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Current Radiopharmaceuticals


ISSN (Print): 1874-4710
ISSN (Online): 1874-4729

Propargyl 4-[18F]fluorobenzoate: A Putatively More Stable Prosthetic Group for the Fluorine-18 Labeling of Biomolecules via Click Chemistry

Author(s): Ganesan Vaidyanathan, Benjamin J. White and Michael R. Zalutsky

Volume 2, Issue 1, 2009

Page: [63 - 74] Pages: 12

DOI: 10.2174/1874471010902010063

Price: $65


Faster and more efficient approaches for radiolabeling biomolecules with short-lived 18F are in dire need. Herein we report a new 18F-labeled prosthetic group containing an acetylene function that permits the labeling of biomolecules via click chemistry. This template, propargyl 4- [18F]fluorobenzoate ([18F]PFB) was synthesized from a quaternary salt precursor in decay-corrected radiochemical yields of 58 ± 31%. Several model compounds containing an azide moiety — benzyl azide, two lysine derivatives and a transglutaminase-reactive peptide — were labeled using [18F]PFB via a click reaction in decay-corrected radiochemical yields of 88 ± 4%, 79 ± 33%, 75 ± 5%, and 37 ± 31%, respectively. Our results suggest that the novel agent [18F]PFB is a potentially useful template for the 18F-labeling of biomolecules via click chemistry.

Keywords: Fluorine-18, click reaction, positron emission tomography, defluorination

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