TMSOTf assisted synthesis of 2’-deoxy-2’-[18F] fluoro-β-D-arabinofuranosylcytosine ([18F] FAC)

Authors

Kishore K. Gangangari, CUNY Hunter CollegeFollow
John L. Humm, Memorial Sloan Kettering Cancer Center
Steven M. Larson, Memorial Sloan Kettering Cancer Center
Naga Vara Kishore Pillarsetty, Memorial Sloan Kettering Cancer Center

Document Type

Article

Publication Date

5-1-2018

Abstract

[¹⁸F]FAC (2’-deoxy-2’-[¹⁸F]fluoro-β-D-arabinofuranosylcytosine, 1) is a versatile probe for imaging deoxycytidine kinase (dCK) expression levels in vivo. dCK is responsible for phosphorylation of deoxycytidine (dC, 2) and other nucleoside analogs, plays a key role in immune activation and has demonstrated to be one of the key enzymes in activating nucleoside based drugs including gemcitabine. Reported synthesis of [¹⁸F]FAC is high yielding but is quite challenging requiring bromination using HBr and careful drying of excess HBr which is critical for successful synthesis. Here in we report a simplified trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted synthesis of [¹⁸F]FAC eliminating the need of bromination and drying. [¹⁸F]FAC (β-anomer) was synthesized with average isolated decay corrected yield of 10.59 + 4.2% (n = 6) with radiochemical purity of >98% and total synthesis time of 158 + 19 min.

Comments

This article was originally published in PLOS One, available at DOI: 10.1371/journal.pone.0196784.

This is an open access article distributed under the terms of the Creative Commons Attribution License 4.0 (CC BY 4.0).