Nebel N, Strauch B, Maschauer S, Lasch R, Rampp H, Fehler S, Bock L, Hübner H, Gmeiner P, Heinrich M, Prante O (2017)
Publication Type: Journal article, Original article
Publication year: 2017
Book Volume: 2
Pages Range: 8649-8659
Journal Issue: 12
18F-Labeled building blocks from the type of [18F]fluorophenylazocarboxylic-tert-butyl esters offer a rapid, mild, and reliable method for the 18F-fluoroarylation of biomolecules. Two series of azocarboxamides were synthesized as potential radioligands for dopamine D3 and the μ-opioid receptor, revealing compounds 3d and 3e with single-digit and sub-nanomolar affinity for the D3 receptor and compound 4c with only micromolar affinity for the μ-opioid receptor, but enhanced selectivity for the μ-subtype in comparison to the lead compound AH-7921. A "minimalist procedure" without the use of a cryptand and base for the preparation of 4-[18F]fluorophenylazocarboxylic-tert-butyl ester [ 18 F]2a was established, together with the radiosynthesis of methyl-, methoxy-, and phenyl-substituted derivatives ([ 18 F]2b-f). With the substituted [18F]fluorophenylazocarbylates in hand, two prototype azocarboxylates radioligands were synthesized by 18F-fluoroarylation, namely the methoxy azocarboxamide [ 18 F]3d as the D3 receptor radioligand and [ 18 F]4a as a prototype structure of the μ-opioid receptor radioligand. By introducing the new series of [18F]fluorophenylazocarboxylic-tert-butyl esters, the method of 18F-fluoroarylation was significantly expanded, thereby demonstrating the versatility of 18F-labeled phenylazocarboxylates for the design of potential radiotracers for positron emission tomography .
APA:
Nebel, N., Strauch, B., Maschauer, S., Lasch, R., Rampp, H., Fehler, S.,... Prante, O. (2017). [18F]Fluorophenylazocarboxylates: Design and Synthesis of Potential Radioligands for Dopamine D3 and μ‑Opioid Receptor. ACS Omega, 2(12), 8649-8659. https://dx.doi.org/10.1021/acsomega.7b01374
MLA:
Nebel, Natascha, et al. "[18F]Fluorophenylazocarboxylates: Design and Synthesis of Potential Radioligands for Dopamine D3 and μ‑Opioid Receptor." ACS Omega 2.12 (2017): 8649-8659.
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