[en] The use of a polymeric solid support loaded with a long alkyl chain quaternary ammonium allows the rapid and efficient recovery of cyclotron produced [18F]F- from [18O]water to a low water content organic solution compatible with fast nucleophilic labelling of most precursors for PET radiopharmaceuticals in high yield.
Research Center/Unit :
GIGA CRC (Cyclotron Research Center) In vivo Imaging-Aging & Memory - ULiège
Disciplines :
Chemistry
Author, co-author :
Aerts, Joël ; Université de Liège - ULiège > Centre de recherches du cyclotron
Voccia, Samuel
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Giacomelli, Fabrice ; Université de Liège - ULiège > Centre de recherches du cyclotron
Goblet, David ; Université de Liège - ULiège > Centre de recherches du cyclotron
Thonon, David ; Université de Liège - ULiège > Centre de recherches du cyclotron
Plenevaux, Alain ; Université de Liège - ULiège > Centre de recherches du cyclotron
Warnock, Geoffrey ; Université de Liège - ULiège > Centre de recherches du cyclotron
Luxen, André ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse - Centre de recherches du cyclotron
Language :
English
Title :
Fast production of highly concentrated reactive [18F] fluoride for aliphatic and aromatic nucleophilic radiolabelling
Publication date :
2010
Journal title :
Tetrahedron Letters
ISSN :
0040-4039
Publisher :
Elsevier, Oxford, United Kingdom
Volume :
51
Pages :
64-66
Peer reviewed :
Peer Reviewed verified by ORBi
Funders :
F.R.S.-FNRS - Fonds de la Recherche Scientifique [BE] EU’s FP6 STRP 516984 MI-Lab-On-Chip
Ametamey S., Honer M., and Schubiger P. Chem. Rev. 108 (2008) 1501-1516
Levin C. Eur. J. Nucl. Med. Mol. Imaging 32 (2005) S325-S345
Padgett H., Schmidt D., Luxen A., Bida G., Satyamurthy N., and Barrio J. Appl. Radiat. Isot. 40 (1989) 433-445
Lemaire C., Damhaut P., Lauricella B., Mosdzianowski C., Morelle J.-L., Monclus M., Van Naemen J., Mulleneers E., Aerts J., Plenevaux A., Brihaye C., and Luxen A. J. Labelled Compd. Radiopharm. 45 (2002) 435-447
Tewson T.J. Nucl. Med. Biol. 6 (1989) 533-551
Nutt R., Vento L., and Ridinger M. Clin. Pharmacol. Ther. 81 (2007) 792-795
Lee C., Sui G., Elizarov A., Shu C., Shin Y., Dooley A., Huang J., Daridon A., Wyatt P., Stout D., Kolb H., Witte O., Satyamurthy N., Heath J., Phelps M., Quake S., and Tseng H. Science 310 (2005) 1793-1796
Hamacher K., Coenen H.H., and Stoecklin G. J. Nucl. Med. 27 (1986) 235-238
Stone-Elander S., and Elander N. J. Labelled Compd. Radiopharm. 45 (2002) 715-746
Kim D.W., Choe Y.S., and Chi D.Y. Nucl. Med. Biol. 30 (2003) 345-350
Kim D.W., Ahn D.-S., Oh Y.-H., Lee S., Kil H.S., Oh S.J., Lee S.J., Kim J.S., Ryu J.S., Moon D.H., and Chi D.Y. J. Am. Chem. Soc. 128 (2006) 16394-16397
Bejot R., Fowler T., Carroll L., Boldon S., Moore J.E., Declerck J., and Gouverneur V. Angew. Chem., Int. Ed. 48 (2009) 586-589
Watson D.A., Su M.S., Teverovskiy G., Zhang Y., García-Fortanet J., Kinzel T., and Buchwald S.L. Science 325 (2009) 1661-1664
Toorongian S., Mulholland G., Jewett D., Bachelor M., and Kilbourn M. Nucl. Med. Biol. 17 (1990) 273-279
Hamacher K., Hirschfelder T., and Coenen H. Appl. Radiat. Isot. 56 (2002) 519-523
Jewett D., Toorongian S., Mulholland G., Watkins G., and Kilbourn M. Appl. Radiat. Isot. 11 (1988) 1109-1111
Preparation of modified support: 25 mg of n-tetradecyl-trimethylammonium bicarbonate (C14HCO3) or n-tetradecyl-trimethylammonium bromide (C14Br) or n-decyltrimethyl-ammonium (C10Br) was dissolved in 1 ml of ACN. The solution was added to 100 mg of N-vinyl lactame/divinylbenzene copolymer sorbent, a typical example is Waters Oasis™ HLB. The suspension was triturated until complete evaporation of the solvent.
Preparation of extraction cartridges: 50 mg or 100 mg of modified support were introduced into an SPE reservoir (Isolute® empty reservoir 1 ml, internal diameter 5-6 mm) between two frits (Isolute® frits 20 μm 1 ml). When using a bromide salt, the solid was conditioned with 200 μl/50 mg of a solution of 50% P/P K2CO3 in water and rinsed with 3 ml of water. When using a bicarbonate salt, the functionalised sorbent was used without conditioning.
Typical [18F]F- recovery procedure: The water solution containing [18F]F- was passed through the extraction cartridge (at 1 ml/min). The cartridge was dried for 4 min with a nitrogen flow (10 l/min, upstream pressure 3.25 bar). The radioactivity was eluted with 1 ml ACN (dried on molecular sieves, <100 ppm water).
A Waters Sep-pak® QMA cartridge was eluted with a mixture of equal volumes of potassium carbonate in water (35 mg/1.5 ml) and Kryptofix K222 in ACN (110 mg/1.5 ml). A 500 μL aliquot was submitted to an azeotropic drying (95 °C, nitrogen flow, 5 min). The residue was dissolved in 1 ml of dry ACN (water <100 ppm) and the mixture was heated at 100 °C in capped reactor to simulate a labelling step. After cooling, the residual water concentration was estimated by Karl Fisher titration (541 ± 118 ppm, n = 3).
Landini D., Maia A., and Rampoldi A. J. Org. Chem. 54 (1989) 328-332
Labelling procedure: A fraction of the [18F]F- solution eluted from a modified support cartridge with an appropriate solvent was introduced into a reactor containing the precursor to be labelled and the additive, if necessary. The final volume was adjusted with the same solvent. The reactor was capped and the solution was heated without agitation. At the end of the labelling step, the reaction mixture was transferred to another vial. The reactor was rinsed with water. The residual activity in the reactor and the transferred activity were measured. The transferred water diluted mixture was analysed by TLC or HPLC to assay the percentage of [18F] incorporation. The yields were calculated from the chromatography results and the transferred percentages of activity.
Goblet, D.; Lemaire, C.; Giacomelli, F.; Plenevaux, A.; Warnock, G.; Franci, X.; Wouters, L.; Luxen, A. Automated synthesis of [18F]fallypride for imaging dopamine D2 receptors: Nice. In World Molecular Imaging Congress, 2008.
Lemaire C., Guillaume M., Cantineau R., and Christiaens L. J. Nucl. Med. 31 (1990) 1247-1251
Li X., Link J.M., Stekhova S., Yagle K.J., Smith C., Krohn K.A., and Tait J.F. Bioconjugate Chem. 19 (2008) 1684-1688
Le Bars D., Lemaire C., Ginovart N., Plenevaux A., Aerts J., Brihaye C., Hassoun W., Leviel V., Mekhsian P., Weissmann D., Pujol J., Luxen A., and Comar D. Nucl. Med. Biol. 25 (1998) 343-350