A new nucleophilic fluorine-18 labeling method for aliphatic mesylates: Reaction in ionic liquids shows tolerance for water

Nuclear Medicine and Biology

Volumn 30, Issue 4, 2003, Pages 345-350

  Kim, Dong Wook ^a   Choe, Yearn Seong ^b   Chi, Dae Yoon ^a  

^a Inha University   (South Korea)

^b Sungkyunkwan University School of Medicine   (South Korea)

Author keywords

Fluorination; Fluorine 18; Ionic liquid; Labeling method; PET; Potassium fluoride

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM TRIFLATE; 2 (3 METHANESULFONYLOXYPROPOXY)NAPHTHALENE; ALKANE DERIVATIVE; FLUORINE; FLUORINE 18; FLUOROALKANE; HALOGENOALKANE; ION; MESYLIC ACID DERIVATIVE; MESYLOXYALKANE; NAPHTHALENE DERIVATIVE; OXYGEN 18; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL MODEL; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; FLUORINATION; ISOTOPE LABELING; LIQUID; MOLECULAR MECHANICS; RADIOCHEMISTRY; RADIOFLUORINATION; TEMPERATURE; TIME;

EID: 0037721073     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(03)00017-9     Document Type: Article

References (14)

1. M.C. Lasne, C. Perrio, J. Rouden, L. Barre, D. Roeda, F. Dolle, C. Crouzel, Chemistry of beta(+)-emitting compounds based on fluorine-18, Contrast Agents II, Topics in Current Chemistry, Springer-Verlag, Berlin, 222 (2002) 201-258.
2. Bolton R. Radiohalogen incorporation into organic systems. J. Labelled Compd. Radiopharm. 45:2002;485-528.
3. Gerstenberger M.R.C., Haas A. Methods of fluorination in organic chemistry. Angew. Chem. Int. Ed. Engl. 20:1981;647-667.
4. Mascaretti O.A. Modern methods for the monofluorination of aliphatic organic compounds. Aldrichimica. Acta. 26:1993;47-58.
5. Chi D.Y., Kilbourn M.R., Katzenellenbogen J.A., Welch M.J. A rapid and efficient method for the fluoroalkylation of amines and amides. Development of a method suitable for incoration of the short-lived positron emitting radionuclide fluorine-18. J. Org. Chem. 52:1987;658-664.
6. Kim D.W., Choi H.Y., Lee K.C., Choe Y.S., Chi D.Y. Synthesis and fluorine-18 labeling of fluoroalkylquinoline-5,8-diones. J. Labelled Compd. Radiopharm. 44S:2001;906-908.
7. 18F]FHBG) A new potential imaging agent for vial infection and gene therapy using PET . Nucl. Med. Biol. 25:1998;175-180.
8. 18F]fluoride production. Int. J. Appl. Radiat. Isot. 36:1985;327-328.
9. Welton T. Room-Temperature ionic liquids. Solvents for Synthesis and Catalysis. Chem. Res. 99:1999;2071-2083.
10. J.D. Holbrey, K.R. Seddon, The phase behaviour of 1-alkyl-3-methylimidazolium tetrafluoroborates; ionic liquids and ionic liquids crystals, J. Chem. Soc. Dalton Trans. (1999) 2133-2139.
11. Wasserscheid P., Keim W. Ionic liquids-New "Solution" for transition metal Catalysis. Angew. Chem. Int. Ed. Engl. 39:2000;3772-3789.
12. Kim D.W., Song C.E., Chi D.Y. New method of fluorination using potassium fluoride in ionic liquid Significantly enhanced reactivity of fluoride and improved selectivity . J. Am. Chem. Soc. 124:2002;10278-10279.
13. 18F]fluoromethylbenzylation of amides and amines . Appl. Radiat. Isot. 49:1998;73-77.
14. S. Rozen, M. Brand, Direct fluorination of lithium enolates with acetyl hypofluorite, Synthesis (1985) 665-667.