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Bifunctional bispidine derivatives for copper-64 labelling and positron emission tomography. | LitMetric

Bifunctional bispidine derivatives for copper-64 labelling and positron emission tomography.

Org Biomol Chem

Laboratoire d'Ingénierie Moléculaire Appliquée à l'Analyse, Université de Strasbourg, CNRS, IPHC UMR 7178, F-67000 Strasbourg, France.

Published: February 2017

AI Article Synopsis

Article Abstract

The first radiolabelling studies of a bispidine (3,7-diazabicyclo[3.3.1]nonane) derivative substituted by a glycinate pendant arm (L1) with Cu are reported. Labelling was fast and easily performed at room temperature and in a wide range of pH values. Under these conditions, radiochemical yields over 90% were achieved within 5 minutes at micromolar concentration of the ligand. A bifunctional analogue of L1 (L2) has been obtained by introducing an l-lysine amino acid on the bispidine skeleton. Ligand L2 demonstrates good radiolabelling capacities at room temperature and in water (pH 4 to pH 6). This new bispidine is a versatile platform which can easily react with NHS esters and can be subsequently coupled to a recognition unit in order to perform targeted Positron Emission Tomography (PET) imaging. As a proof of concept, two new bifunctional chelators (BFCs) with a biotin (L3) or a maleimide functional group (L4) have been synthesized. The biotinylated BFC is very valuable for pretargeting strategies using streptavidin-conjugated antibodies. The reactivity of the maleimide derivative L4 has been studied with the model peptide GP120. Quantitative coupling has been achieved under physiological conditions, showing a good regioselectivity towards cysteine residues versus lysine amino acids.

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Source
http://dx.doi.org/10.1039/c6ob02712aDOI Listing

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