Nuclear Medicine and Molecular Imaging

The Korean Society of Nuclear Medicine (대한핵의학회)
권호 표지

Nucleophilic Fluorination Reactions in Novel Reaction Media for $^{18}F$-Fluorine Labeling Method

$^{18}F$-플루오린 표지를 위한 신개념 반응용매에서 친핵성 불소화 반응

  • Kim, Dong-Wook (Department of Nuclear Medicine, Cyclotron Research Center, Research Institute of Clinical Medicine, Chonbuk National University Medical School and Hospital) ;
  • Jeong, Hwan-Jeong (Department of Nuclear Medicine, Cyclotron Research Center, Research Institute of Clinical Medicine, Chonbuk National University Medical School and Hospital) ;
  • Lim, Seok-Tae (Department of Nuclear Medicine, Cyclotron Research Center, Research Institute of Clinical Medicine, Chonbuk National University Medical School and Hospital) ;
  • Sohn, Myung-Hee (Department of Nuclear Medicine, Cyclotron Research Center, Research Institute of Clinical Medicine, Chonbuk National University Medical School and Hospital)
  • 김동욱 (전북대학교 의학전문대학원 핵의학교실, 사이클로트론연구소, 임상의학연구소) ;
  • 정환정 (전북대학교 의학전문대학원 핵의학교실, 사이클로트론연구소, 임상의학연구소) ;
  • 임석태 (전북대학교 의학전문대학원 핵의학교실, 사이클로트론연구소, 임상의학연구소) ;
  • 손명희 (전북대학교 의학전문대학원 핵의학교실, 사이클로트론연구소, 임상의학연구소)
  • Published : 2009.04.30
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Abstract

Noninvasive imaging of molecular and biological processes in living subjects with positron emission tomography(PET) provides exciting opportunities to monitor metabolism and detect diseases in humans. Measuring these processes with PET requires the preparation of specific molecular imaging probes labeled with $^{18}F$-fluorine. In this review we describe recent methods and novel trends for the introduction of $^{18}F$-fluorine into molecules which in turn are intended to serve as imaging agents for PET study. Nucleophilic $^{18}F$-fluorination of some halo- and mesyloxyalkanes to the corresponding $^{18}F$-fluoroalkanes with $^{18}F$-fluoride obtained from an $^{18}O(p,n)^{18}F$ reaction, using novel reaction media system such as an ionic liquidor tert-alcohol, has been studied as a new method for $^{18}F$-fluorine labeling. Ionic liquid method is rapid and particularly convenient because $^{18}F$-fluoride in $H_2O$ can be added directly to the reaction media, obviating the careful drying that is typically required for currently used radiofluorination methods. The nonpolar protic tert-alcohol enhances the nucleophilicity of the fluoride ion dramatically in the absence of any kind of catalyst, greatly increasing the rate of the nucleophilic fluorination and reducing formation of byproducts compared with conventional methods using dipolar aprotic solvents. The great efficacy of this method is a particular advantage in labeling radiopharmaceuticals with $^{18}F$-fluorine for PETimaging, and it is illustrated by the synthesis of $^{18}F$-fluoride radiolabeled molecular imaging probes, such as $^{18}F$-FDG, $^{18}F$-FLT, $^{18}F$-FP-CIT, and $^{18}F$-FMISO, in high yield and purity and in shorter times compared to conventional syntheses.

Keywords

References

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