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  • [Applied Radiation and Isotopes] One-pot radiosynthesis of O-[18F]fluoromethyl-D-tyrosine via intramolecular nucleophilic 18F-fluorination with 1,2,3-triazolium triflate salt precursor.

    서울의대 / 김호영, 이윤상*, 정재민*

  • 출처
    Applied Radiation and Isotopes
  • 등재일
    February 2018
  • 저널이슈번호
    132:105-109
  • 내용

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    Abstract

    A radiolabeled amino acid O-[18F]fluoromethyl-D-tyrosine (D-[18F]FMT) has been reported to show high tumor uptake. However, introduction of [18F]fluoromethyl group was difficult and was an issue to be solved. We solved it by using a precursor containing 1,2,3-triazolium salt. D-[18F]FMT was synthesized from (R)-1-((4-(2-((tert-butoxycarbonyl)amino)-3-((3,4-dimethylbenzyl)oxy)-3-oxopropyl)phenoxy)methyl)-3-methyl-4-phenyl-1H-1,2,3-triazol-3-ium trifluoromethanesulfonate via intra-molecular 18F-fluorination and subsequent removal of the protecting groups. The total synthesis time was 65min (including purification) and the overall radiochemical yield was 9% based on the isolated product (not decay-corrected). The resulting D-[18F]FMT was obtained with high radiochemical purity (> 99%) and specific activity (100-150 GBq/μmol). D-[18F]FMT also achieved excellent results in pharmacological evaluation such as stability test and protein binding assay. We expect that this simple one-pot labeling method would help using D-[18F]FMT more widely.

     

     

    Author information

    Ho Young Kim a, Chansoo Park b, Ji Youn Lee a c, Dae Yoon Chi b, Yun-Sang Lee a, Jae MinJeong a c d

    a Department of Nuclear Medicine, Seoul National University College of Medicine, Seoul, Republic of Korea
    b Department of Chemistry, Sogang University, Seoul, Republic of Korea
    c Department of Biomedical Sciences, Seoul National University Graduate School, Seoul, Republic of Korea
    d Cancer Research Institute, Seoul National University, Seoul, Republic of Korea

  • 키워드
    Intra-molecular fluorination1,2,3-triazolium saltD-[18F]fluoromethyl tyrosineTumor imaging
  • 편집위원

    종양영상을 위한 PET 방사성의약품 중 하나인 O-[18F]fluoromethyl-D-tyrosine (D-[18F]FMT)의 새로운 합성법에 대한 논문이다. 기존의 D-[18F]FMT 합성은 2 단계를 거쳐서 합성하는 것으로 알려져 왔는데, 이를 1 단계로 줄임으로써 반감기가 짧은 18F 방사성의약품의 효율적인 합성을 위한 개선된 방향을 제시해 주고 있다.

    2018-03-15 16:11:22

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