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Title: 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:
 [1];  [1];  [1];  [1];  [1]
  1. 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) (SC-23)
OSTI Identifier:
1345980
Grant/Contract Number:  
SC0001249
Resource Type:
Journal Article: 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. doi: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. doi: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},
issn = {0002-7863},
number = 17,
volume = 137,
place = {United States},
year = {2015},
month = {4}
}

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Cited by: 16 works
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