Chemie der Positronenemissionstomographie: Aktuelle Fortschritte bei ¹¹C‐, ¹⁸F‐, ¹³N‐ und ¹⁵O‐Markierungsreaktionen

Abstract

Die Positronenemissionstomographie (PET) ist ein molekulares bildgebendes Verfahren, das in vivo quantitative Informationen über Funktion und Metabolismus bei biologischen Prozessen für die Diagnose von Krankheiten und die Therapiebewertung liefert. Die breiten Anwendungsmöglichkeiten und die schnellen Fortschritte bei der PET haben zu einem ansteigenden Bedarf an neuen radiochemischen Methoden zur Synthese hochspezifischer Moleküle mit positronenemittierenden Radionukliden geführt. Dieser Aufsatz gibt einen Überblick über die gängige verwendete Markierungschemie in Bezug auf Beispiele klinisch relevanter PET‐Tracer und zeigt die jüngsten Entwicklungen und bahnbrechenden Erfolge im letzten Jahrzehnt, wobei der Schwerpunkt auf 11C, 18F, 13N und 15O liegt.

Development of a General Automated Flow Photoredox 18F-Difluoromethylation of N-Heteroaromatics in an AllinOne Synthesizer

“…We initially explored the 18 F-difluoromethylation of Acyclovir 2 under the optimum conditions described in our previous study 20 (75 ± 5 % RCY, entry 2, Table 2). Surprisingly, After HPLC purification 3 25 ± 5…”

“…Full three-step synthesis 3 1.4 ± 0. This process was then tested on the AIO, under the optimized conditions, 1 minute residence time (entry 4, was successfully completed in 40 minutes.…”

The Power of Iodane‐Guided C−H Coupling: A Group‐Transfer Strategy in Which a Halogen Works for Its Money

“…Indeed, one of the better studied methods for the synthesis of 18 F-labeled aromatic compounds involves the radiofluorination of diaryliodonium salts. [38] Therefore, considerable efforts in this field are centered on the search for new approaches to access densely functionalized l 3 -iodanes, and this fact has greatly contributed to making such reagents more readily available to the broader synthetic community. It should be noted that although the synthesis of l 3 -iodanes of certain functionalized cores has proven challenging, it is often hard to tell whether this is caused by the intrinsic instability of the target l 3 -iodane or by the incompatibility of the ArI precursor with the oxidizing reaction conditions.…”

Synthesis of 18F-difluoromethylarenes using aryl boronic acids, ethyl bromofluoroacetate and [18F]fluoride

“…Fluorine-18 is a widely used positron emitting radionuclide in part due to its favourable decay properties, and the numerous clinical applications of 2-deoxy-2-[ 18 F]fluoro- d -glucose, a radiopharmaceutical prepared from [ 18 F]fluoride. 1 While radiochemists have in recent years focused their efforts on methods enabling 18 F-fluorination 2 and 18 F-trifluoromethylation of (hetero)arenes, 2 , 3 18 F-difluoromethylation reactions have been less studied despite the importance of the CF 2 H motif 4 in radioligand design for drug discovery programmes. In 2013, we reported a Ag( i )-mediated 18 F-fluorodecarboxylation of 2-fluoro-2-arylacetic acids with [ 18 F]Selectfluor (bis)triflate leading to [ 18 F]ArCF 2 H. 5 Subsequently, we disclosed a Ag( i )-mediated halogen exchange reaction using [ 18 F]fluoride.…”