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Radiochimica Acta

International Journal for chemical aspects of nuclear science and technology

Editor-in-Chief: Qaim, Syed M.


IMPACT FACTOR 2018: 1.339

CiteScore 2018: 1.20

SCImago Journal Rank (SJR) 2018: 0.333
Source Normalized Impact per Paper (SNIP) 2018: 0.720

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2193-3405
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Volume 107, Issue 7

Issues

Copper-catalyzed click reactions: quantification of retained copper using 64Cu-spiked Cu(I), exemplified for CuAAC reactions on liposomes

Karolin Wagener
  • Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
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/ Dennis Renisch
  • Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
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/ Meike Schinnerer
  • Institute of Physical Chemistry, Johannes Gutenberg University, Jakob-Welder-Weg 11, 55128 Mainz, Germany
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/ Matthias Worm
  • Institute of Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany
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/ Yvonne Jakob
  • Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
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/ Klaus Eberhardt
  • Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
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/ Frank Rösch
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  • Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany
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Published Online: 2018-10-26 | DOI: https://doi.org/10.1515/ract-2018-3000

Abstract

The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is a powerful, highly reliable and selective reaction which allows for a rapid synthesis in high yields and under mild conditions (pH, temperature). However, the cytotoxicity of copper requires its complete removal prior to an application in vivo. This is an issue especially when it comes to CuAAC reactions on macromolecular structures or drug delivery systems, as copper might be retained by these systems. Thus, a quantification of the final copper content of these systems is inevitable, which we exemplified for a CuAAC reaction on liposomes using 64Cu-spiked Cu(I). In this respect, a Cu(II) nitrate solution was irradiated at the TRIGA Mark II research reactor Mainz to obtain c.a. [64Cu]Cu(II). The irradiated solution was directly used for a CuAAC on liposomes. After purification, their copper content was calculated utilizing γ-ray spectrometry. Only 0.018% of the added 64Cu-activity was still present in the liposome containing fractions after purification. This refers to a total amount of copper of 0.17 ng. The amount of retained copper is so low, that an in vivo application of the liposomes is absolutely reasonable. Besides this particular study, the experimental methodology may be applied to study many other CuAAC reactions, used for the synthesis of radiolabeled or non-radioactive species, which are intended for human applications.

This article offers supplementary material which is provided at the end of the article.

Keywords: CuAAC; copper-64; quantification of copper; γ-ray spectrometry; liposomes

Dedicated to: The memory of Prof. Dr. Günter Herrmann.

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About the article

Corresponding author: Prof. Dr. Frank Rösch, Institute of Nuclear Chemistry, Johannes Gutenberg University, Fritz-Strassmann-Weg 2, 55128 Mainz, Germany, Tel.: +49 6131 39 25302, Fax: +49 6131 39 25253


Received: 2018-06-06

Accepted: 2018-09-25

Published Online: 2018-10-26

Published in Print: 2019-07-26


Citation Information: Radiochimica Acta, Volume 107, Issue 7, Pages 547–554, ISSN (Online) 2193-3405, ISSN (Print) 0033-8230, DOI: https://doi.org/10.1515/ract-2018-3000.

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