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Synthesis of Optically Pure 4-Fluoro-Glutamines as Potential Metabolic Imaging Agents for Tumors

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† ‡ Departments of †Radiology, ‡Pharmacology, and §Cancer Biology, and ∥Abramson Cancer Centre, School of Medicine, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States
[email protected]; [email protected]
Cite this: J. Am. Chem. Soc. 2011, 133, 4, 1122–1133
Publication Date (Web):December 29, 2010
https://doi.org/10.1021/ja109203d
Copyright © 2010 American Chemical Society
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    Abstract

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    A versatile synthetic route to prepare all four stereoisomeric 4-fluoro-glutamines was developed by exploiting a Passerini three-component reaction. The skeleton of 4-substituted glutamine derivatives was efficiently constructed. Subsequent four-step reactions, highlighted by a “neutralized” TASF fluorination, provided the desired products with high yields and excellent optical purity. The optically pure fluorine-18 labeled 4-fluoroglutamines were also successfully prepared using either a 18-crown-6/KHCO3 or K[222]/K2CO3 catalysis system. Preliminary cell uptake and inhibition studies using the 9L tumor cells and SF188Bcl-xL tumor cells (a glutamine addicted tumor derived from glioblastoma) provided strong evidence for their potential application in conjunction with positron emission tomography (PET) for in vivo imaging of tumors, which use glutamine as an alternative energy source.

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    Full experimental procedures and data, 1H/13CNMR spectra of new compounds, HPLC profiles and reported X-ray structural data. This material is available free of charge via the Internet at http://pubs.acs.org.

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