Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium
Abstract
Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [18F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this paper, we demonstrate the possibility of 18F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile–thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [18F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. Finally, the substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.
- Authors:
-
- David Geffen School of Medicine at Univ. of California, Los Angeles, CA (United States)
- Publication Date:
- Research Org.:
- Univ. of California, Los Angeles, CA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Biological and Environmental Research (BER)
- OSTI Identifier:
- 1345980
- Grant/Contract Number:
- SC0001249
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Journal of the American Chemical Society
- Additional Journal Information:
- Journal Volume: 137; Journal Issue: 17; Journal ID: ISSN 0002-7863
- Publisher:
- American Chemical Society (ACS)
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 60 APPLIED LIFE SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Sergeev, Maxim E., Morgia, Federica, Lazari, Mark, Wang, Jr., Christopher, and van Dam, R. Michael. Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium. United States: N. p., 2015.
Web. doi:10.1021/jacs.5b02659.
Sergeev, Maxim E., Morgia, Federica, Lazari, Mark, Wang, Jr., Christopher, & van Dam, R. Michael. Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium. United States. https://doi.org/10.1021/jacs.5b02659
Sergeev, Maxim E., Morgia, Federica, Lazari, Mark, Wang, Jr., Christopher, and van Dam, R. Michael. Fri .
"Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium". United States. https://doi.org/10.1021/jacs.5b02659. https://www.osti.gov/servlets/purl/1345980.
@article{osti_1345980,
title = {Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium},
author = {Sergeev, Maxim E. and Morgia, Federica and Lazari, Mark and Wang, Jr., Christopher and van Dam, R. Michael},
abstractNote = {Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [18F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this paper, we demonstrate the possibility of 18F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile–thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [18F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. Finally, the substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.},
doi = {10.1021/jacs.5b02659},
journal = {Journal of the American Chemical Society},
number = 17,
volume = 137,
place = {United States},
year = {Fri Apr 10 00:00:00 EDT 2015},
month = {Fri Apr 10 00:00:00 EDT 2015}
}
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