The insertion of [18F] into peptides and proteins is extremely useful for in vivo imaging purposes as well as radiopharmaceutical chemistry, and there are several reported methods for achieving this. However, many of these methods have drawbacks (i.e. harsh radiolabelling conditions, using fluorinated prosthetic groups, special handling). Herein, we describe a novel method for the direct C-F bond formation onto annexin V, a valuable biomarker for apoptosis detection, under mild conditions and straightforward handling. Dehydroalanine (Dha), a chemically modified protein tag, is formed on a single cysteine (C316) by reaction with 2,5-dibromohexadiamide (DBHDA), and is then treated with [18F] Selectfluor bis(triflate) to give the [18F]-radiolabelled annexin V (C316Dfa). Subsequently, the resulting radiotracer was used in an animal model study monitored by positron emission tomography (PET), demonstrating the effectiveness of this new method for the [18F]-radiolabelling of proteins.

Site-selective and direct electrophilic C-F bond formation onto proteins

251st National Meeting (2016)

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