surrogate Marker for the Human Endocrine Pancreas
Eriksson O., Espes D., Selvaraju R.K., Jansson E., Antoni G., Sörensen J., Lubberink M., Biglarnia A., Eriksson J.W., Sundin A., Ahlström H., Eriksson B., Johansson L., Carlsson P., Korsgren O., et. al.
Diabetes , 2014
57.
[11C]5-HTP and microPET are Not Suitable for Pharmacodynamic Studies in the Rodent Brain
Visser A.K., Ramakrishnan N.K., Willemsen A.T., Di Gialleonardo V., de Vries E.F., Kema I.P., Dierckx R.A., van Waarde A.
Journal of Cerebral Blood Flow and Metabolism , 2013
58.
Nuclear Medicine Imaging of Neuroendocrine Tumors
Brabander T., Kwekkeboom D.J., Feelders R.A., Brouwers A.H., Teunissen J.J.
Frontiers of Hormone Research , 2015
59.
Epidemiology of Neuroendocrine Tumors
Fraenkel M., Faggiano A., Valk G.D.
Frontiers of Hormone Research , 2015
60.
Manipulation of [11C]-5-Hydroxytryptophan and 6-[18F]Fluoro-3,4-Dihydroxy-l-Phenylalanine Accumulation in Neuroendocrine Tumor Cells
Neels O.C., Koopmans K.P., Jager P.L., Vercauteren L., van Waarde A., Doorduin J., Timmer-Bosscha H., Brouwers A.H., de Vries E.G., Dierckx R.A., Kema I.P., Elsinga P.H.
Cancer Research , 2008
61.
Improved Staging of Patients With Carcinoid and Islet Cell Tumors With 18F-Dihydroxy-Phenyl-Alanine and 11C-5-Hydroxy-Tryptophan Positron Emission Tomography
Koopmans K.P., Neels O.C., Kema I.P., Elsinga P.H., Sluiter W.J., Vanghillewe K., Brouwers A.H., Jager P.L., de Vries E.G.
Journal of Clinical Oncology , 2008
62.
Bjurling P., Antoni G., Watanabe Y., Långström B., Yamada H., Långström B., Tokii T.
Acta Chemica Scandinavica , 1990
63.
Demonstration of [11C] 5-hydroxy-L-tryptophan uptake and decarboxylation in carcinoid tumors by specific positioning labeling in positron emission tomography.
Sundin A., Eriksson B., Bergström M., Bjurling P., Lindner K., Öberg K., Långström B.
Nuclear Medicine and Biology , 2000
64.
Highlighting the versatility of the Tracerlab synthesis modules. Part 2: fully automated production of [11C]-labeled radiopharmaceuticals using a Tracerlab FXC-Pro
Shao X., Hoareau R., Runkle A.C., Tluczek L.J., Hockley B.G., Henderson B.D., Scott P.J.
Journal of Labelled Compounds and Radiopharmaceuticals , 2011
65.
rcr_89_9_879bib65
Comar
1973
66.
A new and simple on-line method for the preparation of n.c.a. [11C]methyl iodide
Holschbach M., Schüller M.
Applied Radiation and Isotopes , 1993
67.
Production of [11C]CH3I by single pass reaction of [11C]CH4 with I2
Link J.M., Krohn K.A., Clark J.C.
Nuclear Medicine and Biology , 1997
68.
Synthesis of [11C]iodomethane by iodination of [11C]methane
Larsen P., Ulin J., Dahlstrøm K., Jensen M.
Applied Radiation and Isotopes , 1997
69.
rcr_89_9_879bib69
Chaly
J. Nucl. Med , 1988
70.
Further investigation on the radiosynthesis of α-[11C]methyl-tryptophan
Suehiro M., Ravert H.T., Wilson A.A., Scheffel U., Dannals R.F., Wagner H.N.
Journal of Labelled Compounds and Radiopharmaceuticals , 1992
71.
Asymmetric radiosynthesis of α-[11C]methyl-l-tryptophan for PET studies
Mzengeza S., Venkatachalam T.K., Diksic M.
Nuclear Medicine and Biology , 1995
72.
Enantioselective synthesis of n.c.a. (S)-l-([α-11C]methyl)-tryptophan
Plenevaux A., Lemaire C., Delfiore G., Comar D.
Applied Radiation and Isotopes , 1994
73.
A high-yield and simplified procedure for the synthesis of α-[11C]Methyl-l-tryptophan
Chakraborty P.K., Mangner T.J., Chugani D.C., Muzik O., Chugani H.T.
Nuclear Medicine and Biology , 1996
74.
Design and automated production of 11C-alpha-methyl-l-tryptophan (11C-AMT)
Huang X., Xiao X., Gillies R.J., Tian H.
Nuclear Medicine and Biology , 2016
75.
Automated GMP-production of α -[11 C]methyl-L-tryptophan using a tracer production system (TPS)
Nordeman P., Yngve U., Wilking H., Gustavsson S.Å., Eriksson J., Antoni G.
Journal of Labelled Compounds and Radiopharmaceuticals , 2018
76.
A New Method to Measure Brain Serotonin Synthesis in vivo. I. Theory and Basic Data for a Biological Model
Diksic M., Nagahiro S., Sourkes T.L., Yamamoto Y.L.
Journal of Cerebral Blood Flow and Metabolism , 1990
77.
Metabolism of α-methyltryptophan
Madras B.K., Sourkes T.L.
Biochemical Pharmacology , 1965
78.
Stability of α-[11C]methyl-l-tryptophan brain trapping in healthy male volunteers
Rosa-Neto P., Diksic M., Leyton M., Mzengeza S., Benkelfat C.
European Journal of Nuclear Medicine and Molecular Imaging , 2005
79.
rcr_89_9_879bib79
Diksic
J. Psychiatry Neurosci. , 2001
80.
rcr_89_9_879bib80
Greig
J. Pharmacol. Exp. Ther. , 1959
81.
Distribution of Monoamine Oxidase Proteins in Human Brain: Implications for Brain Imaging Studies
Tong J., Meyer J.H., Furukawa Y., Boileau I., Chang L., Wilson A.A., Houle S.
Journal of Cerebral Blood Flow and Metabolism , 2013
82.
rcr_89_9_879bib82
Perreau-Linck
J. Psychiatry. Neurosci. , 2007
83.
An index of 5-HT synthesis changes during early antidepressant treatment: α-[11C]methyl-l-tryptophan PET study
Berney A., Nishikawa M., Benkelfat C., Debonnel G., Gobbi G., Diksic M.
Neurochemistry International , 2008
85.
Brain Regional α-[11C]Methyl-L-Tryptophan Trapping in Medication-Free Patients With Obsessive-Compulsive Disorder
Berney A., Leyton M., Gravel P., Sibon I., Sookman D., Rosa Neto P., Diksic M., Nakai A., Pinard G., Todorov C., Okazawa H., Blier P., Nordahl T.E., Benkelfat C.
Archives of General Psychiatry , 2011
86.
Brain serotonin synthesis capacity in obsessive-compulsive disorder: effects of cognitive behavioral therapy and sertraline
Lissemore J.I., Sookman D., Gravel P., Berney A., Barsoum A., Diksic M., Nordahl T.E., Pinard G., Sibon I., Cottraux J., Leyton M., Benkelfat C.
Translational Psychiatry , 2018
87.
Abnormal brain tryptophan metabolism and clinical correlates in Tourette syndrome
Behen M., Chugani H.T., Juhász C., Helder E., Ho A., Maqbool M., Rothermel R.D., Perry J., Muzik O.
Movement Disorders , 2007
88.
Brain serotonin synthesis in MDMA (ecstasy) polydrug users: an alpha-[11 C]methyl-l -tryptophan study
Booij L., Soucy J., Young S.N., Regoli M., Gravel P., Diksic M., Leyton M., Pihl R.O., Benkelfat C.
Journal of Neurochemistry , 2014
92.
NIMG-38MULTIMODAL IMAGING OF SPATIAL PATTERNS OF POST-TREATMENT GLIOBLASTOMA PROGRESSION
Bosnyak E., Kamson D., Robinette N., Barger G., Mittal S., Juhasz C.
Neuro-Oncology , 2015
93.
Multi-modal imaging of tumor cellularity and Tryptophan metabolism in human Gliomas
Jeong J., Juhász C., Mittal S., Bosnyák E., Kamson D.O., Barger G.R., Robinette N.L., Kupsky W.J., Chugani D.C.
Cancer Imaging , 2015
94.
Differential kinetics of α-[11C]methyl-l-tryptophan on PET in low-grade brain tumors
Juhász C., Muzik O., Chugani D.C., Chugani H.T., Sood S., Chakraborty P.K., Barger G.R., Mittal S.
Journal of Neuro-Oncology , 2010
95.
Multimodal imaging-defined subregions in newly diagnosed glioblastoma: impact on overall survival
John F., Bosnyák E., Robinette N.L., Amit-Yousif A.J., Barger G.R., Shah K.D., Michelhaugh S.K., Klinger N.V., Mittal S., Juhász C.
Neuro-Oncology , 2018
96.
N1-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase
Henrottin J., Zervosen A., Lemaire C., Sapunaric F., Laurent S., Van den Eynde B., Goldman S., Plenevaux A., Luxen A.
ACS Medicinal Chemistry Letters , 2015
97.
rcr_89_9_879bib97
Silk
2011
98.
Tryptophan degradation in women with breast cancer: a pilot study
Lyon D.E., Walter J.M., Starkweather A.R., Schubert C.M., McCain N.L.
BMC Research Notes , 2011
99.
Tryptophan metabolism in breast cancers: molecular imaging and immunohistochemistry studies
Juhász C., Nahleh Z., Zitron I., Chugani D.C., Janabi M.Z., Bandyopadhyay S., Ali-Fehmi R., Mangner T.J., Chakraborty P.K., Mittal S., Muzik O.
Nuclear Medicine and Biology , 2012
102.
Inhibition of Indoleamine 2,3-Dioxygenase in Dendritic Cells by Stereoisomers of 1-Methyl-Tryptophan Correlates with Antitumor Responses
Hou D., Muller A.J., Sharma M.D., DuHadaway J., Banerjee T., Johnson M., Mellor A.L., Prendergast G.C., Munn D.H.
Cancer Research , 2007
103.
Indoximod: An Immunometabolic Adjuvant That Empowers T Cell Activity in Cancer
Fox E., Oliver T., Rowe M., Thomas S., Zakharia Y., Gilman P.B., Muller A.J., Prendergast G.C.
Frontiers in Oncology , 2018
105.
rcr_89_9_879bib105
Xie
Sci. Rep. , 2015
106.
Loss of IDO1 Expression From Human Pancreatic β-Cells Precedes Their Destruction During the Development of Type 1 Diabetes
Anquetil F., Mondanelli G., Gonzalez N., Rodriguez Calvo T., Zapardiel Gonzalo J., Krogvold L., Dahl-Jørgensen K., Van den Eynde B., Orabona C., Grohmann U., von Herrath M.G.
Diabetes , 2018
107.
rcr_89_9_879bib107
Coenen
2007
108.
Synthesis of11C,18F,15O, and13N Radiolabels for Positron Emission Tomography
Miller P., Long N., Vilar R., Gee A.
Angewandte Chemie - International Edition , 2008
110.
18F-labelling innovations and their potential for clinical application
Coenen H.H., Ermert J.
Clinical and Translational Imaging , 2018
111.
Fundamental Limits of Spatial Resolution in PET.
Moses W.W.
Nuclear Instruments and Methods in Physics Research, Section A: Accelerators, Spectrometers, Detectors and Associated Equipment , 2011
112.
Positron flight in human tissues and its influence on PET image spatial resolution
S�nchez-Crespo A., Andreo P., Larsson S.A.
European Journal of Nuclear Medicine and Molecular Imaging , 2004
113.
Synthesis of f-18 labelled fluoro-melatonins and 5-hydroxy-fluoro-tryptophans
Chirakal R., Sayer B.G., Firnau G., Garnett E.S.
Journal of Labelled Compounds and Radiopharmaceuticals , 1988
114.
Synthesis and evaluation of l-5-(2-[18F]fluoroethoxy)tryptophan as a new PET tracer
Li R., Wu S., Wang S., Fu Z., Dang Y., Huo L.
Applied Radiation and Isotopes , 2010
115.
Characterization of 5-(2-18F-fluoroethoxy)-L-tryptophan for PET imaging of the pancreas
Abbas A., Beamish C., McGirr R., Demarco J., Cockburn N., Krokowski D., Lee T., Kovacs M., Hatzoglou M., Dhanvantari S.
F1000Research , 2016
116.
5-(2-18F-Fluoroethoxy)-l-Tryptophan as a Substrate of System L Transport for Tumor Imaging by PET
Krämer S.D., Mu L., Müller A., Keller C., Kuznetsova O.F., Schweinsberg C., Franck D., Müller C., Ross T.L., Schibli R., Ametamey S.M.
Journal of Nuclear Medicine , 2012
117.
Radiosynthesis of 1-[18F]fluoroethyl-L-tryptophan as a novel potential amino acid PET tracer
Sun T., Tang G., Tian H., Wang X., Chen X., Chen Z., Wang S.
Applied Radiation and Isotopes , 2012
118.
Fully automated radiosynthesis of N1-[18F]fluoroethyl-tryptophan and study of its biological activity as a new potential substrate for indoleamine 2,3-dioxygenase PET imaging
Henrottin J., Lemaire C., Egrise D., Zervosen A., Van den Eynde B., Plenevaux A., Franci X., Goldman S., Luxen A.
Nuclear Medicine and Biology , 2016
119.
Challenges in the automated synthesis of [ 18 F]-1-fluoroethyl tryptophan: Formation of both O- and N-alkylated products
Venkatachalam T.K., Stimson D.H., Pierens G.K., Bhalla R., Reutens D.C.
Applied Radiation and Isotopes , 2018
120.
Automated Synthesis of18F-Fluoropropoxytryptophan for Amino Acid Transporter System Imaging
Shih I., Duan X., Kong F., Williams M.D., Yang K., Zhang Y., Yang D.J.
BioMed Research International , 2014
121.
Synthesis and biological evaluation of 18F-labeled fluoropropyl tryptophan analogs as potential PET probes for tumor imaging
Chiotellis A., Mu L., Müller A., Selivanova S.V., Keller C., Schibli R., Krämer S.D., Ametamey S.M.
European Journal of Medicinal Chemistry , 2013
122.
Advances in neuro-oncology imaging
Langen K., Galldiks N., Hattingen E., Shah N.J.
Nature Reviews Neurology , 2017
123.
Synthesis, Radiolabeling, and Biological Evaluation of 5-Hydroxy-2-[18F]fluoroalkyl-tryptophan Analogues as Potential PET Radiotracers for Tumor Imaging
Chiotellis A., Müller Herde A., Rössler S.L., Brekalo A., Gedeonova E., Mu L., Keller C., Schibli R., Krämer S.D., Ametamey S.M.
Journal of Medicinal Chemistry , 2016
125.
Evaluation of l-1-[18F]Fluoroethyl-Tryptophan for PET Imaging of Cancer
Xin Y., Gao X., Liu L., Ge W., Jain M.K., Cai H.
Molecular Imaging and Biology , 2019
126.
Assessment of Tryptophan Uptake and Kinetics Using 1-(2-18F-Fluoroethyl)-l-Tryptophan and α-11C-Methyl-l-Tryptophan PET Imaging in Mice Implanted with Patient-Derived Brain Tumor Xenografts
Michelhaugh S.K., Muzik O., Guastella A.R., Klinger N.V., Polin L.A., Cai H., Xin Y., Mangner T.J., Zhang S., Juhász C., Mittal S.
Journal of Nuclear Medicine , 2016
127.
PET imaging of medulloblastoma with an 18F-labeled tryptophan analogue in a transgenic mouse model
Xin Y., Yue X., Li H., Li Z., Cai H., Choudhary A.K., Zhang S., Chugani D.C., Langhans S.A.
Scientific Reports , 2020
128.
Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung
Balz G., Schiemann G.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1927
129.
The preparation of fluorine-18 labelled radiopharmaceuticals
Palmer A.J., Clark J.C., Goulding R.W.
The International Journal of Applied Radiation and Isotopes , 1977
130.
rcr_89_9_879bib130
Atkins
J. Nucl. Med. , 1972
131.
Radiosynthesis of 4-[ 18 F]fluoro- l -tryptophan by isotopic exchange on carbonyl-activated precursors
Weiss P.S., Ermert J., Castillo Meleán J., Schäfer D., Coenen H.H.
Bioorganic and Medicinal Chemistry , 2015
133.
A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET Imaging
Lee E., Kamlet A.S., Powers D.C., Neumann C.N., Boursalian G.B., Furuya T., Choi D.C., Hooker J.M., Ritter T.
Science , 2011
134.
rcr_89_9_879bib134
Lee
J. Am. Chem. Soc. , 2012
135.
Synthesis and imaging validation of [¹⁸F]MDL100907 enabled by Ni-mediated fluorination.
Ren H., Wey H., Strebl M., Neelamegam R., Ritter T., Hooker J.M.
ACS Chemical Neuroscience , 2014
136.
A Practical One-Pot Synthesis of Positron Emission Tomography (PET) Tracers via Nickel-Mediated Radiofluorination
Zlatopolskiy B.D., Zischler J., Urusova E.A., Endepols H., Kordys E., Frauendorf H., Mottaghy F.M., Neumaier B.
ChemistryOpen , 2015
137.
Copper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium Salts
Ichiishi N., Brooks A.F., Topczewski J.J., Rodnick M.E., Sanford M.S., Scott P.J.
Organic Letters , 2014
138.
A general copper-mediated nucleophilic 18F fluorination of arenes.
Tredwell M., Preshlock S.M., Taylor N.J., Gruber S., Huiban M., Passchier J., Mercier J., Génicot C., Gouverneur V.
Angewandte Chemie - International Edition , 2014
139.
Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids
Mossine A.V., Brooks A.F., Makaravage K.J., Miller J.M., Ichiishi N., Sanford M.S., Scott P.J.
Organic Letters , 2015
140.
Copper-Mediated Radiofluorination of Arylstannanes with [18F]KF
Makaravage K.J., Brooks A.F., Mossine A.V., Sanford M.S., Scott P.J.
Organic Letters , 2016
141.
Copper‐Mediated Aminoquinoline‐Directed Radiofluorination of Aromatic C−H Bonds with K 18 F
Lee S.J., Makaravage K.J., Brooks A.F., Scott P.J., Sanford M.S.
Angewandte Chemie - International Edition , 2019
142.
Copper-mediated aromatic radiofluorination revisited: efficient production of PET tracers on a preparative scale.
Zlatopolskiy B.D., Zischler J., Krapf P., Zarrad F., Urusova E.A., Kordys E., Endepols H., Neumaier B.
Chemistry - A European Journal , 2015
143.
Neither azeotropic drying, nor base nor other additives: a minimalist approach to 18F-labeling
Richarz R., Krapf P., Zarrad F., Urusova E.A., Neumaier B., Zlatopolskiy B.D.
Organic and Biomolecular Chemistry , 2014
144.
Preparation of No-Carrier-Added 6-[18F]Fluoro-l-tryptophan via Cu-Mediated Radiofluorination
Schäfer D., Weiß P., Ermert J., Castillo Meleán J., Zarrad F., Neumaier B.
European Journal of Organic Chemistry , 2016
145.
Alcohol-Enhanced Cu-Mediated Radiofluorination.
Zischler J., Kolks N., Modemann D., Neumaier B., Zlatopolskiy B.D.
Chemistry - A European Journal , 2017
146.
Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo
Zlatopolskiy B.D., Zischler J., Schäfer D., Urusova E.A., Guliyev M., Bannykh O., Endepols H., Neumaier B.
Journal of Medicinal Chemistry , 2017
147.
C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines
Loach R.P., Fenton O.S., Amaike K., Siegel D.S., Ozkal E., Movassaghi M.
Journal of Organic Chemistry , 2014
148.
Preparation and evaluation of L- and D-5-[ 18 F]fluorotryptophan as PET imaging probes for indoleamine and tryptophan 2,3-dioxygenases
Tang T., Gill H.S., Ogasawara A., Tinianow J.N., Vanderbilt A.N., Williams S., Hatzivassiliou G., White S., Sandoval W., DeMent K., Wong M., Marik J.
Nuclear Medicine and Biology , 2017
149.
Giglio B.C., Fei H., Wang M., Wang H., He L., Feng H., Wu Z., Lu H., Li Z.
Theranostics , 2017
150.
rcr_89_9_879bib150
Galldiks
Q. J. Nucl. Med. Mol. Imaging , 2015
151.
System l amino acid transporter LAT1 accumulates O-(2-fluoroethyl)-l-tyrosine (FET)
Habermeier A., Graf J., Sandhöfer B.F., Boissel J.-., Roesch F., Closs E.I.
Amino Acids , 2014
153.
Indoleamine 2,3-dioxygenase activity and l-tryptophan transport in human breast cancer cells
Travers M.T., Gow I.F., Barber M.C., Thomson J., Shennan D.B.
Biochimica et Biophysica Acta - Biomembranes , 2004
154.
Altered serotonin physiology in human breast cancers favors paradoxical growth and cell survival
Pai V.P., Marshall A.M., Hernandez L.L., Buckley A.R., Horseman N.D.
Breast Cancer Research , 2009
155.
Isotope effects and alternative substrate reactivities for tryptophan 2,3-dioxygenase.
Leeds J.M., Brown P.J., McGeehan G.M., Brown F.K., Wiseman J.S.
Journal of Biological Chemistry , 1993
156.
Heme-Containing Oxygenases
Sono M., Roach M.P., Coulter E.D., Dawson J.H.
Chemical Reviews , 1996