Skip to main content
Disciplines
Automotive Business IT + Informatics Construction + Real Estate Electrical Engineering + Electronics Energy + Sustainability Insurance + Risk Finance + Banking Management + Leadership Marketing + Sales Mechanical Engineering + Materials
Events
DE
EN
Books
Journals
Topic Page
Marketing
Start single access now
Access for companies
EXTENDED SEARCH
Log in
Top
Published in:
Cover of the book

2020 | OriginalPaper | Chapter

Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography

Authors : Jian Rong, Steven H. Liang

Published in: Fluorination

Publisher: Springer Singapore

Log in

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Excerpt

Positron emission tomography (PET) is a noninvasive medical imaging technique that has been rapidly developing in the past several decades. By imaging the uptake and distribution of a radiolabeled molecule, PET is an important diagnostic tool for investigating diverse types of diseases in preclinical and clinical research and drug development. Compared to other imaging techniques, such as magnetic resonance imaging (MRI), computed tomography (CT), X-ray, or ultrasound which provide structural and anatomical information, PET provides quantitative functional information about biological process at the molecular level. Following by in vivo injection of molecules labeled with positron-emitters, PET imaging is accomplished by the detection of two gamma ray photons (511 keV, ~180° apart) from annihilation of a positron (from β+-decay from radiolabeled molecules) and an electron in proximity. Frequently used positron-emitting radionuclides include carbon-11 (11C, half-life 20.4 min), nitrogen-13 (13N, half-life 10.0 min), oxygen-15 (15O, half-life 2.0 min), fluorine-18 (18F, half-life 109.8 min), as well as radiometals, such as copper-64 (64Cu, half-life 12.7 h), gallium-68 (68Ga, half-life 68 min), yttrium-86 (86Y, half-life 14.7 h), and zirconium-89 (89Zr, half-life 78.4 h). In particular, fluorine-18 has distinct characteristics as positron-emitting radionuclide, such as high positron emission pattern (97% β+-decay ratio), reasonable half-life (109.8 min), which not only allows sufficient time for 18F-incorporation of target molecules and 18F-labeled molecules to reach and bind molecular targets (compared to 11C), but also provides reduced radiation dosimetry for patients (compared to long-lived radiometals). The relatively low positron energy (0.635 MeV) limits fluorine-18 to short travel path, leading to high-resolution PET images. Nowadays, 18F is the most widely used positron-emitting radioisotope probably attributed to the widely used PET pharmaceutical, 2-[18F]fluoro-2-deoxy-D-glucose ([18F]FDG) which is used clinically to assess cancers, cardiovascular and neurological diseases. The favorable characteristics of fluorine-18 generate a continuous need to develop novel 18F-labeled PET molecules and related chemical methods for radiofluorination in order to study various disease conditions and conduct thorough investigation of diverse biological process. …

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

inform now

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

inform now
next chapter Aminosulfur Trifluoride Deoxofluorination
Literature
1.
Bergman J, Solin O (1997) Fluorine-18-labeled fluorine gas for synthesis of tracer molecules. Nucl Med Biol 24:677-683PubMed
2.
Ehrenkaufer RE, MacGregor RR (1983) Synthesis of [18F]perchloryl fluoride and its reactions with functionalized aryl lithiums. Int J Appl Radiat Isot 34 (3):613-615
3.
Neirinckx RD, Lambrecht RM, Wolf AP (1978) Cyclotron isotopes and radiopharmaceuticals-XXV: an anhydrous 18F-fluorination intermediate: trifluoromethyl hypofluorite. Int J Appl Radiat Isot 29:323-327
4.
Chirakal R, Firnau G, Couse J, Garnett ES (1984) Radiofluorination with 18F-labelled acetyl hypofluorite: [18F]L-6-fluorodopa. Int J Appl Radiat Isot 35 (7):651-653
5.
Sood S, Rirnau G, S. GE (1983) Radiofluorination with xenon difluoride: a new high yield synthesis of [18F]2-fluoro-2-deoxy-D-glucose. Int J Appl Radiat Isot 34 (4):743-745PubMed
6.
Schrobilgen G, Firnau G, Chirakal R, S. GE (1981) Synthesis of [18F]XeF, a novel agent for the preparation of 18F-radiopharmaceuticals. J Chem Soc Chem Commun 0:198-199
7.
Oberdorfer F, Hofmann E, Maier-Borst W (1988) Preparation of a new 18F-labelled precursor: 1-[18F]fluoro-2-pyridone. Int J Radiat Appl Instrum Part A 39 (7):685-688
8.
Teare H, Robins EG, Årstad E, Luthra SK, Gouverneur V (2007) Synthesis and reactivity of [18F]-N-fluorobenzenesulfonimide. Chem Commun 43 (23):2330-2332
9.
Teare H, Robins EG, Kirjavainen A, Forsback S, Sandford G, Solin O, Luthra SK, Gouverneur V (2010) Radiosynthesis and evaluation of [18F]Selectfluor bis(triflate). Angew Chem Int Ed 49:6821-6824
10.
Stenhagen IS, Kirjavainen AK, Forsback SJ, Jorgensen CG, Robins EG, Luthra SK, Solin O, Gouverneur V (2013) [18F]fluorination of an arylboronic ester using [18F]selectfluor bis(triflate): application to 6-[18F]fluoro-L-DOPA. Chem Commun 49:1386-1388
11.
Oberdorfer F, Hofmann E, Maier-Borst W (1988) Preparation of 18F-labeled N-fluoropyridinium triflate. J Label Comp Radiopharm 25:999-1005
12.
Ido T, Wan C-N, Casella V, Fowler JS, P. WA (1978) Labeled 2-deoxy-D-glucose analogs—18F-labeled 2-deoxy-2-fluoro-D-glucose, 2-deoxy-2-fluoro-D-mannose and 14C-2-deoxy-2-fluoro-D-glucose. J Label Comp Radiopharm 14:175-183
13.
Dolbier WR, Li A-R, Koch CJ, Shiue C-Y, Kachur AV (2001) [18F]-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure. Appl Radiat Isot 54:73-80PubMed
14.
Nodwell MB, Yang H, Colovic M, Yuan Z, Merkens H, Martin RE, Benard F, Schaffer P, Britton R (2017) (18)F-Fluorination of unactivated C-H bonds in branched aliphatic amino acids: direct synthesis of oncological positron emission tomography imaging agents. J Am Chem Soc 139:3595-3598PubMed
15.
Hamacher FK, Coenen HH, Stöcklin G (1986) Efficient stereospecific synthesis of no-carrier-added 2-[18F]-fluoro-2-deoxy-D-glucose using aminopolyether supported nucleophilic substitution. J Nucl Med 27:235-238.PubMed
16.
Tang G, Wang M, Tang X, Gan M, Luo L (2005) Fully automated one-pot synthesis of [18F]fluoromisonidazole. Nucl Med Biol 32 (5):553-558PubMed
17.
Mukherjee J, Yang Z-Y, Das MK, Brown T (1995) Fluorinated benzamide neuroleptics-III. Development of (S)-N-[(1-allyl-2-pyrrolidinyl)methyl]-5-(3-[18F]fluoropropyl)-2,3-dimethoxybenzamide as an improved dopamine D-2 receptor tracer. Nucl Med Biol 22 (3):283-296PubMed
18.
Machulla H-J, Blocher A, Kuntzsch M, Piert M, Wei R, R. GJ (2000) Simplified labeling approach for synthesizing 3′-deoxy-3′-[18F]fluorothymidine ([18F]FLT). J Radioanal Nucl Ch 243 (3):843-846
19.
Mori T, Kasamatsu S, Mosdzianowski C, Welch MJ, Yonekura Y, Fujibayashi Y (2006) Automatic synthesis of 16α-[18F]fluoro-17β-estradiol using a cassette-type [18F]fluorodeoxyglucose synthesizer. Nucl Med Biol 33 (2):281-286PubMed
20.
Kim DW, Ahn D-S, Oh Y-H, Lee S, Kil HS, Oh SJ, Kim JS, Ryu JS, Moon DH, Chi DY (2003) A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: reaction in ionic liquids shows tolerance for water. Nucl Med Biol 30 (4):345-350PubMed
21.
Kim DW, Ahn D-S, Young-Ho O, Sungyul L, Seup KH, Jun OS, Ju LS, Seung KJ, Sook RJ, Hyuk MD, Yoon CD (2006) A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules. J Am Chem Soc 128:16394-16397PubMed
22.
Chaly T, Dhawan V, Kazumata K, Antonini A, Margouleff C, Dahl JR, Belakhlef A, Margouleff D, Yee A, Wang S, Tamqnan G, Neumeyer JL, Eidelberg D (1996) Radiosynthesis of [18F]N-3-fluoropropyl-2-β-carbomethoxy-3-β-(4-iodophenyl)nortropane and the first human study with positron emission tomography. Nucl Med Biol 23:999-1004PubMed
23.
Nielsen MK, Ugaz CR, Li W, Doyle AG (2015) PyFluor: A low-cost, stable, and selective deoxyfluorination reagent. J Am Chem Soc 137 (30):9571-9574PubMed
24.
Liang SH, Vasdev N (2014) Csp3-18F bond formation by transition-metal-based [18F]fluorination. Angew Chem Int Ed 53:11416-11418
25.
Hintermann L, Läng F, Maire P, Togni A (2006) Interactions of cationic palladium(II)- and platinum(II)-η3-allyl complexes with fluoride: is asymmetric allylic fluorination a viable reaction? Eur J Inorg Chem 2006 (7):1397-1412
26.
Hollingworth C, Hazari A, Hopkinson MN, Tredwell M, Benedetto E, Huiban M, Gee AD, Brown JM, Gouverneur V (2011) Palladium-catalyzed allylic fluorination. Angew Chem Int Ed 50:2613-2617
27.
Topczewski JJ, Tewson TJ, Nguyen HM (2011) Iridium-catalyzed allylic fluorination of trichloroacetimidates. J Am Chem Soc 133 (48):19318-19321PubMed
28.
Benedetto E, Tredwell M, Hollingworth C, Khotavivattana T, Brown JM, Gouverneur V (2013) Regio- and stereoretentive synthesis of branched, linear (E)- and (Z)-allyl fluorides from allyl carbonates under Ir-catalysis. Chem Sci 4 (1):89-96
29.
Huang X, Liu W, Ren H, Neelamegam R, Hooker JM, Groves JT (2014) Late stage benzylic C-H fluorination with [18F]fluoride for PET imaging. J Am Chem Soc 136 (19):6842-6845PubMed
30.
Liu W, Huang X, Placzek MS, Krska SW, McQuade P, Hooker JM, Groves JT (2018) Site-selective 18F fluorination of unactivated C–H bonds mediated by a manganese porphyrin. Chem Sci 9:1168-1172PubMed
31.
Kalow JA, Doyle AG (2010) Enantioselective ring opening of epoxides by fluoride anion promoted by a cooperative dual-catalyst system. J Am Chem Soc 132:3268-3269PubMed
32.
Graham TJ, Lambert RF, Ploessl K, Kung HF, Doyle AG (2014) Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins. J Am Chem Soc 136 (14):5291-5294PubMed
33.
Onega M, Winkler M, O’Hagan D (2009) Fluorinase: a tool for the synthesis of 18F-labeled sugars and nucleosides for PET. Future Med Chem 1 (5):865-873PubMed
34.
Martarello L, Schaffrath C, Deng H, Gee AD, Lockhart A, O’Hagan D (2003) The first enzymatic method for C-18F bond formation: the synthesis of 5′-[18F]-fluoro-5′-deoxyadenosine for imaging with PET. J Label Comp Radiopharm 46 (13):1181-1189
35.
Deng H, Cobb SL, Gee AD, Lockhart A, Martarello L, McGlinchey RP, O’Hagan D, Onega M (2006) Fluorinase mediated C-18F bond formation, an enzymatic tool for PET labelling. Chem Commun 42 (6):652-654
36.
Yang B, Chansaenpak K, Wu H, Zhu L, Wang M, Li Z, Lu H (2017) Silver-promoted (radio)fluorination of unsaturated carbamates via a radical process. Chem Commun 53 (24):3497-3500
37.
Cortés González MA, Nordeman P, Bermejo Gómez A, Meyer DN, Antoni G, Schou M, Szabó KJ (2018) [18F]fluoro-benziodoxole: a no-carrier-added electrophilic fluorinating reagent. Rapid, simple radiosynthesis, purification and application for fluorine-18 labelling. Chem Commun 54 (34): 4286-4289
38.
Zhang M-R, Suzuki K (2007) [18F]Fluoroalkyl agents: synthesis, reactivity and application for development of PET ligands in molecular imaging. Curr Top Med Chem 7:1817-1828PubMed
39.
Kniess T, Laube M, Brust P, Steinbach J (2015) 2-[18F]Fluoroethyl tosylate – a versatile tool for building 18F-based radiotracers for positron emission tomography. MedChemComm 6 (10):1714-1754
40.
van der Born D, Pees A, Poot AJ, Orru RVA, Windhorst AD, Vugts DJ (2017) Fluorine-18 labelled building blocks for PET tracer synthesis. Chem Soc Rev 46 (15):4709-4773PubMed
41.
Pretze M, Pietzsch D, Mamat C (2013) Recent trends in bioorthogonal click-radiolabeling reactions using fluorine-18. Molecules 18 (7):8618-8665PubMedPubMedCentral
42.
Metadata
Title
Aliphatic [18F]Fluorination Chemistry for Positron Emission Tomography
Authors
Jian Rong
Steven H. Liang
Copyright Year
2020
Publisher
Springer Singapore
Book
Fluorination

Print ISBN: 978-981-10-3895-2

Electronic ISBN: 978-981-10-3896-9

Copyright Year: 2020

DOI
https://doi.org/10.1007/978-981-10-3896-9_38

Premium Partners

    Image Credits