Synthesis of ¹⁸F‐labelled biotin analogues

Abstract

A one-step 18 F-labelling strategy was used to prepare three labelled analogues of the vitamin biotin, which can be useful as tracers because of biotin's high affinity for avidin. The labelled compounds were obtained in decay-corrected yields of up to 35% and specific radioactivity of 320GBq/mmol. When evaluated in situ, the analogues showed good affinity for avidin: 60-75% of the radiolabelled compounds were bound to avidin within 5minutes. The binding was site-specific, as shown by blocking experiments with native biotin.

Avidin/Biotin Bioinspired Platform for Dual In Vivo 18F-PET/NIRF Molecular Imaging

“…In the first case, Shoup et al synthesized two [ 18 F]­fluoroalkyl-biotin derivativesusing a mesyloxy precursor for labelingbut the yields were lower (12% to 20% non-decay-corrected) than those we obtained for longer synthesis times (90 min) . Blom et al proposed three [ 18 F]­fluoroalkyl- and [ 18 F]­fluoroalkoxy-biotin derivatives prepared in moderate to good yields (13% to 35% decay-corrected) and with high MA (320 GBq/μmol) . Compared to these two examples, the strategy that we have developed allows the production of an original [ 18 F]­pyridinyl-biotin derivative in 30% to 80% higher radiochemical yields.…”

“…5 Blom et al proposed three [ 18 F]fluoroalkyl-and [ 18 F]fluoroalkoxy-biotin derivatives prepared in moderate to good yields (13% to 35% decaycorrected) and with high MA (320 GBq/μmol). 6 Compared to these two examples, the strategy that we have developed allows the production of an original [ 18 F]pyridinyl-biotin derivative in 30% to 80% higher radiochemical yields. Claesener et al also synthesized another [ 18 F]fluoroalkyl-biotin derivative, using a tosyloxy precursor too.…”