[18F]–NHC–BF3 adducts as water stable radio-prosthetic groups for PET imaging

Kantapat Chansaenpak; Mengzhe Wang; Zhanhong Wu; Rehmat Zaman; Zibo Li; François P. Gabbaï

doi:10.1039/C5CC04545B

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[¹⁸F]–NHC–BF₃ adducts as water stable radio-prosthetic groups for PET imaging†‡

Kantapat Chansaenpak,§^a Mengzhe Wang,§^b Zhanhong Wu,^b Rehmat Zaman,^a Zibo Li ¶*^b and François P. Gabbaï ¶*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Texas A&M University, College Station, Texas 77843, USA
E-mail: gabbai@mail.chem.tamu.edu

^b Department of Radiology, Biomedical Research Imaging Center, University of North Carolina, Chapel Hill 27599, USA
E-mail: ziboli@med.unc.edu

Abstract

The radiofluorination of N-heterocyclic carbene (NHC) boron trifluoride adducts affords novel [¹⁸F]–positron emission tomography probes which resist hydrolytic fluoride release. The labelling protocol relies on an ¹⁸F–¹⁹F isotopic exchange reaction promoted by the Lewis acid SnCl₄. Modification of the NHC backbone with a maleimide functionality provides access to a model peptide conjugate which shows no evidence of defluorination when imaged in vivo.

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Article information

DOI: https://doi.org/10.1039/C5CC04545B
Article type: Communication
Submitted: 03 Jun 2015
Accepted: 25 Jun 2015
First published: 26 Jun 2015

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Chem. Commun., 2015,51, 12439-12442

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[¹⁸F]–NHC–BF₃ adducts as water stable radio-prosthetic groups for PET imaging

K. Chansaenpak, M. Wang, Z. Wu, R. Zaman, Z. Li and F. P. Gabbaï, Chem. Commun., 2015, 51, 12439 DOI: 10.1039/C5CC04545B

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Chemical Communications