Radiopharmaceutical Chemistry Laboratory, Turku PET Centre, University of Turku, Turku, Finland.
Mol Imaging Biol. 2013 Apr;15(2):131-5. doi: 10.1007/s11307-012-0584-9.
We have studied the utility of [(18)F]ClF electrophilic addition to the carbon-carbon double bond of analogues of a model positron emission tomography (PET) tracer, [(18)F]EF5. The consequence of simultaneous chlorine/fluorine addition on lipophilicity and biological activity of the molecule is evaluated.
Post-target produced [(18)F]F2 was reacted with Cl2 to produce [(18)F]ClF, which was used in electrophilic addition.
[(18)F]ClF was produced and used to label chlorinated analogues of [(18)F]EF5. The chlorinated analogues, [(18)F]EF4Cla and [(18)F]EF4Clb, were synthesized simultaneously. The in vivo uptake of the analogues compared well with [(18)F]EF5 uptake in tumor-bearing mice.
[(18)F]ClF is a suitable labeling reagent for electrophilic addition to double bonds of PET tracers. The results show that the modification of the pentafluoro group of [(18)F]EF5 by monofluorine-for-chlorine exchange affected the lipophilicity, but the hypoxia avidity of these molecules was not apparently altered.
我们研究了 [(18)F]ClF 的亲电加成反应在模型正电子发射断层扫描 (PET) 示踪剂 [(18)F]EF5 类似物的碳-碳双键中的应用。评估了氯/氟同时加成对分子亲脂性和生物活性的影响。
靶后产生的 [(18)F]F2 与 Cl2 反应生成 [(18)F]ClF，用于亲电加成。
[(18)F]ClF 被合成并用于标记 [(18)F]EF5 的氯化类似物 [(18)F]EF4Cla 和 [(18)F]EF4Clb。这些类似物在荷瘤小鼠体内的摄取与 [(18)F]EF5 的摄取相当。
[(18)F]ClF 是一种适合用于 PET 示踪剂双键的亲电加成反应的标记试剂。结果表明，[(18)F]EF5 的五氟基团被单氟-氯取代的修饰影响了亲脂性，但这些分子的缺氧亲和力并没有明显改变。
