Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent.

Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Research Abstract Details 

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Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Abstract Text:

Sang Ju Lee,Seung Jun Oh,Dae Yoon Chi,Hee Seup Kil,Euy Nyong Kim,Jin Sook Ryu,Dae Hyuk Moon,Sang Ju Lee,Seung Jun Oh,Dae Yoon Chi,Hee Seup Kil,Euy Nyong Kim,Jin Sook Ryu,Dae Hyuk Moon,

PURPOSE: The aim of this study was to develop a method of radiochemical synthesis of 3'-deoxy-3'-[18F]fluorothymidine ([18F]FLT) with an improved radiochemical yield using nucleophilic substitution catalyzed by protic solvent. METHODS: We introduced t-butanol (t-BuOH) as a new reaction solvent for nucleophilic [18F]fluorination with [18F]fluoride using (5'-O-DMTr-2'-deoxy-3'-O-nosyl-beta-D-threo-pentofuranosyl)-3-N-BOC-thymine to synthesize [18F]FLT. [18F]F- was eluted with (1) tetrabutylammonium bicarbonate (TBAHCO3), (2) Cs2CO3 and kryptofix 2.2.2 (K222) after trapping of [18F]F- on an ion exchange cartridge, or (3) addition of tetrabutylammonium hydroxide (TBAOH) and [18F]F- to the reactor without trapping [18F]F- on an ion exchange cartridge. We optimized [18F]fluorination conditions with t-butanol and then applied them to automatic synthesis using commercially available radiochemistry modules (TracerLab MX, GE Healthcare). RESULTS: We achieved a high radiochemical yield of 85.3+/-3.5% by radio-TLC with TBAHCO3 as an elution solvent and 20 mg of precursor at 100 degrees C (n=4). With the same labeling conditions, use of Cs2CO3 and K222 with t-BuOH and TBAOH with t-BuOH generated radiochemical yields of 57.1+/-22.5% and 55.0+/-18.8% by radio-TLC, respectively (n=3 for each condition). Automated synthesis with TBAHCO3 and 20 mg of precursor at 120 degrees C for 10 min of [18F]fluorination led to radiochemical yields of 60.2+/-5.2% after HPLC purification with an MX module (n=10). Synthesized [18F]FLT was stable for 6 h. CONCLUSION: [18F]FLT was synthesized with a significantly improved radiochemical yield by nucleophilic substitution catalyzed by protic solvent with mild reaction conditions and a short preparation time.

Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Publishing Authors By Initials

SJ Lee,SJ Oh,DY Chi,HS Kil,EN Kim,JS Ryu,DH Moon,SJ Lee,SJ Oh,DY Chi,HS Kil,EN Kim,JS Ryu,DH Moon,

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Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: European journal of nuclear medicine and molecular

VOLUME: 34

Page Numbers: 1406-9

Journal Abbreviation: Eur. J. Nucl. Med. Mol. Imagin

ISSN: 1619-7070

DAY: 24

MONTH: 03

YEAR: 2007

Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent. Information

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LANGUAGE: eng

NlmUniqueID: 101140988

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Grant and Affiliation Information for Simple and highly efficient synthesis of 3'-deoxy-3'-[18F]fluorothymidine using nucleophilic fluorination catalyzed by protic solvent.

AFFILIATION: Department of Nuclear Medicine, Asan Medical Center, University of Ulsan College of Medicine, 388-1 Pungnap-dong, Songpa-gu, Seoul, 138-736, South Korea.

Country: Germany

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MEDLINETA: Eur J Nucl Med Mol Imaging

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