Journal Article Epublish 1 citation
PubMed: 38352831 DOI: 10.1021/acsmedchemlett.3c00557
Design of Novel F-Labeled Amino Acid Tracers Using Sulfur F-Fluoride Exchange Click Chemistry.
ACS Med Chem Lett 15(2):294-301
Authors: Yong Huang, Hualong Chen, Lu Zhang, Yi Xie, Chengze Li, Ziyue Yu, Zeng Jiang, Wei Zheng, Zhongjing Li, Xuan Ge, Ying Liang, Zehui Wu
Affiliations
- Department of Nuclear Medicine, National Cancer Center, National Clinical Research Center for Cancer, Cancer Hospital & Shenzhen Hospital, Chinese Academy of Medical Sciences and Peking Union Medical College, Shenzhen 518116, China.
- Beijing Institute of Brain Disorders, Laboratory of Brain Disorders, Ministry of Science and Technology, Collaborative Innovation Center for Brain Disorders, Capital Medical University, Beijing 100069, China.
Abstract
[F]Gln-OSOF, [F]Arg-OSOF, and [F]FSY-OSOF were designed by introducing sulfonyl F-fluoride onto glutamine, arginine, and tyrosine, respectively. [F]FSY-OSOF can be prepared directly by sulfur F-fluoride exchange, while [F]Gln-OSOF and [F]Arg-OSOF require a two-step labeling method. Those tracers retain their typical transport characteristics for unmodified amino acids. Both PET imaging and biodistribution confirmed that [F]FSY-OSOF visualized MCF-7 and 22Rv1 subcutaneous tumors with high contrast, and its tumor-to-muscle ratio was better than that of [F]FET. However, [F]Gln-OSOF and [F]Arg-OSOF poorly image MCF-7 subcutaneous tumors, possibly due to differences in the types and amounts of transporters expressed in tumors. All three tracers can visualize the U87MG glioma. According to our biological evaluation, none of the tracers evaluated in this study exhibited obvious defluorination, and subtle structural changes led to different imaging characteristics, indicating that the application of sulfur F-fluoride exchange click chemistry in the design of radioactive sulfonyl fluoride amino acids is feasible and offers significant advantages.
MeSH
Neoplasms, Amino Acids, Click Chemistry