ACS Chemical Neuroscience
Page 6 of 7
assistance. The results of the ligand docking were obtained
14.
Schwarcz, R.; Bruno, J. P.; Muchowski, P. J.; Wu, H. Q.,
1
2
3
4
5
6
7
8
using computing resources of Supercomputer Center,
the Peter the Great’s St. Petersburg Polytechnic University
Kynurenines in the mammalian brain: when physiology meets
pathology. Nat Rev Neurosci 2012, 13 (7), 465-77.
15.
Chugani, D. C.; Muzik, O.; Behen, M.; Rothermel, R.;
Janisse, J. J.; Lee, J.; Chugani, H. T., Developmental changes in
brain serotonin synthesis capacity in autistic and nonautistic
children. Ann Neurol 1999, 45 (3), 287-95.
REFERENCES
16.
Chiotellis, A.; Mu, L.; Muller, A.; Selivanova, S. V.;
Keller, C.; Schibli, R.; Kramer, S. D.; Ametamey, S. M., Synthesis
and biological evaluation of (1)(8)F-labeled fluoropropyl
tryptophan analogs as potential PET probes for tumor imaging.
Eur J Med Chem 2013, 70, 768-80.
1.
Chaly, T.; Diksic, M., Synthesis of "no-carrier-added"
alpha-[11C]methyl-L-tryptophan. J Nucl Med 1988, 29 (3), 370-
9
4.
2.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Leklem, J. E., Quantitative aspects of tryptophan
17.
Chiotellis, A.; Muller Herde, A.; Rossler, S. L.; Brekalo,
metabolism in humans and other species: a review. Am J Clin
Nutr 1971, 24 (6), 659-72.
A.; Gedeonova, E.; Mu, L.; Keller, C.; Schibli, R.; Kramer, S. D.;
Ametamey, S. M., Synthesis, Radiolabeling, and Biological
Evaluation of 5-Hydroxy-2-[(18)F]fluoroalkyl-tryptophan
Analogues as Potential PET Radiotracers for Tumor Imaging. J
Med Chem 2016, 59 (11), 5324-40.
3.
Chugani, D. C.; Muzik, O., Alpha[C-11]methyl-L-
tryptophan PET maps brain serotonin synthesis and
kynurenine pathway metabolism. J Cereb Blood Flow Metab
2000, 20 (1), 2-9.
18.
Giglio, B. C.; Fei, H.; Wang, M.; Wang, H.; He, L.; Feng,
4.
Bosnyak, E.; Kamson, D. O.; Guastella, A. R.;
H.; Wu, Z.; Lu, H.; Li, Z., Synthesis of 5-[(18)F]Fluoro-alpha-
methyl Tryptophan: New Trp Based PET Agents. Theranostics
2017, 7 (6), 1524-1530.
Varadarajan, K.; Robinette, N. L.; Kupsky, W. J.; Muzik, O.;
Michelhaugh, S. K.; Mittal, S.; Juhasz, C., Molecular imaging
correlates of tryptophan metabolism via the kynurenine
pathway in human meningiomas. Neuro Oncol 2015, 17 (9),
1284-92.
19.
Henrottin, J.; Zervosen, A.; Lemaire, C.; Sapunaric, F.;
Laurent, S.; Van den Eynde, B.; Goldman, S.; Plenevaux, A.;
Luxen, A., N (1)-Fluoroalkyltryptophan Analogues: Synthesis
and in vitro Study as Potential Substrates for Indoleamine 2,3-
Dioxygenase. ACS Med Chem Lett 2015, 6 (3), 260-5.
5.
Zitron, I. M.; Kamson, D. O.; Kiousis, S.; Juhasz, C.;
Mittal, S., In vivo metabolism of tryptophan in meningiomas is
mediated by indoleamine 2,3-dioxygenase 1. Cancer Biol Ther
2013, 14 (4), 333-9.
20.
Kuznetsova, O. F.; Schweinsberg, C.; Franck, D.; Muller, C.;
Ross, T. L.; Schibli, R.; Ametamey, S. M., 5-(2-18F-
fluoroethoxy)-L-tryptophan as substrate of system
transport for tumor imaging by PET. J Nucl Med 2012, 53 (3),
434-42.
Kramer, S. D.; Mu, L.; Muller, A.; Keller, C.;
6.
Malachowski, W. P.; Winters, M.; DuHadaway, J. B.;
Lewis-Ballester, A.; Badir, S.; Wai, J.; Rahman, M.; Sheikh, E.;
LaLonde, J. M.; Yeh, S. R.; Prendergast, G. C.; Muller, A. J., O-
alkylhydroxylamines as rationally-designed mechanism-based
inhibitors of indoleamine 2,3-dioxygenase-1. Eur J Med Chem
2016, 108, 564-576.
a
L
21.
Zlatopolskiy, B. D.; Zischler, J.; Schafer, D.; Urusova,
E. A.; Guliyev, M.; Bannykh, O.; Endepols, H.; Neumaier, B.,
Discovery of 7-[(18)F]Fluorotryptophan as a Novel Positron
Emission Tomography (PET) Probe for the Visualization of
Tryptophan Metabolism in Vivo. J Med Chem 2018, 61 (1), 189-
206.
7.
Juhasz, C.; Muzik, O.; Lu, X.; Jahania, M. S.; Soubani,
A. O.; Khalaf, M.; Peng, F.; Mangner, T. J.; Chakraborty, P. K.;
Chugani, D. C., Quantification of tryptophan transport and
metabolism in lung tumors using PET. J Nucl Med 2009, 50 (3),
356-63.
22.
John, F.; Muzik, O.; Mittal, S.; Juhasz, C., Fluorine-18-
8.
M. Z.; Bandyopadhyay, S.; Ali-Fehmi, R.; Mangner, T. J.;
Chakraborty, P. K.; Mittal, S.; Muzik, O., Tryptophan
Juhasz, C.; Nahleh, Z.; Zitron, I.; Chugani, D. C.; Janabi,
Labeled PET Radiotracers for Imaging Tryptophan Uptake and
Metabolism: a Systematic Review. Mol Imaging Biol 2019.
metabolism in breast cancers: molecular imaging and
immunohistochemistry studies. Nucl Med Biol 2012, 39 (7),
926-32.
23.
Tredwell, M.; Preshlock, S. M.; Taylor, N. J.; Gruber,
S.; Huiban, M.; Passchier, J.; Mercier, J.; Genicot, C.;
Gouverneur, V., A general copper-mediated nucleophilic 18F
fluorination of arenes. Angew Chem Int Ed Engl 2014, 53 (30),
7751-5.
9.
Chugani,
D.
C.,
alpha-methyl-L-tryptophan:
mechanisms for tracer localization of epileptogenic brain
regions. Biomark Med 2011, 5 (5), 567-75.
24.
Schäfer, D.; Weiß, P.; Ermert, J.; Castillo Meleán, J.;
10.
Chugani, H. T.; Luat, A. F.; Kumar, A.; Govindan, R.;
Zarrad, F.; Neumaier, B., Preparation of No-Carrier-Added 6-
[18F]Fluoro-l-tryptophan via Cu-Mediated Radiofluorination.
Eur J Med Chem 2016, 2016 (27), 4621-4628.
Pawlik, K.; Asano, E., alpha-[11C]-Methyl-L-tryptophan--PET in
191 patients with tuberous sclerosis complex. Neurology 2013,
81 (7), 674-80.
25.
Yanagida, O.; Kanai, Y.; Chairoungdua, A.; Kim, D. K.;
11.
Sakai, Y.; Nishikawa, M.; Diksic, M.; Aube, M., alpha-
Segawa, H.; Nii, T.; Cha, S. H.; Matsuo, H.; Fukushima, J.;
Fukasawa, Y.; Tani, Y.; Taketani, Y.; Uchino, H.; Kim, J. Y.;
Inatomi, J.; Okayasu, I.; Miyamoto, K.; Takeda, E.; Goya, T.;
Endou, H., Human L-type amino acid transporter 1 (LAT1):
characterization of function and expression in tumor cell lines.
Biochim Biophys Acta 2001, 1514 (2), 291-302.
[11C] methyl-L tryptophan-PET as a surrogate for interictal
cerebral serotonin synthesis in migraine without aura.
Cephalalgia 2014, 34 (3), 165-73.
12.
Erhardt, S.; Schwieler, L.; Imbeault, S.; Engberg, G.,
The kynurenine pathway in schizophrenia and bipolar
disorder. Neuropharmacology 2017, 112 (Pt B), 297-306.
26.
Singh, N.; Scalise, M.; Galluccio, M.; Wieder, M.;
13.
Brundin, L.; Sellgren, C. M.; Lim, C. K.; Grit, J.;
Seidel, T.; Langer, T.; Indiveri, C.; Ecker, G. F., Discovery of
Potent Inhibitors for the Large Neutral Amino Acid
Transporter 1 (LAT1) by Structure-Based Methods. Int J Mol Sci
2018, 20 (1).
Palsson, E.; Landen, M.; Samuelsson, M.; Lundgren, K.;
Brundin, P.; Fuchs, D.; Postolache, T. T.; Traskman-Bendz, L.;
Guillemin, G. J.; Erhardt, S., An enzyme in the kynurenine
pathway that governs vulnerability to suicidal behavior by
regulating excitotoxicity and neuroinflammation. Transl
Psychiatry 2016, 6 (8), e865.
27.
Yan, R.; Zhao, X.; Lei, J.; Zhou, Q., Structure of the
human LAT1-4F2hc heteromeric amino acid transporter
complex. Nature 2019, 568 (7750), 127-130.
6
ACS Paragon Plus Environment