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High-Yielding Aqueous 18F-Labeling of Peptides via Al18F Chelation

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Immunomedics, Inc., 300 American Road, Morris Plains, New Jersey 07950, United States
Garden State Cancer Center, Center for Molecular Medicine and Immunology, Morris Plains, New Jersey 07950, United States
§ Hunter College of the City University of New York, New York, New York 10065, United States
For C.A.D.: e-mail, [email protected].; phone, 973-605-8200, extension 299; fax, 973-605-1340. For D.M.G.: e-mail, [email protected]
Cite this: Bioconjugate Chem. 2011, 22, 9, 1793–1803
Publication Date (Web):July 30, 2011
https://doi.org/10.1021/bc200175c
Copyright © 2011 American Chemical Society

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    Abstract

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    The coordination chemistry of a new pentadentate bifunctional chelator (BFC), NODA-MPAA 1, containing the 1,4,7-triazacyclononane-1,4-diacetate (NODA) motif with a methylphenylacetic acid (MPAA) backbone, and its ability to form stable Al18F chelates were investigated. The organofluoroaluminates were easily accessible from the reaction of 1 and AlF3. X-ray diffraction studies revealed aluminum at the center of a slightly distorted octahedron, with fluorine occupying one of the axial positions. The tert-butyl protected prochelator 7, which can be synthesized in one step, is useful for coupling to biomolecules on solid phase or in solution. High yield (55–89%) aqueous 18F-labeling was achieved in 10–15 min with a tumor-targeting peptide 4 covalently linked to 1. Defluorination was not observed for at least 4 h in human serum at 37 °C. These results demonstrate the facile application of Al18F chelation using BFC 1 as a versatile labeling method for radiofluorinating other heat-stable peptides for positron emission imaging.

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    HPLC chromatograms, crystallographic data, and CIF file. This material is available free of charge via the Internet at http://pubs.acs.org.

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