高等学校化学学报

高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (07): 1486.doi: 10.3969/j.issn.0251-0790.2012.07.022

• 有机化学 • 上一篇    下一篇

整合素αvβ3 靶向PET探针 18 F-c(RGDfK) 在Cu(Ⅰ)催化体系中的点击合成

施玲丽1,2, 李剑波1,2, 王成1,2, 贾丽娜1,2, 汪勇先1, 张岚1   

  1. 1. 中国科学院上海应用物理研究所, 上海 201800;
    2. 中国科学院研究生院, 北京 100049
  • 收稿日期:2011-09-22 出版日期:2012-07-10 发布日期:2012-07-10
  • 通讯作者: 张 岚, 男, 博士, 研究员, 主要从事放射性药物研究. E-mail: Zhanglan@sinap.ac.cn E-mail:shilingli@yahoo.cn
  • 基金资助:

    国家自然科学基金(批准号: 10805069, 10875163)资助.

Synthesis of 18F-c(RGDfK) as Integrin αvβ3 Targeted PET Tracer via Click Chemsitry with Cu(Ⅰ) Catalyst Systems

SHI Ling-Li1,2, LI Jian-Bo1,2, WANG Cheng1,2, JIA Li-Na1,2, WANG Yong-Xian1, ZHANG Lan1   

  1. 1. Shanghai Institute of Applied Physics, Chinese Academy Sciences, Shanghai 201800, China;
    2. Graduate University of Chinese Academy of Sciences, Beijing 100049, China
  • Received:2011-09-22 Online:2012-07-10 Published:2012-07-10

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摘要： 通过2-叠氮乙基对甲苯磺酸酯的18F-亲核取代反应, 制备了[18F]2-氟叠氮乙烷, 并与丙炔酸修饰的c(RGDfK)反应, 采用常用的CuSO4/NaVc催化体系, 并尝试了CuI(s)和CuI/NH4OH 2种催化体系, 通过点击化学方法合成了整合素αvβ3靶向PET探针[18F]氟乙基-1,4-取代1,2,3-三唑c(RGDfK)[18F-c(RGDfK)]. 在CuSO4/NaVc的催化下, 18F-c(RGDfK)的总合成时间约为60 min, 总收率62%(从[18F]F-起计, 经过衰变校正). 实验结果表明, 点击化学方法高效便捷, 适于多肽的18F标记.

关键词: 点击化学, 18F标记, 1,3-偶极环加成, 叠氮化物, 精氨酸-甘氨酸-天冬氨酸(RGD)序列

Abstract: As one of the most important types of Click chemistry, copper-catalyzed 1,3-dipolar cycloaddition reaction has attracted great attention. In this study, 2-[18F]fluoroethyl azide([18F]FEA) was synthesized by nucleophilic substitution of 18F-. Then, [18F]fluoroethyl-1H-1,2,3-triazole-4-c(RGDfK)[18F-c(RGDfK)] was radio-synthesized as integrin αvβ3 targeted PET tracer fast and efficiently via Click reaction of [18F]FEA with propioloyl c(RGDfK). Three catalyst systems of click reaction were investigated: CuSO4/NaVc, CuI(s) and CuI/NH4OH, the last two have been used in peptide-click-labeling for the first time. While CuSO4/NaVc catalysing the Click reaction, the total radio-chemistry yield of 18F-c(RGDfK) was 62% and the synthesis time was about 60 min(decay-corrected). Click chemistry has demonstrated to be an extraordinarily efficient and convenient method for the preparation of 18F labeled peptides.

Key words: Click chemistry, 18F-labeling, 1,3-Dipolar cycloaddition, Azide, RGD

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