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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Main Authors:	Tryfon Zarganes-Tzitzikas, Gonçalo S. Clemente, Philip H. Elsinga, Alexander Dömling
Format:	Article
Language:	English
Published:	MDPI AG 2019-04-01
Series:	Molecules
Subjects:	multicomponent reactions fluor-18 positron emission tomography radiochemistry boronic pinacol esters
Online Access:	https://www.mdpi.com/1420-3049/24/7/1327

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spelling	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	AT tryfonzarganestzitzikas mcrscaffoldsgethotterwithsup18supflabeling AT goncalosclemente mcrscaffoldsgethotterwithsup18supflabeling AT philiphelsinga mcrscaffoldsgethotterwithsup18supflabeling AT alexanderdomling mcrscaffoldsgethotterwithsup18supflabeling
_version_	1716795567141552128

MCR Scaffolds Get Hotter with <sup>18</sup>F-Labeling

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