Figure 2. Representative radio-HPLC (coinjected with the authentic compound) and radio-TLC chromatogram.
Figure 1. Elution efficiency with different PTA amount in Table 2.
Table 1. Comparison of elution efficiency with different phase transfer agents and organic solventsa)
Table 2. Study of elution efficiency with different amount of PTA eluentaa)
Table 3. Effect of total organic content on elution efficiency
Table 4. Radiofluorination with different organic content in reaction medium (DMSO)a)
References
- Phelps ME. Positron emission tomography provides molecular imaging of biological processes. Proc. Natl. Acad. Sci. U.S.A. 2000;97:9226-9233. https://doi.org/10.1073/pnas.97.16.9226
- Ametamey SM, Honer M, Schubiger PA. Molecular Imaging with PET. Chem. Rev. 2008;108:1501-1516. https://doi.org/10.1021/cr0782426
- Jacobson O, Kiesewetter DO, Chen X. Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic Routes. Bioconjug Chem. 2015;26:1-18. https://doi.org/10.1021/bc500475e
-
Miller PW, Long NJ, Vilar R, Gee AD. Synthesis of
$^{11}C$ ,$^{18}F$ ,$^{15}O$ , and$^{13}N$ Radiolabels for Positron Emission Tomography. Angew. Chem. Int. Ed. 2008;47:8998-9033. https://doi.org/10.1002/anie.200800222 -
Cai L, Lu S, Pike VW. Chemistry with [
$^{18}F$ ]Fluoride Ion. Eur. J. Org. Chem. 2008;2853-2873. - Kwon Y-D, Son J, Yun M, Chun J-H. Azeotropic drying-free aliphatic radiofluorination to produce PET radiotracers in a mixed organic solvent system. Tetrahedron Lett. 2018;59:2848-2852. https://doi.org/10.1016/j.tetlet.2018.06.033
- Kim DW, Choe YS, Chi DY. A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water. Nucl. Med. Biol. 2003;30:345-350. https://doi.org/10.1016/S0969-8051(03)00017-9
-
Brichard L, Aigbirhio FI. An Efficient Method for Enhancing the Reactivity and Flexibility of [
$^{18}F$ ] Fluoride Towards Nucleophilic Substitution Using Tetraethylammonium Bicarbonate. Eur. J. Org. Chem. 2014;6145-6149. -
Aerts J, Voccia S, Lemaire C, Giacomelli F, Goblet D, Thonon D, Plenevaux A, Warnock G, Luxen A. Fast production of highly concentrated reactive [
$^{18}F$ ] fluoride for aliphatic and aromatic nucleophilic radiolabelling. Tetrahedron Lett. 2010;51:64-66. https://doi.org/10.1016/j.tetlet.2009.10.085 -
Lemaire CF, Aerts JJ, Voccia S, Libert LC, Mercier F, Goblet D, Plenevaux AR, Luxen AJ. Fast Production of Highly Reactive No-Carrier-Added [
$^{18}F$ ]Fluoride for the Labeling of Radiopharmaceuticals. Angew. Chem. Int. Ed. 2010;49:3161-3164. https://doi.org/10.1002/anie.200906341 -
Mossine AV, Brooks AF, Ichiishi N, Makaravage KJ, Sanford MS, Scott PJH. Development of Customized [
$^{18}F$ ]Fluoride Elution Techniques for the Enhancement of Copper-Mediated Late-Stage Radiofluorination. Sci. Rep. 2017;7:233. https://doi.org/10.1038/s41598-017-00110-1 - Chun J-H, Telu S, Lu S, Pike VW. Radiofluorination of diaryliodonium tosylates under aqueous-organic and cryptand-free conditions. Org. Biomol. Chem. 2013;11:5094-5099. https://doi.org/10.1039/c3ob40742j
- Obermayer D, Znidar D, Glotz G, Stadler A, Dallinger D, Kappe CO. Design and Performance Validation of a Conductively Heated Sealed-Vessel Reactor for Organic Synthesis. J. Org. Chem. 2016;81:11788-11801. https://doi.org/10.1021/acs.joc.6b02242
- Kim DW, Ahn D-S, Oh Y-H, Lee S, Kil HS, Oh SJ, Lee SJ, Kim JS, Ryu JS, Moon DH, Chi DY. A New Class of SN2 Reactions Catalyzed by Protic Solvents: Facile Fluorination for Isotopic Labeling of Diagnostic Molecules. J. Am. Chem. Soc. 2006;128:16394-16397. https://doi.org/10.1021/ja0646895
- Kim DW, Jeong H-J, Lim ST, Sohn M-H, Katzenellenbogen JA, Chi DY. Facile Nucleophilic Fluorination Reactions Using tert-Alcohols as a Reaction Medium: Significantly Enhanced Reactivity of Alkali Metal Fluorides and Improved Selectivity. J. Org. Chem. 2008;73:957-962. https://doi.org/10.1021/jo7021229
- Shinde SS, Lee BS, Chi DY. Synergistic Effect of Two Solvents, tert-Alcohol and Ionic Liquid, in One Molecule in Nucleophilic Fluorination. Org. Lett. 2008;10:733-735. https://doi.org/10.1021/ol702679d