MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling
Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high st...
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doaj-13c5eaaea8244176b9f4c82b490e90ce2020-11-24T20:53:58ZengMDPI AGMolecules1420-30492019-04-01247132710.3390/molecules24071327molecules24071327MCR Scaffolds Get Hotter with <sup>18</sup>F-LabelingTryfon Zarganes-Tzitzikas0Gonçalo S. Clemente1Philip H. Elsinga2Alexander Dömling3Department of Drug Design, Groningen Research Institute of Pharmacy, University of Groningen, 9713 AV Groningen, The NetherlandsDepartment of Nuclear Medicine and Molecular Imaging, University Medical Center Groningen, University of Groningen, 9713 GZ Groningen, The NetherlandsDepartment of Nuclear Medicine and Molecular Imaging, University Medical Center Groningen, University of Groningen, 9713 GZ Groningen, The NetherlandsDepartment of Drug Design, Groningen Research Institute of Pharmacy, University of Groningen, 9713 AV Groningen, The NetherlandsImaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high structural diversity can be synthesized via convergent multicomponent reactions (MCRs). The combination of PET labeling with MCR synthesis of biologically active compounds can greatly simplify radioanalytical and imaging-based analysis. In a proof-of-concept study, we optimized robust on-site radiolabeling conditions that were subsequently applied to several structurally different drug-like MCR scaffolds (e.g., arenes, β-lactam, tetrazole, and oxazole). These labeled scaffolds were synthesized via pinacol-derived aryl boronic esters (arylBPin) by copper-mediated oxidative <sup>18</sup>F-fluorination with radiochemical conversions (RCCs) from 15% to 76%.https://www.mdpi.com/1420-3049/24/7/1327multicomponent reactionsfluor-18positron emission tomographyradiochemistryboronic pinacol esters |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Tryfon Zarganes-Tzitzikas Gonçalo S. Clemente Philip H. Elsinga Alexander Dömling |
spellingShingle |
Tryfon Zarganes-Tzitzikas Gonçalo S. Clemente Philip H. Elsinga Alexander Dömling MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling Molecules multicomponent reactions fluor-18 positron emission tomography radiochemistry boronic pinacol esters |
author_facet |
Tryfon Zarganes-Tzitzikas Gonçalo S. Clemente Philip H. Elsinga Alexander Dömling |
author_sort |
Tryfon Zarganes-Tzitzikas |
title |
MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling |
title_short |
MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling |
title_full |
MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling |
title_fullStr |
MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling |
title_full_unstemmed |
MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling |
title_sort |
mcr scaffolds get hotter with <sup>18</sup>f-labeling |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2019-04-01 |
description |
Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high structural diversity can be synthesized via convergent multicomponent reactions (MCRs). The combination of PET labeling with MCR synthesis of biologically active compounds can greatly simplify radioanalytical and imaging-based analysis. In a proof-of-concept study, we optimized robust on-site radiolabeling conditions that were subsequently applied to several structurally different drug-like MCR scaffolds (e.g., arenes, β-lactam, tetrazole, and oxazole). These labeled scaffolds were synthesized via pinacol-derived aryl boronic esters (arylBPin) by copper-mediated oxidative <sup>18</sup>F-fluorination with radiochemical conversions (RCCs) from 15% to 76%. |
topic |
multicomponent reactions fluor-18 positron emission tomography radiochemistry boronic pinacol esters |
url |
https://www.mdpi.com/1420-3049/24/7/1327 |
work_keys_str_mv |
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