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. 2024 May 17;30(28):e202400581.
doi: 10.1002/chem.202400581. Epub 2024 Apr 4.

Intramolecular Friedel-Crafts Acylation of [11C]Isocyanates Enabling the Radiolabeling of [carbonyl-11C]DPQ

Marius Ozenil  1 , Lukas Kogler  2   3 , Braeden A Mair  4   5 , Marcus Hacker  1 , Wolfgang Wadsak  1   3 , Benjamin H Rotstein  4   5   6 , Verena Pichler  2
Affiliations

Intramolecular Friedel-Crafts Acylation of [11C]Isocyanates Enabling the Radiolabeling of [carbonyl-11C]DPQ

Marius Ozenil et al. Chemistry. .

Abstract

α,β-aromatic lactams are highly abundant in biologically active molecules, yet so far they cannot be radiolabeled with short-lived (t1/2=20.3 min), β+-decaying carbon-11, which has prevented their application as positron emission tomography tracers. Herein, we developed, optimized, and applied a widely applicable, one-pot, quick, robust and automatable radiolabeling method for α,β-aromatic lactams starting from [11C]CO2 using the reagent POCl3⋅AlCl3. This method proceeds via intramolecular Friedel-Crafts acylation of in situ formed [11C]isocyanates and shows a broad substrate scope for the formation of five- and six-membered rings. We implemented our developed labeling method for the radiosynthesis of the potential PARP1 PET tracer [carbonyl-11C]DPQ in a clinical radiotracer production facility following the standards of the European Pharmacopoeia.

Keywords: PARP; PET tracer; carbon-11.

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References

    1. G. Costantino, A. Macchiarulo, E. Camaioni, R. Pellicciari, J. Med. Chem. 2001, 44, 3786–3794.
    1. J. R. Atack, A. Pike, G. Marshall, J. Stanley, R. Lincoln, S. M. Cook, R. T. Lewis, W. P. Blackaby, S. C. Goodacre, R. M. McKernan, G. R. Dawson, K. A. Wafford, D. S. Reynolds, Neuropharmacology 2006, 50, 677–689.
    1. E. O. Hexner, C. Serdikoff, M. Jan, C. R. Swider, C. Robinson, S. Yang, T. Angeles, S. G. Emerson, M. Carroll, B. Ruggeri, P. Dobrzanski, Blood 2008, 111, 5663–5671.
    1. None
    1. P. J. H. Scott, Angew. Chem. Int. Ed. Engl. 2009, 48(33), 6001–60004;

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