Home / Articles / 18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects

18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects

,  , 
Irina Anatol'evna Veselova 1
Irina Anatol'evna Veselova
,  , 
Valentin Georgievich Nenajdenko 1
Valentin Georgievich Nenajdenko
1 Lomonosov Moscow State University, Faculty of Chemistry
10.1070/RCR4752
Published 30 November 2017
Review , RCR4752, Volume 87, Issue 4, 350-373
11
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Vatsadze S. Z. et al. 18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects // Russian Chemical Reviews. 2017. Vol. 87. No. 4. pp. 350-373.
GOST all authors (up to 50)
Copy cite
Vatsadze S. Z., Eremina O. E., Veselova I. A., Kalmykov S. N., Nenajdenko V. G. 18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects // Russian Chemical Reviews. 2017. Vol. 87. No. 4. pp. 350-373.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR4752
UR - https://rcr.colab.ws/publications/10.1070/RCR4752
TI - 18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects
T2 - Russian Chemical Reviews
AU - Vatsadze, Sergey Zurabovich
AU - Eremina, Olga Evgen'evna
AU - Veselova, Irina Anatol'evna
AU - Kalmykov, Stepan Nikolaevich
AU - Nenajdenko, Valentin Georgievich
PY - 2017
DA - 2017/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 350-373
IS - 4
VL - 87
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2017_Vatsadze,
author = {Sergey Zurabovich Vatsadze and Olga Evgen'evna Eremina and Irina Anatol'evna Veselova and Stepan Nikolaevich Kalmykov and Valentin Georgievich Nenajdenko},
title = {18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects},
journal = {Russian Chemical Reviews},
year = {2017},
volume = {87},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4752},
number = {4},
pages = {350--373},
doi = {10.1070/RCR4752}
}
MLA
Cite this
MLA
Copy cite
Vatsadze, Sergey Zurabovich, et al. “18F-Labelled catecholamine type radiopharmaceuticals in the diagnosis of neurodegenerative diseases and neuroendocrine tumours: approaches to synthesis and development prospects.” Russian Chemical Reviews, vol. 87, no. 4, Nov. 2017, pp. 350-373. https://rcr.colab.ws/publications/10.1070/RCR4752.
Views / Visits / Downloads
26 / 25 / 5

Abstract

The pathogenesis of many socially significant diseases such as neurodegenerative dementias and neuroendocrine tumours involves imbalance of neurotransmitters. Among the known neuroimaging methods, positron emission tomography (PET) is the most perfect and informative technique for diagnosing these diseases. The potential of PET is largely determined by the inventory of available radiopharmaceuticals, that is, biologically active molecules containing short-lived nuclides with positron decay. This review gives a systematic account of the application of fluorine-18-labelled catecholamine type radiopharmaceuticals in clinical investigations of the sympathetic and central nervous systems. The methods for the synthesis of these agents and existing problems are considered. The material is arranged according to the mechanisms of reactions that underlie the synthetic approaches: electrophilic, nucleophilic and metal-catalyzed reactions.

The bibliography includes 198 references.

Funders

Russian Science Foundation
16-13-00114

References

1.
rcr_87_4_350_bib1
Ugryumov
2014
3.
rcr_87_4_350_bib3
Ramanan
Am. J. Neurodegener. Dis. , 2013
5.
Neuroendocrine tumours.
Barakat M.T., Meeran K., Bloom S.R.
Endocrine-Related Cancer , 2004
6.
The diagnosis and medical management of advanced neuroendocrine tumors.
Kaltsas G.A., Besser G.M., Grossman A.B.
Endocrine Reviews , 2004
7.
rcr_87_4_350_bib7
Schuller
2007
8.
Catecholamine Metabolism: A Contemporary View with Implications for Physiology and Medicine
Eisenhofer G., Kopin I.J., Goldstein D.S.
Pharmacological Reviews , 2004
9.
Spreading of pathology in neurodegenerative diseases: a focus on human studies
Brettschneider J., Tredici K.D., Lee V.M., Trojanowski J.Q.
Nature Reviews Neuroscience , 2015
10.
Neuroendocrine tumor disease: an evolving landscape.
Frilling A., Åkerström G., Falconi M., Pavel M., Ramos J., Kidd M., Modlin I.M.
Endocrine-Related Cancer , 2012
11.
Characteristics of Tau and Its Ligands in PET Imaging
Harada R., Okamura N., Furumoto S., Tago T., Yanai K., Arai H., Kudo Y.
Biomolecules , 2016
12.
PET/SPECT imaging agents for neurodegenerative diseases.
Zhu L., Ploessl K., Kung H.F.
Chemical Society Reviews , 2014
13.
The use of PET in Alzheimer disease
Nordberg A., Rinne J.O., Kadir A., Långström B.
Nature Reviews Neurology , 2010
15.
rcr_87_4_350_bib15
Loane
Am. J. Transl. Res. , 2011
17.
PET in the Diagnosis of Neuroendocrine Tumors
SUNDIN A., ERIKSSON B., BERGSTRÖM M., LÅNGSTRÖM B., ÖBERG K., ÖRLEFORS H.
Annals of the New York Academy of Sciences , 2004
18.
Positron emission tomography in oncology: a review.
Wood K.A., Hoskin P.J., Saunders M.I.
Clinical Oncology , 2007
19.
Methods for determining neurotransmitter metabolism markers for clinical diagnostics
Veselova I.A., Sergeeva E.A., Makedonskaya M.I., Eremina O.E., Kalmykov S.N., Shekhovtsova T.N.
Journal of Analytical Chemistry , 2016
21.
rcr_87_4_350_bib21
Kaprin
2017
22.
rcr_87_4_350_bib22
Krivonos
Saratov. Nauchno-Med. Zh. , 2013
23.
rcr_87_4_350_bib23
Belousov
Kachestv. Klin. Praktika , 2009
25.
rcr_87_4_350_bib25
Heitz
1987
26.
miR-195 and miR-483-5p Identified as Predictors of Poor Prognosis in Adrenocortical Cancer
Soon P.S., Tacon L.J., Gill A.J., Bambach C.P., Sywak M.S., Campbell P.R., Yeh M.W., Wong S.G., Clifton-Bligh R.J., Robinson B.G., Sidhu S.B.
Clinical Cancer Research , 2009
27.
Is the New Classification of Neuroendocrine Pancreatic Tumors of Clinical Help?
Schindl M., Kaczirek K., Kaserer K., Niederle B.
World Journal of Surgery , 2000
28.
Neuroendocrine Pancreatic Tumors: Guidelines for Management and Update
Burns W.R., Edil B.H.
Current Treatment Options in Oncology , 2011
30.
Ways toward an early diagnosis in Alzheimer's disease: The Alzheimer's Disease Neuroimaging Initiative (ADNI)
Mueller S.G., Weiner M.W., Thal L.J., Petersen R.C., Jack C.R., Jagust W., Trojanowski J.Q., Toga A.W., Beckett L.
Alzheimer's and Dementia , 2005
32.
Role of imaging techniques in the diagnosis of dementia.
O'BRIEN J.T.
British Journal of Radiology , 2008
33.
Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes
Jacobson O., Kiesewetter D.O., Chen X.
Bioconjugate Chemistry , 2014
34.
Synthesis and Evaluation of 11C-Labeled 6-Substituted 2-Arylbenzothiazoles as Amyloid Imaging Agents
Mathis C.A., Wang Y., Holt D.P., Huang G., Debnath M.L., Klunk W.E.
Journal of Medicinal Chemistry , 2003
35.
rcr_87_4_350_bib35
Ryzhkova
Sib. Onkol. Zh. , 2013
36.
rcr_87_4_350_bib36
Bejot
2012
37.
rcr_87_4_350_bib37
Lu
Quant. Imaging Med. Surg. , 2015
38.
PET and SPECT Radiotracers for Alzheimer's Disease.
Oukoloff K., Cieslikiewicz-Bouet M., Chao S., Costa Branquinho E., Bouteiller C., Jean L., Renard P.
Current Medicinal Chemistry , 2015
41.
Krasikova Raisa Nikolaevna, Aliev Ramiz Avtandilovich, Kalmykov Stepan Nikolaevich
Mendeleev Communications , 2016
42.
The [18F]Fluorodeoxyglucose Method for the Measurement of Local Cerebral Glucose Utilization in Mane
Reivich M., Kuhl D., Wolf A., Greenberg J., Phelps M., Ido T., Casella V., Fowler J., Hoffman E., Alavi A., Som P., Sokoloff L.
Circulation Research , 2012
43.
Automated synthesis of [18F]FDG using tetrabutylammonium bicarbonate
Culbert P.A., Adam M.J., Hurtado E.T., Huser J.M., Jivan S., Lu J., Ruth T.J., Zeisler S.K.
Applied Radiation and Isotopes , 1995
44.
Effectiveness and Safety of 18F-FDG PET in the Evaluation of Dementia: A Review of the Recent Literature
Bohnen N.I., Djang D.S., Herholz K., Anzai Y., Minoshima S.
Journal of Nuclear Medicine , 2011
45.
Relationship of Cerebrospinal Fluid Markers to 11C-PiB and 18F-FDDNP Binding
Tolboom N., van der Flier W.M., Yaqub M., Boellaard R., Verwey N.A., Blankenstein M.A., Windhorst A.D., Scheltens P., Lammertsma A.A., van Berckel B.N.
Journal of Nuclear Medicine , 2009
46.
18F‐flutemetamol amyloid imaging in Alzheimer disease and mild cognitive impairment: A phase 2 trial
Vandenberghe R., Van Laere K., Ivanoiu A., Salmon E., Bastin C., Triau E., Hasselbalch S., Law I., Andersen A., Korner A., Minthon L., Garraux G., Nelissen N., Bormans G., Buckley C., et. al.
Annals of Neurology , 2010
47.
Amyloid Imaging with 18F-Florbetaben in Alzheimer Disease and Other Dementias
Villemagne V.L., Ong K., Mulligan R.S., Holl G., Pejoska S., Jones G., O'Keefe G., Ackerman U., Tochon-Danguy H., Chan J.G., Reininger C.B., Fels L., Putz B., Rohde B., Masters C.L., et. al.
Journal of Nuclear Medicine , 2011
48.
Amyloid-β assessed by florbetapir F 18 PET and 18-month cognitive decline
Doraiswamy P.M., Sperling R.A., Coleman R.E., Johnson K.A., Reiman E.M., Davis M.D., Grundman M., Sabbagh M.N., Sadowsky C.H., Fleisher A.S., Carpenter A., Clark C.M., Joshi A.D., Mintun M.A., Skovronsky D.M., et. al.
Neurology , 2012
49.
Comparison of the binding characteristics of [18F]THK-523 and other amyloid imaging tracers to Alzheimer’s disease pathology
Harada R., Okamura N., Furumoto S., Tago T., Maruyama M., Higuchi M., Yoshikawa T., Arai H., Iwata R., Kudo Y., Yanai K.
European Journal of Nuclear Medicine and Molecular Imaging , 2012
50.
18F-THK5351: A Novel PET Radiotracer for Imaging Neurofibrillary Pathology in Alzheimer Disease
Harada R., Okamura N., Furumoto S., Furukawa K., Ishiki A., Tomita N., Tago T., Hiraoka K., Watanuki S., Shidahara M., Miyake M., Ishikawa Y., Matsuda R., Inami A., Yoshikawa T., et. al.
Journal of Nuclear Medicine , 2015
51.
Preclinical Evaluation of [18F]THK-5105 Enantiomers: Effects of Chirality on Its Effectiveness as a Tau Imaging Radiotracer
Tago T., Furumoto S., Okamura N., Harada R., Adachi H., Ishikawa Y., Yanai K., Iwata R., Kudo Y.
Molecular Imaging and Biology , 2015
52.
Longitudinal Assessment of Tau Pathology in Patients with Alzheimer’s Disease Using [18F]THK-5117 Positron Emission Tomography
Ishiki A., Okamura N., Furukawa K., Furumoto S., Harada R., Tomita N., Hiraoka K., Watanuki S., Ishikawa Y., Tago T., Funaki Y., Iwata R., Tashiro M., Yanai K., Kudo Y., et. al.
PLoS ONE , 2015
53.
Comparison of New Tau PET-Tracer Candidates With [18F]T808 and [18F]T807
Declercq L., Celen S., Lecina J., Ahamed M., Tousseyn T., Moechars D., Alcazar J., Ariza M., Fierens K., Bottelbergs A., Mariën J., Vandenberghe R., Andres I.J., Van Laere K., Verbruggen A., et. al.
Molecular Imaging , 2016
54.
Early clinical PET imaging results with the novel PHF-tau radioligand [F-18]-T807.
Chien D.T., Bahri S., Szardenings A.K., Walsh J.C., Mu F., Su M., Shankle W.R., Elizarov A., Kolb H.C.
Journal of Alzheimer's Disease , 2013
55.
Visual Assessment Versus Quantitative Assessment of 11C-PIB PET and 18F-FDG PET for Detection of Alzheimer's Disease
Ng S., Villemagne V.L., Berlangieri S., Lee S.-., Cherk M., Gong S.J., Ackermann U., Saunder T., Tochon-Danguy H., Jones G., Smith C., O'Keefe G., Masters C.L., Rowe C.C.
Journal of Nuclear Medicine , 2007
56.
Dopamine visualized in the basal ganglia of living man
Garnett E.S., Firnau G., Nahmias C.
Nature , 1983
57.
rcr_87_4_350_bib57
Ibrahim
Am. J. Nucl. Med. Mol. Imaging , 2016
59.
Blood-brain barrier unlocked
Goldstein N., Goldstein R., Terterov D., Kamensky A.A., Kovalev G.I., Zolotarev Y.A., Avakyan G.N., Terterov S.
Biochemistry (Moscow) , 2012
60.
[(18)F]-Group 13 fluoride derivatives as radiotracers for positron emission tomography.
Chansaenpak K., Vabre B., Gabbaï F.P.
Chemical Society Reviews , 2016
61.
rcr_87_4_350_bib61
Fedorova
Luch. Diagnost. Terap. , 2015
62.
New functional imaging modalities for chromaffin tumors, neuroblastomas and ganglioneuromas
Ilias I., Shulkin B., Pacak K.
Trends in Endocrinology and Metabolism , 2005
63.
Whole-body 18F dopa PET for detection of gastrointestinal carcinoid tumors.
Hoegerle S., Altehoefer C., Ghanem N., Koehler G., Waller C.F., Scheruebl H., Moser E., Nitzsche E.
Radiology , 2013
64.
rcr_87_4_350_bib64
Becherer
J. Nucl. Med. , 2004
65.
18F-DOPA PET and PET/CT
Nanni C., Fanti S., Rubello D.
Journal of Nuclear Medicine , 2007
66.
Comparison of [111In]pentetreotide‐SPECT and [18F]FDOPA‐PET in the localization of extra‐adrenal paragangliomas: the case for a patient‐tailored use of nuclear imaging modalities
Charrier N., Deveze A., Fakhry N., Sebag F., Morange I., Gaborit B., Barlier A., Carmona E., De Micco C., Garcia S., Mancini J., Palazzo F.F., Lavieille J.P., Zanaret M., Henry J.F., et. al.
Clinical Endocrinology , 2010
67.
Functional imaging of SDHx-related head and neck paragangliomas: comparison of 18F-fluorodihydroxyphenylalanine, 18F-fluorodopamine, 18F-fluoro-2-deoxy-D-glucose PET, 123I-metaiodobenzylguanidine scintigraphy, and 111In-pentetreotide scintigraphy.
King K.S., Chen C.C., Alexopoulos D.K., Whatley M.A., Reynolds J.C., Patronas N., Ling A., Adams K.T., Xekouki P., Lando H., Stratakis C.A., Pacak K.
Journal of Clinical Endocrinology and Metabolism , 2011
68.
18F-FDOPA: A Multiple-Target Molecule
Minn H., Kauhanen S., Seppänen M., Nuutila P.
Journal of Nuclear Medicine , 2009
69.
18F-FDOPA PET and PET/CT Accurately Localize Pheochromocytomas
Imani F., Agopian V.G., Auerbach M.S., Walter M.A., Imani F., Benz M.R., Dumont R.A., Lai C.K., Czernin J.G., Yeh M.W.
Journal of Nuclear Medicine , 2009
70.
Comparison of 18F-fluoro-L-DOPA, 18F-fluoro-deoxyglucose, and 18F-fluorodopamine PET and 123I-MIBG scintigraphy in the localization of pheochromocytoma and paraganglioma.
Timmers H.J., Chen C.C., Carrasquillo J.A., Whatley M., Ling A., Havekes B., Eisenhofer G., Martiniova L., Adams K.T., Pacak K.
Journal of Clinical Endocrinology and Metabolism , 2009
71.
6-l-18F-Fluorodihydroxyphenylalanine PET in Neuroendocrine Tumors: Basic Aspects and Emerging Clinical Applications*
Jager P.L., Chirakal R., Marriott C.J., Brouwers A.H., Koopmans K.P., Gulenchyn K.Y.
Journal of Nuclear Medicine , 2008
72.
123I-meta-iodobenzylguanidine scintigraphy for the detection of neuroblastoma and pheochromocytoma: results of a meta-analysis.
Jacobson A.F., Deng H., Lombard J., Lessig H.J., Black R.R.
Journal of Clinical Endocrinology and Metabolism , 2010
73.
Jindal T., Kumar A., Venkitaraman B., Dutta R., Kumar R.
Korean Journal of Internal Medicine , 2010
74.
Comparison of somatostatin analog and meta-iodobenzylguanidine radionuclides in the diagnosis and localization of advanced neuroendocrine tumors.
Kaltsas G., Korbonits M., Heintz E., Mukherjee J.J., Jenkins P.J., Chew S.L., Reznek R., Monson J.P., Besser G.M., Foley R., Britton K.E., Grossman A.B.
Journal of Clinical Endocrinology and Metabolism , 2001
75.
Effects of ring fluorination on the cardiovascular actions of dopamine and norepinephrine in the dog.
Goldberg L.I., Kohli J.D., Cantacuzene D., Kirk K.L., Creveling C.R.
Journal of Pharmacology and Experimental Therapeutics , 1980
76.
Effects of fluoro-dopamines on dopamine receptors (D1, D2, D3, sites).
Firnau G., Garnett S., Marshall A.M., Seeman P., Tedesco J., Kirk K.L.
Biochemical Pharmacology , 1981
77.
Functional imaging of endocrine tumors: role of positron emission tomography.
Pacak K., Eisenhofer G., Goldstein D.S.
Endocrine Reviews , 2004
79.
rcr_87_4_350_bib79
Nie
Med. Chem. Res. , 1996
80.
The binding of fluorocatecholamines to adrenergic and dopaminergic receptors in rat brain membranes.
Nimit Y., Cantacuzene D., Kirk K.L., Creveling C.R., Daly J.W.
Life Sciences , 1980
81.
Syntheses of (R)- and (S)-2- and 6-fluoronorepinephrine and (R)- and (S)-2- and 6-fluoroepinephrine: effect of stereochemistry on fluorine-induced adrenergic selectivities.
Lu S., Herbert B., Haufe G., Laue K.W., Padgett W.L., Oshunleti O., Daly J.W., Kirk K.L.
Journal of Medicinal Chemistry , 2000
82.
6-[18F]Fluorodopamine Positron Emission Tomographic (PET) Scanning for Diagnostic Localization of Pheochromocytoma
Pacak K., Eisenhofer G., Carrasquillo J.A., Chen C.C., Li S., Goldstein D.S.
Hypertension , 2012
83.
rcr_87_4_350_bib83
Pacak
J. Clin. Endocrinol. Metab. , 2001
84.
Diagnostic Localization of Pheochromocytoma
PACAK K., EISENHOFER G., CARRASQUILLO J.A., CHEN C.C., WHATLEY M., GOLDSTEIN D.S.
Annals of the New York Academy of Sciences , 2002
87.
Efficient automated syntheses of high specific activity 6-[18F]fluorodopamine using a diaryliodonium salt precursor.
Neumann K.D., Qin L., Vāvere A.L., Shen B., Miao Z., Chin F.T., Shulkin B.L., Snyder S.E., DiMagno S.G.
Journal of Labelled Compounds and Radiopharmaceuticals , 2015
88.
Nucleophilic routes to selectively fluorinated aromatics
Adams D.J., Clark J.H.
Chemical Society Reviews , 1999
89.
Selective fluorodenitration of chloronitroaromatics
Beaumont A.J., Clark J.H., Boechat N.A.
Journal of Fluorine Chemistry , 1993
91.
Applications of Fluorine in Medicinal Chemistry
Gillis E.P., Eastman K.J., Hill M.D., Donnelly D.J., Meanwell N.A.
Journal of Medicinal Chemistry , 2015
92.
rcr_87_4_350_bib92
Nenajdenko
Tetrahedron , 1994
93.
rcr_87_4_350_bib93
Nenajdenko
2014
94.
Reaction of CBrF2–CBrF2 with hydrazones of aromatic aldehydes
Nenajdenko V.G., Varseev G.N., Korotchenko V.N., Shastin A.V., Balenkova E.S.
Journal of Fluorine Chemistry , 2004
95.
The catalytic olefination reaction of aldehydes and ketones with CBr3CF3
Nenajdenko V.G., Varseev G.N., Shastin A.V., Balenkova E.S.
Journal of Fluorine Chemistry , 2005
97.
Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate).
Teare H., Robins E., Kirjavainen A., Forsback S., Sandford G., Solin O., Luthra S., Gouverneur V.
Angewandte Chemie - International Edition , 2010
99.
Recommendations for fluorine-18 production
Guillaume M., Luxen A., Nebeling B., Argentini M., Clark J.C., Pike V.W.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1991
100.
rcr_87_4_350_bib100
2012
101.
Optimization of nucleophilic fluorination step in the synthesis of various compounds labelled with fluorine-18 for their use as pet radiotracers
Gomzina N.A., Zaitsev V.V., Krasikova R.N.
Journal of Labelled Compounds and Radiopharmaceuticals , 2001
103.
rcr_87_4_350_bib103
Lehn
1971
104.
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
106.
Chemistry with [18F]Fluoride Ion
Cai L., Lu S., Pike V.W.
European Journal of Organic Chemistry , 2008
107.
Total Radiosynthesis: Thinking outside "the box".
Liang S.H., Vasdev N.
Australian Journal of Chemistry , 2015
110.
Solvent extraction of Th(IV) from aqueous solution with methylimidazole in ionic liquid
Li W., Yang S., Lv H., Liu Z., Wu J., Li S., Shen Y.
Radiochimica Acta , 2016
111.
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
112.
The dimethylsulfonium moiety as a leaving group in aromatic radiofluorination using tetra-n-butylammonium [18F]fluoride
Maeda M., Fukumura T., Kojima M.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1987
113.
Aromatic n.c.a. labelling with 18F- by modified Balz-Schiemann-decomposition☆
Knöchel A., Zwernemann O.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1991
114.
Syntheses of 5-fluoro-d/l-dopa and [18F]5-fluoro-l-dopa
Argentini M., Wiese C., Weinreicht R.
Journal of Fluorine Chemistry , 1994
116.
N.C.A. 18F‐fluoroalkylation of H‐acidic compounds
Block D., Coenen H.H., Stöcklin G.
Journal of Labelled Compounds and Radiopharmaceuticals , 1988
118.
Efficient O‐ and N‐(β‐fluoroethylation)s with NCA [18F]β‐fluoroethyl tosylate under microwave‐enhanced conditions
Lu S., Chin F.T., McCarron J.A., Pike V.W.
Journal of Labelled Compounds and Radiopharmaceuticals , 2004
120.
Radioactive Labeling of Defined HPMA-Based Polymeric Structures Using [18F]FETos for In Vivo Imaging by Positron Emission Tomography
Herth M.M., Barz M., Moderegger D., Allmeroth M., Jahn M., Thews O., Zentel R., Rösch F.
Biomacromolecules , 2009
123.
4-[18F]fluoroarylalkylethers via an improved synthesis of n.c.a. 4-[18F]fluorophenol.
Ludwig T., Ermert J., Coenen H.H.
Nuclear Medicine and Biology , 2002
124.
Oxidation of substituted 4-fluorobenzaldehydes: application to the no-carrier-added syntheses of 4-[18F]fluoroguaiacol and 4-[18F]fluorocatechol.
Chakraborty P.K., Kilbourn M.R.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1991
125.
[18F]fluorination/decarbonylation: new route to aryl [18F]fluorides.
Chakraborty P.K., Kilbourn M.R.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1991
126.
6-[18F]fluorometaraminol: a radiotracer for in vivo mapping of adrenergic nerves of the heart.
Mislankar S.G., Gildersleeve D.L., Wieland D.M., Massin C.C., Mulholland G.K., Toorongian S.A.
Journal of Medicinal Chemistry , 1988
127.
Synthesis of 4-[18F]fluoro-L-m-tyrosine: a model analog for the in vivo assessment of central dopaminergic function.
Perlmutter M., Satyamurthy N., Luxen A., Phelps M.E., Barrio J.R.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1990
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.
rcr_87_4_350_bib129
Barré
J. Labelled Compd. Radiopharm. , 1994
131.
Bis(4-benzyloxyphenyl)iodonium salts as effective precursors for the no-carrier-added radiosynthesis of 4-[¹⁸F]fluorophenol.
Helfer A., Castillo Meleán J., Ermert J., Infantino A., Coenen H.H.
Applied Radiation and Isotopes , 2013
132.
Spirocyclic hypervalent iodine(III)-mediated radiofluorination of non-activated and hindered aromatics.
Rotstein B.H., Stephenson N.A., Vasdev N., Liang S.H.
Nature Communications , 2014
133.
Comparison of pathways to the versatile synthon of no‐carrier‐added 1‐bromo‐4‐[18F]fluorobenzene
Ermert J., Hocke C., Ludwig T., Gail R., Coenen H.H.
Journal of Labelled Compounds and Radiopharmaceuticals , 2004
135.
Synthesis of 6-[18F] and 4-[18F]fluoro-L-m-tyrosines via regioselective radiofluorodestannylation.
Namavari M., Satyamurthy N., Phelps M.E., Barrio J.R.
Applied Radiation and Isotopes , 1993
136.
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
137.
Metal-free oxidative fluorination of phenols with [18F]fluoride.
Gao Z., Lim Y.H., Tredwell M., Li L., Verhoog S., Hopkinson M., Kaluza W., Collier T.L., Passchier J., Huiban M., Gouverneur V.
Angewandte Chemie - International Edition , 2012
141.
Nucleophilic Deoxyfluorination of Phenols via Aryl Fluorosulfonate Intermediates.
Schimler S.D., Cismesia M.A., Hanley P.S., Froese R.D., Jansma M.J., Bland D.C., Sanford M.S.
Journal of the American Chemical Society , 2017
143.
Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands.
Taylor N.J., Emer E., Preshlock S., Schedler M., Tredwell M., Verhoog S., Mercier J., Genicot C., Gouverneur V.
Journal of the American Chemical Society , 2017
144.
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
145.
Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination ofN-Arylsydnones
Narayanam M.K., Ma G., Champagne P.A., Houk K.N., Murphy J.M.
Angewandte Chemie - International Edition , 2017
146.
A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging.
Huiban M., Tredwell M., Mizuta S., Wan Z., Zhang X., Collier T.L., Gouverneur V., Passchier J.
Nature Chemistry , 2013
147.
A universal procedure for the [¹⁸F]trifluoromethylation of aryl iodides and aryl boronic acids with highly improved specific activity.
van der Born D., Sewing C., Herscheid J.K., Windhorst A.D., Orru R.V., Vugts D.J.
Angewandte Chemie - International Edition , 2014
148.
Concerted nucleophilic aromatic substitution with 19F− and 18F−
Neumann C.N., Hooker J.M., Ritter T.
Nature , 2016
149.
Reaction of [18F]acetyl hypofluorite with derivatives of dihydroxyphenylalanine: Synthesis of l-[18F]6-fluorodopa
Adam M.J., Grierson J.R., Ruth T.J., Jivan S.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1986
150.
Yusubov M.S., Yoshimura A., Zhdankin V.V.
Arkivoc , 2016
152.
Novel electrophilic synthesis of 6-[18F]fluorodopamine and comprehensive biological evaluation
Eskola O., Grönroos T.J., Naum A., Marjamäki P., Forsback S., Bergman J., Länkimäki S., Kiss J., Savunen T., Knuuti J., Haaparanta M., Solin O.
European Journal of Nuclear Medicine and Molecular Imaging , 2012
153.
Enhanced copper-mediated (18)F-fluorination of aryl boronic esters provides eight radiotracers for PET applications.
Preshlock S., Calderwood S., Verhoog S., Tredwell M., Huiban M., Hienzsch A., Gruber S., Wilson T.C., Taylor N.J., Cailly T., Schedler M., Collier T.L., Passchier J., Smits R., Mollitor J., et. al.
Chemical Communications , 2016
154.
Radiofluorinated N-Octanoyl Dopamine ([18F]F-NOD) as a Tool To Study Tissue Distribution and Elimination of NOD in Vitro and in Vivo.
Pretze M., Pallavi P., Roscher M., Klotz S., Caballero J., Binzen U., Greffrath W., Treede R., Harmsen M.C., Hafner M., Yard B., Wängler C., Wängler B.
Journal of Medicinal Chemistry , 2016
155.
rcr_87_4_350_bib155
Lee
J. Am. Chem. Soc. , 2012
156.
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
158.
rcr_87_4_350_bib158
Firnau
J. Nucl. Med. , 1984
160.
[(18)F]6-fluoro-3,4-dihydroxy-L-phenylalanine--recent modern syntheses for an elusive radiotracer.
Edwards R., Wirth T.
Journal of Labelled Compounds and Radiopharmaceuticals , 2015
161.
rcr_87_4_350_bib161
Chaly
J. Nucl. Med. , 1986
162.
Kinetics of in vitro decarboxylation and the in vivo metabolism of 2-18F- and 6-18F-fluorodopa in the hooded rat.
Cumming P., Häusser M., Martin W.R., Grierson J., Adam M.J., Ruth T.J., McGeer E.G.
Biochemical Pharmacology , 1988
163.
Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF: a high yield synthesis of 6-[18F]Fluoro-L-dopa.
Namavari M., Bishop A., Satyamurthy N., Bida G., Barrio J.R.
International Journal of Radiation Applications and Instrumentation Part A Applied Radiation and Isotopes , 1992
164.
Fully automated synthesis module for the high yield one-pot preparation of 6-[]fluoro-l-DOPA
de Vries E.F., Luurtsema G., Brüssermann M., Elsinga P.H., Vaalburg W.
Applied Radiation and Isotopes , 1999
166.
Electrophilic synthesis of 6-[18F]fluoro-L-DOPA using post-target produced [18F]F2
Forsback S., Eskola O., Haaparanta M., Bergmann J., Solin O.
Radiochimica Acta , 2008
167.
Synthesis of [18F]-L-DOPA radiopharmaceutical on a modified GE TracerLAB Fx F-E platform
Antuganov D.O., Zykov M.P., Ryzhkova D.V., Zykova T.A., Vinal’ev A.A., Antuganova Y.O., Samburov O.P.
Radiochemistry , 2016
168.
[18F]fluorination of an arylboronic ester using [18F]selectfluor bis(triflate): application to 6-[18F]fluoro-L-DOPA.
Stenhagen I.S., Kirjavainen A.K., Forsback S.J., Jørgensen C.G., Robins E.G., Luthra S.K., Solin O., Gouverneur V.
Chemical Communications , 2013
169.
18F labeling of arenes.
Tredwell M., Gouverneur V.
Angewandte Chemie - International Edition , 2012
170.
rcr_87_4_350_bib170
Shah
1998
171.
Nucleophilic 18F-fluorination of heteroaromatic iodonium salts with no-carrier-added [18F]fluoride.
Ross T.L., Ermert J., Hocke C., Coenen H.H.
Journal of the American Chemical Society , 2007
173.
Convenient Synthesis of Diaryliodonium Salts for the Production of [18F]F‐DOPA
Edwards R., Westwell A.D., Daniels S., Wirth T.
European Journal of Organic Chemistry , 2014
175.
rcr_87_4_350_bib175
2015
176.
rcr_87_4_350_bib176
2010
178.
A general procedure for the fluorodenitration of aromatic substrates
Maggini M., Passudetti M., Gonzales-Trueba G., Prato M., Quintily U., Scorrano G.
Journal of Organic Chemistry , 1991
179.
rcr_87_4_350_bib179
Attiná
1983
180.
New fluorine-18 labeled benzaldehydes as precursors in the synthesis of radiopharmaceuticals for positron emission tomography
Orlovskaja V.V., Fedorova O.S., Studentsov E.P., Golovina A.A., Krasikova R.N.
Russian Chemical Bulletin , 2016
181.
Synthesis of high specific activity 6-[18F]fluorodopamine for positron emission tomography studies of sympathetic nervous tissue.
Ding Y.S., Fowler J.S., Gatley S.J., Dewey S.L., Wolf A.P., Schlyer D.J.
Journal of Medicinal Chemistry , 1991
183.
Catalytic enantioselective synthesis of 18F-fluorinated alpha-amino acids under phase-transfer conditions using (S)-NOBIN.
Krasikova R.N., Zaitsev V.V., Ametamey S.M., Kuznetsova O.F., Fedorova O.S., Mosevich I.K., Belokon Y.N., Vyskočil Š., Shatik S.V., Nader M., Schubiger P.A.
Nuclear Medicine and Biology , 2004
184.
No carrier added synthesis of O-(2'-[18F]fluoroethyl)-L-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff base.
Krasikova R.N., Kuznetsova O.F., Fedorova O.S., Maleev V.I., Saveleva T.F., Belokon Y.N.
Bioorganic and Medicinal Chemistry , 2008
185.
Production at the Curie Level of No-Carrier-Added 6-18F-Fluoro-l-Dopa
Libert L.C., Franci X., Plenevaux A.R., Ooi T., Maruoka K., Luxen A.J., Lemaire C.F.
Journal of Nuclear Medicine , 2013
186.
Synthesis of high specific activity (+)- and (-)-6-[18F]fluoronorepinephrine via the nucleophilic aromatic substitution reaction.
Ding Y.S., Fowler J.S., Gatley S.J., Dewey S.L., Wolf A.P.
Journal of Medicinal Chemistry , 1991
187.
Enzymatic synthesis of no-carrier-added 6-[18F]fluoro-l-dopa with β-tyrosinase
Kaneko S., Ishiwata K., Hatano K., Omura H., Ito K., Senda M.
Applied Radiation and Isotopes , 1999
188.
Cu-catalyzed fluorination of diaryliodonium salts with KF.
Ichiishi N., Canty A.J., Yates B.F., Sanford M.S.
Organic Letters , 2013
189.
rcr_87_4_350_bib189
Vavere
J. Nucl. Med. , 2014
190.
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
191.
rcr_87_4_350_bib191
Qiao
2011
192.
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
193.
Development of new methods in modern selective organic synthesis: Preparation of functionalized molecules with atomic precision
Ananikov V.P., Khemchyan L.L., Ivanova Y.V., Bukhtiyarov V.I., Sorokin A.M., Prosvirin I.P., Vatsadze S.Z., Medved'ko A.V., Nuriev V.N., Dilman A.D., Levin V.V., Koptyug I.V., Kovtunov K.V., Zhivonitko V.V., Likholobov V.A., et. al.
Russian Chemical Reviews , 2014
194.
Chevalme Y., Montravers F., Vuillez J., Zanca M., Fallais C., Oustrin J., Talbot J.
Brazilian Archives of Biology and Technology , 2007
195.
Alcohol-Enhanced Cu-Mediated Radiofluorination.
Zischler J., Kolks N., Modemann D., Neumaier B., Zlatopolskiy B.D.
Chemistry - A European Journal , 2017
196.
Stereoelectronic Chameleons: The Donor–Acceptor Dichotomy of Functional Groups
Vatsadze S.Z., Loginova Y.D., dos Passos Gomes G., Alabugin I.V.
Chemistry - A European Journal , 2016
197.
Fluorine in Pharmaceuticals: Looking Beyond Intuition
Müller K., Faeh C., Diederich F.
Science , 2007
198.
Organic chemistry. History and mutual relations of universities of Russia
Antipin I.S., Kazymova M.A., Kuznetsov M.A., Vasilyev A.V., Ishchenko M.A., Kiryushkin A.A., Kuznetsova L.M., Makarenko S.V., Ostrovskii V.A., Petrov M.L., Solod O.V., Trishin Y.G., Yakovlev I.P., Nenaidenko V.G., Beloglazkina E.K., et. al.
Russian Journal of Organic Chemistry , 2017