18F-PEG-biotin: Precursor (boroaryl-PEG-biotin) synthesis, 18F-labelling and an in-vitro assessment of its binding with Neutravidin™–trastuzumab pre-treated cells

Abstract

Biotin can be functionalised with boroaryl and readily 18F -radiolabelled in aqueous solution and will bind to cells pre-incubated with Neutravidin™-antibody conjugates.

Boron–18F containing positron emission tomography radiotracers: advances and opportunities

“…This could offer an indirect way of radiolabelling antibodies for use as PET biomarkers (49). This could offer an indirect way of radiolabelling antibodies for use as PET biomarkers (49).…”

“…Smith and co-workers developed a high-yielding method for conjugation of both boronic esters and aryltrifluoroborates to amine-terminating molecules (see Scheme 9) (49,50). The initial reaction was carried out using the commercially available 2,6-difluoro-4-formylphenylboronic acid pinacol ester with (o-carboxymethyl)hydroxylamine and Hünig's base.…”

“…Smith and co-workers have recently developed a new approach for labelling biotin owing to its high strong binding affinity with avidin (in this case, deglycosylated avidin) that can be conjugated to antibodies. This could offer an indirect way of radiolabelling antibodies for use as PET biomarkers (49). This method for radiolabelling biotin uses a PEG linker as a spacer between the biomolecule and the boronic group for fluorination.…”

“…The reaction was also attempted using the tetraphenyl benzopinacolate derivative, which gave the desired product in a 79% yield, with no deboronated by-product present (44). Smith and co-workers developed a high-yielding method for conjugation of both boronic esters and aryltrifluoroborates to amine-terminating molecules (see Scheme 9) (49,50). The initial reaction was carried out using the commercially available 2,6-difluoro-4-formylphenylboronic acid pinacol ester with (o-carboxymethyl)hydroxylamine and Hünig's base.…”

Abstracts of the 20th International Isotope Society (UK group) Symposium: Synthesis & Applications of Labelled Compounds 2011

“…We have developed three biotin precursors for [ 18 F] labelling: oxy‐amine‐biotin conjugate. which was labelled using [ 18 F]FDG as a prosthetic group; a conjugate of biotin and boroaryl, which was [ 18 F]labelled in aqueous solution; a conjugate of biotin with 4, 8 and 16 branched dendrons functionalised with trifluoroboroaryl, which were labelled using isotopic exchange.…”