Molecules 2013, 18(7), 8618-8665; doi:10.3390/molecules18078618

Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18

1 Institut für Radiopharmazeutische Krebsforschung, Helmholtz-Zentrum Dresden-Rossendorf, Bautzner Landstraße 400, D-01328 Dresden, Germany 2 Institut für Klinische Radiologie und Nuklearmedizin, Medizinische Fakultät Mannheim der Universität Heidelberg, Theodor-Kutzer-Ufer 1-3, D-68167 Mannheim, Germany
* Author to whom correspondence should be addressed.
Received: 13 June 2013; in revised form: 11 July 2013 / Accepted: 15 July 2013 / Published: 22 July 2013
(This article belongs to the Special Issue Advances in Click Chemistry)
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Abstract: The increasing application of positron emission tomography (PET) in nuclear medicine has stimulated the extensive development of a multitude of novel and versatile bioorthogonal conjugation techniques especially for the radiolabeling of biologically active high molecular weight compounds like peptides, proteins or antibodies. Taking into consideration that the introduction of fluorine-18 (t1/2 = 109.8 min) proceeds under harsh conditions, radiolabeling of these biologically active molecules represents an outstanding challenge and is of enormous interest. Special attention has to be paid to the method of 18F-introduction. It should proceed in a regioselective manner under mild physiological conditions, in an acceptable time span, with high yields and high specific activities. For these reasons and due to the high number of functional groups found in these compounds, a specific labeling procedure has to be developed for every bioactive macromolecule. Bioorthogonal strategies including the Cu-assisted Huisgen cycloaddition and its copper-free click variant, both Staudinger Ligations or the tetrazine-click reaction have been successfully applied and represent valuable alternatives for the selective introduction of fluorine-18 to overcome the afore mentioned obstacles. This comprehensive review deals with the progress and illustrates the latest developments in the field of bioorthogonal labeling with the focus on the preparation of radiofluorinated building blocks and tracers for molecular imaging.
Keywords: Staudinger ligation; Huisgen click reaction; bioorthogonal; radiolabeling; tetrazine

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MDPI and ACS Style

Pretze, M.; Pietzsch, D.; Mamat, C. Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18. Molecules 2013, 18, 8618-8665.

AMA Style

Pretze M, Pietzsch D, Mamat C. Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18. Molecules. 2013; 18(7):8618-8665.

Chicago/Turabian Style

Pretze, Marc; Pietzsch, Doreen; Mamat, Constantin. 2013. "Recent Trends in Bioorthogonal Click-Radiolabeling Reactions Using Fluorine-18." Molecules 18, no. 7: 8618-8665.

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