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[ 18 F]FPyZIDE: A versatile prosthetic reagent for the fluorine‐18 radiolabeling of biologics via copper‐catalyzed or strain‐promoted alkyne‐azide cycloadditions
Author(s) -
Roche Mélanie,
Specklin Simon,
Richard Mylène,
Hinnen Françoise,
Génermont Kevin,
Kuhnast Bertrand
Publication year - 2019
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3701
Subject(s) - cycloaddition , chemistry , reagent , alkyne , azide , combinatorial chemistry , fluorine , radiosynthesis , aryl , click chemistry , molecule , chemical synthesis , pyridine , catalysis , organic chemistry , in vitro , biochemistry , alkyl , microbiology and biotechnology , in vivo , biology
Methods for the radiolabeling of biologics with fluorine‐18 have been of interest for several decades. A common approach consists in the preparation of a prosthetic reagent, a small molecule bearing a fluorine‐18 that is conjugated with the macromolecule to an appropriate function. Click chemistry, and more particularly cycloadditions, is an interesting approach to radiolabel molecules thanks to mild reaction conditions, high yields, low by‐products formation, and strong orthogonality. Moreover, the chemical functions involved in the cycloaddition reaction are stable in the drastic radiofluorination conditions, thus allowing a simple radiosynthetic route to prepare the prosthetic reagent. We report herein the radiosynthesis of 18 F‐FPyZIDE, a pyridine‐based azide‐bearing prosthetic reagent. We exemplified its conjugation via copper‐catalyzed cycloaddition (CuAAC) and strain‐promoted cycloaddition (SPAAC) with several terminal alkyne or strained alkyne model compounds.