Copper-catalyzed click reactions: quantification of retained copper using 64Cu-spiked Cu(I), exemplified for CuAAC reactions on liposomes
-
Karolin Wagener
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.
Dedicated to: The memory of Prof. Dr. Günter Herrmann.
Acknowledgment
The authors are very grateful to the Max-Planck Graduate Center (MPGC, K. Wagener) as well as to the DFG in the context of the SFB 1066 for financial support. K. Wagener and M. Schinnerer and M. Worm are members of the Graduate School of the SFB 1066.
References
1. Kettenbach, K., Schieferstein, H., Ross, T. L.: 18F-labeling using click cycloadditions. Biomed. Res. Int. 2014, 361329 (2014).10.1155/2014/361329Search in Google Scholar PubMed
2. Meyer, J.-P., Adumeau, P., Lewis, J. S., Zeglis, B. M.: Click chemistry and radiochemistry: The first 10 years. Bioconjug. Chem. 27, 2791 (2016).10.1021/acs.bioconjchem.6b00561Search in Google Scholar PubMed
3. Nwe, K., Brechbiel, M. W.: Growing applications of ‘click chemistry’ for bioconjugation in contemporary biomedical research. Cancer Biother. Radiopharm. 24, 289 (2009).10.1089/cbr.2008.0626Search in Google Scholar
4. Mamat, C., Ramenda, T., Wuest, F. R.: Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging. Mini-Rev. Org. Chem. 6, 21 (2009).10.2174/157019309787316148Search in Google Scholar
5. Bock, V. D., Hiemstra, H., Van Maarseveen, J. H.: CuI-catalyzed alkyne-azide ‘click’ cycloadditions from a mechanistic and synthetic perspective. Eur. J. Org. Chem. 2006, 51 (2006).10.1002/ejoc.200500483Search in Google Scholar
6. Ross, T. L.: The click chemistry approach applied to fluorine-18. Curr. Radiopharm. 3, 202 (2010).10.2174/1874471011003030202Search in Google Scholar
7. Kolb, H. C., Finn, M. G., Sharpless, K. B.: Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40, 2004 (2001).10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5Search in Google Scholar
8. Marik, J., Sutcliffe, J. L.: Click for PET: rapid preparation of [18F]fluoropeptides using CuI catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett. 47, 6681 (2006).10.1016/j.tetlet.2006.06.176Search in Google Scholar
9. Bost, M., Houdart, S., Oberli, M., Kalonji, E., Huneau, J.-F., Margaritis, I.: Dietary copper and human health: current evidence and unresolved issues. J. Trace Elem. Med. Biol. 35, 107 (2016).10.1016/j.jtemb.2016.02.006Search in Google Scholar PubMed
10. Turnlund, J. R.: Human whole-body copper metabolism. Am. J. Clin. Nutr. 67, 960S (1998).10.1093/ajcn/67.5.960SSearch in Google Scholar PubMed
11. Cerchiaro, G., Manieri, T. M., Bertuchi, F. R.: Analytical methods for copper, zinc and iron quantification in mammalian cells. Metallomics 5, 1336 (2013).10.1039/c3mt00136aSearch in Google Scholar PubMed
12. Wagener, K., Worm, M., Pektor, S., Schinnerer, M., Thiermann, R., Miederer, M., Frey, H., Rösch, F.: Comparison of linear and hyperbranched polyether lipids for liposome shielding by 18F-radiolabeling and Positron emission tomography. Biomacromolecules 19, 2506 (2018).10.1021/acs.biomac.8b00115Search in Google Scholar PubMed
13. Gaetke, L. M., Chow, C. K.: Copper toxicity, oxidative stress, and antioxidant nutrients. Toxicology 189, 147 (2003).10.1016/S0300-483X(03)00159-8Search in Google Scholar PubMed
14. Pretze, M., Kuchar, M., Bergmann, R., Steinbach, J., Pietzsch, J., Mamat, C.: An efficient bioorthogonal strategy using CuAAC click chemistry for radiofluorinations of SNEW peptides and the role of copper depletion. ChemMedChem. 8, 935 (2013).10.1002/cmdc.201300053Search in Google Scholar PubMed
15. Reibel, A. T., Müller, S. S., Pektor, S., Bausbacher, N., Miederer, M., Frey, H., Rösch, F.: Fate of linear and branched polyether-lipids in vivo in comparison to their liposomal formulations by 18F-radiolabeling and positron emission tomography. Biomacromolecules 16, 842 (2015).10.1021/bm5017332Search in Google Scholar PubMed
16. Rokka, J., Snellman, A., Zona, C., La Ferla, B., Nicotra, F., Salmona, M., Forloni, G., Haaparanta-Solin, M., Rinne, J. O., Solin, O.: Synthesis and evaluation of a 18F-curcumin derivate for β-amyloid plaque imaging. Bioorg. Med. Chem. 22, 2753 (2014).10.1016/j.bmc.2014.03.010Search in Google Scholar PubMed
17. Carneiro De Sousa, F. N., Eichholz, G. G.: Dosimetry of gamma rays from nitrogen-16 decay. Int. J. Appl. Radiat. Isot. 36, 981 (1985).10.1016/0020-708X(85)90260-1Search in Google Scholar PubMed
18. Tahir, S. N. A., Chettle, D. R.: Identification of oxygen-19 during in vivo neutron activation analysis of water phantoms. Physiol. Meas. 36, N127 (2015).10.1088/0967-3334/36/12/N127Search in Google Scholar PubMed
19. Bé, M.-M., Chisté, V., Dulieu, C., Browne, E., Chechev, V., Kuzmenko, N., Helmer, R., Nichols, A., Schönfeld, E., Dersch, R.: Table of radionuclides (Vol. 1 – A=1 to 150). Le bureau international des poids et mesures, sèvres 2004.Search in Google Scholar
20. Horen, D. J., Meyerhof, W. E.: Decay of copper-66. Phys. Rev. 111, 559 (1958).10.1103/PhysRev.111.559Search in Google Scholar
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/ract-2018-3000).
©2019 Walter de Gruyter GmbH, Berlin/Boston
Articles in the same Issue
- Frontmatter
- Preface
- Günter Herrmann (1925–2017): A tribute to his research and organizational achievements
- The research reactor TRIGA Mainz – a strong and versatile neutron source for science and education
- Copper-catalyzed click reactions: quantification of retained copper using 64Cu-spiked Cu(I), exemplified for CuAAC reactions on liposomes
- Reactions of fission products from a 252Cf source with NO and mixtures of NO and CO in an inert gas
- From SRAFAP to ARCA and AIDA – developments and implementation of automated aqueous-phase rapid chemistry apparatuses for heavy actinides and transactinides
- Production and study of chemical properties of superheavy elements
- Precise ground state properties of the heaviest elements for studies of their atomic and nuclear structure
- Modeling the sorption of Np(V) on Na-montmorillonite – effects of pH, ionic strength and CO2
- Determination of complex formation constants of neptunium(V) with propionate and lactate in 0.5–2.6 m NaCl solutions at 22–60°C using a solvent extraction technique
- Nuclear forensics on uranium fuel pellets
- Recent developments in resonance ionization mass spectrometry for ultra-trace analysis of actinide elements
- Measurement of the laser resonance ionization efficiency for lutetium
Articles in the same Issue
- Frontmatter
- Preface
- Günter Herrmann (1925–2017): A tribute to his research and organizational achievements
- The research reactor TRIGA Mainz – a strong and versatile neutron source for science and education
- Copper-catalyzed click reactions: quantification of retained copper using 64Cu-spiked Cu(I), exemplified for CuAAC reactions on liposomes
- Reactions of fission products from a 252Cf source with NO and mixtures of NO and CO in an inert gas
- From SRAFAP to ARCA and AIDA – developments and implementation of automated aqueous-phase rapid chemistry apparatuses for heavy actinides and transactinides
- Production and study of chemical properties of superheavy elements
- Precise ground state properties of the heaviest elements for studies of their atomic and nuclear structure
- Modeling the sorption of Np(V) on Na-montmorillonite – effects of pH, ionic strength and CO2
- Determination of complex formation constants of neptunium(V) with propionate and lactate in 0.5–2.6 m NaCl solutions at 22–60°C using a solvent extraction technique
- Nuclear forensics on uranium fuel pellets
- Recent developments in resonance ionization mass spectrometry for ultra-trace analysis of actinide elements
- Measurement of the laser resonance ionization efficiency for lutetium
