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A Flexible Synthesis of 68Ga-Labeled Carbonic Anhydrase IX (CAIX)-Targeted Molecules via CBT/1,2-Aminothiol Click Reaction

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molecules-24-00023.pdf (2.42 MB)

Date

2018-12-21

Authors

Chen, Kuo-Ting
Nguyen, Kevin
Ieritano, Christian
Gao, Feng
Seimbille, Yann

Journal Title

Journal ISSN

Volume Title

Publisher

MDPI

Abstract

We herein describe a flexible synthesis of a small library of 68Ga-labeled CAIX-targeted molecules via an orthogonal 2-cyanobenzothiazole (CBT)/1,2-aminothiol click reaction. Three novel CBT-functionalized chelators (1–3) were successfully synthesized and labeled with the positron emitter gallium-68. Cross-ligation between the pre-labeled bifunctional chelators (BFCs) and the 1,2-aminothiol-acetazolamide derivatives (8 and 9) yielded six new 68Ga-labeled CAIX ligands with high radiochemical yields. The click reaction conditions were optimized to improve the reaction rate for applications with short half-life radionuclides. Overall, our methodology allows for a simple and efficient radiosynthetic route to produce a variety of 68Ga-labeled imaging agents for tumor hypoxia.

Description

Keywords

carbonic anhydrase IX, 68Ga-labeling, click reaction, compound library

LC Keywords

Citation

URI

https://doi.org/10.3390/molecules24010023
 http://hdl.handle.net/10012/16489

Collections

Waterloo Research
Chemistry