Browse > Article

A Novel Aromatic Fluorine-18 Labeling Method Using Iodonium Salts Precursor  

Moon, Byung-Seok (Institute of Radiation Medicine, Seoul National University Medical Research Center & Department of Nuclear Medicine, Seoul National University Bundang Hospital)
Lee, Byung-Chul (Institute of Radiation Medicine, Seoul National University Medical Research Center & Department of Nuclear Medicine, Seoul National University Bundang Hospital)
Kim, Sang-Eun (Institute of Radiation Medicine, Seoul National University Medical Research Center & Department of Nuclear Medicine, Seoul National University Bundang Hospital)
Publication Information
Nuclear Medicine and Molecular Imaging / v.43, no.1, 2009 , pp. 1-9 More about this Journal
Abstract
As many new drug substances contained various aromatic rings and fluorine attached to an electron rich aromatic ring or on the meta-position, a strategy towards improvement in aromatic fluorination of these compounds is highly desirable. The introduction of fluorine-18 onto aromatic rings showed in the limited condition containing electron withdrawing group (EWG) on the para- or ortho-position to get reasonable radiochemical yield so far. No-carrier added (NCA) [$^{18}F$]fluoroarene syntheses by iodonium salts recently reported that has the potential to greatly increase the yield in systems or positions that normally not reactive enough to give sufficient yields in simple model reaction. This review describes the methodological approach towards effective aromatic fluorination by diaryliodonium salts and future prospects in an application of novel PET radiotracer.
Keywords
Aromatic fluorination; fluorine-18; diaryliodonium salts; PET;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
연도 인용수 순위
1 Chi DY. The development of radiopharmaceuticals for human body imaging. J Korean Ind Eng Chem 2003;14:253-62
2 Katsifis A, Hamacher K, Schnitter J, Stocklin G. Synthesis of fluorine-18-labelled 5- and 6-fluoro-2-pyridinamine. Appl Radiat Isot 1993;44:1015-20   DOI   ScienceOn
3 Ogawa M, Hatano K, Oishi S, Kawasumi Y, Fujii N, Kawaguchi M, et al. Direct electrophilic radiofluorination of a cyclic RGD peptide for in vivo $a_v_3$ integrin related tumor imaging. Nucl Med Biol 2003;30: 1-9   DOI   ScienceOn
4 Kilbourn MR, Welch MJ, Dence CS, Tewson TJ, Saji H, Maeda M. Carrier-added and no-carrier -added syntheses of $[^{18}F]$spiroperidol and $[^{18}F]$haloperidol. J Appl Radiat Isot 1984;35:591-8   DOI   ScienceOn
5 Imahori Y, Ueda S, Ohmori Y, Kusuki T, Ono K, Fujii R, et al. Fluorine-18-labeled fluoroboronophenylalanine PET in patients with glioma. J Nucl Med 1998;39:325-33   PUBMED   ScienceOn
6 Satyamurthy N, Bida GT, Phelps ME, Barrio JR N-[$^{18}F$]Fluoro-N-alkylsulfonamides: novel reagents for mild and regioselective radiofluorination. Appl Radiat Isot 1990;41:733-8   DOI   ScienceOn
7 Pike VW, Aigbirhio FI. Reactions of cyclotron-produced [$^{18}F$]fluoride with diaryliodonium salts-a novel single-step route to no-carrier-added [$^{18}F$]fluoroarenes. J Chem Soc Chem Commun 1995;2215-6
8 Shah A, Pike VW, Widdowson DA. The synthesis of [$^{18}F$]fluoroarenes from the reaction of cyclotron-produced [$^{18}F$]fluoride ion with diaryliodonium salts. J Chem Soc Perkin Trans 1 1998;2043-6
9 Kazmierczak P, Skulski L, Kraszkiewicz. Syntheses of (diacetoxyiodo )arenes or iodylarenes from iodoarenes, with sodium periodate as the oxidant. Molecules 2001;6:881-91   DOI
10 Kitamura T, Matsuyuki J, Nagata K, Furuki R, Taniguchi H. A concenient preparation of diaryliodonium triflates. Synthesis 1992;945-6   DOI
11 Lee BC, Dence CS, Zhou H, Parent EE, Welch MJ, Katzenellenbogen JA. Fluorine-18 labeling and biodistribution studies on peroxisome proliferator-activated receptor-gamma (PPARg) ligands: potential positron emission tomography (PET) imaging agents. Nucl Med Biol 2009;36:147-53   DOI   ScienceOn
12 Kilbourn MR. Nucl. Sci. Series, NAS-NS3203, National Academy Press, Washington DC, 1990
13 Ermert J, Hocke C, Ludwig T, Gail R. Comparison of pathways to the versatile synthon of no-carrier-added 1-bromo-4-[$^{18}F]fluorobenzene. J Labell Compd Radiopharm 2004;47:429-41   DOI   ScienceOn
14 Zhang M-R, Kumata K, Suzuki K. A practical route for synthesizing a PET ligand containing [$^{18}8F]fluorobenzene using reaction of diphenyliodonium salt with [$^{18}8F]F. Tetrahedron Lett 2007;48:8632-5   DOI   ScienceOn
15 Coenen HH. In Synthesis and Application of Isotopically Labeled Compounds (Eds.: T. A. Bailey, J. R Jones), Elsevier, Amsterdam, 1989, pp. 4334-48
16 Luxen A, Perlmutter M, Bida GT, Van Moffaert G, Cook JS, Satyamurthy N, et al. Remote, semiautomated production of $6-[^{18}F]$fluoro-L-dopa for human studies with PET. Appl Radiat Isot 1990;41:275-81   DOI   ScienceOn
17 Knochel A, Zwememann O. Aromatic n.c.a. labelling with $^{18}F$ by modified Balz-Schiemann-decomposition. Appl Radiat Isot 1991;42:1077-80   DOI   ScienceOn
18 Kitamura T, Matsuyuki J, Taniguchi H. Improved preparation of diaryliodonium triflates. Synthesis 1994; 147-8   DOI   ScienceOn
19 Moon BS, Kim JH, Lee KC, An GI, Cheon GJ, Chun KS. Production of $[^{18}F]F_2$ gas for electrophilic substitution reaction. Nucl Med Mol Imaging 2006;40:228-32   과학기술학회마을
20 Oberdorfer F, Hofmann E, Maier-Borst W. Preparation of $^{18}F$-labelled 5-fluorouracil of very high purity. J Labell Compd Radiopharm 1989;27: 137-45   DOI   ScienceOn
21 Sawaguchi M, Ayuba S, Hara S. A practical synthetic method of iodoarene difluorides without fluorine gas and mercury salts. Synthesis 2002;13:1802-3
22 Kim DW, Ahn DS, Oh YH, Lee S, Kil HS, Oh SJ, et al. A new class of $SN_2$ reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules. J Am Chern Soc 2006;128:16393-7   DOI   ScienceOn
23 Balz G, Schiemann G. ber aromatische fluorverbindungen, I: Ein neues verfahren zu ihrer darstellung. Ber Dtsch Chem Ges 1927;60:1186-90   DOI
24 Wallach O. Ueber das verhalten einiger diazo- und diazoamidoverbindungen. Justus Liebigs Ann Chem 1886;235:233-55   DOI
25 Simon FG, Pike VW. Radiosyntheses of 2-[$^{18}F$]fluoro-1,3-thiazoles. J Labell Compd Radiopharm 2005;48(Suppl 1):S158
26 Koser GF, Wettach RH, Smith CS. New methodology in iodonium salt synthesis. Reactions of [hydroxy(tosyloxy)iodo]arenes with aryltrimethylsilanes. J Org Chem 1980;45:1543-4   DOI
27 Oberdorfer F, Hofmann E, Maier-Borst W. Preparation of a new $^{18}F$-labelled precursor: 1-[$^{18}F$]fluoro-2-pyridone. Appl Radiat Isot 1988;39:685-8   DOI   ScienceOn
28 Shah A, Pike VW, Widdowson DA. Synthesis of functionalized unsymmertrical diaryliodonium salts. J Chem Soc Perkin Trans 1 1997;2463-5
29 Karramkam M, Hinnen F, Berrehourna M, Hlavacek C, Vaufrey F, Halldin C, et al. Synthesis of a [6-pyridinyl-$^{18}F$]-labelled fluoro derivative of WAY-100635 as a candidate radioligand for brain $5-HT_{1A}$ receptor imaging with PET. Bioorg Med Chem 2003;11:2769-82   DOI   ScienceOn
30 Lee BC, Lee KC, Lee H, Mach RH, Katzenellenbogen JA. Strategies for the labeling of halogen-substituted peroxisome proliferator-activated receptor gamma ligands: potential positron emission tomography and single photon emission computed tomography imaging agents. Bioconjugate Chem 2007;18:514-23   DOI   ScienceOn
31 Pages T, Langlois BR. Fluorination of aromatic compounds from 1-aryl-3,3-dimethyltriazenes and fluoride anions in acidic medium: 1. A model for $^{18}F$ labelling. J Fluorine Chem 2001;107:321-7   DOI   ScienceOn
32 Hamacher K, Hamkens W. Remote controlled one-step production of $^{18}F$ labeled butyrophenone neuroleptics exemplified by the synthesis of n.c.a. $[^{18}F]$N-methylspiperone. Appl Radiat Isot 1995;46:911-6   DOI   ScienceOn
33 Hess E, Sichler S, Kluge A, Coenen HH. Synthesis of $2-[^{18}F]$fluoro-L-tyrosine via regiospecific fluoro-de-stannylation. Appl Radiat Isot 2002;57:185-91   DOI   ScienceOn
34 Purrington ST, Jones WA. 1-Fluoro-2-pyridone: a useful fluorinating reagent. J Org Chem 1983;48:761   DOI
35 Pages T, Langlois BR, Le Bars D, Landais P. Fluorination of aromatic compounds from 1-aryl-3,3-dimethyltriazenes and fluoride anions in acidic medium: 2. Synthesis of (S)-[$^{18}F$]-3-fluoroa-methylphenylalanine. J. Fluorine Chem 2001;107:329-35   DOI   ScienceOn
36 Carroll MA, Nairne J, Woodcraft JL. Diaryliodonium salts: a solution to 3-[$^{18}F$]fluoropyridine. J Labell Compd Radiopharm 2007;50:452-4   DOI   ScienceOn
37 Moon BS, Shim AY, Lee KC, Lee HJ, Lee BS, An GI, et al. Synthesis of F-18 labeled capecitabine using $[^{18}F]F_2$ gas as a tumor imaging agent. Bull Korean Chem Soc 2005;26:1865-8   DOI   ScienceOn
38 Oberdorfer F, Hofmann E, Maier-Borst W. Preparation of $^{18}F$-labelled N-fluoropyridinium triflate. J Labelled Compd Radiopharm 1988;25:999-1005   DOI   ScienceOn
39 Pike VW, Butt F, Shah A, Widdowson DA. Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributy-Istannanes with Koser's reagent. J Chem Soc Perkin Trans 1 1999:245-48
40 Namavari M, Bishop A, Satyamurthy N, Bida G, Barrio JR. Regioselective radiofluorodestannylation with $[^{18}F]F_2$ and $[^{18}F]CH_3COOF$; A high yield synthesis of $6-[^{18}F]$fluoro-L-dopa. Appl Radiat Isot 1992;43:989-96   DOI   ScienceOn
41 Pascali C, Lutbra SK, Pike VW, Price GW, Ahier RG, Hume SP, et al. The radiosynthesis of [$^{18}sF$]PK 14105 as an alternative radioligand for peripheral type benzodiazepine binding sites. Appl Radiat Isot 1990;41:477-82   DOI   ScienceOn